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A friend and I were texting a while ago about what boots people would be wearing with tights this year — after all, donchaknow, knee-high boots are totally and completely dead.
And while manufacturers and fashion magazines would really like you to think that… I'm still seeing a lot of people wearing them, particularly for commuting, in part because it's so hard to find a flat boot that looks as good with tights (that is also warm and generally weatherproof).
So we will include a few knee high boots in this roundup — with the caveat that they're probably not the trendy pick (and you're really not advised to spend big money on them this year).
So ladies — what boots are you pulling out to wear with tights as we head into winter? What will you wear for commuting, what will you wear around the office, what will you wear on dates?
We've got a few options for you below… and if you're hunting for tights, these are our favorites!
(plus Berkshire for plus sizes — and here are two great fleece-lined options — and here's a great way to store tights!)
The Best Boots to Wear with Tights to Work
The Best Heeled Low Boots for Work Outfits
As of 2024, some of our favorite general boots for work outfits include the ones below…
The Best Knee-High Heeled Boots for Work
As of 2024, knee-high boots with a heel are making a comeback — some of the best-looking options include these from J.Crew, Everlane, Veronica Beard and Stuart Weitzman. If you're looking for an affordable alternative to try the style, check out these boots at Loft, or these boots at Amazon, both under $100.
Boots To Wear On Your Commute
Like I said earlier, knee high boots are generally out but they are certainly very practical! If you're looking to buy a new pair this year, I'd say focus on function over form — you can get a classic look like a Hunter or everyone's perennial Frye favorite boot, or perhaps look to an affordable brand known for comfort, such as Born or Aerosoles.
Obviously, over the knee boots at the office can be a dicey choice — AND they may be on their way out — so unless you really need the extra few inches for warmth (or you find some on a great sale), be wary of spending a ton of money on them this season.
As of 2024, these are some of our latest favorite weatherproof knee-high boots for work…
You can also get lower waterproof boots, like the best-sellers featured in our post on weatherproof shoes for work.
Hunting for weatherproof shoes for work? As of 2024, these are some of our favorites — also check out waterproof sneakers like Allbirds, and Tory Burch's rain loafers.
Trendy Boots to Wear With Tights Or Bare Legs (but know your office!)
As of 2024, some of our favorite general boots for work outfits include the ones below…
I tend to think of these mid-calf boots as the most modern, trendy look — but that may mean it can look a little weird to people in your office who aren't super trendy, so know your office well.
If you work in creative or in a locale with lots of creatives (NYC, LA) you may also be able to get away with wearing them with bare legs, should you want to from a weather/comfort perspective.
That said, I like a lot of these mid-calf boots — preferably with a super high, stacked or block heel — for wearing to work. A lot of these are called sock boots/stretch boots because of the way the upper is meant to hug your leg (like, ahem, a sock) — you also may find these in textures like velvet a lot.
(2018 Update: Check out our most recent roundup of stylish high-heeled boots for work!)
Other Shoes to Wear with Tights to the Office
Call me crazy, but I've always thought that if you have narrow heels, the best shoes to wear with tights to the office are almost all strappy. Accordingly, here are some of our favorite strappy heels and flats…
The Best Strappy Heels In General
As of 2024, these are our latest favorite strappy heels for work (below) — also check the brands J.Crew, Valentino, and Jennifer Chamandi for strappy pumps. If you’re looking for strappy commuting shoes with heels to maintain a hem length, we recommend Dansko or Fly London.
The Best Strappy Flats in General
Stylish strappy flats can be hard to find! As of 2024, these are some of our favorites — also, in general, check J.Crew, Boden, and Valentino (on the pricier side, obviously). Nordstrom also has a surprisingly large selection!
The Best Mary Jane Heels
There aren't a ton of Mary Jane pumps that I know of in 2024 — Manolo Blahnik has had this heeled Mary Jane for years, and Jennifer Chamandi has some cute styles now, as does Tory Burch. In terms of affordable options that are less than $350, Amazon also has a “limited time sale” on these SJP by Sarah Jessica Parker Mary Jane pumps, and these Kurt Geiger pumps are only $150 at Dillards. If you prefer wedges, Theory has some Mary Jane wedges. (Also, take a look at the trend of Mary Jane flats…)
The Best T-Strap Heels
As of Sept. 2023, these are some of our favorite T-strap pumps for work:
The Best Ankle Strap Heels
Ankle-strap pumps can be slightly hard to find in 2024… one of our longtime favorites is this affordable option from Anne Klein, and Nordstrom has a surprisingly large selection of ankle-strap heels right now. If you prefer flats, Dream Pairs has a bunch of options (such as this or this), and Eileen Fisher usually does as well.
Sleek, Sophisticated Shooties to Wear With Tights
As of 2024, shooties, aka shoe booties, are not terribly in right now… if you're looking for a heeled version you can still find these stacked shooties from Gentle Souls, as well as a lot of affordable options from Lifestride. You may also want to consider a heeled oxford (like this, this, or this) or a heeled loafer, or some of our favorite strappy pumps… our latest favorite shooties, from the very small selection out there, are below…
These aren't super trendy, and they're not on their way out — but the tradeoff here is that in order to look the sleekest, these booties often have to have a pretty high heel in order to avoid the frump factor.
