The Hunt: Flat Dressy Boots

flat dressy boots for work

2017 Update: We still like a lot of these flat dressy boots, but you may also want to check out our most recent round-up of the best knee-high boots for commuting, work, and beyond, as well as our most recent discussion on what boots to wear with tights to work (which includes some flat dressy boots both high and low).

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.

Flat dressy boots are one of those know-your-office situations — just a few years ago they were fairly scandalous, but now they’re everywhere.  We haven’t done a roundup in a year (here’s our 2013 and 2012 roundups), so I thought I’d poke around… these are my favorites.  First, a few specialty categories that may be of interest — note that if you’re really on the hunt for a custom style, check out  Duo boots — you have the ability to tailor your fit, but they already have a large sale section that is up to 30% off today.

Ladies — have you bought any great flat boots for work lately? What are the top qualities you look for in an office-appropriate boot?

Volatile WickerI’ve had a pair of Volatile shoes, and they were comfortable enough that I’m going to start today’s roundup with these $32 flat knee-high option, which comes in three colors and a lot of sizes.  It’s a faux leather upper and man-made lining, so note that these won’t be as warm as leather/natural linings (and likely won’t hold up as well), but if you’re looking for a bargain, I’d start here. They were $69, but are now marked to $32. VOLATILE Wicker
Sole Society Bria Leather Knee High BootI’ve heard great things about the comfort of Sole Society boots, and a number of them are available for $83 — Nordstrom has a small selection, such as this nice Bria boot in two colors; the Sole Society website has a ton more marked 40% off (mostly under $90). Sole Society Bria Boot
Anne Klein ColdfeetAnne Klein’s iFlex line is one of my favorite budget comfort shoe lines, so it’s a mystery to me why you can only see that it’s an iFlex shoe if you look at the picture of the bottom of the sole. In any event: these come in five color options, have nice traction on the outsole, and simple buckle accents at the ankle. They’re available in sizes 5-11 for $169. Anne Klein Coldfeet
Cole Haan Dorian Stretch BootThese Dorian stretch boots come in three colors.  I particularly like that they’re leather on the front, but stretchy on the back — perfect if you’re like me and your calves are too big for most regular sizes, but too small for most “wide calf” sizes. (Note that the Cole Haan Jodhpur Boot has similar elements, but is marked down as low as $139 over at 6pm.) The pictured boots are $298. Cole Haan Dorian Stretch Boot
Frye Melissa Harness Inside ZipIt’s hard to imagine doing a boot roundup without including Frye — I’ve thought of them for years as having a great selection of well-made, durable, comfortable, and stylish boots. Their Melissa boots are one of their most popular styles, and it’s spawned a zillion different mini-styles — Melissa Harness! Melissa Tall Riding! Melissa Logo! Melissa Over the Knee! Melissa Extended Calf Sizes! Both Nordstrom and Zappos have a ton of them, and they’re all highly rated. For the office I like these Melissa Harness Inside Zip Boot, $428 at Zappos. Melissa Harness Inside Zip Boot
Loeffler Randall Matilde BootThese Loeffler Randall wedge boots are some of my favorites on the roundup. Not only are they best sellers at Bloomingdale’s (but on deeper sale at Amazon), they come in four colors, have a teeny tiny wedge of 1.25″, and — if you’re a shortie — have only a 16.5″ shaft height. (Similar, but for $126: the Steven Intyce wedge.) The pictured shoes are $373-$695 at Amazon. Loeffler Randall Tall Wedge Boots – Matilde

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  1. There is a great selection of flat boots @ Macy’s. I recommend looking on line first, then trying them on in the store as sizing varies.

    BTW, where is Ellen? I am sure she would have some inkling as to where the best boots can be found!

  2. I have wide calves and a harder to find shoe size and have had AMAZING luck with Duo. They certainly aren’t priced as starters, but are beautiful, fit and wear well.

  3. This is very timely as I am currently on the hunt for a low heel/flat black boot.
    I’d say that while none of these are wildly inappropriate, I would only really wear the Loeffler Randall happily all day at work. I think the buckles on all the rest make them look less sleek and thus less work appropriate. Again, not to say anyone will faint if you wear them, but I think this is one of the reasons I’m finding my quest for a good work boot so difficult. My other requirements are that the leg be relatively un-slouchy and the shoe/toe itself be almond or pointy, not too square or rugged.

    • N.C. anon :

      I am also anti-buckles. I love my Ciao Bella boots as recommended by Belle at CapHillStyle. She is no longer pleased with them lately, but does recommend Corso Como boots. Both are lovely and buckle-free.

      I would also add that the Frye Melissas are nice. I got a pair on a Black Friday sale a few years ago; they don’t even have a zipper. However, this means the ankle is a little loose, which I dislike. I’m hoping a last or boot tree will fix this.

    • I recently bought the Frye Melissa boots. Stiff leather so they were difficult to break in, but I’m happy with them now. They seem to fit your criteria!

