How to Wear a Hat with Style & Confidence - 7 Tips to Look Great in Men's Hats

We discuss 7 tips to help you be confident and stylish while wearing classic hats: gentl.mn/styling-classic-hats
#menshats #howto #notsponsored
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GUIDES YOU DON'T WANT TO MISS:
→ Trilby, Homburg, & Pork Pie Hat Guide: gentl.mn/3oGwHT4
→ How to Get the Right Hat: gentl.mn/3mYS9C9
→ How To Find The Right Colors For Your Skin Tone: gentl.mn/372PcuX
→ The Black Tie Guide: gentl.mn/345hlPP
→ How to Use the Color Wheel to Assemble Superior Outfits: gentl.mn/3a5jgbe
→ How to Pair Overcoats with Gloves and Scarves: gentl.mn/3a4ltne
→ Straw Boater Hat Guide: gentl.mn/3ndmpJH
→ The Formality Scale: gentl.mn/345TuQ4
→ Men’s Hat Etiquette Guide: gentl.mn/3oKosVP
→ Disconnected Undercut: gentl.mn/2KmN08n
→ 11 Easy Hair Hacks for Men: gentl.mn/3mcg4ge
→ Hairstyles for Gentlemen: gentl.mn/37dGpGB
→ How to Accept a Compliment Like A Gentleman: gentl.mn/379dm6Y
VIDEO CREDITS:
→ Script: Preston Schlueter
→ Camera: Chris Dummer
→ Editing: Jonathan Oster
→ AMC
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00:00 Introduction
Longtime viewers are sure to know that we’re no strangers to the subject of classic hats; we’ve produced videos on specific hat styles, how to select a hat, hat-wearing etiquette, and more.
While hats were once a requirement for any man in a public setting, societal changes through the 20th and into the 21st century have now made hats entirely optional in all but the most niche of settings. Today, we discuss wearing classic hat styles as a modern man and how to do so confidently and stylishly.
01:00 The Fall of the Hat-Wearing Tradition
7 Tips to Look Great in Classic Men’s Hats
If you’re looking to transition more often from ball caps and beanies to more classically styled hats, we’ve got seven tips today on how you can do so effectively.
03:20 1. Find a hat style that complements your face shape
04:22 2. Make sure that your chosen hat complements your skin tone
06:38 3. The hat color you choose must harmonize with your outfit
08:40 4. Pay attention to the weather
09:56 5. Be mindful of the overall formality of your outfit
11:26 6. Be mindful of hat etiquette
13:11 7. General Hat Style Tips
Finally, here’s a piece of good news: while the evidence isn’t exactly scientific, history and aesthetics tell us that wearing a hat can actually make you more confident because a hat will often make you look taller.
It can, therefore, send a subconscious signal of increased strength or power. This is evidenced by the fact that many police and military dress uniforms often feature a hat, as did many other types of uniforms in past centuries. So, let this confidence spur you on to more hat wearing. Combine it with all of the tips that we laid out today, and you’ll be well on your way to making classic hats a staple of your wardrobe.
15:00 Outfit Rundown

[@themoderndandy713]

The fact you didn't mention Panama hats in that list drove me a little bit crazy. It's the only main one missing!

[@gentlemansgazette]

Thanks for pointing this out! Panamas (as well as other non-boater straws like my coconut pork pie) would rank just below fedoras, trilbies, and felt pork pies on the formality scale, given that they're similar in shape, with straw being inherently less formal than felt. - Preston

[@branislavjeriga6762]

It was shown with summer hats...

[@1Retsuki]

Preston looks like he goes door to door trying to sign people up for Vault-Tec. Love the content as usual, guys!

[@davianjanvierto4679]

His look resembles as the Vault-Tec Rep isn't it?

[@1Retsuki]

@@davianjanvierto4679 certainly does!

[@davianjanvierto4679]

​@@1Retsuki Haha! I knew it!

[@FadingNewDawn]

I started wearing a fedora about 3 1/2 years ago. I was definitely a bit self-conscious at first, but got over it pretty quickly. Now I wear one almost every single day. I even got a burgundy hat last year. Was definitely nervous about the bold color at first, but now I wear it without even thinking. Thank you for the video (and all of the others) about hats. They are always my favorites.

