The Top 14 googled Hat related Questions, Answered
Article by Maddison McKinley, in collaboration hat experts. The products featured in this article were sourced independently and chosen for the benefit of the reader. Daily Inspirato doesn’t financially benefit if you buy any of these products.
Have you ever wondered where do to start when looking for a hat? What hat colors go best with blonde, light, or dark hair? How to know if you’ve found the right one for you (once it’s on)? I’ve compiled your top questions and asked hat experts from across the country answer your burning questions!
Quick preview of questions, answered (click on the question below to jump ahead).
What colors go best with blonde, light, or dark hair when it comes to hats?
How do I know if I’ve found the right one for me (once it’s on)?
What if I have a big/small head, how do I find a hat that works for me?
I have short/long/curly hair, how do I find the one that works best for me?
What are the benefits of working with a milliner to make a hat?
Hat Experts Across the Country Provide Masterful Takes On Your Top Hat Questions
#NormalizeHats
In today’s article, I’ve compiled the top Googled questions around hats and asked hat experts across the country to answer your burning questions. We’ll have you picking out and rocking a hat in NO time.
Dear Reader,
If you are a fledgling hat wearer, you’ll see hats throughout the story that you may feel you’d never wear. I get it. I’m not suggesting you immediately begin dressing like Audrey Hepburn from Breakfast At Tiffany’s. (Though, how chic would that be?!) My goal is to ease you into hat-wearing by answering your top questions. I hope to inspire you to start wherever you’re comfortable. Maybe that’s a wide-brimmed floppy hat at the beach, a small fascinator for an upcoming garden-themed cocktail party, or a felt fedora with a cool feather in it. Even though hats aren’t as commonly worn as they were at one time, that doesn’t mean you shouldn’t wear them. They’re a completely underused accessory in day-to-day life that often make an outfit stand head and shoulders above its peers.
One of the hat experts in this article, Lisa McFadden says,
“Generally, if you’re not a hat wearer, don’t force it, but stay open to conversion :) If it’s the right one, you’re sure to smile. Hats should make you happy, not conflicted.”
Lisa’s email signature is literally:
So with that, let’s get it into it!
Meet the Hat Experts
Katie Allen of Lifted Millinery
Taking inspiration from historic Hollywood style, milliner Katie Allen creates high-fashion hats and headpieces. Incorporating vintage and antique materials whenever possible, each piece is truly one-of-a-kind. Katie’s background includes a BA in Costume Design and Technology and extensive work in regional theatre, independent film, and historic interpretation. Prior to launching her millinery label, Lifted, Katie spent years constructing bespoke garments and accessories for private clients. Her combined love of history and vintage materials are a special offering to North Carolina’s fashion scene.
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Shop Lifted Millinery
Amy Jo of Amy Jo Original Hats
Amy Jo is the expert on Southern Hat Style. She creates custom pieces for Mobile, Alabama debutantes, Kentucky Derby spectators, and everyone in between. A client of Amy Jo’s won the 2019 Kentucky Oaks Fashion contest wearing an Amy Jo Original, and she is a member of the Milliners Guild USA, a group consisting of the best hat makers across the U.S.
“As a Southern Girl, hats are an essential part of my wardrobe. They have a way of finishing off an outfit and making it look perfect!”
- Amy Jo
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Shop Amy Jo Original Hats
Etsy: https://www.etsy.com/shop/AmyJoOriginalHats
Direct: https://www.amyjooriginalhats.com/
Instagram: https://www.instagram.com/amyjooriginalhats/
Hats: A Docuseries
Samantha Valentina and Talia Jaclyn Bornstein are the creators behind Hats: A Docuseries. This docuseries is a playful examination of different cultures through an accessory found everywhere—the hat. Part travel documentary and part edutainment, Hats was born out of discovering a French beret made in China. This artifact of contemporary globalization compelled the two curious Americans to answer the question: What makes a symbol authentic to a culture?
