When and How To Wear Hats

Kate Hepburn, "Bringing Up Baby"Reader E writes to us with a request for an accessories post on hats:

I would love to see a post on how to wear hats, not winter hats, but some of the more structured 50’s-esque hats that seem to be everywhere. I imagine they aren’t appropriate for a conservative office environment but where exactly are they okay to where? Only outside? I love these hats and would like to incorporate them into my wardrobe but I’m just not sure how.

To be honest, whenever I think of hats I think of one of my favorite movies, “Bringing Up Baby,” in which Kate Hepburn wears a lot of, um, interesting hats. Oh, and I think of that show “Blossom,” also. But let’s not let my mild dislike of hats (except for comic relief) stand in our way.

That said — some of my friends look great in hats, and celebrities do seem to wear them a lot.  The key to wearing them does seem to be integrating them into your outfit as an essential component.  This isn’t going to be like a purse that you can wear with everything — you have to think about your outfit’s proportions, and colors, and the general “statement” you hope to make with it (as well as whether the hat looks attractive on you given your facial features in general).  You may want to start with a cowboy hat or a fedora, as those seem to be the styles I see most — and then work your way up to something a bit more unique or with vintage appeal.  Another popular look these days is the headband-so-large-it-could-be-a-hat, similar to the peacock one below — that might also be a dip your toe into the waters of headwear.

Volcom - Frankie Fedora (Black) - Hats

Volcom - Frankie Fedora (Black) - Hats, available at Zappos for $38

Raffia Crochet Cowboy Hat

Raffia Crochet Cowboy Hat, available at ShopBop.com for $49 (was $50)

Peacock Feather Headband with Polka Dots and White Goose Feathers

Peacock Feather Headband with Polka Dots and White Goose Feathers, available at Etsy from seller intothelookinglass for $12.50.

As for WHEN, I would limit wearing a hat to your off hours — I doubt I’d bring one anywhere near an office (but maybe that’s just me?).  I seem to see them a lot when worn at parties and BBQs, or Sunday brunch kind of events — where you’re still casual, but want your outfit to look deliberate.

Readers, what are your thoughts on hats? How do you wear them, or choose one that fits best with your style and face? Would you ever wear one anywhere near the office (not counting winter hats)?


  1. Marinemarie :

    This is a funny world, there was a time when a conservative office would require hats.

  2. I have a headband that is a very scaled down version of the peacock feather example that you show on the right — my headband is thin and brown, and has a brown feather / flower (noticeable, but not overly so — I have brown hair). I wore it to a ladies’ luncheon yesterday with a knit dress that is pumpkin / brown. I am considering wearing this headband to a client later on this month with a camel-colored thin-corduroy jacket, chocolate brown pants and flats, a dark green shell and accessories. The outfit is on the plainer side by itself so the headband would function as the interesting accessory (a la a scarf or brooch). Having said that – I am leading a workshop for 50+ people at my client’s — they will all be in business casual / casual dress — and it’s ok if I wear something a little more notable, as my goal is to stand out / provide leadership and creativity, not blend in with the rest of them.

    • This sounds lovely! I’m loving the orange and green I see in stores. Pairing either with chocolate brown sounds so autumnal and cool. (Can you tell I’m sick of hot, sticky weather in Florida?)

    • Love hats (but have a pixie so would look weird in them – I think). That said, I adore headbands worn by others with short hair – very Audrey Hepburn in Sabrina.

  3. North Shore :

    Oh man, I was just checking out a cute motorcycle-type jacket at nordstrom.com when you had to remind me of Joey Lawrence from Blossom. Whoa! Now I can’t buy it.

  4. divaliscious11 :

    Love Hats, and preferred style is either a cloche or a fedora. Rarely wear to the office as all day wear, but when I usually pair with something like a knee length knit dress, tights and dress boots and a cloche. Fedora’s are a little trickier, particularly now that my 8 year associates them with the “Smooth Criminal” video. I save those for the weekends with jeans, although I could wear on Friday (jean day).