So, you may be better off just going wearing tights with strappy pumps for the office instead.
Classic & Comfortable: Low-Heeled, Knee-High Boots for Work
These aren't terribly fashionable or trendy — but you will still see a TON of people wearing these. If you're on the hunt for a pair yourself, here are our latest favorites:
Stay tuned for a roundup of our latest favorite knee-high boots under 2.5″! As of 2024, J.Crew, Naturalizer and Vince all have nice options — and you can drool over these gorgeous ones from Totême.
Stay tuned for a roundup of our latest favorite knee-high boots under 2.5″! As of 2024, J.Crew, Naturalizer and Vince all have nice options — and you can drool over these gorgeous ones from Totême.
Hunting for black knee-high boots? Here are some of our long-standing favorites as of 2024 (pictured below). HEELED knee-high boots are starting to trend again, also — some of the best looking options include these from J.Crew, Everlane, Veronica Beard and Stuart Weitzman (not pictured).
OK readers, let's open up discussion — what boots are you seeing with tights around your office? What new boots are you excited to pull out this year (or which boots will you be hunting for in the coming deluge of sales)? If you prefer to wear flats, what are you wearing with skirts and dresses — boots? oxfords? Do tell…
Updated stock images (red sweater, tights) via Stencil. Original social media pictures (black tights with wedge booties) credit: Deposit Photos / Voyagerix. That's a stock photo so I'm not sure which exact wedge bootie is pictured, but…
In 2024, wedge booties are hard to find, although platform booties and thick lug soles are very popular. Some sleek options for work might include these affordable wedge boots from Dream Pairs, these comfortable Dr. Scholl's wedge boots, and these nice Anne Klein wedges.
C
I still wear knee high black leather boots with a 1 inch block heel (very similar to #2 above) with black tights and dresses/skirts and I’m not alone in doing so in my office. Call me old-fashioned, but I think a black tall boot is like a tan trenchcoat or a good cashmere sweater- it’ll never truly be out of style.
Panda Bear
I agree. I still happily wear (and see colleagues wearing) knee high boots regularly, because they are just the warmest and most practical thing for cold and/or wet days. Sometimes I change out of them post-commute, but sometimes I can’t be bothered to take them off. My office is casual enough that a flat, knee high leather boot with skirts and tights is a perfectly acceptable look. I for one am not going to trade my tall boots in for colder booties just because they are arbitrarily no longer trendy.
MJ
Reporting from Boston here, where it is wicked windy. There is NO WAY that booties will be my pick when it is 28 with massive windchill, as it is today. Sorry, booties don’t work for my commute. Boston weather is no joke. All of you wearing “fashion” boots in the South and CA, bootie on. Where it’s cold, you can pry my classic knee-high riding boots off my cold dead (large) feet.
RK
Agreed. I’m not giving up my black tall boots. Or, for that matter, my gray suede tall boots, my lovely camel-colored tall boots, or my dark brown tall boots. I spent too much money on them to abandon them! I think they will always look chic with pencil skirts, and I am also in Boston where booties just aren’t that practical. But I am abandoning the skinny jeans with tall boots look, at least for now.
Anonymous
You can have my knee height boots when you pry them from my cold dead feet. No! No! No!
boots time
I wear ankle boots and tall boots with tights. I wouldn’t wear the middle set of boots with bare legs or tights… it just seems weird to me to have not-quite-calf-high boots. I have thin calves, so the boots would have a big gap if they didn’t come closer to my knees. I wear all styles of skirts/dresses with my boots, and I have a mix of heels and flats. Then again, I don’t think I’m particularly stylish!
Kk
I think the casual look of jeans, tall boots, a waterfall sweater, (a la mormon mommy bloggers) is out, but I think sleek tall black boots with black tights and a pencil skirt or a slim dress will never go out of style- it’s professional, warm, and stylish!
Ellen
I still wear this on weekends. The large sweater tends to cover my tuchus, which is a good thing, and alot better then a pencil skirt b/c pencil skirts assume that I have a small tuchus when I do NOT. FOOEY!
L
I regularly wear knee high boots and so do most people. They definitely aren’t dead in DC. I actually don’t like ankle boots with tights because they make me feel like an elf. Knee high boots look polished and are practical.
Anonymous
+1. Black knee high boots will never be out here in DC.
anon
I’m all about the ankle boot in fall and early spring, but when the cold weather REALLY hits, I am super grateful for tall boots! Not only do they cover more skin area, but they disguise my very warm, comfy socks. If my feet are cold, so is the rest of my body.
genabee
Same, I love my warm and comfy socks. Although with brown knee-high boots, I don’t disguise them – I just wear really long knitted fisherman’s wool socks and fold the edges over the top of the boot. So cozy and cute!