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Check out Hats: A Docuseries
LISAMCFADDEN MILLINERY
Lisa McFadden is a New York City designer with over 20 years of experience in the fashion industry. Lisa studied millinery while earning her BFA in Fashion Design from American Intercontinental University in Atlanta, Georgia and graduated with top craftsmanship honors. She was critiqued by French couturier Pierre Cardin who, upon seeing her student work, said she was a designer who “knows her job.”
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Shop LISAMCFADDEN
Hat Confidence
“Sunday Style...wardrobe indecision. Hat or fascinator? Help me decide!”
“What a difference a hat can make!”
A hat can completely change an outfit and prolong its shelf life. Check out these pictures of Amy Jo of Amy Jo Original Hats.
Wearing a bold hat is the highest form of confidence and self-expression that one can manifest. Not only do hats add to our height, but they also sit upon our greatest asset: our faces!
The word I hear most commonly coupled with “hat” is “intimidating.” I think we’re intimidated by hats because they make us uncomfortable. But you know the old adage: “face your fears!” The more we confront what intimidates us, the more comfortable we become with it.
With hats, there are considerations of scale, occasion, and, even the 4Cs (Cut, Color, Cloth, Comfort) when selecting the right piece to don your crown, but it’s nothing you can’t handle when you know what to consider.
That’s why we’re focusing on answering your top questions about hats in this article so that you feel comfortable trying a few on for size. Have a question not listed here? Let me know!
#1: Where do I start when I’m looking to select a hat?
Savannah: “If you’re looking for a cute, cheap souvenir or something that will keep the sun out of your eyes, get something from a gift shop. That’s fine, no shame! If you’re looking for something that will protect you from the cold or heat, that will last ages, that has a history, that’s authentic, check out specialty hat shops and manufacturers for whatever specific hat calls to you.”
Talia: “Speaking from the view of our docuseries, authenticity is important in more ways than one. Consider looking into your culture—almost every culture has a hat associated with it. Personally, as a pretty secular Jew, I probably won’t start donning a Yarmulke everyday, but I’m also American. Cowboy hats are culturally American, and stylish as hell. But that’s just one way to pick out a hat—no matter what though, authenticity first. Look around, experiment, try some different styles on and see what feels good to you.”
“Be mindful of the event”
“Go to a Millinery shop and try everything you can on … Start looking well in advance of your event. Just like you spend time looking for the dress and shoes, the hat should be a conscious decision.”
“Make sure you love your dress and shoes first, then choose a hat with a Milliner.”
“Don’t rush the process.”
Before you even try on a hat, there are some questions you can ask yourself to get a sense of what types of hats might work best for your personal style. In typical Daily Inspirato format, we’ve broken it down by the 4Cs—Cut, Color, Cloth, (Comfort comes once you’ve tried it on!).
CUT
Begin by asking yourself what style hat you are most drawn to? Don’t worry about anything other than that to begin.
There are many types of hats in the world, just take the following as a few of the most popular examples.
Baseball Cap
$23—Shop the Baseball Cap from TouchStoneThread’s Etsy Store
Bucket
$32— Shop the Bucket hat from LorienStern.com
Fedora
$175 - Shop the Fedora from LiftedMillinery.com
Boater
$18—Shop the Straw Boater hat from Asos.com
Beanie
$15—Shop the Beanie from Zumiez.com
Cap
$350—Shop the Woven Cap from EastVillageHats.nyc
Cowboy
$215—Shop the Cowboy hat from Stetson.com
Turban
$290—Shop the Turban from Bongenie Grieder.com
Beret
$24—Shop the Beret from LanaBluDesign’s Etsy Store
Fascinator
$225 - Shop the Fascinator from AmyJoOriginalHats.com
Pillbox
$250—Shop the Pillbox from AmyJoOriginalHats.com
Sunhat
$295 - Shop the Sunhat from EastVillageHats.nyc
Tradition Note: Traditionally with hats, the brim goes from wide to narrow as the day goes on because it follows the trajectory of the sun. A wide-brimmed floppy hat works great at the beach to protect your skin in the noontime sunshine, and the cocktail fascinator is worn at night because it has a small to nonexistent brim and is purely for aesthetics and not function. This isn’t to say that you can’t rock a Stetson at night (Texans do), it’s just a traditional perspective.
