The Hunt: Flat, Tall Boots

Boutique 9 'Zanny' Boot

2017 Update: Check out our most recent round-up of the best knee-high boots for commuting, work, and beyond!

Sure, we all know what basics professional women are supposed to have in their closets, but if you’re buying one for the first time or replacing one you’ve worn into the ground, it can be a pain to find exactly the right incarnation in stores. In “The Hunt,” we search the stores for a basic item that every woman should have.

By reader request, I’m focusing today’s Hunt on the flat tall boot. I must admit: I’m kind of iffy on wearing these to the office. I know Capitol Hill Style says she rocks her flat boots with a skirt suit all the time, but I really think this is the kind of thing that you need to make sure that you know your office, and that your outfit is “intentional” enough that you avoid looking like you never changed out of your commuting shoes. When looking for a pair of flat boots to wear around the office, I think you want to avoid a few features — the overly slouchy boot, the Western-style boot, or anything with serious treads (too reminiscent of rain boots).  Readers, do you wear flat boots with skirts to the office?  Which features do you look for (or avoid)?  Have you made any recent purchases (share the brand/style name if possible!)

Chinese Laundry 'Spring Street' BootFirst up: these affordable boots from Chinese Laundry (which, reading reviews, sound like they might work if you have calves on the wider side). I particularly like the almond toe. They’re available in black and cognac leather at Nordstrom for $99.95. Chinese Laundry ‘Spring Street’ Boot
Buckleup I really like the ever-so-slight, 1″ wedge on these Nine West Buckleup boots — I think this would be a great boot for the office. It’s available in black, dark brown, and “medium natural” leather for $109.99 at Another good option from Nine West: this “Watermelon” boot, available at Amazon on sale (was $169, now $119).
Steven IntyceAgain, I like the slight wedge on these Intyce boots by Steve Madden’s sister company, Steven. They’re available in 6 colors (including a kind of great wine color) for $104-$149 at Zappos. Steven Intyce
Boutique 9 'Zanny' BootThese boots have a 1.5″ heel, but I think they look great, in part because they’re completely devoid of any details. No buttons, no buckles, nothing (just a muted zipper in the back). They’re $214.95 at Nordstrom (available in both burgundy and black). Boutique 9 ‘Zanny’ Boot
Frye Melissa Button Back ZipFrye boots are, of course, legendary for comfort — but can the usually rugged look work for the office? They have a huge number of boots with heels under 2″ — I think this is my favorite of the bunch: The Melissa Button Back Zip. I could do without the buckle detail at the back of the shoe, but that’s ok. I think these would be a really versatile pair to wear both on the weekend and for work. They’re $348 at Zappos (available in 10 colors). Frye Melissa Button Back Zip
Stuart Weitzman JustmineGorgeous! I really like these Stuart Weitzman boots. It doesn’t say exactly how tall the wedge is inside, but on the video it looks to be about 1.5″ — I also like that it has goring in the back to help with fit. These babies are $595 at Zappos (available in black and brown). Stuart Weitzman Justmine

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  1. I love the look but these fatted calves just can’t do it. I tried on skinny jeans the other day, baggy in the hips and thighs and completely stretched over my calves. Damn my love for hilly cities.

    • I have MASSIVE calves that I’ve never been able to fit into any tall boots. But, I ordered Bandolino’s “Cabeza Wide” flat boots to see if I could squeeze in- they’re a slight bit snug around the tops, but if I wear them with tights and a skirt, they fit fine. They’re also extremely comfortable and break in really well. Here they are:

      The women in my office do tend to wear the tall boots with skirts and dresses. As long as everything else looks polished, they’re fine.

    • S in Chicago :

      I bought some adjustable calf ones at Nordstrom a few years ago by a company named Sanzia. I love them because I can adjust so they always look nice whether wearing over tights or thick jeans. Other places sell them. I totally recommend– I’ve had the sole dyed once where some of the finish was flaking off, but otherwise they have held up amazingly well with frequent wear. Super comfortable footbed, too.

      • kerrycontrary :

        For some reason I feel fine in a dress and boots and tights, but I feel silly in a pencil skirt and tall boots. I feel like my pencil skirts always call for heels.

        • des-pairing :

          Same here. I think it’s because I’m short, so the boots+pencil skirt combo make me even shorter by breaking me into 3 equally tiny chunks, whereas the dress creates one long line

    • I have heavy calves, too, and live in the Steven Intyces. Just an FYI.

