A Fashionable Resolution: Wear Hats with Confidence!

I felt all eyes on me the first time I wore one. Sure, I had worn winter caps and slouchy berets before, but the first time I took a real chance and wore a vintage hat in public, I was terrified. Would I look like a goon? What would people think? But it was 2010, and this was the year I had firmly resolved to wear more hats. Although stepping away from the mirror and stepping out in public, I was so close to giving up on the whole silly New Year’s resolution.

Maybe it was the fear of what horrible hat hair laid beneath, but I resisted the temptation to leave the hat in my car, and to my surprise, I received so many compliments and delighted looks throughout my whole day! When I got home and put my hat back into its box, my feelings of insecurity had been changed into the heroic sentiments of a do-gooder. Really, wearing hats does make the world a bit of a better place!

It’s true that wearing a hat these days can take quite a bit of courage. They’re an endangered species, so wearing a hat will steal your anonymity and invite attention from strangers. But if you’re like I was, always admiring women who wear hats and wishing you could pull it off, you might decide to make a fun resolution this new year and commit to giving hats a chance. What’s there to lose? Okay, so there’s a little at stake. You don’t want to waste your hard-earned dollars on something you might never wear. So you’ll want to find a hat that you can wear with confidence. One that seamlessly blends in with your wardrobe and makes you feel like Audrey Hepburn reincarnate. Or Anna Karina. You just want to exude awesomeness. So let’s talk about some guidelines and tips that will get you to Awesometown.

things to consider when buying a hat

Some might say the most important thing to consider when choosing a hat is your face type. But I believe the most important factor in hat selection is your personal style. When I first started wearing hats, I had a variety of styles that I would wear, depending on my outfit, but now that I’ve refined my personal style, I seem to go for the same type of hat over and over again. My style is preppy with plenty of 1960s influence, and after browsing fashion photos from that era, I found that I really liked the look of a rolled brim schoolgirl hat. If you already know your personal style, I have some ideas for hat types that might fit in nicely with your wardrobe.

  • Bohemian: slouchy berets, floppy wide brims, large fur hats, wide brim fedoras
  • Preppy: structured wide brim hats like picture hats, bretons and boaters, structured berets, cloches, fedoras
  • Tomboy: newsboy cap, fedoras, bowlers, boaters, ball caps, beanies
  • Vintage glamour: smaller pill-box types, fascinators, structured wide brims, wide-brim cloches
  • Grunge: bowlers, slouchy berets or beanies, structured rolled wide brims, ball caps

finding the right hat for your hair style

When I cut my hair, I was surprised to find that most of my hats looked better without long locks hanging limp past my shoulders. When it was really short, picture hats and cloches worked great, with little bits of hair peeking out around the crown. And when my hair was longer, I found that my vintage styled hats looked great when I wet set my hair and styled it in an vintage fashion (like here and here). I believe that hats can work with any face shape you have, but your hair style really plays a big part in making them work. I suggest finding a hair stylist trained to find a style suited to your face type, but while considering what hat type to go with your current hairdo, just remember that balance is key.

  • Long bohemian hair: beret. fedoras, floppy, bowlers
  • Pixie cuts and bobs: cloches, picture hats, bretons, rolled brims, floppy wide brims, some pill box styles
  • Shoulder-length: cloches, wide brims of any kind, fedoras, pill box styles (better with curls), boaters, bowlers
  • Bangs: hats that go up away from your forehead, or if they do come down, are wider, like a wide-brim cloche

finding the right hat for your face shape

I think any hat-wearing rules based on face shape are trumped by proper hair styling techniques. I also think that trial and error is the best way to find a hat type that will work with your style and facial appearance. Nevertheless, there are some set millinery standards for matching hat styles with your face shape.

  • Round: Look for wide brim hats, angular hats, and cloches that balance out the soft shape of your face with harder angles.
  • Heart & Triangular: Try wide brim hats, picture hats, rounded styles, and styles that go up and away from your forehead.
  • Square: Soften the hard angles of your face with rounder styles, and stay away from brims that come out from the side of your face, like a fedora or boater worn straight.
  • Long: Look for hats that come down onto your forehead, or style them so that they do. Tilt wide-brim fedoras over your forehead, utilize floppy hats, and try cloches.

the right hat for each season

This one’s kind of a no-brainer, but still, it’s something that should be considered with choosing a hat. Wool and fur hats are great for the wintertime, whereas straw and floppy hats are typically reserved for the summertime- although sometimes you can find wool hats in a floppy style too. There’s no need to over-think this when selecting a hat- just don’t wear a wool hat in the Summer, or you might melt away.

tips for selecting a hat

If you’re still unsure about wearing hats, don’t give up yet! Something as simple as finding the right size for your head can make you love or hate wearing a hat. A too large hat will not only look silly, but might keep falling off, causing a lot of stress to the wearer. When my hats are too small, they also fall off, which makes me feel anxious the whole time I’m wearing it. Not worth it. So, find a hat that fits!