    Modcloth has great hats, as does stores like H&M etc…. Having spent a significant amount of the last 20 years in and out of Europe, I tend to pick up accessories there. there is a great accessories (hats & scarves) shop in Heathrow and Gatwick (London) as well as usually a good selection in the Madrid Airport- MANGO often has cute stuff at the airport in Madrid also.
    Big fan of H&M/Zara IN Spain, in the US, not so much…..

    • I’m with you on cloches! Some of the smaller ones look smashing with slim or pegleg pants tucked into boots, and a long jacket for the whole equestrian vibe.

    • May be I am misreading, but I thought you’re not really supposed to wear hats “inside” — so Friday or not, wouldn’t it be weird to wear a hat “all day” in the office?

      • divaliscious11 :

        I’ve always associated that rule with men…. but could be because I grew up with too many luncheons and teas etc… where hats were part of the outfit, and with aunts who left the house with gloves and hats as young women.

        • According to Ms. Manners, “what is clearly a lady’s hat — something with flowers, veils or other such frivolity — may be worn inside, as well as outdoors (although never at home or after dark). Unisex hats [e.g. baseball caps] must be removed.”

          • That seems sound. I would not think it odd if someone wore an easter bonnet indoors for some brunch type occasion, but I would definitely think it was odd if someone I worked with wore a fedora around the office all day.

          • divaliscious11 :

            Well cloches are clearly ladies hats….and as I said fedoras are trickier

  5. I like hats. I think some people can pull them off really well, to the office and otherwise. Others, sadly, don’t have a prayer. I think its about looking intentional, as Kat said, and also just about having the confidence to really “own” the look.

    I would recommend, however, that rather than starting with random hats (like a cowboy hat for no reason), the OP wait for it to get a bit chilly (or take a sunny day) and just wear a not so ostentatious hat that looks suited for the time of year. It will help make the look feel purposeful & logical — as opposed to “woo-hoo, I’m wearing a hat!”

  6. If you like the feathered headband a really fun thing to go for is a Fascinator… They’ve been a big part of British fashion for ages, and more recently are becoming a trendier look. I love them, especially the ones with the mesh netting that covers a bit of your face.
    Kind of a happy medium between a headband and a hat.
    http://www.fashionfascinators.com/ – Just for some ideas, most of these are a bit too extreme for anything but a derby or a wedding.

    • divaliscious11 :

      CUTE! I could totally see wearing one with say a black strapless cocktail dress…..

      • ADORE these!! I wish I had places to go (atleast once in my life) where I could wear any of them…sigh….

    • San Francisco :

      Um, I kind of love these. Sadly, I can’t imagine where I could wear one here in California…

  7. Threadjack –

    I have read one too many stories about bedbugs (another one in the NYTimes today!) and I’m starting to get nervous. I’m looking at buying a mattress cover designed to keep my mattress safe. I’m considering the “Bed Bug Blocker” brand (a few reviews on amazon and overstock – all look good but none with first hand experience in terms of having a bedbug-infested apartment where the mattress actually stayed safe due to the cover or anything like that to prove it really “works”) but I’m open to suggestions. What other precautions are people taking?

    • quantjockette :

      @E – Having lived through the hell that is a bed bug infestation, I can say that your mattress is only one of several places the little nasties like to call home. They follow body heat, so they travelled from our bed to our living room furniture. When we had the apartment prepped for treatment, we hired a service that vacuumed every (and I mean EVERY) surface and item – books, stuffed animals, etc. – and then bagged up all our earthly possessions for the treatment period (2 consecutive treatments, two weeks apart). All our clothes were either tossed in the dryer on high heat for 30 minutes, or sent to the dry cleaner. We had to have multiple treatments before our apartment was finally declared bed bug free.

