Reader mail: Which winter hats are professional?

which winter hats are professional?2017 Update: We still think this is an interesting discussion on which winter hats are professional — but you may also want to check out our recent discussion on how to dress professionally on the coldest days. You may also want to check out more of our general advice on commuting to work.

Today’s reader question has to do with finding professional winter hats, and we are eager to hear what our readers say — ultimately, she’s wondering which winter hats are professional. Hmmmn…

Will you please consider writing a post about winter hats? It seems like an appropriate time to cover winter hats, especially with the snow storms crossing the country this week. I often walk to work but have never been able to find a suitable winter hat. I need a hat that covers my ears as well as the top of my head. I have found that the cute hats don’t cover my ears. Another frustration is that the winter hats I have all flatten my hair. Perhaps that is inevitable. However, my hair tends to be curly and after putting a hat on, my hair is flat and straight by the time I get to work.

Tricky. First, we have yet to find a functional winter hat that doesn’t look dorky. But, given that a) we grew up in the Midwest b) went to college in a city where windchill is a major consideration, and c) often walk to/fro work in NYC, we don’t discriminate against “dorky” hats — it’s cold outside, yo. And even if someone recently said it’s a myth that 80% of your heat escapes from your head… well, we don’t believe it. To make matters worse, this author’s hair seems to get curlier with each passing year — and it now seems impossible to wear many of our old hats without totally killing the curls.  So, like we said, we are eager to hear what our readers say.

which winter hats are professional?In the past (when our hairstyle was blown straight) we went with floppy (not felted) berets.  They’re easy to keep in the pocket of jackets (one can “live” in every coat; also, a hat you can stuff in your pocket is hard to lose), and, as a classic style, the dork factor is on an acceptable scale. We just lost the only one we had with a silky lining, though — which seemed to be the only one that didn’t crush the curls.  So we’re in the market for one.  After a quick survey of the market for hats on Shopstyle, we like the looks of this knit hat (pictured above and at right) — non-itchy, fleece lining, looks cute — but doubt it would work well with our curly hair.   Solid Knit Hat, available at Athleta for $40.

Readers, what are your solutions?

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Picture via Stencil.the best winter hats for your commute to work

A reader wondered which winter hats are professional -- functional and warm for her commute, without leaving her hair a flattened mess.



  1. I’ve been wearing a gray felt cloche with a gray felt flower on the side. It’s all very gray, but it’s structured and crisp enough that I feel professional in it.

    • I love my grey felt cloche! Darn deep south non-winters …

      • Never ever saw the word Cloche EVER until this day. And I thought I was “educated” ha!

    • Me too!

      I just bought this one, in charcoal, from a local shop:

    • I got my black cloche hat at Target. It’s is wonderful and works fine with my curly hair.

      • Agreed! I have a black felt cloche from H+M that I paid like 4 dollars for. It’s been my savior– big head + curly hair…. it’s just long enough to cover my ears sufficiently.

        • I also have a felt cloche (white) from H&M and always get comments whenever I wear it. I actually have shoulder length straight hair and it looks great too. Because the hat has a little structure, it doesn’t seem to flatten out the little volume I do have.

  2. If it’s really cold, you don’t care what you look like. Everyone looks just as dorky as you.

  3. C, thanks for the few tiny details about the region where you grew up, etc. And we now know you have curly hair. Sure wish you could go “public.” Would fashion blogging interfere with your BigLaw persona? Not being nosey, I’m just a naturally curious person. Feels so weird to have the disembodied “C” voice… but you do seem like a really nice, relate-able person!

  4. I wear a white wool skull cap but it does make the hair go limp. I do the grannieish scarf head wrap with a large warm scarf if its essential for me to have a good hair day and its really cold.

  5. Corporate Tool :

    I would also suggest the knit “berets” that are very much in style right now. Warm, ear-covering, and they don’t mess up your hair too much if you get a non-wool one (lessening the chances of static).

    I have black, white and gray, and I love them.

