What Boots to Wear With Tights to Work

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?

Pictured at top: tall / flat / mid-calf.

We’ve got a few options for you below…

This post contains affiliate links and Corporette® may earn commissions for purchases made through links in this post. For more details see here. Thank you so much for your support!

Boots To Wear On Your Commute

boots to wear on your commute

Pictured: All of these boots are highly rated, and many on sale today! one / two / three / four

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. You can also get lower waterproof boots, like the best-sellers featured in our post on weatherproof shoes for work. (To be totally clear about the boots pictured above: I wouldn’t recommend wearing #3 anywhere but your commute, probably layered with boot socks — #1, #2, and #4 may work for “just got in from my commute” type meetings, networking events, and more.)

Trendy Boots to Wear With Tights Or Bare Legs (but know your office!)

Pictured: one / two / three / four

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.

Sleek, Sophisticated Booties to Wear With Tights

Pictured above: one / two / three / four.

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. (#3 may be the rare exception, and it’s from one of the reader favorite brands for comfortable heels — but brand new to Zappos so there are no reviews yet.) Pictured above: one / two / three / four. Not pictured: this unusual boot is highly rated, so also worth knowing about if you’re hunting for a lower-heeled shoe/bootie.

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…

Social media picture credit: Deposit Photos / Voyagerix. That’s a stock photo so I’m not sure which exact wedge bootie is pictured, but here are three similar options, all under $150: one / two / three

Rumor has it that knee-high boots and OTK boots are dead -- but what the heck do you wear with tights to work then? We rounded up some of the best boots and booties to wear to work... in 2017 and 2018!



  1. 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.

    • 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.

    • 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.

    • You can have my knee height boots when you pry them from my cold dead feet. No! No! No!

  2. 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!

  3. 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!

    • 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!

  4. 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.

  5. 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.

    • 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!

  6. 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.

    • 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?

  7. 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.

    • 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.

        • 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!

  8. 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.

  9. 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

  10. 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.

  11. 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.

  12. 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

  13. 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!

  14. 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/

  15. For the second set of boots, link 3 opens up to the same Stuart W. boot for link 2.

Add a Comment

Your email address will not be published.

Thank you for commenting. On the off chance that your comment goes to moderation, note that a moderation message will only appear if you enter an email address. If you have any questions please check out our commenting policy.