      As for precautions, we put bed bug covers on all mattresses, box springs, and pillows (the AllerZip brand), and vacuumed luggage after travel. We used lint rollers like fiends (offices are rife with infestations these days), and sealed all cracks in our apartment, as multiple apartments in our line had infestations.

      I wouldn’t wish a bed bug infestation on my worst enemy. I am itching just typing this message.

      • You guys are making me nervous. I just got back from vacation . . . and I didn’t even think to vacuum my luggage.

        • I have read to NEVER keep your suitcases anywhere near your bedroom, despite the convenience of storing them under the bed. There’s now bedbugs that jump from hotel rooms and other luggage into yours. FUN! And of course, the little guys are can be dormant for months, so it’s best to NEVER keep your luggage close to places that bedbugs could hide. Yes…this is making me itchy too.

          My parents got bedbugs upon return from Tahiti, of all places.

    • Ew. That freaks me out. I had mice in my city apartment once and I turned into a wreck. I think bed bugs would be farrrr worse.

      Has anyone had an infestation anywhere other than NYC?

      • They’re starting to pop up in Texas (in homes, I don’t know if hotels have had any outbreaks recently). I know that several people’s outbreaks here have to do with the college kids coming home from New York and bringing them with them on suitcases/laundry what-have-you.

        This gives me the heebie-jeebies just thinking of it.

      • my brother had them in Alabama. They’re definitely spreading. Apparently they used to be a lot easier to kill before DDT was banned, but since it’s been a few decades… they’re back.

      • We had them in Philly. Moved into an apartment- within a week had over 20 bites. I didn’t even know that bed bugs were real things.

        Two floors of the building were infested with them. They lived in the walls, but set up nests in our mattress, sofa, and pet bed. After washing our clothes in hot water, we had to keep them in giant plastic bags so they wouldn’t get reinfested. We had to have an exterminator come for a month and a half before they were gone.

        I still shudder thinking about it. I’ll take mice or roaches any day.

  8. I think you could wear a fascinator in the office (not on business formal days though) but I would be wary of an actual hat. Perhaps if your workplace is more quirky a rather tame hat, like a cloche, would be fine. I do see headwraps regularly on African women and no one bats an eye, but it seems to be something you can’t get away with if you’re a red-blooded American.

    At outdoor business events, I think conservative/non-flamboyant hats are fine. I always wear a big floppy hat in the sun and I get compliments on it; several of my male higher-ups have told me it’s very classy. I think elegance is key. Don’t wear anything flamboyant or potentially awkward (something that could slide askew, for instance, or that will draw a lot of attention) and hats should be fine.

    • I assume you’re not suggesting that women of African descent cannot also be “red-blooded Americans”?!

      You were probably trying to be sensitive, but it might have been less potentially offensive (and more accurate) to just say that women of color can wear headwraps, but white women can’t really pull them off.

      • Glitterachi :

        I think Eponine actually means women born and raised in Africa. I have never seen a woman of color born and raised in the US wear an African headdress, and frankly, I think I would find it odd if she did. But to each their own!

        • divaliscious11 :

          fyi …. Lots of Black, American born and raised women wear head wraps or head scarves.

        • I have seen women of color born and raised in the US wear African style headwraps.

          I also wonder how, walking down the street, you’d be able to tell whether or not the woman walking past you in an African style headwrap is born and raised in the US or born and raised in Africa.

          • I think this was directed at another poster, not me, but just in case – I know for a fact which of my colleagues are African and which are not and the ones who wear headwraps at the office are all from Africa. Now that I think about it, occasionally one or two women from the Caribbean wear them too. I’ve never seen Americans of any race wear them at the office. I am white and I like to wear headwraps on the weekends sometimes, though. I just think that in a professional setting, wearing the national dress of your nationality is generally considered appropriate but it’s generally considered inappropriate to wear an “ethnic” style when you’re of a different ethnicity. I see the occasional sari, salwar kameez, thobe, indigenous-style Central American skirts, etc, even once a kimono, in my office, but I’d never consider it appropriate for me to wear any of these items in a professional setting. OK, I’m getting way off topic so I’ll stop here.