How you wear your hair will also affect how hats look on you. Lots of ’40s to ’60s era hats were designed to be worn with more elaborate up-dos than we typically do in our modern culture, so they might look out of balance if you have straight hair, especially if it’s long. Something as simple as a side chignon might help, but if you really love older hats, you might want to experiment with some vintage hair styles (like this one, perhaps?). You might also try pinning back your bangs for styles worn low on the forehead, or part them off to the side.

Smaller hats, like a pillbox style, need the assistance of pins to stay in place. Even larger hats can benefit from the use of a hat pin, especially if the crown is shallow. I wear a pin mostly every time I wear a hat that isn’t super snug. To wear a hat pin, you’ll need to have a foundation to pin it in, so if your hair is down, use hairspray and tease the hair at the place you wish to pin the hat (usually at the base of your head, or wherever works to keep the pin in place). If your hair is up, you’ll probably also want to have it teased, and sometimes even just having bobby pins in place can create a great place to slip a hat pin. To use the pin, pierce one side of the hat, then put the hat on your head, push the pin through the teased hair or bobby-pinned area, and out the other side of the hat.

One last tip I have is for those who may be a bit shy about wearing hats in public. Especially for the bolder hat, I suggest pairing it with a simply styled outfit. A basic black dress is nice on its own, but worn with a stylish hat, your simple dress can become a really chic outfit, and nothing to be shy about!

the best places to buy vintage hats

Would you believe I’ve never been to a millinery shop? I live in a smaller city, and have never come across a hat shop for women. But I do know that larger cities have millinery shops where you can buy quality hats that are handmade and sized perfectly to your head’s shape and size. Keep in mind that a new hat from a millinery shop will be an investment, so make sure you know what you want before making a purchase.

I bought my first nice hat at a vintage shop. Usually you can find lots of different styles and sizes at a well stocked vintage shop, and it’s lots of fun to try them all on and experiment with different styles. Depending on where you live or depending on the particular store, vintage shops can be a pretty affordable place to get a hat. In the northeast Ohio area, you can find a hat anywhere from $10 to $100, depending on the quality (minor flaws are expected with worn vintage) and depending on if you’re looking at a designer item. Most of my hats from vintage shops were purchased for around $10 to $30. If you’re a regular visitor to your area vintage shops, you could probably score a return customer discount, if you charm the local shop ladies!

I wouldn’t recommend buying hats online until after you’ve found a style that works for you and you know your hat size (or head circumference). I have never bought a new hat from shops like Topshop or ASOS, because they are usually one-size, and not all heads are the same size. If you have an average head size, maybe you won’t have any trouble. But I didn’t know I had a larger head until I started trying on hats at a vintage shop. Once you know your size and style, the best way to find a hat on Etsy or eBay is by searching for a specific style or decade, and then reading each item’s description to check out the size. Most sellers don’t put sizes in the title, so don’t bother searching for sizes- you might miss out on some great hats that way! Also, be aware that a lot of sellers don’t know hat terminology or dating, so if you have some time, you should look through results for broader search terms like “wide brim hat,” “black hat,” or “round hat.”

rules for wearing hats

I’m usually the first person to ignore rules when it comes to fashion. But if you have a hat you really love, you’d better take care of it! Many hats aren’t made to be worn in rain or snow, so pay attention to the fibers in your hat when deciding what to wear for the weather. Wool will resist water for a short period of time, but then will soak it up, possibly resulting in shrinking or reshaping. Leather and fur could also be damaged by water, so be careful! Besides the weather, you should also consider the design of a hat when deciding how to wear it. For instance, if a hat has an elastic band, most likely the band is meant to be worn behind the neck under a fashioned hair style. If you wear the strap under your chin, you risk damaging the strap or even causing it to pull a hole through your hat.