COLOR
If you’re going to invest in a hat, I recommend choosing a color that is going to go with everything. I love the idea of a bright pink Stetson hat, but I’m going to get the black one if I’m spending $215 because I’ll be able to wear it more. Black and ivory are great neutrals that will go with any outfit and any hair color. Other wearable neutrals are beige, brown, and natural green.
Pro Tip: Invest in a hatbox if you get an ivory hat! They get dirty easily.
Speaking of hair color, be sure to try on the hat you’re interested in to make sure it doesn’t clash with the tones of your skin or hair.
#2: What colors go best with blonde, light, or dark hair when it comes to hats?
“What is framing your face should complement your skin-tone, so avoid hats that blend with your hair color.”
"Details on a hat don't show up as well against hair colors that blend or match with it. If you do want to wear a hat in a similar hue as your hair make sure the texture, trim, or shape provides a good contrast."
If your hair is tied back, then it’s not much of a problem since your hair isn’t the focus of the look.
If you’re doing a head-to-toe event where the hat and the shoes are all being considered—Take your hat to your hair stylist and have them work the hat in with your hairstyle. They will consider the elastic, and how the hat sits on your head.
CLOTH
Depending on the season, material plays a functional role. For warm months, cashmere or wool will keep you warm, while for spring and summer a cotton bucket hat or linen summer hat are more comfortable and seasonally appropriate.
#3: How do I know if I’ve found the right one for me (once it’s on)?
Savannah: “Do you feel good in it? When you look at yourself in the mirror, do you feel empowered by it? Obviously, not every accessory you wear has to be empowering, but hats are a statement piece. They send out a message. What do you want that message to be and is it helping you express that? When I picked out my first Stetson, I picked the one I did because I’m very drawn to leather. I’m a very tactile person who loves textures. Talia for example hates velvet and suede but I love [them] and seek [them] out. Leather, to me, demands respect. It’s powerful. It’s sensual. It makes you look.”
Talia: “Confidence is key. When you know, you know. Dr. Debbie Henderson, a hat historian we’ve spent a lot of time interviewing, really drove home for us the fact that hats are an extension of one’s self. If it feels natural on you, it’s right.”
COMFORT
Ask yourself, is the hat comfortable on your head (does it fit)? If the answer’s no, then try to size up/down, or nix that particular size/brand.
Comfort is key when it comes to picking the right hat for you.
For years I tried wearing women’s cowboy hats that never quite fit (I’d have to rest them on the back of my head instead of the brim resting level on my head). It wasn’t until I took a trip to the Stetson store in Tombstone, Arizona that I found out I’m a size 7.5 (at least 2 sizes up from what I had been wearing). Now the hat fits flawlessly, hitting just above my ears and sitting snugly around my head. Proper fitting is so important!
CUT
Do you like the general shape of the hat? Don’t worry if it doesn’t feel natural to wear yet … it may feel “intimidating,” but that feeling will pass. The question is: do you like the way it makes you feel? Does it jive with the vision you have of your personal style?
COLOR
Does the color make your skin look healthy? Does the hat’s color complement your hair and skin tone rather than replicate it?
CLOTH
Do you like the material? Does it feel ready for “all day wear”? Not itchy? Appropriate for the weather?
# 4: Is there a hat that works for everyone?
Amy Jo of Amy Jo original hats says “yes!”
“Some people don’t look good in certain styles ... I don’t look good in certain styles! But you learn what you look good in and go with it. There’s a style of hat that looks good on nearly everyone. I’ve found the asymmetric brim is the go-to hat for the people who don’t think they look good in a hat.”
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$395—Navy and Oyster Giraffe Wide Brim Hat
“A hat that sits at an angle whether it’s a fascinator or with a brim will work on most face shapes.”
An angled topper gives an alluring look to any ensemble.
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Contact Lisa to custom order your hat confections.
“A small button fascinator, fedora, or headbands, are universal and work well for everyone”
Katie mentions that scale is important, meaning, you want to consider your face size and match it accordingly with the width and height of the piece you choose.
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$175—Marie in Wool
$55—Luna Headband (I ordered one :) LiftedMillinery.com
#5: What if I have a big/small head, how do I find a hat that works for me?