LG
I do like the look of the mid-calf bootie but I do not know how to wear them with jeans at all. I work in a casual office where everyone wears jeans and most women wear skinny jeans on a regular basis. But I can’t figure out where/how skinny jeans fall with the mid-calf booties. Do I cuff the skinny jeans? Stuff them into the bootie? I don’t love either look. Wear cropped skinny jeans? Trouser jeans? Help a lady out!
Also sad to report that in my very fashion forward office, no one wears tall boots anymore. I wear them into the office b/c it’s too cold but switch to different shoes (including the vexing mid-calf bootie) once in.
AZCPA
I love mid calf boots and wear them all the time with jeans. I usually tuck my skinny jeans into the boots, but with jeans that are wider at the bottom, I cuff them. Just like when booties started becoming popular, it takes some getting used to visually.
Anonymous
I feel like none of my skinny jeans (or even leggings) tuck into mid calf boots well. My ankles are skinny compared to the rest of me, so maybe that’s the issue… Or the boots are not wide enough to accommodate the width.
Stupid question on cuffing (CA person who is transitioning to North East), how do you keep the sliver of leg between jeans and top of boots warm? Socks? If so, what kind of height/thickness do you recommend?
Anonymous BigLaw Associate
Women don’t wear boots to work at my office. I would have never thought to, aside from with casual clothes for coming in the weekend etc. Maybe it is a CA thing.
Sorry but a lot of what is above seems really out of style and/or dowdy, especially the row of “booties,” that I think are actually shooties. But the terminology is besides the point.
Anon
So what are people wearing in your fashion forward office? I’m in Biglaw in a medium-sized city and boots and booties are everywhere.
Anonymous BigLaw Associate
Pumps and dress flats are pretty much it. That may not be as fashion forward, as it is traditional.
Anon
Do people wear these with tights? I like wearing flats but I don’t like wearing them with tights, and now it feels too cold for bare legs (in CA).
Anonymous BigLaw Associate
Yeah, me and other people will wear tights when it gets cold, but there are been very few days yet this year where it was cold enough for that. I probably wear tights a dozen times in a year?! It is currently in the 70s and sunny, and is going to be like 90 degrees later this week. Not really tights weather even though it is fall. I’d sweat like crazy, particularly with the intense afternoon sun my office gets.
Perhaps someone wears booties and bare legs like the poster below mentioned, but haven’t noticed it. Will have to look around, and maybe will have to do booties one day. Always considered them more weekend-wear. But currently wear a pair of purple alligator pumps, so tied to traditional lawyer-wear.
Anonymous
I’m in LA, and wear mid-calf booties to the office with bare legs.
FWIW, I tend to be a bit fashion forward, or at least someone who likes to bring in my personal style (life prior to corporate tended towards punk). Honestly can’t say if the rest of my office wears them. I feel like I should be paying attention to these things!
Anonymous
Reporting from Boston, where everyone still wears tall boots for warmth.
I don’t like block heel, midcalf boots. I think they make people look short and stumpy.
London Junior Associate
The block heel, mid calf boot is all i’m seeing in London this season. I can’t do them because I have fat calves and it’s just not a good look on me. I have a pair of knee-high black boots that I wear some, but generally I just don’t wear boots to the office.
I bought Harrow booties from Rag and Bone in black last year and I wear them with black tights all the time on the weekends, but they feel too clunky for work
Boston and Toronto
I spend most of my time in Boston and Toronto and live in wool pencil skirts, dresses, tights and flat knee high boots in cold weather. Tory Burch in nice (dry) weather, Aquatalia for elements.
Leslie
It’s true that booties are more “in,” but I work with a lot of really young women, and they are all wearing OTK boots and sometimes knee-high boots. They aren’t dead yet. Agree that sometimes, booties just don’t cut it.
Nancy
I would be happy to find a pair of stylish boots in Wide width that allows me to put in my custom orthotics (for plantar fascilitis)….besides Munro (very limited options this year…cute booties but suede..not good for midwest winters). Want something more stylish than Dansko. Any suggestions?
Martin nuala
Have you considered Frye? Not fashion forward but relatively simple styles.
Anonymous
I just looked at Frye’s site and I do not see wide width or removable insoles. I think Frye has some great boots but need to insert my orthotics which are a 9.5 Wide
Anonymous
So . . . it’s OK style-wise to wear a mid-calf boot with tights and a skirt or dress as an all-day outfit (not just for the commute)?
Also, If one wears a shorter boot with a slightly cropped pant (not skinny), I’d think the boot should go under the pant w/no exposed skin? But if the pant is skinny and not tucked in, there should be some skin showing?
Thanks for helping a clueless person!
Irina
I think your boots should be short, that’s why I recommend wearing ankle boots. Go for neutral color, the best one is black. Keep it as simple as possible.
Irina || http://imogentrend.com/
Ash
For the second set of boots, link 3 opens up to the same Stuart W. boot for link 2.