  6. Anonymous :

    I’ve never found a hat that won’t mess up my hair. I always get a jacket with a big hood – keeps my hair from blowing around on a windy day, and warmer than a hat for my long walk in the cold. I have a tailored, long black down jacket with a big (faux) fur hood.

    • I have to wear a hat if there is the least bit of moisture/humidity/precipitation outside. I have thick, frizzy, half-wavy hair that I flat-iron most days, and walking from the car into school is enough to undo all of my flat-ironing completely. Wearing a hat outside is the only thing that works for me if it’s wet/humid.

      • Oh, and I have a black cloche with a black flower on the side that I like to wear when it’s moderately cold, but on days like today when the high is 12 and the wind chill is -10, I go with either a white fluffy nice-looking winter hat or my trusty school logo/colors knit hat (with matching gloves and scarf!).

      • Have you tried a big silk scarf, 1960s-style?

  7. I combine a hat with a hood. I use either a plain wool one that can slide over my hair/ears, or one with a band and a floppier, looser knit. My favorite one is crocheted on top but all the essentials are covered. But in the winter, I generally give in with my hair. It’s thick and very curly, I just put it in a bun or a low ponytail if its cold and I need to wear a hat.

  8. I wear a dark brown (which matches my gloves and goes well with my coat), cashmere, ribbed knit cap or, if it’s snowing and I want something with a brim, a camel-colored, wool, newsboy-style cap. Cashmere doesn’t mess up my hair, and my newsboy-style one is lined with a satiny fabric.

    I’ve noticed some truly fabulous hats at Nordstrom lately, if you want something stylish but classic.

  9. I would second the beret suggestion. I usually buy them at H&M because I always lose them!

  10. Anonymous :

    For days when I wear my hair up I wear the ear covers that look like a thick band and velcro at the back of your neck. I have straight hair so I just wear a regular old hat w/ my hood over it.

  11. target fleece velour hat in black….about $10.. it has very subtle ear flaps that fold down and a brim that you can wear down or pushed up. I wear this under a hood if necessary… Another good possibility are ear muffs…actual fur, faux fur or the ones that wrap around the back of your neck (180s). I have an LLBean “Trapper Hat” too, but it has not been cold enough to need to wear it…some day. It IS dorky, but when it gets that cold, I will be immune to criticism.

  12. I wear a tight cream wool hat I got at Nordstroms that can pull over the ears. It does flatten the hair so I’ve been teasing it a bit in the back after I take it off. But, it is coordinated with my coat/gloves/scarf so looks pretty good and keeps me warm. Except my forehead gets itchy after about 10 minutes so it’s only good for short walks. This is a conundrum for us ladies.

  13. Oh, do tell! Did you go to college in Chicago or Minneapolis? Brrrr!

    What about earmuffs? They don’t give you the same hat-head.

    • My boyfriend just gave me these grey shearling earmuffs from J. Crew to congratulate me on finishing up two very intense weeks of brief writing:

      I absolutely love them and get lots of complements on them. Plus, they don’t mess up my hair at all.

      • I might be in the minority as I’ve seen people sporting ear muffs around DC during the last week but I just don’t think ear muffs are professional. I also agree with C that you need to actually cover your head to keep in real warmth.

        It doesn’t get that cold here and other than walking to/from the courthouse, I can stay mostly indoors/in the car for my job so I tend to go without a hat or use a thin cashmere beanie I got from Nordstroms a few years ago. It’s not particularly warm but it takes the bite out of the wind chill.

  14. Snood? Wouldn’t work in wind though…

  15. operaghost :

    I wear my suit, high heels, black pea coat, scarf, gloves… and my Western Michigan University ski cap. I probably look like an idiot, but if anyone really wants to poke fun at me in the morning when I’m a) half-awake, b) crabby, and c) freezing, joke’s on them because I will TOTALLY punch them out.

  16. I agree with everyone who said hood. I either wear a coat with a hood or a hooded sweatshirt or lighter jacket under my coat (you can always take it off!) and then wrap my scarf around the whole deal so the hood stays up. It doesn’t crush your hair and it’s surprisingly warm when your whole head is encased…keeps your cheeks warm too.