Savannah: “A hat that works for you is a hat that you can put on your head and when you shake your head like you’re quickly saying “no,” it doesn’t fall off. We learned that tip in Tucson at Arizona Hatters.”
Talia: “As a member of the big-headed community, I’d like to highlight the fact that also, if you have the cash to do so, you can get your head measured and get a custom hat made just for you.”
“Don't give up at just one hat. Persevere because there’s a hat for everyone”
With the number of hat styles out there, there is bound to be something that will work for you. It’s about trying different styles, seeing what works, and getting them in your size!
“Once you know that your head measurement requires special sizing ... I would suggest a Google search for hatmakers who can customize a hat for your needs. Looking for brands that offer large-sized hats or made-to-order services will help streamline the process.”
“Go get measured, not just around, but also ear to ear.”
Katie makes a great point in that we get measured for bras, which we’d all agree is critical to a proper fit. The same goes for hats.
Also, know that milliners like Katie and Amy Jo work virtually, too, so you don’t have to have a milliner locally to get fitted. You can meet with a milliner online!
How to Measure Your Head Video
Check out Lisa McFadden’s “how to measure” video! So helpful!
#6: How to wear a hat with big ears?
Savannah: “Who cares?”
Talia: “Totally understand insecurities, but typically what you’re insecure about is also what makes you unique. Show off your ears, boo.”
“A sizing band allows the hat to sit up a bit higher so you’re ears aren’t rubbing up on the brim (you can snug the band up, or down, depending on your ears)”
“It depends on if you’re trying to minimize the size of your ears or show them off. A haircut will do the trick either way. Now, if you have a little bit of Will Smith going on, then you can always wear a beanie or beret for a snug, yet comfortable fit. Another possibility is to wear a brimmed hat with a slightly larger fit, tilted toward the back of your head [to cover} the top of the ears. This also works great with bangs and glasses.”
Check out Lisa’s CRUSH Hair Hat Journey YouTube series for a variety of solutions.
“Fit is so important. Do you want your ears to show or not? A fascinator is always a great choice, or a hatinator, for those concerned about ears because you can conceal the ear with your hairstyle.
If your ears are bothered by close fitting headbands, a soft, unstructured, hat is going to sit on your head with less rigid contact. Katie also likes the tactic of creating a soft little loop across the ear with some hair.
Kate Middleton commonly uses this:
Elastic bands can help prevent earitation (see what I did there!?) like The Gilda on LiftedMillinery.com ($255).
#7: How to wear a hat with glasses?
Savannah: “This order is very important. Glasses first, hat second.”
Talia: “You put on your glasses, and then you put on your hat. Don’t be afraid to wear more than one accessory— forget about that Coco Chanel quote. She was a Nazi anyway. Make maximalism work for you!”
“There are headbands that can be tied behind the ears, which can help”
Take Katie Allen’s Vita headband (love) - $235—Vita on LiftedMillinery.com
“If the hat sits above your ears, it’s not going to be a problem.”
There are hat styles that don’t hit the ears, like a beret, that will rest comfortably on your head without disturbing your glasses. When you can, go for a thin elastic band that will work around your glasses.
Shop the Celeste Beret on LiftedMillinery.com $185).
#8: I have short/long/curly hair, how do I find the one that works best for me?
Talia: “As someone with short hair, it literally doesn’t matter. Hats actually save my self esteem in a huge way on bad hair days.“
Savannah: “I would say hair length and texture actually matters very little, but hair density is huge. Thick hair can make it hard to get hats securely on your head, so the way you style your hair and what size hat you get definitely matters. It’s all about strategy.”
“The density of the hair is taken into account when a Milliner measures your head, since the hair adds to your head size. The great thing about the elastic and thin headbands is that you can tint them to your hair color so that the headband disappears. Plus, you can get an elastic size that’s stretchy enough to work for your thick or curly hair.”
“For women who have gone through chemo, we can use toupee tape and custom colored elastic to match their skin tone.”
“For short hair, you can use a comb to attach the hat to the hair, or an elastic band.”