          • Yes – this was definitely not directed at you, Eponine.

            Also, I realize that I did not express myself very clearly. My point was not about whether or not an individual will be able to tell if a coworker or other woman personally known to her is born and raised in the US or in Africa – it was a more general response to the comment of having never seen a woman of color born and raised in the US wear a head wrap. I see many, many women of color in head wraps at my local grocery store, and the only way to know where they were born/raised is to engage them in conversation and ask – you’ll get everything from Topeka to Timbuktu.

          • I agree with Eponine regarding the appropriateness of wearing “ethnic” dress in the workplace when you are of a different ethnicity. I don’t, however, think that whether or not you were born and raised in that ethnicity’s common country of origin necessarily weighs into whether or not the national dress is acceptable. For example, I think a kimono would be equally appropriate for a Japanese woman born and raised in Tokyo and one born and raised in New York, but not for me because I’m not Japanese.

          • No way would a kimono be appropriate office-wear for someone born and raised in New York! I work at a Japanese firm in NY and I have never seen anyone in a kimono. We have many people who work here who came from Japan, many who have Japanese parents buts were raised in the US, and constant streams of visitors from Japan. I’ve also been to visit our main office in Tokyo several times (and I’ve always been very interested in what everyone was wearing) and no one was dressed in a kimono at the office. If someone from Japan came to visit and happened to be wearing a kimono, I guess I wouldn’t be shocked and certainly not offended, but I just wanted to point out that this is not common and not really within the realm of appropriate office attire.

          • My point was simply that, if you are in an environment where “ethnic” dress is appropriate (some workplaces yes, others no), it would be equally appropriate for someone born/raised in that country of ethnic-dress to wear it as someone of that ethnicity born/raised in the States.

      • I meant African women, not African-American.

      • Can’t speak for Eponine, but the African American women in my office do not wear headwraps, while I have seen them on women living or raised in Africa. I read her reference to Americans as all-inclusive.

  9. Glitterachi :

    A vintage-y style hat can sometimes be pulled off, if you have the chutzpah, with a skirt suit that has a vintage flair (30s and 40s style suits, for instance). Obviously, it doesn’t not have to be an actual vintage suit, nor a direct replica, but definitely heavily influenced. I find that this makes more of an appropriate look, as this era was when women would actually wear hats with their suits.

    And personally, the movie I always think of with regard to hats, especially the issue of wearing them to work, is My Girl Friday!

  10. I wear hats all the time on weekends, but I do not think they are suited for the current American workplace. On the weekend I wear a cloche or sunhat to synagogue and whenever I am outside in the sun. The bigger the brim, the better for keeping the sun off my face all summer. I also think that berets can be worn in several fun and interesting ways (Rachel Bilson has done this a lot).

    In my opinion, fascinators have no place (yet?) in stateside business settings. They are much too unusual to be part of a conservative office outfit.

    If you are getting started with hats, I agree that it makes sense to wear one with a purpose: warmth, shade, etc. See how it feels, get used to having it on your head (some hats cause headaches or make marks on your forehead that can last for hours). Like all fashion, you will look good only if you feel good; if the hat hurts, toss it.

    A brand to check out: Louise Green for cloches (relatively expensive but really beautiful and high quality).

    Another note: keep in mind seasonality. Winter hats (wool, felt) typically are worn between Labor Day and Easter. Summer hats (straw) are usually debuted around Easter. Sometimes this is silly (we have lots of hot days in September) but it is the general rule.

  11. To me, the big issue with choosing a hat is how it works with your hairstyle. I think many hats work best with very short or very sleek hair (think pulled back in a ponytail.) Something about long, loose hair under a hat looks messy to me unless the hat is very casual, like a cowboy hat.

    My ex-mother in law designed hats, and in a fit of pique during my divorce, I gave away all the ones she made. Too bad; they were gorgeous.

