Reader mail: Which winter hats are professional?

Gifts: Solid Knit Hat - BlackToday’s reader question has to do with finding professional winter hats, and we are eager to hear what our readers say…

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.

Gifts: Solid Knit Hat - BlackIn 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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  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.

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