  17. Chloe all the way. Cheap even at the department stores. I’d rather have flattened hair than my nose instantly begin to run in the cold/wind.

  18. I use a beret from Target. My hair is the kind of straight that will get an annoying crease from wearing a knit cap that is tight enough to stay on my head for more than 5 minutes. My hair is shoulder-length, so I just put it all in the beret (so the only creases are on my forehead & neck – sad that this is the better option) and shake it out as soon as possible. This also works for the ambitious days when I try to curl my hair. BTW, I am *fascinated* by the word/concept of cloche. Very The Changeling.

  19. I found a black wool fedora with satin lining at Banana Republic a couple seasons back that I LOVE. Not as much ear-coverage as my cloche, but it’s got the Jane Bond vibe going, so I feel slightly less dorky. (Okay, I’ll admit it: it makes me feel like a badass. Don’t judge!) I’ve also discovered that sizing up in most hats doesn’t crush my hair as badly, but you have to keep a hand on it when the wind picks up.

  20. I have a light-weight pashmina that I wrap around my head–very cosy, and it does less damage to my hair. For days when I do want a hat, I just purchased an adorable asymmetrical cloche at Macy’s.

  21. Having a gigantic head (friends tell me it doesn’t LOOK enormous, but my hat size is an impossible-to-shop-for 7&3/4…), I go with a knit hat in light brown and blue that matches my scarf.

    To avoid flattening hair, I part my hair on the opposite side before putting on the hat and walking out the door. When I get to the office, I change the part back to its normal spot, do the “crunching” action with my hands up to the roots a couple of times, then spritz it with travel-sized hairspray. Takes about 30 seconds, and leaves my hair probably more volumized than during non-winter months.

    I’m impressed that many of you can wear hoods with jackets. I never could figure out how to make them stay UP!! Even with the elastic strings to tighten them, I have terrible luck unless I’m standing perfectly still…

    • Anonymous :

      I wrap a scarf around the hood – whether this deal goes around only my neck or envelopes my entire face depends on how cold and windy it is.

    • Anonymous :

      You need to try on jackets with hoods to see if they have enough room for your head/hair. I have a nice long down jacket from Eddie Bauer and the hood is cut/attached in such a way that it never falls down.

  22. Liz (Europe) :

    I wear like the one on the right:

  23. Hoods! It took me forever and a day to find a peacoat with a hood that was decent enough to wear to work and professional-looking. (Also removable). Although really, if it’s crazy windy and cold enough to wear a hat, I’ll pull on my north face skull cap that has a fleece lining. Super warm. And I won’t care how I look because my ears will not fall off.

    I went to school in upstate NY – you get over the dorky factor really quickly once that temperature drops and you can only tell who your friends are from the blurbs of coats on campus.

  24. I’m in Minneapolis and it’s below zero with a wind chill in the WHAT ARE YOU DOING OUTSIDE?!? range, so my solution was an Eddie Bauer knit hat (lined) in men’s sizes (it’s black and red and matches my black down EB coat), so I can pull it over a ponytail/bun and not worry about it.

    Of course, I’m just going to school at this point, so if my hair flattens out on top, no one cares. However, at some point, especially up here, the weather trumps fashion. I vaguely envy those of you who can get away with a lightweight scarf around your head.

    • Oh, c’mon, its 3 degrees outside and the wind’s barely blowing. :) At least the predicted high is above zero. You ain’t seen nothing yet – the real cold doesn’t happen until January.

  25. I am one that doesn’t particularly care how dorky I look when it’s freezing outside, so long as I’m warm, I’m happy. That said I purchased a classic Burberry Cloche at a mens store that is my go to hat for the cold when I need to appear professional. It’s in a super think wool that is the neutral camel color plaid, so it blends nicely with all my wool coats, but has the silk lining. It rides low on my head and covers my ears nicely without crushing my hair. And because it’s not structured like many Cloche/Fedora style hats are, I can easily fold it up and put it in my pocket. I’m also a big fan of simply wrapping my head/ears in a thick scarf.