  12. If you want to try wearing them to the office, I’ve found it easy enough to substitute regular hats for winter hats on milder days. Where I live, winter lasts an eternity, so wearing a few different hats is perfectly normal. I do take them off inside, though.

  13. I’ve worn fedoras to and from the office a bunch of times last winter, got compliments on them and actually had the judge I was clerking for buy me a scarf as a Christmas present to match. (Of course, I also had an attorney think it was funny to grab it off my desk and try it on. A male attorney.)

  14. The only hats I wear are baseball hats (go sox!), a tilley hat, and fleece winter hats. I have a gigantic head and fashion hats do not fit me at ALL. Too bad, bc I would love to wear them on the weekends!

  15. I love wearing hats- have several vintage ones that I got from my grandmothers and great aunts. I might wear them in route to work but never wear them all day in the office. I’ve been seeing lots of great hats in the stores the last couple of weeks and I’m itching to add a few more to my collection.

    As someone up-thread mentioned, it used to be that a lady was never seen out of the house with out some sort of head covering or gloves for that matter. Times certainly do change.

  16. My orthodox Jewish friend and colleague used to wear the most elegant hats to our office in NYC. It wasn’t BigLaw, but it was a very conservative office, and her headwear fit in just fine.

    • I should clarify, she wore the hats *in* the office (not “to” the office), as part of her normal office attire, every day, for religious reasons.

  17. Lauren Hill is a “redblooded American” and also black. She often wears headweaps, as do plenty of other black women. Not sure if willful exculsion or ignorance is the problem, but that comment made my head spin.

    on the topic of hats: I never felt comfortable in one til I went to the hat store in Lex KY and had the owner help me select appropriate style/fit for my face and the function I needed one for. That hat was not cheap but his advice was like the ad says–priceless!

    • legalicious07 :

      I think the original poster meant well, but it was a bit insensitive (albeit unintentionally so).

      As a African-American, I know for a fact that many, many, many “redblooded” black women in this country wear headwraps and scarves. I do too. But I would also point out that very few of said black women wear their headwraps and scarves in corporate/professional settings. So I think there’s a little truth on both sides of this friendly debate. :-)

  18. Funny, I just saw three different women in three very different neighborhoods all wearing similar straw cowboy hats this morning as I was driving to court, and I thought, hmm, I had no idea those were the new trend. Then you had this post up. Well, I admit I like it, even though I just noticed it today. Woo–time to dig that old cowboy hat out of the closet!

  19. Congresswoman Bella Abzug was known for her big hats. This is her explanation of how she came to wear them:
    “When I went to represent my law firm anywhere—I was a young kid just out of college—I said, “How do you do? I’m Bella Abzug from the law firm of such and such,” and people would say, “Yes, fine, fine, sit down.” So I’d wait and nothing much would happen, so finally I’d clear my throat and say, “I’m Bella Abzug from the law firm of such and such,” and they’d say, “Yes, we know, but we’re waiting.” I’d say, “What are we waiting for?” And they’d say, “We’re waiting for the lawyer.” They thought I was the secretary. So I had this identity crisis.
    I went home and discussed it with my husband, Martin. In those days professional women wore hats—and gloves, so I put on gloves and a hat. And every time I went anywhere for business, with the hat and gloves, they knew I was there for business.”
    Excerpt from Bella Abzug Interview with Global Education Motivators, April 24, 1997.
    Abzug contested society’s expectations for women in order to battle for justice directly and publicly. Her appearance, manner, and words all communicated a message of liberation. She refused to hide her strength, intelligence, love of life, and fury.
    When Bella Abzug was a young attorney, people often ignored and dismissed her, mistaking her for a secretary. To overcome this discrimination, she decided to wear a hat and gloves so that people would see her as a professional. By the time Abzug became a prominent political figure in the 1970s, a hat no longer symbolized the professional role which she had sought to represent. By then, her flamboyant hats had become a singular emblem that symbolized her bold, valiant, and indefatigable spirit. Thus, her costume allowed her to be seen as the truly powerful woman she was.
    Abzug began to challenge societal expectations of women early in her life.
    From childhood, Abzug aspired to become an attorney. When she was rejected from Harvard Law School, because it didn’t admit women, she went to Columbia University’s law school on a scholarship at a time when few lawyers were women.
    Abzug took vocal and visible stands on the issues of civil rights, the environment, women’s rights, nuclear weapons, the Vietnam War and gay rights. She was one of the few attorneys willing to fight against the House Un-American Activities Committee during the McCarthy era. In 1950, Abzug risked her life in Mississippi to plead for clemency in a rape trial against a black man. Pregnant and alone, she spent the night locked in a bathroom in a bus station to avoid the Ku Klux Klan.
    Although times have certainly changed, I have found that a good hat will still give you “presence.” In the winter I usually wear a hat to court, but remove it. However, the very elegant woman who was my mentor often wore a hat to argue in court. People also enjoy seeing a woman wearing a hat. Whenever I wear a good hat, strangers on the street, both men and women, often compliment my hat. Try it and see the reaction!

