How to Wear Flats in the Winter

How to Wear Flats in Winter | CorporetteIn cold weather, what are the best ways to wear flats to work? With socks? Tights? Reader E wonders…

Could you recommend some ways to style flats for the winter? In years past I have worn skirts and opaque tights with pumps or booties in cold weather (I don’t live in a particularly cold climate), but earlier this year I decided to give up on heels altogether because of some foot problems I’ve been having. I’m happy with my flats for summer looks, but ballet flats just look so odd with tights to me. I’m hoping for some better style ideas! What flat shoes work best for winter looks? Thanks!

Great question, Reader E — and even though it still feels kind of warm outside, the cold will be upon us in no time. (Winter is coming!) We’ve talked about wearing flats all the time, as well as interviewing in flats, but not in a while. Obviously you can just wear flats where you would have worn pumps, but if you can’t walk in flats with tights (I can’t!), or if you feel like something is off with the silhouette, then we need to dive a bit deeper.  I’m curious to hear what readers think, but here are some of my thoughts:

  • Know your best silhouettes, both based on your own body type as well as your clothes. On my own body type (curvy), I think some silhouettes inherently look better with a bit of a heel — for example, a pencil skirt or a sheath dress — but on others they look great with flats. This is partly trial and error on your part; go with your comfort level. Notice which styles are flattering when you wear the flats and clothes you already have, and then make adjustments to your wardrobe from there.
  • Know the appropriate hem lengthsIf your pants are hemmed for heels right now, you may have to get them hemmed again for flats — even with flats you don’t want anything dragging on the ground, because your pants will suffer.
  • Reconsider the bare-feet-in-flats look. We’ve talked about what you can’t wear in winter, and it’s also important to “know your office” and your region well. In New York City, wearing flats with bare feet would only work up until November or so at the absolute latest — walking, even just to or from the subway with exposed feet and ankles, just isn’t doable… and there are a million other cute options.
  • For flats with tights and a skirt: Look for strappy flats (unless I am the only weirdo who can’t walk in flats in tights — some nice current options pictured below), short booties, calf-high booties, knee-high boots (but know your office), and over-the-knee boots (but really know your office). Some points:
    • Try to match your tights to your shoes if possible (but see our old thoughts on what tights to wear with navy).
    • If possible look for booties with a slight dip in the front, which is usually a million times more flattering, even with tights.  (…and I can’t for the life of me find an example that is totally flat.  These 2″ heeled booties from comfort brand Mephisto might be a help to you, though; this low Eileen Fisher bootie with cutouts also looks cute….)
  • For flats with socks: This comes back to the bare-feet-in-winter conundrum, but for milder temperatures, note that it’s becoming more acceptable to keep your ankles exposed by wearing low, hidden socks with your booties. Another trend: wearing slouch socks with booties. Of the two I tend to think the first look is sleeker than the second, but common sense obviously has to play a part here.
  • For really cold weather when bare ankles would just look silly, try fleece tights, which have been hugely popular with readers recently, perhaps for just this reason. They offer a great middle ground because your legs are warm, you look like you have common sense, and you can still wear your flats and be comfortable. Another great look (also trendy): flared trousers. Note that a slight point to your boot or flat (at least) tends to look best with flared trousers, and know where the hem should fall. (It should graze the top of the vamp, leaving about 1/2″ of your flat heel showing in the back.)
  • Try commuting in different shoes. It’s 100% acceptable to commute in different flats; after all, slush, snow, road salt, and rain can damage your shoes (and not feel so great on your feet — or tights, yuck — either). Rainboots, snowboots… it’s all acceptable (but see our older posts on colors, as well as when to change out of your commuting boots). The trick is twofold: for commuting shoes you want to get a functional look that, even if it’s a bit uglier than what you normally wear, could actually fly in your office if push came to shove (so skip the Minnie Mouse rainboots, for eample).  The second trick is to make it look as if your final office look COULD have been worn outside — you never want to look like you’re dressing for a Miami summer when it’s a Northeast winter.

For those of you looking for strappy flats to wear with tights, here are three options right now — note also that the oxford look is very in right now, and this sleek patent leather one from Kate Spade could look very cute with tights.  Clockwise: 1) The ballerina style is very popular right now; the pictured shoe is only $79 but you can get versions all the way up to $675.  2) Kate Spade’s very clean take on the oxford.  3) The Rockstud look may be on the wane, but these cute Halogen flats (pictured) are much more affordable and still look nice (and they come in a zillion colors).  4) If full on comfort is what you’re looking for, these Eileen Fisher flats look really great.


Readers, what are your thoughts — are there any tricks to wearing flats in the winter? What are your favorite flats to wear this winter, and which silhouettes do you like to wear them with the best?