[@akirak1871]

My first REAL hat was a burgundy fedora from Bailey of Hollywood. I too was bit self-conscious, but I got comfortable with it very quickly. In fact, for all the fedora hate you hear about on the Internet, countless people (total strangers) have complimented me on my hats but not one person has said anything negative about them. I have a whole collection and even had to install some pegs in the wall so I'd have a place to hang all of them! I've even been rocking a bowler hat lately, which is a bit more adventurous (I've been experimenting with a streak of late-1800s fashion lately).

[@mungulor]

Once one gets over that initial shock of an appearance change, it becomes second nature to don a hat before stepping out the door. Now I can't leave the house without a lid on

[@fredperry9235]

Embrace your flamboyance

[@TexasNightRider]

Your comment was helpful. I am a retiree who sports a shaved head. I'm tired of wearing a baseball cap in cooler weather so I have a couple of not too expensive fedoras coming in. I do expect to feel a bit self- conscious at first with a fedora but I'm glad to see others have experienced the same thing.

[@jasonkelsey3441]

I previously wore a fedora almost everyday. Not sure why I stopped as I love them. Watched this video a few months ago and my fedora acquisition disorder flared up. I bought 11 hats in 2 months! Fedoras, panamas, trilby, and homburgs. All bought vintage. Still looking for the elusive bowler. I thank you @gentlmen'sGazett for lighting my fedora fire again. My bank account curses you ;)

[@piccalillipit9211]

*I NEVER GO OUT WITHOUT A HAT ON* and you should definitely not feel self-conscious - hats are the thing I get complimented on most often... The other this is a walking cane. People simply like to see people with a hat and cane.

[@johanjohansen7572]

This video had the perfect timing, I just bought my first fedora some hours ago.

[@armink9686]

I personally wear a homburg almost every day, in different settings, even with leather jackets. My personal secret is to not fetishize the hat, it's literally just headwear, it doesn't carry any magical powers, have fun with hats. The less I think about it, the better it is. I've only gotten positive comments even though I am young and am very mobile in terms of social circles.

[@OrrosGG]

That’s a good way to bring it back.

[@timboi3399]

the one thing I love about Preston's is that because he doesn't have thousands of clothes like raph or even as many as Kyle it's great to see his videos because you can see how his wardrobe is growing

[@richardordonez8331]

We wore straw boater hats as part of our uniform back in the early 80's when I worked at a full service butcher shop. I thought we looked pretty sharp

[@mzlww]

Want to convince my bf to wear hats so I sent him this...thanks for making it!

[@carltrotter7622]

Just don’t push a Top Hat on him too soon.

[@piccalillipit9211]

He should definitely wear a hat. I started about 2 years ago and now I wear one every day. Why? Cos I get so many compliments about the hat. It sets you apart and people LIKE to see other people in hats, its as simple as that.

[@MartinParnham]

My wife hates my flat cap but I love it and have had compliments so you definitely should recommend it :-)

[@1Thunderfire]

@@MartinParnham I've always considered flat caps to be pretty stylish (I'm female but I like watching these anyway as they're quite relaxing). If I wore hats, I'd likely wear caps but my thick hair plus a hat would make my head too hot.

[@reedolightningweaver2732]

@@1Thunderfireyou could always just wear them in the winter

[@taki-wayra]

Got myself a flat cap, peaky blinders style made of Harris tweed. I‘m lovin‘ it.

[@bdcochran01]

1. I probably have 15 hats, including 3 top hats. When the country is not locked down, I wear a tuxedo about twice a month with top hat. When I wear a suit, I have a Borsalino fedora. 2. For health reasons, I wear a modified Rhodesian Army hat with side panels everyday as I walk and exercise outdoors - avoids skin problems. 3. In a world in which guys wear baseball hats backwards, wearing a proper hat draws the attention and admiration of women. It goes with the concept of looking your best when you venture out into the world.

[@mattmorelli9833]

Second comment: i just want to say how impressive this program has become over time. Good on you guys for not only rocking this style but also heading out there to shoot all this "walking" footage in so many different locations etc. Jeez, and all these little spin-frame and slide edits and smooth camerawork. Aside from the writing of this narration and however many takes it took.

[@MrFagedaboudit]

As an observant Jew I wear a hat daily for most of the day (it's a sign of respect for us). I've been wearing black Fedoras and Trilby's for many decades. The high quality rabbit pelt used by Borsalino holds up well over many years and shapes itself to the head comfortably over time. All that's needed is a shoebrush, and a new band every so often together with a steam clean. I also have 2 black Bailey's Trilby's from 1972, which are like new. Yes, quality materials and workmanship are worth it!