  20. I work in the southern US, at a pretty conservative firm, but I always wear a headcovering for religious reasons. For court, I tend towards 30s/40s inspired skirt suits, and wear a vintage or vintage-inspired hats to match. Some people do seem to think it’s a little old-fashioned, but it’s the most modern covering I can think of (I wear a veil type scarf or Mennonite style cap outside of work).

  21. I would love to wear hats. But I have a short neck and broad shoulders and somehow, it ends up looking like a hat is sitting on my torso with no head or neck in between. Like a defensive lineman in drag. I have tried many styles of hats over the years and all of them give this effect. I have major hat envy and always love it when I see a British wedding on TV or in the movies and all the ladies are in fabulous hats. Of course, if I wore a hat like that anywhere in my area, people would think I had lost my marbles. And then plopped a hat on top of the squishy remnants of my head.

  22. I was indifferent toward hats until I bought the cutest cloche winter hat last year, which totally changed my opinion on hats. I really want them to come back into fashion. (I feel the same way about brooches. I feel like they’re making progress, but I would still feel a little self-conscious wearing them regularly because they seem more appropriate for an older age group than me)

    • I definitely think cloches are back in style. I feel like I see them around alot. Though I do see it as more of a wintery hat.

  23. I kind of feel like Americans just don’t really do hats much anymore. Except baseball caps or cowboy hats. But there really aren’t that many place that they’re that appropriate anymore. If you ever move to an office in London, you’d probably have better luck with that as the British still seem to love their hats.

  24. I just returned from DC where I was visiting my sister. She wears a super cute hat to and from work. She is pasty white and uses the hat to keep the sun out of her face. She looks really great in the hat and I complemented her every time she put it on. She is petite and the hat is black with a small white and black flower. She can totally pull it off. I don’t think I could.

  25. I would not wear hats except for skiing. I think they mess up your hair – when they come off, you never know what will be underneath. I think that I made an exception when was a tourst in Mexico and wore a strw hat. I really don’t see any females wearing a hat in this part of the country. Possibly because it is windy here – it would blow right off your head!

  26. In Britain they do love their hats, but not for work. They are widely worn to weddings. It would be inappropriate for work there, much as it (mostly) is here.

    I primarily wear hats to protect my skin, so basically weekends only. The number of weddings I’m invited to is dwindling as I get older, but if the wedding is outside, then I’m excited to break out one of my pretty hats.

  27. Senior Attorney :

    I’m de-lurking to say that I have a colleague (my age, late 40s) who prides herself on her Bella Abzug-like hat collection, and honestly, I find it kind of offputting. She is the kind of person who sucks all the air out of any room she’s in, anyway, and the hat collection seems to scream “Look at me!!” in a not-very-attractive way.