#9: What if I'm not ready to commit to a hat?
Custom Headbands start at $75 and are available on amyjooriginalhats.com
Not feeling ready to dive into hats quite yet? Start small with other crown accessories like headbands, clips, head scarves, or scrunchies.
“Generally, if you're not a hat wearer, don't force it, but stay open to conversion :) If it's the right one, you're sure to smile. Hats should make you happy, not conflicted.”
Lisa’s email signature is literally:
Many thanks and remember ...
For everyone there is a hat!
#10: How do I accessorize a hat?
You can style a hat a million different ways from adding a pendant, a neat ribbon or a horsehair hatband around your cowboy hat.
![“A few unconventional ideas to wrap around your crown:A necktie wrapped around and held in place with a [pin, pendant] or colored jumbo paper clips.Try cutting pantyhose or tights [across the thigh].. Once cut, they will stretch over the crown. Mix …](https://images.squarespace-cdn.com/content/v1/5a5bb2d44c326d0693be1df9/1618366168268-GYPOS14VY7MLYNHSYC2M/Lisa+McFadden+Icon.jpg)
“A few unconventional ideas to wrap around your crown:
A necktie wrapped around and held in place with a [pin, pendant] or colored jumbo paper clips.
Try cutting pantyhose or tights [across the thigh].. Once cut, they will stretch over the crown. Mix and match textures/ colors.”
#11: How do I keep a hat on if it’s windy?
Hatpins are the answer. They are essentially a needle that goes through the hat, grabs some hair, and then comes out the other side. The end of the needle is fastened with some sort of safety cap to make sure you don’t impale yourself.
Depending on the design and thickness of the material, not all hats allow for a hat pin. Fascinators and hatinators supplement form with the function of elastic straps. Looking for a DIY solution? Try this clever trick using nothing more than safety pins and a hair band.
“If it’s windy, avoid brims. Wind picks the brim up and takes the hat away.”
#12: What is the best way to store and care for a hat?
Katie of Lifted Millinery has a few notes about taking care of your hat. Like many things we love, we can keep them around for a long time if we treat them well. This is particularly true of hats. Proper storage is the key to making a hat last.
Katie’s recommendations:
STORE IT: Depending on how you buy the hat, it may come with a box. If you purchase the hat from a milliner, take a picture of how the hat is stored in the box before you take it out. That way, you know exactly how to store it when you’re ready. If you didn’t buy the hat from a Milliner, store the hat in a dry, cool, breathable (not plastic), container so that it won’t misshapen from items hitting it. Don’t hang your hat up! Warping happens easily.
WATER = BAD: For the love of God, do not get your hat WET. Scotch Guard your hat to protect it from the elements, or get one made to withstand inclement conditions. Don’t leave a hat exposed to humidity and moisture.
DUST IT: Use a nylon bristle baby brush or a hat brush to regularly dust off your hat.
#13: What are the benefits of working with a milliner to make a hat?
The three images above are courtesy of @SallyCaswellHat. Hat blocks are the traditional way Milliners created a hat—they wrapped the material around the hat block. In the case above, you’ll see that the hat can be worn a few different ways. The image with the hat centered is the original design, while the image with the hat slightly off-kilter is the same hat, just sitting differently on the head which makes it look like a different hat!
A benefit of working with a milliner is that they will evaluate your unique features. They look at face shape, hair length, height, your outfit, and hair and skin tone to make hat recommendations. There are a wealth of milliners who will be more than happy to consult with you on your needs.
MILLINERS GUILD SITE: https://www.millinersguild.org/
#14: Can you restore a hat?
Yes! You can restore a hat. See Katie of Lifted Millinery bringing a 1960s hat back to life through the images below.
When a milliner creates a hat by hand they can disassemble and reassemble a piece by restoring, reworking, restyling, and retrimming.
Take your cue from jewelry. It is commonplace to rework grandmother's gem into a setting and band that’s more your style. Do the same with a hat! Bring grandma’s 1920s hat into the 2020s! Because these hats were usually made with high-quality materials and techniques, they are worth saving.
Bringing a hat back to life is the sustainable choice and it’s custom. No one will have anything else like it.