  26. I live in Minneapolis and bus to work, which requires standing outside in sub-zero weather without any shelter while waiting for the bus. I wear a fleece sock hat pulled down over my ears and to my eyebrows. I also wear Ugg boots for the commute, which I love because I can tuck my pants into them. I do try to minimize my hat-wearing time by removing it during my 40-minute bus ride and once I get into the skyway system.

    Bizarrely, I think my hair looks better after I wear the sock hat. I’ve got very straight hair and it seems to hang better after being scrunched down for a bit.

    I do think the expectations may be different when one lives in a cold-weather climate.


  28. Earbands. Earbands. Earbands. They’re like thick but functional headbands that keep you warm & even give a little volume-boost at the roots.
    The trick is to wear it under your hair rather than over. I’ve found lots of nice alternatives to the ugly fleece band, like pointelle.

  29. I, too, have the curly hair thing going on. After years of struggle, I have settled on three options, depending upon the level of cold:

    1. For serious cold, I go for the giant granny scarf over the head and shoulders. This actually works great when I have my shoulder briefcase to hold it down and also protects my coat shoulders if I am wearing a fur. Sometimes I pin the scarf in place. I have an extra large Burberry plaid cashmere scarf that works great for this purpose.

    2. For moderate cold or heavy wind, I use a headband that can be worn over the ears and under the hair in back. I have about three of these, including a really cute quilted fleece one that came with matching gloves and scarf. I have in fact toyed with getting one of the really cute fur headbands, but I often leave the house with a wet head (my curls frizz if they are blown dry) and fear water-staining a silk linking.

    3. For mild cold, or if my hair is dry or can be pinned up, I go with a structured fedora or cowboy-style hat. I have a black wool fedora with a cute applique on the side and a black leather fedora (very Run DMC) that I wear with pant coats. My cowboy-style hat is black wool in a Stetson-type shape, but with a smooth brim. It has a snakeskin hatband and I cock it over one eye. (@Ash – so I totally get the”badass vibe”!).

  30. honestly, even more than hats, i want a post about curly hair. i feel like there is almost no way to make it look professional. if i ever wear it and curly in the office, i get comments about how i’ve let my hair ‘go wild.’

    • Agreed. I straightened my hair every day for work until a 3 month trial from hell had me billing 400+ hours and that went completely out the window and I spent weeks on end looking like I’d been caught in a wind tunnel. Since then I’ve settled on straightening my bangs and keeping my hair well conditioned and adding gel to keep frizz to a minimum. I feel like then it looks like I spent some time on my hair as long as I don’t come in with it wet. In the end, there’s nothing you can really do except to keep down the frizz and keep it out of your face. I may have also informed all of my female coworkers who ever comment on the curly hair just how long it takes to blow dry/straighten curly hair. That generally cuts down the chatter.

      • I was told by a hiring partner that he wouldn’t have hired me had he known I had such curly hair (I had straightenend my hair for the interviews, but then let it go natural when I started working). He was only partially kidding. After years of struggle, I’ve gone the Karatin treatment route. It is very expensive, but cuts my hair care time by 75% and I don’t have to weep when it’s humid out or when I get caught in the rain.

        • That’s ridiculous that someone wouldn’t hire you just b/c your hair’s curly — as if you could control how your hair naturally behaves. I would think long curls could also be worn “up” several ways to look more professional too, but my hair is straight/wavy.

          • Anonymous :

            Wow, that hiring partner stinks. I have very long, curly hair, and I don’t straighten it. I get compliments on it frequently (at work, and the only reason I mention this is to point out that not all conservative workplaces frown on curls). Sometimes I wear it pulled back or in a ponytail, but mostly I wear it down. I use leave-in conditioner and a bit of gel to define the curls, but otherwise leave it alone (no elaborate cut, no blowdrying). I don’t think curls look unprofessional at all.

            Frankly, I’d be concerned if my hiring partner was more concerned with my hairstyle than my capabilities (or thought that extra daily hour was better served straightening my natural curls than working, spending time with family, volunteering, etc). Which isn’t to say those of us with natural curls shouldn’t straighten them – just that it really isn’t anyone else’s business, nor should it be a hiring criteria.