    • I wear a 4-6 and have tiny ankles, but my calves are shaped like flower vases, so even “wide calf” boots sometimes won’t even pull on over the widest part of my leg.

  2. Always a NYer :

    I love my Duo Ravenna boots. Today I’m wearing them with slim fit black pants tucked in. Where I’m currently interning is business casual and since the pants/boots are both black it doesn’t bother me. I’d probably wear them with a skirt or dress if I were also wearing black tights.

  3. La Canadienne has lots of models like the Frye one. Waterproof, warm, and rubber soles.

  4. style advice needed... :

    Calling for lady docs/scientists who wear “white coats” every day…

    What are you wearing now, in the winter?

    Do you wear sweaters under the coat, or still stick with lighter blouses/tops etc… since you are layered? What kind?

    What is your winter coat like, that hopefully covers your long white coat?

    What are you wearing on your feet, that works with winter (snowy?) weather and allows you to walk among hospitals/clinic building in weather and still works when you enter the hospital and transition to patient care?


    • LadyEnginerd :

      I wear a lab coat and run around between buildings but have no patient contact and there’s no institutional expectation of professionalism (hooray science). When I lived in a cold place I liked silk blend turtleneck sweaters for under the lab coat as the right level of warmth. Since my neck is always cold, I preferred turtlenecks because I can’t accessorize with scarves for safety reasons. My favorite was purchased at Banana yeeears ago – maybe the “essential turtleneck” is this year’s version? On the feet? Clarks ankle booties with smartwool cable-knit socks. Comfy enough to wear when I’m on my feet all day, reasonably weatherproof, and reasonably professional looking poking out from under trousers.

      Can’t help on the coat front, since I’d just make mad dashes between buildings sans coat.

      • OMG, the silk turtleneck under a lab coat brings back memories of my biology professor in college.

        She would wear the thin silk turtlenecks that were designed as long underwear. You know, the kind that became transparent when stretched over one’s rounder parts? Yeah, and then she’d take off her lab coat to lecture, and we could see her “rounder parts” quite plainly…and she didn’t wear a bra…

        • LadyEnginerd :

          Oh jeez. I didn’t mean underwear-as-outerwear! I swear I have more fashion sense than that!
          Here’s what I was thinking of…

    • For tops I prefer thin sweaters and long sleeve Tshirts. I can dress them up with nicer jewelry and cardigan layers I take off when I put on a labcoat. Our labcoats live in the lab, we don’t bring them into the office and have different ones for different labs, we would not wear them between buildings.
      I commute in shoes that can take the weather and keep nicer looking ones in the offices. I prefer Oxford styles that strike a balance between comfort and safety.

      • style advice needed... :

        Thanks. What are your favorite T shirts that look nice enough with that much exposure? Are they nicer fabrics (ex. silk/blends) or simply sturdy cotton?

        • I prefer cotten to expensive tops, I think that inexpensive Tshirts wear fine. Lands End is my favorite source but I also have ones from H&M and Kohls.

    • I have patient contact, but my lab coat stays in my office when I leave the building. I wear layers, sheath dress + cardi, or pencil skirt, tights (mostly fleece lined), and tall boots. Although not everyone can pull off the boot/skirt combo, it is just too cold for nylons and heels. That and the constant running around the hospital is a hassle in heels. I have some Born boots for my 1/2 mile walk from the parking lot, and there is a lot of ice and snow here….they are perfect without being too clunky.

    • sweaters under the lab coat, sure, it’s pretty cold with the air conditioning needed in our lab.

      however! the lab coat never leaves the lab! first rule drummed into the heads of unwilling students, techs, etc. by health and safety.

    • Late reply :

      On days where I’m in clinic, I tend to wear long-sleeve cotton or cotton-blend shirts, or possibly a lighter weight sweater, because sometimes I get too warm otherwise. Usually I wear pants and silk long underwear. I leave my white coat at work. In the past when that wasn’t an option, I put it in a bag to hopefully not transfer germs to my other clothing. Honestly, I haven’t cared too much about my shoes (either boots, sometimes clogs and sometimes a Mary Jane-type flat shoe) but that’s easier with pants. If you have to walk outside a lot, perhaps a nicer boot would be an option (La Canadienne, maybe Aquaitalia?).