[@Sancte_Benedicte]

I got my first Bowler/Derby yesterday and I absolutely love it.

[@therealmalik]

Nothing classier than a nice hat.

[@locklear2478]

I started with a Stetson Bozeman last winter and then bought a Panama this summer. I’m hooked!

[@robertdee648]

I'm not a hat wearer, but I nonetheless really enjoyed this video. Preston, you nailed the outfit. You were most dapper.

[@natalya6091]

Thank you, dear Preston. Have a nice day!

[@Mr19thcenturyman]

As a kid I collected hats....for fun. As a youth I collected hats for...antique interest. And as an an adult I collect hats to keep me warm and protected from the sun and other elements.

[@gdretired4385]

Great video! I’ve worn classic hats for many years. I have a trilby, a felt fedora, a Panama hat, and a few flat caps that I’ve had since the 1980s. The flat caps are my workhorse hats through the winter months.

[@joshuarivera6195]

I like all your dress styles!

[@anthonys5568]

Well said young man!

[@timcampbell4267]

Gray Stetson Sovereign fedora here. I've always thought the car headrest contributed to the decline in hats. You really can't wear a brimmed hat in a car without awkwardly leaning forward.

[@reedolightningweaver2732]

Yeah the only option is to put the seat back a little farther and sit up straight. Probably better for my poster though lol!

[@meptune]

I have always worn a Hawes and Curtis black bowler. I wear it with absolute confidence and I always get compliments.

[@str8shooter36]

I've always gravitated towards the traditional look like my grandfather used to wear.

[@raleighsanford5111]

I think the biggest renaissance in hats for men, at least in Texas and the South, is skin cancer. That is my motivation, and I know others as well. In retrospect, white men stopping to wear hats in Texas was a poor decision. So in Texas, brim is key, not as much in the short winter that we have, but ears and nose needs to be covered. The top of your head if you are bald. The key to confidence in wearing a hat is to not worry about what other people think about your hat! If you like it, eventually other people will like it. One thing I used when I started was that I my look odd in hat, but not as bad as if I had scars from where a Dr cut skin cancer off my face.

[@ritvatoiviainentoiviainen6486]

Great video, I recently had my hair cut, it was exactly like Raphael’s hair, but just all over the head. I can now wear my favourite hats without bushy tufts of hair flying out from underneath

[@spyro1159]

I know you've already made videos on Smart Casual and Business Casual outfits, but I think you should make a video directly comparing the two styles. I'm asking this because I was doing some research on both of these styles last night and realized that it can be hard to tell the two dress codes apart from even an image search on the two. I hope you gentlemen consider my video idea! Happy Holidays!

[@MartinIrwin]

They’re not real dress codes. Plus, I’m sure Raphael has compared them before in a video, but either way, their content is superb, so I’m looking for more.

[@lynnglidewell7367]

I have dozens of hats ( not ball caps) colors,styles,seasons, occasions. I wear them year round. I have an off white straw Trilby with a multicolor ban around it that gathers more compliments then any other. Even from strangers who approach me in public. It's a great hat because it matches anything I wear during warm months of the year.

[@ghw7192]

I am a fedora znd flat cap fan and get a lot of positive commrntd.

[@Jedwbpm]

Very nice video. As the former retail manager at one of America’s oldest and largest hats shops and now a sales rep for the largest hat manufacturer in the US. I would suggest a Gray hat for your first purchase it will go with the most of your clothing. Next would be a brown hat. Silverbelly don’t be afraid that it will show dirt it won’t . Silverbelly is my goto hat color when I just need to grab a hat and run out the door.

[@edgarbernardoorellanahered5261]

Bringing the PIPM style back !

[@OrrosGG]

Awesome timing, today I was rockin’ my DB Pinstripe navy suit and grey homburg with black accents.

[@paulmathers6753]

I never go out without wearing a hat, I would feel wrong. It used to be a baseball cap until I turned 50, at which point I felt that looked silly and started experimenting with other headgear. In summer I like linen based Panama style hats. In winter I have a number of styles, my favourite in winter are my newsboy's caps, which are as versatile as baseball caps, but much more stylish. When I wear my felt fedora's in winter I am often complimented, but that is because I use the tips you have shared over the years on how to wear hats and match to colours. The main reason for commenting is, however, to thank you for all your videos in this very strange year, and can I wish you happy holidays and the best for 2021, to you and your families. And to use an old Mancunian expression [which I made up as an "Old Mancunian", Manchester UK incidentally] Stay safe, take care, don't do anything daft. If I may say..... and see you next year.