        • You should have replied “I wouldn’t have accepted the offer if I’d known you were such a jerk” and smiled.

        • I can’t believe a hiring partner would say that. I have very thick curly hair which I wear natural, at about shoulder length. I have to admit that straight hair does seem so much more sleek and professional at times, but I have stuck with my curls anyway. I hardly ever straighten it – too time-consuming and my kids look like they don’t quite recognize me when my hair is straight. Anyway, I think we need to get over this whole curly-hair-isn’t-professional thing, and just be ourselves.

          As for hats, this is a HUGE problem for me. I have one black H&M hat that I love, but I get a red line across my forehead when I wear it. Plus, I live in a cold-weather, conservative rust-belt city where high fashion is not the norm, so I’ve gotten a few weird comments when I wear my stylish hat… Not sure if its my head or my hair, but most hats do not fit me – it is so frustrating.

    • I also have very curly hair, and will under very few circumstances blow it out. Those circumstances do not include a job. Costume party, yes. Job, no. I have a haircut that makes me not have a fro, I wash and condition every day, and use styling creme and hairspray. Peeps can be happy with that.

      Curly hair may be the only thing in this world where a person’s natural hair is considered unprofessional.

      • “Curly hair may be the only thing in this world where a person’s natural hair is considered unprofessional.”

        Not nearly as much so as African hair.

    • I would have told the person who made that comment to go —- himself.

      Then again, I haven’t straightened my hair since I was 15 or so, and I’m not going to start. I can’t stand the fascist “women have to spend an hour in the bathroom torturing their hair with hot irons to look professional” mentality, or the fact that so many women go along with it.

    • For all you curly girls, I absolutely swear by The Cream by Paul Mitchell. Just wash and condition your hair, then gently squeeze out the extra water, and scrunch The Cream into your hair section by section. Keep the roots lifted and try not to separate the curls too much. Then, you absolutely must air dry or use a diffuser. (I have about 1.0 to 1.5 hours from the time I style my damp hair, get ready, get the kids ready, drop everyone off, and get to the office. A few final scrunches in the elevator gives extra volume and softness to the hair.) My extremely thick curly/wavy hair turns out very shiny and smooth with this stuff. It’s the only thing I’ve found that works. And with a good haircut by someone who knows how to cut curly hair, you can look very professional without straightening. Plus your hair is so much healthier without all that harmful blow-drying. Oh, also coloring makes curls much, much less frizzy.

  31. I find the Ugg Bucket Hat to be great. Personally, as far as practical hats go it’s pretty decent looking. Also, it pulls over your ears and forehead (so amazingly wind resistant!); since the inside is fleece the hat stays put without being too fitted- so much so that my hair can be in a bun or ponytail and still fit. It causes some fly-aways but I find those are fairly easy to tame.

    Also I don’t know if anyone else does this: but I always put my gloves inside my hat when I’m not wearing them; I’ve lost a lot less gloves since I started to do this.

    • Anonymous :

      I found that the back of this hat and the top of my coat collar kept bumping into each other, the result being that the hat was pushed up off my head :(

  32. I like the Ugg bucket hat above. IMO, the one C pictured is as dorky as it gets.

  33. divaliscious11 :

    Seriously????? Do winter hats have to be professional…or merely functional, ie…warm, provide appropriate coverage and removable? Is anyone conducting outdoor meetings? I am happy to chat about nice hats, but this is getting ridiculous….

  34. freeeezing :

    I bought this bucket hat last winter and love it–it has an extra swath of fabric that covers my ears when it’s really cold, but that part tucks up into the hat nicely when it’s just a tad chilly (or drizzling outside).

    I bought it in the biggest size, and it’s fairly lightweight (but still very warm), so it doesn’t crush my curls too terribly. It also looks professional in its dark gray wool.

    • freeeeezing – That hat is very cute. Is the large really large though? I have very thick curly hair and hats (especially structured ones) almost never fit my head.