  5. I purchased the Steve Madden boots above, wore them once, and think I’m going to donate them. The size 8 was so large that my heels were slipping out of them, and the 7.5 was so tight that they tore my feet up. They are nice for larger calves though. I know other women on here love them so YMMV.

  6. I have a pair of Ciao Bella flat boots that I wear with black tights and dresses/pencil skirts to the office once or twice a week in the winter. They’re similar to the Boutique 9 boots above (sans wedge), very sleek and without any buckles, slouch, etc.

  7. Diana Barry :

    I only have flat boots and wear them all the time to the office in fall/winter/spring. I have one pair of (brown) Timberlands (wide in the foot but not the calf) and one pair of (black) Clarks (I got them stretched). I don’t wear them with suits, but with skirts/dresses, tights, and blazer.

  8. My coworker has the Steve Madden boots above, and I think those particular boots really are too casual for office wear, unless you have the sort of office like ours that lets you wear jeans to work (looks down at jeans and J.Crew riding boots).

    I love those Boutique 9 boots, though.

    • Research, Not Law :

      I frequently wear a very similar pair with tights and pencil skirt to the office and get complements. (It’s not a conservative office, though.)

  9. I picked these up the “Miz Mooz Boot” in brown few weeks ago from Nordstrom and LOVE them. They look great with dresses, skinny jeans, under bootcut jeans, tights, bare legs, you name it.

  10. I’m in a California law office and women (partners too) wear tall boots to the office all the time, but people also wear jeans mid-week and it’s an admittedly more casual environment, so.. grains of salt etc.

    I totally agree with your criteria. I would add that I personally find a pointier toe to be more “formal” looking and more office-friendly as a result, but that may just be my own thing. I just bought these:

    And so far I’m loving them, especially for the price. They’re not totally flat, but they’re close.

  11. I can vouch for Chinese Laundry.. I have two pairs of knee high boots and want more. I also like these boots which are on sale for $80 right now.. such a steal ( The reviews are pretty accurate. They’re perfect except they bulge a little around the ankles. I have slim calves though. The leather is SO soft. I also have the Steve Madden Candence boots which are great. I’m curious to see everyone else’s reviews as I’m tall and prefer flat boots.

  12. As someone who is only 5′ tall, I will be really happy when this trend for boots right up to the knees is done. Those are always WAY too high for me and though I need a new black boot, I have found absolutely nothing in my price range this year that wouldn’t make me look oddly shrunken PLUS kind of trashy with over-the-knee-boots. Sigh.

    • Reallllyyy?! I’m just under 5’2, and I love the knee boots! In fact, knee-high, flat boots are my favourite kind of shoe.

      I feel like they are flattering on me…but I am am very short through the torso, so I feel like they even me out somehow, and I love how they look with a mid-thigh coat.

      I got a sweet pair from Naturalizer recently, and they’re awesome (they made me a Naturalizer convert, I’ve always avoided that store, but gosh, their shoes are comfy, and as long as you look for the youthful styles, they’re cute). They were under $200, waterproof, leather, and I think they’re having a sale on right now…

      (…as an aside, isn’t it weird that Canadians, though metric, have broadly failed to adopt centimeters as our height unit? I know people that use kgs not lbs, but not a single person that says “oh yes, I’m 158 cm tall”…)

      • Do they actually sit at/below your knee? Because on me, they’re often closer to thigh boots than knew boots. Clearly not work appropriate – or at all my style. Maybe next year, lol.

        • *knee boots. Not knew boots.

        • Yup, they do sit at my knee, they’re the Juletta ones- but, as I said, I’m super short through the torso, so my legs, while short, are long for my height (my legs are too long to wear petite pants, they flop around at the ankles, but regular pants are just slightly too long….I need like a 31.5 inseam).

          • Lucky you, lol. The Juletta ones are fab. I’m the opposite. Short legs, long torso. Knees boots are a fail for me :(

    • darjeeling :

      right there with you. I have had the damnedest time finding 13-14″ boot shafts and have pretty much just given up.

  13. I wear la canadienne flat boots with a dress or skirt and tights all the time. I think it works for our fairly formal (but more flats than heels) office.

  14. Weekend Getaway :

    What are some nice weekend getaway activities away from NYC?