[@mrcvry]

You are right! Baseball caps are better left to baseball players! 😉

[@dr.excalibur9818]

My favorite hat is the bowler

[@Eirik_Bloodaxe]

I mostly wear a chromatic black and white style. But I guess I’m also here to learn. Also I’ve always thought of the “Panama cover” as a Soviet military hat lol.

[@staguar]

Got my wolf t-shirt and cargo shorts ready to go, just need to grab my trench coat and trilby and I'm gonna look awesome.

[@dennistennis2225]

M'lady, do you like neckbeards?

[@staguar]

@@dennistennis2225 *tips fedora*

[@heinzguderianbutmoreyounge9659]

Hat is a mandatory piece of clothing for me!like just walkibg around in a dress shirt with panama or stetson Or homburg,fedora and bowler for suit wearing,and top hats for cutaway and tails,hat is a great piece of wardrobe,and to from my pov i think every gentleman who want an old school charm should own an hat,whether its a fur felt,wool felt,straw,even silk plush,and i always wanted a video from you guys talking about hard hats,like bowler and top hats,especialy top hats is something that was fascinating because the best one are made from silk plush that have the luxorius and glamorous shine to it,looking forward to it!

[@yashyadav_29]

These hats are amazing than modern hats 🙏

[@micaylab1]

Anyone who Agrees that Gentlemen’s Gazette and the other KZbinr Kirby Allison should get together and Do A Cross Over Video, please say Yes!😄

[@mattmorelli9833]

Wore fedoras and panama hats through high school and into college. Strangely I've only taken up ball caps or beanies in my mid 20s and now 30s. Perhaps I'll go back to my old hat days. Remember fellas the more of us that bring hats back, the more successful the trend will be!

[@Aaronjames2007]

Yes another upload!!

[@paulamorris7466]

A ladies version of this channel would be amazing!!

[@rl6319]

I wear my fedoras and cowboy hats with black T-shirts and blue jeans I collect hats and I love them all

[@Methodsaimon]

im impreston how good this channel is had alot of influence on my wardrobe!

[@meptune]

Regarding black and formal. I have always worn a black Hawes and Curtis bowler with absolute confidence and I always get compliments. It works great with formal wear (as you pointed out) but it also works really well with rock and roll wear. I wear jeans and a black t-shirt when I go to rock concerts and everyone loves it. The bowler can be an informal hat.

[@chocothemagnificent1019]

Hats are the most important statement a person makes when they wear one!

[@michaelgoodman3845]

I love you guys. Everytime any of you model the presentation is executed with so much confidence and deservingly so. You guys look great and thanks for the energy 😊

[@food2430]

Looks kinda weird😂

[@Nero0108]

@@food2430 no

[@temoharri8848]

this was an informative and enjoyable video. Thanks a lot for this.

[@ravipeiris4388]

Great video, thank you 🌚

[@areguapiri]

The Homburg hat is my favorite. It's much easier to wear traditional hats and nice, formal clothing in cooler climates.

[@davidminken4094]

My tip: give some thought to how your hat pairs with your choice of shoes. These two elements bracket the entire outfit.

[@mathias369]

Preston rocks! Great video ma boy! 👍🏻

[@MichaelOssen]

Love wearing hats!

[@kendrickoyola4290]

Agree

[@1Thunderfire]

I think that flat caps have come back in fashion in the UK; probably in part due to Peaky Blinders. I tell my Grandad that he's cool again because he's always worn one! 😁 (Admittedly, this is for practical reasons considering his lack of hair but still.)

[@gvcfashion8160]

This hats are lovely 😘

[@Eric19401]

Raphael's hat hair at 12:19 was a pleasant surprise. 🙂

[@PlutoProtogen]

i would love to spend a few days wih you guys, i love the style, respect the knowledge and i gotta say,men should take pride in how they dress

[@emrahercancakir]

This is great. Can you also please do a video on how to swap the ribbon band on a fedora and/or panama hat?

[@ivanlazarev6414]

Great job! Could you please also make a video on wearing the beret as this headgear is common in many European countries?

[@adrianostberg2337]

You should do a full video on the bowler hat

[@almatttt6081]

Pls make video about British Warm overcoat!