Be mindful of how you store your hats when they’re not on your head. Sometimes I hang my hats on the wall and change them out with the seasons, but if you are storing your hats in a room with sunlight, you will definitely want to keep them in hat boxes to avoid the fading that will occur with sun damage. Boxes also keep your hats dust-free and safe from getting crushed. If your hat did get crushed somehow, try using steam to soften the felt or straw of the hat and work with your hands or a form to reshape it.

As you all know, I’m not one for rules in fashion, but hat etiquette is about being polite to those around you, not about following rules. Women are lucky in that they can wear hats indoors for almost any occasion (fashion hats, that is, not unisex hats like ball caps). But you should remove your hat when participating in audience events, like concerts or sporting events, where your hat might block someone’s view. If your hat is small enough not to block anyone’s view, go ahead and leave it on. You’ll also not want to wear a hat when working indoors or when hosting a party in your own home. But at all other events, even during the playing of the national anthem, women need not worry about removing their fashion hats.

28 Responses

  1. Nicole says:

    thank you! this is very helpful.

  2. Becky Bedbug says:

    I was always convinced that no hats looked good on me. Then I tried a woolen beret and it looked great. Turns out those are the only types of hat I can wear, as well as bowler hats. I’m on the lookout for a red bowler.


  3. Et tu, tutu? says:

    This is a really fun article! I don’t wear hats often, but maybe I’ll try and find a cool one. :)


  4. Juliet says:

    Great article! If you ever make it down to Dayton, you should definitely visit Brim, a fabulous neighborhood hat shop in the Oregon District.

  5. Eugénie says:

    You’re my queen. Your article makes me want to wear more hats than ever… I have two cloches and one black beret (héhé I am French). I love them, but I don’t wear them as often I would like. I have a little question and maybe you could give me a piece of advice : I wear glasses and I don’t know if it fits with hats, I fear that my face dispears. What do you think about hat+glasses ?

    • Mandi says:

      That’s a good question I hadn’t considered! I wear contacts, but occasionally wear glasses. And now that you mention it, I rarely wear hats when I wear glasses. Though sometimes I will wear a simple black wide brim bowler style hat, or a beret while wearing glasses. My advice would be to somewhat match the style of your glasses to the style of your hat. I wouldn’t wear wire rim glasses with a 40s-60s era hat. But that’s just my personal opinion. I’ve been dying for a pair of cat eye glasses- nothing too dramatic, but just a subtle cat eye. I think they would look great with lots of older vintage styles.

  6. Cyndi says:

    This is so useful! I was recently diagnosed with alopecia, and have huge bald spots all over my scalp. I bought 10 hats on sale after Christmas at a millinery shop and I love them so much! I also have vintage hats that look like they came from Mad Men. People compliment me all the time, which is great because I’ve felt so ugly since losing my hair. Fashionable hats are a great confidence booster :) I frequently look through your archives for style inspiration because you wear hats all the time and look fantastic!

  7. irene wibowo says:

    nice post! :)Irene Wibowo

  8. Kati says:

    Thanks so much for these tips – I really like hats on other people but haven’t been brave enough yet to wear one myself…


  9. Kristian says:

    I adore wearing hats (and ironically have most of the hats you recommended for longer hair, which I have! Good to know I’m kn the right track…or at any rate have it explained why these hats worked for me and other styles didn’t). Think I’ll share this on twitter so more people will wear hats too!


    • Mandi says:

      That’s great to hear! I’m glad things work our more than just in theory. haha But I do believe there are exceptions to every rule, and you can always work around the rules. :)

  10. RM says:

    Thanks for this. As a transplanted Kentucky girl, I always want a nice big Derby hat, but I hate spending money on them because I have no idea where else to wear them. Maine is such a laid-back place, it seems I never have occasion to dress up. Can you talk a bit about where you wear hats?

  11. Maya says:

    I particularly like your hints about matching hats to face shape- but am really pleased by how much overlap there is between different shapes. As someone who covers my hair, finding ways to either fit my (long, straight) hair under my hat, or make the hat look right when there isn’t hair peeping out is often a challenge for me. It’s easier for me to stick with my tried and true scarves and wraps. This is great inspiration to play with more hats. Thank you! (I’ll be sharing the link on my blog, as well…)

  12. Victoria says:

    I’ve been wearing hats daily for several years now. I agree with pretty much everything you have here.