  15. I have medium brown Bandolino boots called “Ajern Tall Wedge Boots” that I don’t wear to the office (personal preference but certainly could). I live in them outside the office. They have a slight wedge and I have walked miles in them in complete comfort and I am a wuss about heels and shoes in general. I highly recommend them. They are on sale at Macy’s too!

  16. Does anyone have any recommendations for boots that don’t sag around the ankle? Boots tend to have saggy, wrinkly ankles on me and I’m not sure if I’m over-thinking it too much or what. I have a pair of knee-high Cole Haan riding boots that are mostly ok, but I wanted to try another brand/style.

  17. Bereavement Leave :

    If you have used bereavement leave, did work need to see a death certificate?

    Briefly, my office has been very stingy with approving time off. I am taking four days off for Christmas (traveling to visit family). My grandparent died this weekend, and I want to take bereavement leave after the new year to help my family. I don’t think two “vacations” in one month would be seen fondly, so I’m considering not telling anyone at work about the death until I return. I think I were to tell them about my plans to take the leave now, they would tell me I couldn’t take my Christmas time off. I want to avoid having them know that I sat on the info, though.

    I know that sounds bad, but I don’t want to choose between helping my parent in the wake of their parents’ death and helping my husband and children see their family for the first time in over a year.

    • Mine did. And grandparents didn’t count – only immediate family. I was allowed to use sick leave or vacation time instead.

    • Wow, no I’ve never had to present a death certificate! I can’t even imagine. I’ve taken leave for two grandparents, once when I was with a small firm and later while with BigLaw. I will say that for the second grandparent (BigLaw), I did work out of the firm’s office that was located near where my family lives. So I wound up really taking off a total of two days over the course of a week (a half day to go make the arrangements, a full day for the funeral, and another half day to help sort through things). But it came right on the heels of a holiday when I took some leave to travel for the holiday so I had the same holiday + bereavement leave.

    • No Problem :

      Mine didn’t. It seems a little farfetched to ask employees to provide a death certificate for that reason. If they did need proof, maybe a copy of the obituary could suffice?

      Does your company have a written policy on bereavement? My company’s lists the family members for whom you are permitted to take bereavement and the number of days per year allowed.

      As a side note, I find it entirely ridiculous that the OP is even in this predicament (and I’m not saying she’s wrong for bringing it up, just that the fact that your company is so stingy that you have anything to worry about is really sad). What employer is so cold-hearted that upon finding out an employee wishes to take bereavement leave to help her family cope with their loss they would consider not letting her take her pre-approved Christmas vacation?

    • Meg Murry :

      Could you let them know that your grandparent died but that you aren’t sure as to when there will be a memorial service, etc, so you will let them know when you need to take the time? That way you aren’t sitting on the info but telling them the truth – you will need to take time off in the future, but you aren’t sure of the date. They might want you to take vacation time as opposed to bereavement leave if they have strict policies as to the number of days you can take for specific relatives, but I would hope that they wouldn’t deny you the leave to visit your family and pay your respects to your grandfather.

    • I was asked and I didn’t provide one. It was not a problem. Someone from HR called and asked and I said it was a bit difficult at the moment and they let it go.

    • S in Chicago :

      Do you have an HR manual you can check? Our is very specific, and it allows for grandparents. I didn’t have to show anyone any documentation, but I’ve also worked for my company for a long time so have a ton of time stockpiled. Our HR also tends to leave a lot to the discretion of supervisors–and the person I report to tends to be pretty laid back on this sort of thing. (Probably because he realizes so much time has stockpiled because I never get a freaking day off from things. Grrr.)

      If post-holiday time off isn’t doable, any chance you can maybe bargain a remote work situation instead?

      So awful anyone should have to choose between Christmas and managing after a funeral. I’m so sorry you’re even having to think about this.

    • Bereavement Leave :

      Thank you for your responses.

      I should have specified that grandparents are eligible for our policy and that the policy is vague about what kind of documentation is required. (No form needed, but “verification” may be). It seems like it’s up to the discretion of the supervisor, but sounds like a program from the service would work.

      Unfortunately working remotely isn’t a reasonable possibility for either trip due to some quirks about the locations and schedules.

      I’m considering the “heads up” approach, but I suspect it would not help or even make them more jumpy. If I tell them there’s a good chance I’ll need upcoming leave, they are going to want to review my entire upcoming leave regardless of how fixed the additional leave would be.