N.B. These substantive posts are intended to be a source of community comment on a particular topic, which readers can browse through without having to sift out a lot of unrelated comments. And so, although of course we highly value all comments by our readers, we’re going to ask you to please keep your comments on topic; threadjacks will be deleted at our sole discretion and convenience. Thank you for your understanding!


  1. lawsuited :

    Along with Oxfords, I think a suped-up moc or loafer can be great too. The MK Fulton moccasins are my year-round go-to – they’re not a ballet flat so don’t look silly in the winter.

    I just ordered these fantastic loafers from Talbots that look like some awesome Ernest Hemingway smoking slipper menswear-as-womenswear dream come true:

    • Love these! Do you think that you could wear them with trouser socks (with nice jeans or slacks)? I’m always trying to find something slip-on to wear (casually) when it’s too cold for bare ankles but I just don’t feel like boots.

      • lawsuited :

        I’m definitely planning to wear the loafters with ankle pants and trouser socks, so I vote it’s okay!

  2. Aunt Jamesina :

    I love oxfords. I got the Tahari Latrice oxfords this summer and just started wearing them this week. They’re comfortable and neutral but still interesting. And I got a bunch of compliments on them :)

    • Aunt Jamesina :

  3. I do NOT wear flat’s in the winter (outside) b/c I alway’s step in schlush and it get’s RIGHT into my shoes in NYC. There should be a rule that all corners have to be cleared of schlush within 2 hours of a snow storm — otherwise you get schlush all over your shoe’s and stocking’s. I wear LLBean muck Boot’s that are waterproof b/c my Fry boot’s got ruined from the salt. This should be told to ALL women who come to NYC between November 1 and April 30. YAY!!!

  4. Diana Barry :

    For in-between seasons, I like mocs and oxfords in addition to ballet flats. In the winter I normally wear flat boots with pants and knee-high boots (also almost flat) with skirts.

  5. I do trouser socks with pants, or tights with shooties or flat boots.

  6. As far as boots with that “dip” in front go- I have these and they’re comfortable and flattering (and under $100!)

  7. I strongly disagree with matching color between shoes and tights when you are wearing flat shoes. When you’re in heels, the matching serves to elongate, but to my eye, in flats, this just makes you look stumpy. For example, black tights with a camel or nude shoe, especially with a pointed toe, looks much better than a black shoe.


    • Totally disagree. I always feel like Minnie Mouse when my tights are darker than my shoes. I think your second link exemplifies that perfectly.

      • Come to think of it, maybe it’s only because I wear a size 10 shoe and have tiny ankles. Can’t get more Minnie Mouse than that. :)

  8. Oops – sent my comment to moderation by including some links, but just wanted to register that I don’t agree with the suggestion to match tight and shoe colors for flats. A nice contrasting neutral, like camel or grey, that coordinates well with the rest of your outfit, to me looks much more stylish than black + black.

    • Anonymous :

      I also love matching my skirt color with my tights, and wearing a pop of a shoe color that works well with the outfit. Usually heels, but not always. If shoe pops, skirt/tights are subdued neutrals

  9. I don’t really think that ballet flats and tights look weird, as long as you have more wintry ballet flats–suede, tweed, darker colors that extend the line of the tights.

    I lived in cold climates for years and never had boots, ever, mostly because I have super-skinny ankles and boots look ridiculous on me. Also, (and I have written on this site about this before), but back in the day, high boots were not considered business formal, and in some cases, were considered trashy. Not the case anymore–boots are pretty ubiquitous, but I still don’t wear boots to work. Not a look I endorse due to my old-school prejudices, although it works for some (and is wholly necessary in certain climes).

  10. Keilexandra :

    I think that D’Orsay flats and any others with significant cutouts should be reserved for barefoot wear. It’s like wearing tights with sandals, or with peeptoe heels where the peeptoe is on the larger side–not really my cup of tea. Another downside is that they offer absolutely zero protection from light rain or puddles.

  11. I recently bought loafers to wear from commuting for transitional weather (which isn’t that long in NYC!). They provide a little more hell support than a flat and slightly more feminine than an oxford.

  12. I have Reynaud’s so my toes lose feeling if they get too cold. It’s pretty unpleasant. And I don’t wear heels. And live in Chicago. What has worked so far is either commuting in weather appropriate footwear and changing when I get to work, or I also have flat ankle booties that I wear with dress pants. They look like they could be heeled boots. I don’t 100% love the look but I love that my feet aren’t cold.

  13. What about a pair of dressier booties? I’m in Montreal and see lots of lawyers downtown wearing ones like these:

work fashion blog press mentions