      I have the extended (wide calves) but they come in regular too

      • Those are really cute! But they still have a (small) back buckle. Maybe this is my white whale but I am holding out for the perfect pair for work boots.

        • I also have the Melissa and share your criteria for boots. I’d say the Melissa is a great casual boot, but not a sleek office boot, which I am also looking for.

    • Coach Laura :

      AIMS I agree that too much hardware makes the boots less formal, as do slouchy boots and those with square toes. I do have a knee-height pair with a belt-and-buckles at the top and they do look a bit casual with formal outfits.

    • I like a smooth, sleek look, too, and I got the Sam Edelman Penny. I think the black is much more polished looking than the cognac (I have both).

    • TO Lawyer :

      I love the Loeffler Randall boots. I agree – everything else seems too slouchy or adorned for work. Slouchy is actually one of my biggest pet peeves with boots – I like the smooth look but most of the boots I try are slouchy around my ankles. The only way I’ve found to get around that are boots that zip up the entire way

  4. As a tall person, I’m glad that OTK boots are in… they usually don’t go over my knee!

  5. As a tall person, I’m glad that OTK boots are in… they usually don’t go over my knee!

  6. Pretty Primadonna :

    I would not feel comfortable wearing OTK boots to work, even on casual Friday, but because links to those were included, I have to wholeheartedly recommend the Vince Camuto Karita boot. They are beautiful, very comfortable, fit my very narrow calves, and look like 5050’s.

  7. lucy stone :

    I have wide calves and wide feet. I have a great pair of Fitzwells from Zappos that are six years old and just now started to show wear. I just replaced them with the Frye Veronica Slouch Extended Calf. Today’s their first wearing but they are comfortable and stretching nicely.

    Because I have big legs, my main goal is to avoid too much elastic, which seems to be the default method of making wide calf boots. I also feel like back zippers aren’t appropriate for the office, but maybe that’s just me.

  8. I have wide feet and most boots that look good are too tight. As a result, I wind up with ugly boots that are functional but make me look like a Russian Cossack that has gone wild on steroids. As a result, men can’t wait to run in a different direction. Is there anyplace that has stylish boots for people with wide feet?

  9. I love this post. I just bought new black flat boots from TJM for $40. They’re Franco Sarto “Carta” and I love them. Very smooth/sleek. No embellishments or anything.

  10. Anonymous :

    I’m short, and I’m sure this influences my feelings on the matter, but I can’t wear flat boots with a non-casual outfit without feeling super frumpy.

  11. I just bought the Blondo Venise flat boots, and I love them. Very comfortable and waterproof, too. The hardware puts them on the more casual side, but it is pretty restrained and “classic.”

  12. I just purchased the Crown by Born Roxie Boot, which is very very similar to a previous Born boot I owned (the zippers had broken like a bazillion times and I think the cobbler would have killed me if I brought them in to be fixed again, especially considering it was (a) my fault for not storing them correctly and (b) really tedious for him to fix.)

    They’re 25% off at Nordies right now, with most colors and sizes left. And the calf is a bit larger for those of us with Thor-like calves.

  13. KS IT Chick :

    I’ve picked up a couple pairs of Bussola (www bussolastyle com). The cognac pair I got last winter (Bucarest style) and is a side zip only, while the black pair I bought this weekend is lace/buckles/size zip (listed as the Trapani style).

  14. Maybe someone here is smart and knows the answer to this – for “shaft height,” where are they measuring from on the boot, and where should I measure my leg from and to?

    Is that from bottom of boot heel to top of boot? From insole to top of boot?

    And when they give the circumference, where is that measured? the top of the boot opening? Widest part of the calf? My knees are narrower than my calves and I assume knee-high boots are also narrower at the opening for that reason?


    Devoted Online Shopper who is Quite Tall with Fatted Calves

    • Anonymous :

      Unless the boots have a zipper or elastic back, they are going to be at least as wide at the opening so that you can get your calves in them. I have pretty muscular calves but bony knees, so I tend to stick to pairs with zippers for that reason. The pull-on styles look like wellies on me.

  15. Shopping challenge :

    Flat boots office inappropriate? I find them far more appropriate than boots with high heels, which are too sexy for work. Then again. I may be a stick in the mud, having seen enough streetwalkers in otk boots that I’d never wear them anywhere.

    Whether hardware makes them less dressy depends on the hardware.

  16. cavity maker :

    When I was looking, I went to DSW, and saw what they had on sale in my size. I’ve never been let down, and haven’t paid more than $100 for a pair of boots. It was a great way to get a starter pair to see if I would wear them often– and I do.

  17. Annalyn Kraft :

    I just have a quick question regarding wearing flat boots with suit. I saw Sarah Palin pulled it off but with heels. I don’t want to sacrifice beauty over comfort but I’m afraid that wearing skirt suit with flat black boots may look mismatch to other people. Any advice would be very helpful and appreciated.

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