      My office is generally relaxed, but getting time off has become a real issue. I’m not sure what caused the tightened fist about a year or two ago. Your responses have assuaged my guilt some, though, since their attitude sounds unusual.

      • I would go with the suggestion above that you let them know there has been a death in the family, and plans are still up in the air. Then you can let them know when you need to take the leave. I think you are likely going to get even less push back because a death over the holidays is an extra-bummer.

        I have taken bereavement twice, never had to produce evidence…but I would think anything (memorial service program, obit, note from funeral home…) would work. I suppose “proof” must be required in some cases because of abuse…but it has never been an issue with me.

      • Death certificates often take weeks or months to get. So I doubt they’ll require a death certificate.

        My sympathies. This must be extra tough around the holidays.

    • My work accepted a letter from the mortuary that did the funeral service to “authenticate” the death. Airlines used to accept this letter as well (if you are trying to get bereavement fares). The mortuary was familiar with what I needed and happy to provide the letter.

    • PharmaGirl :

      Never had to produce a death certificate and was given bereavement leave for grandparents. I was offered 3 days in each case but, if memory serves, I only took 1-2.

    • Mine did not ask, but we’re pretty lax about time off, despite the fact that we’re a huge national company. I even took more bereavement leave than we apparently are allowed, and no one cared.

      Honestly, I don’t know what I would’ve done in my situation. My grandmother lived overseas in Asia, so I have no idea what sort of death certificate I would’ve produced.

    • First of all, I’m so sorry for your loss. I recently had a death in the family but it was complicated. I told my manager and director I had to deal with a family emergency but then when I got back, I talked to HR and explained why I wanted to use bereavement leave and they were okay with it. I’ve had to take bereavement leave at two different jobs now and no one has ever asked me for a death certificate. Do you think the obituary would suffice? Best wishes.

  18. emcsquared :

    I bought a pair of Bare Traps tall black boots – I had thought I would need a wide calf boot, but these aren’t wide calf and fit perfectly. Not sure of the style, although they have a stretchy black panel that makes them much more comfortable. Only weird thing is that one foot fits much more tightly than the other, which I’ve never experienced before (so it’s probably the boots).

    I was also surprised that a pair of my jeans that are close fitting but not skinny jeans fit inside them too. Plus they only cost $80 the day after Thanksgiving…

  19. TJ: What do people think of Warby Parker glasses? I’m looking into getting a spare pair of glasses for those days – like today – when I have apparently lost a contact and have to get rid of the other one to prevent serious headaches.

    Not having to squint at the screen would be awesome.

    • I haven’t purchased them (they’re on my list for my next trip stateside) but I think they’re adorable!

    • eastbaybanker :

      Love mine. They’re a good value. At $99, they are a pretty low commitment so I found myself pushing the style envelope a bit.

    • I just checked them out. Now I want a pair, they have lots of cute frames, and well…there’s never any harm in having another spare pair of glasses.

    • They’re good basic glasses. The lenses are not fancy though – so glare, etc. will not be great. But I only wear mine when watching TV or going to a show, so they suit me fine for those purposes.

    • My husband has them and loves them.

    • East Coaster :

      I got my new Warby Parkers on Friday. Highly recommend!

      I have a very high prescription, so my glasses this year were going to be upwards of $700 for 1 pair, and it was too much (including high index, anti -reflective coating and everything else). I ordered 5 pairs to try on, and then had to order another 5, but I found a frame that fits nicely. My glasses through WP were $125 including the high index lenses. Of course, they are not as nice as the designer glasses, but for the price difference I’ll take them!

    • I think they’re good value for money. My SO has a pair and has managed to keep them a year without destroying them (a real first!). Maybe the chunky hipster frames are better able to take a beating than wire frames!

    • Patent Pending :

      I haven’t had a problem with glare but some reason they get much dirtier then other glasses. I just use hand soap or dish soap to clean them, but I do find that even a passing brush with my hand makes them really dirty. That’s my only complaint. Note they don’t have nose pads–I think that is the main difference with other glasses.

      • Yes on both counts. Although the odd dirtiness is less of a problem with my more recent pair than the first. Maybe they have fixed it somewhat. I usually carry a cloth with me and just wipe down, so not a huge problem.

      • I haven’t noticed this problem. I have two pair of eyeglasses and one sunglasses, & I’ve been happy with them.