    One thing you left out that I have found vitally important to successful hat wearing is to treat the hat like it’s a part of the outfit you’ve put on, not an afterthought. Hats has the same level of importance as shoe choice on overall presentation. Most women don’t wear sneakers with cocktail dresses, so don’t wear a straw cowboy hat with one either. (A top hat or highly styled fedora, however, would work just fine) Nor would pair a stylish felt fedora with ripped jeans and a t-shirt. (I’d go with a woven straw fedora with grunge.) Matching colors or materials or themes/styles extends the wearing of hats in a wonderful mix-or-match way.

    Hats shouldn’t look like afterthoughts or something you slapped on your head on the way out the door.

    Eugénie – I wear hats with glasses. Just remember, both glasses and hats are what I call “head accents”. As a rule, smaller framed glasses work better with hats. Large frames and large hats tends to make people look like a starlet gone incognito. If your frames flatter your face, 95% of the time will work with the hat that also flatters your face. If your glasses literally bump with your hat, one, or both, of those items are the wrong size.

    I could go on endlessly about how to deal with long-term hat wear, plus refreshing old head gear, but I’ll restrain myself.

  13. Pippi says:

    What a great article! I’ve always admired your braveness for wearing hats in public. I’ve got a collection of hats too and it took me ages to build up my confidence to wear them. The problem is that I’m a university student so I can wear one during the day but I find I often have to take them off as I’ll be indoors for a few hours at a time, so I have to make sure my hair survives the hat! I think you’ve just inspired me to wear my hats more often :)

  14. One of my resolutions this year is to wear more hats, so this was the perfect post to read! I’ve purchased several vintage hats throughout the years, but never actually worn them. So this year, I’m going to put those pretty things to good use and work them into my daily style.

  15. I’m not much for hats, but I was given loads of vintage hats that you reminded me just now that I still need to photograph to sell. You are so good at hats!!!

  16. Cassandra says:

    I just bought myself an adorable dull navy straw fedora on a total whim. I was shopping with my eldest son, I picked it up in a men’s store for less than half price! It looks great (if I do say so myself).

    I find the trick with wearing a hat is habit or practice. Once you forget you’re wearing it, you’re not so conscious of it, it will just become part of you. All your hints and ideas just make me want to wear them more!

  17. Hats are freaking glorious! These are some great tips – especially about proper storage and weather conditions.
    I am a Victorian-era freak and love to emulate men’s fashion from that time period. I bought myself a bowler hat yesterday and it just feels right! (You can see a picture of my new hat if you please, here: http://www.flickr.com/photos/91233450@N04/8390151195/) I plan to wear this daily and to follow the hat etiquette to the best of my ability – taking it off when going indoors, tipping my hat as a greeting, etc. I did find myself getting a few more looks than usual, but that has always been a secret thrill for me. Bring it on, world! Look all you want! We need more dandy ladies out there!
    I am a new reader, by the way. Your blog is awesome :D

  18. Dana says:

    So glad I can across this article. I had neck surgery over the summer and wore floppy summer hats to shade my scar. Now that fall is here, I can’t wait to experiment with call hats. It’s nice to know I am not the only female that thinks hats can be part of a basic wardrobe and make it great. Please post more.

    • Mandi says:

      I had neck surgery over the summer too! I gave up trying to make my scar less noticeable, though. I just kind of roll with it now. It makes me look really tough! haha!

  19. Kierstin says:

    I love hats. I love, love, love hats. Not that I’ve ever been able to “wear” one, but I love hats. A few days ago (just in time for my bonnie and clyde costume) my brother bought me a vintage fur pillbox hat, I put it atop my head and about fell in love. I’d never even attempted to wear a pillbox hat, thinking I had too much of a face shape to my face to wear one. Lo and behold, I put it on, and fell in love. Thanks to your article, I shall be on the look out for more of a variety of hats, and will be wearing my pillbox to death! :) (and maybe making an offsetting black veil for it)

  20. Irene says:

    I’ve been collecting vintage hats since I was 14. This has unfortunately been made considerably harder due to my local hat shop closing. My go to hat is the fedora of which I have a few, but I also wear the trilby, bowler, cloche, and several large ladies straw hats. I have noticed over the years how my hairstyle had impacted the look these hats have given me over the years, and I would like to ad that having a very finely boned face I’m able to wear a fedora with my pixie cut without fighting much femininity. It is however a far more severe look than my previous shoulder length curls. I definitely feel as though it gives me a more no-nonsense appearance.

  21. ida hunter says:

    I always wanted to wear more hats but I also wear eyeglasses and the two never seem to look right together. Whats your opinion on eyeglasses and hats?

  22. professor says:

    Just bought a custom cloche online. Boy did I get lucky because it looks and fits great!