  35. My solution when I was in school in Minneapolis was combination 180s earmuffs + a “sock hat” made out of a double layer of fleece. When commuting by bicycle at minus crazy degrees, I added a fleece neckwarmer and a pair of ski goggles, so I didn’t have any exposed skin to get frostbite. THAT maxxed out the dorky scale.

    p.s. second for curly hair discussion – now that I’m out of school, I try to limit ponytail days to when I’m going to be out on jobsites (there is no way for a hardhat to not smash curls), but my curls have a bad tendency to get in my face and annoy me by the end of the day.

  36. Anne Vohl :

    Cloche! I can’t believe it. That would look just crazy here. For people who need to cover the head, a hooded coat is the best idea. But here’s a funny story. A few years ago on a snowy day in Chicago, I was at a bus stop in front of the Art Institute and I asked a fellow passenger for some directions. This passenger was in her 50’s and was wearing a dorky knitted hat (red) with many tassels. On the bus, I got to chatting with her, and found that she is a senior partner in a very important Chicago law firm. So…..

    • If she was taking the bus, she obviously wasn’t a typical biglaw attorney (let alone partner). Also, once you’ve made senior partner, you can be as eccentric as you want to be. I have pretty eccentric tastes in my personal life, but I tone it down at work because I know that on the occasions I’ve let them show people have made it clear they think I’m a little weird. The senior partner I work with, though, is full-on wacky, and while people might wonder about it behind her back, no one would ever say anything about it and it obviously is too late for it to affect her career progress.

  37. I’m surprised there are so many hood fans! They do have the convenience factor of being attached to the coat, so you don’t have to worry about where to put them, or losing them, true – but so not worth the loss of peripheral vision. I tend to go with some sort of bucket hat (fabric dependent on whether there is precipitation) or just a basic knit skullcap or similar. On the hair front, I have wavy hair that *can* go straight or curly, but easily ends up in some ridiculous semi-squashed in-between land. I generally put the sides up with a couple of bobby pins, then hat on top, which a) looks decent with the hat on, and b) gives me a little volume when I get to the office, remove hat and bobby pins, and give it a quick shake and finger comb, with a quasi-french twist as my backup strategy (hats tend to sit oddly on top of the twist, so I wait until I’m at the office). I really need to find more of the super-long bobby pins I use for my quick twists – I used to have a dozen and I’m down to two :(

  38. Love, love, love my Giant Dwarf flower hat. I get tons of compliments, its cute, but sophisticated. Plus, the artist is awesome and they are all made from recycled sweaters.

  39. Well, I’d like to up the ante, but this is not for those who lost hats.

    I am allergic to wool, but I like fancy cashmere. I have really curly hair–ringlets (Irish descent) and my favorite caps are from here:

    Brora, a UK based luxury cashmere purveyor

    You will not be disappointed with the quality of either of these outfits, but there is wallet shock involved.

    Brora ships to the US, no problem.
    and Golightly Cashmere

    • Hmm. Well I did have to pick myself up from the floor when I saw the $699.00 pillbox that was featured on the Harlems Heaven’s site that was suggested quite a few posts back. So the prices on the site you’ve suggested are a steal.

    • Land’s End has surprisingly good cashmere, often on sale. That’s where I got my cashmere hat.

  40. I like a thick beret with a band – stuff all your hair up inside. Also works with fleece hats

    When it is cold (under 20) I will also wear a hood and scarf.

  41. Anonymous :

    I was thinking about this is a winter hat. Thoughts? I live in Minneapolis.

  42. I have a pair of J.Crew earmuffs that I wear most of the winter, but when it gets bitter cold (under 10 or so) I wear hats. I don’t care about being stylish, I just want to be warm, so I wear big wool hats with earflaps. I was in court last week on a cold day and the judge was wearing a college tassel hat, so I don’t think anyone judges for style at that point!

    I have big hair that I blow straight and flatten, and I’ve found that wearing a headband under my hat can help. When I was in school in Minneapolis, I’d often wear earmuffs under a hat — anything to make the bus stop warmer!

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