  20. Has anyone come across a nice maroon leather skirt? I love the Madewell zipping skirt, but only size 14 available. I’d like something similar — real leather, not faux and reasonably priced. I know leather is pricey, but I think under $300 is my range.

    • Zipline. Damn you, autocorrect.

    • You didn’t specify your size. This one is available in a 4:

  21. Maddie Ross :

    I wear my Frye Melissas (not the back zip — the plain ones) to work all the time. Not with suits, but definitely with skirts/blazers and skirts/sweaters. I could be persuaded to wear them with a suit if it ever really snowed where I am, but since it doesn’t, I generally wear actual hose and heels with suits.

  22. I love my Gore-Tex Ecco corse boots: they fit perfectly because of the stretchy fabric, but are (to my opinion) still elegant enough to wear to the office. And they feel like slippers, so comfy!
    Still looking for comfortable, waterproof yet elegant brown boots. I have too many high heeled boots, and we’ve already had so much snow that high heels are not a good idea.
    Suggestions welcome, but I’m in Europe so non EU-based shops are out due to high customs-fees.

  23. eastbaybanker :

    Is the red pants trend officially over? I’m thinking of buying a pair, but wondering if that ship has sailed….

    • I just bought some, but I tend to do what I want. It seems like there are still a large number of different colored pants in the market still – so I would think it would be ok.

      • eastbaybanker :

        Thanks for the input! I guess worst case scenario I can always just wear them around the holidays.

        • Moving to the City :

          I still wear and love my yellow skinny pants! I vote buy them.

    • Red is a neutral.

  24. Gail the Goldfish :

    How timely as I want a pair of flat, dark brown riding boots for Christmas. Does anyone have a favorite for skinnier calves? Most boots have at least an inch or two of extra room in the calves on me.

    • kerrycontrary :

      I have a pair of clarks riding boots that I love. I have a little room in the calf, but it doesn’t look silly (and I have thin legs)

    • I’m also looking for the same thing. 6pm lets you filter by circumference, but I wasn’t in love with any of the 14″ boots.

    • Try Franco Sarto’s “Clint” style. My calves are average-sized and usually fit into any pair of boots I please, but I had to return these because they ran very narrow. The Friar Brown is gorgeous, and I was super bummed they didn’t work out!

      • Gail the Goldfish :

        those look perfect, thanks! (Well, actually the LK Bennetts linked below look absolutely perfect, but these look perfect in a within-my-budget-and-not- sold-out sort of way)

    • Seattle Freeze :

      Cole Haan Tenleys (mentioned below by another poster) – nice looking, very comfortable, and don’t gape on my <14" calves.

      Zappos also allows searching by calf circumference.

    • Anonymous :

      This may be too late, but I have pretty slim calves and I prefer Steve Madden boots. I have three pair that zip up either the side or back and my legs don’t swim around in them bare legged or with skinny jeans/leggings, etc.

    • The naturalizer juletta is one to check out. I wear a 10.5 and have calves that measure about 13.5 inches around and these were snug on me. I did go down a half size and likely could have went down a full size.

    • I have the Frye Melissas Kat posted (those exact ones with the back zip) in a gorgeous dark brown and they are perfect on my smaller calves.

  25. I got these (link to follow) and have been really happy with them. They’re Donald J. Plainer and were a great price at Last Call. The leather is very nice & they’re dressy enough for my office and have just enough of a heel to wear them with pants without looking like Man Shoes.

  26. I agree with Kat that simple works best here. On that basis, I actually don’t really like options 1-3 for the office. I think the buckles are a bit unnecessary. And the CL ones look like they may be “over the knee” (in style at least, if not in practice), which I think is probably too much for the office.

    I wear plain black and brown leather boots, flat and heeled, to the office regularly (weather permitting). I don’t wear them on especially formal days but I think for the most part they are fine and my office is on the more conservative side. But one observation: if you’re going to wear knee high boots, make sure you wear dark tights and make sure your skirt is not too short. Something about bare legs and tall boots or a shorter skirt and tall boots, or especially both, just seems way too overtly sexy for the office.

    • Actually, on second thought, I don’t think buckles are per se not good for the office. But I think a buckled boot needs to be a lot more structured. E.g., I would wear these boots to the office any day or the week:

  27. Posting here because I feel weird posting something relatively trivial under the Coffee Break above, but I’m in need of the collective wisdom of the hive in navigating some family holiday drama.

    DH and I have been spending Christmas with my family (about 1.5 hours away) for most of the time we’ve been together. After we got married a couple years ago, my in-laws started coming down for Christmas Eve dinner. Last year, for the first time they stayed overnight and joined in the Christmas day festivities. Recently my mom confessed to me that she hasn’t enjoyed the years when my MIL and FIL join us, even though they like each other just fine. So this year she invited them for Christmas Eve dinner but suggested that maybe it would be easier if they didn’t stay over because they got a new dog, she’s renovating the house and the guest room is full of stuff, etc.

    Now DH is upset and saying that if his family isn’t welcome, then he feels unwelcome too and maybe he’ll go back with his family instead of staying overnight with me. That plan obviously upsets me, which he understands, and I think if I push he’ll stay, but then I feel like I’m putting my family ahead of him. I feel like I’m caught in the middle and am looking for a way to make everybody happy when it’s largely out of my hands but can’t help wanting to fix it so we can have a happy holiday. One option DH and I discussed is offering to pay for a hotel room for his parents, but that still doesn’t fix the awkwardness. I understand my mom’s frustration and reasons, but I’m also a bit resentful that she created this situation even if that’s selfish. I’d offer to host, but I think I’d be met with resistance from my family for several (somewhat valid) reasons.

    If anybody has any thoughts on how to approach a conversation with my mom, or how to make DH feel like I’m validating his feelings (and also my in-laws, although they’re being gracious and have accepted the dinner invite and said nothing further about it to us) I’d love to hear it.

    • Merabella :

      It may be time to instate the every other year rule for your family if they can’t hang out together – or you can tell your mom that if she isn’t comfortable having your in-laws there that you may go up to stay with them this year.

      Then you alternate between Christmas and Thanksgiving – we did this when I was a kid with divorced parents, but I think it works well with dealing with in-laws as well.

      • Merabella :

        Just re-read, maybe tell your mom that you will be coming for Christmas Eve, but since your in-laws aren’t invited that you all will be spending Christmas day with them at your house.

        Next year you may want to institute the every other year rule in order to prevent this issue from coming up again.

    • Your DH is being a 12 year old girl.

      Pick a proper holiday schedule, carve up the time appropriately and stick to it. Don’t “play this by ear” or “try to be nice” or “make everyone happy”. One set of parents gets X time. The other parents gets X time. Done.

    • I have all sorts of “they get along fine, but it’s still awkward” issues with sharing holidays between my parents and my in-laws. I hate to say it because I completely understand, but I think it’s not really fair for your parents to get the full Christmas holiday, every year. Having your in-laws come and share the holiday is a fine solution, but it sounds like that’s not possible anymore. In that case, I agree with the above-posters who said that you have to start splitting the holidays 50/50. This year is already awkward because Christmas is a week away, but can your mom compromise on having them over one last time, and then next year you’ll do the full holiday at your in-laws’ house instead?

      • I should have been a bit clearer above. My in-laws are Jewish so don’t really celebrate Christmas at all (or Hanukkah, for that matter, they’re not big “celebrate the holidays” people). They just like to spend time as a family. So while I’d love the idea of alternating, it would basically mean ditching my family to sit at home and not celebrate. Oh, also, I’m basically all the family my mom and brother have left. Although you’re right that it’s not fair for my mom to do it all every year. I really would love to host, and will probably start my campaign this year in the hopes of taking it over next year.

        • Research, Not Law :

          Since they don’t celebrate Christmas, couldn’t you spend time with them on another date, like the 26-27th?

          I feel for your mom, actually. If they don’t care about celebrating the holidays, there are hundreds of other days that you could all be together that wouldn’t affect your mom’s Christmas with her family.

        • Susan (edna_mode_nyc) :

          Today’s been the day for difficult parent/in-law dynamics, and I’m sorry to see that.

          I have a similar situation (lack of religious connection to Christmas in my family), and while my parents and in-laws like each other, my parents just don’t want to take part in any of the religious Christmas stuff. I’m circumventing this by hosting (also, to prevent my brother-in-law from bullying my MIL), so I think your idea to host is a good one. No “turf” issues!

    • Could you and your ILs stay in a hotel this year? That should make it less awkward to have them stay in a hotel.

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  30. DC Lawyer :

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