[@Tomatohater64]

I personally just love Trilbys and Newsboy caps. Any color is good by me but I tend to prefer darker hues.

[@baklei7100]

whaaa presque le million d'abonné, ca monte vite !!! bravo à vous !!

[@utkarshchourasiya5309]

Have been wearing Flat caps. Will start with a Trilby and Hombourg in winter and a boater in Summer. Please share all the recommendations, they are welcome.🙏 :)

[@Dantheman1342]

I wear a hat every day. Fedora or western style, not concerned at all what others think of my hat choice. If I like it, I wear it. Be who you are, wear what you like.

[@redscale82]

I loves hats. Mostly I wear a cowboy hat. Good protection against bad weather. Flat cap around wintertime.

[@renkenner]

Thanks. I’ll save my black Stormy Kromer for formal events.

[@newtonmenlo]

If you're going to wear a hat, find a comfortable hat and STOP TOUCHING IT! Nothing signals that you're a newbie hat wearer like constantly touching and adjusting your hat. Just a pet peeve of mine but I had to say it.

[@Isitbecauseimpanduh]

I started wearing wide brim fedoras after I watched some of your videos. I have gotten a lot of compliments and feel weird not wearing one out to do thinga

[@Clarkson350]

Trilby hats are hard to find but worth the seach

[@clownworldresidentii5184]

a dress watch would compliment the attire well. Like an IWC Portuguese

[@testaccount4830]

I have got to say, I do quite like the classic looks although I don't have the money to pull it off properly. I personally quite like the good old fashioned 1800s look but the 1950s are also quite dapper.

[@jorgecabal8720]

I've got a boater on the way, I cant wait to wear it out!

[@True_Christian]

I'm assuming it's used? I can't find any place that sells good boaters that are newly-made. Sure wish there was one though.

[@jimstevens1726]

@@True_Christian Check Amazon. They have some nice Italian made ones in the classic style. I own two Boaters. Bought one in the 1950s and one in the 1960s. They still made good ones then. The Italian made ones on Amazon may be a little expensive, but they look well made and the right proportions. Be careful ordering a Boater when it comes to size. The hat is stiff and hard. The one in this video he is wearing looks bad as it is too big for his head. Hats should never rest on your ears. If you get a hat that is a little big, buy some foam weather-stripping and stick it under the inner band to size your hat.

[@mitchellsmith4690]

I'v been wearing hats for 45 years...just put it on and go...and stuff everybody else's expectations...from fedoras to pith helmets, my methode works.

[@canadiansensei]

14:30 - Love it! Details on this hat please?

[@AxelAlexK]

I do wish hats like this other than baseball caps and beanies were more popular. Even wearing a flat cap I feel takes quite a bit of confidence.

[@samcooper430]

I live in a flat cap & I think hats are awesome. I grew up hating hats & now I Love them although I am not a fan of ball caps.

[@AxelAlexK]

@@samcooper430 Yeah, same here. Never wore hats growing up but when my hair went it's become basically a necessity half the year. Protect it from sunburn in the summer and keep it warm in the winter. I have a flatcap and wear it sometimes though I do feel more comfortable in a baseball cap or beanie just because I won't get tons of attention and comments about it.

[@mrcvry]

@@AxelAlexK Leave the baseball caps to baseball players and kids.

[@stefanlaskowski6660]

I started wearing fedoras just a couple of years ago. Contrary to some videos, I usually get compliments on my hats.

[@vqo0]

I've just started trying to get my hands on a fedora

[@Randy-1967]

I wear felt year round

[@stanisawzokiewski3308]

Could i ask for advice on a very specific topic? I need an elegant suit that would still allow for full range of motion. I attend sword cutting competitions where its expected to drees formally but its rather obvious that its needed to be able to move to perform the techniques properly. Usuwally i just wear a white shirt dark blue suit pants and black boxing shoes for good footwork. But i was wonder if you know a company that makes suit that would allow for uninhibited motion. (Im not going to be running just need full range of motion in place). And if any formal shoes that have very good grip on the ground. Or should i just stick to the shirt?

[@BBS_Robski]

my hat journey started with beanies then I started wet shaving my head & the beanies rode up like bobble hats, moved on to flat caps then switched to trilbies which I wear daily. I also have a bowler & Homburg + a porkpie hat (which I don't wear at all), I'm not sure I can pull the bowler or Homburg off just yet ..........

[@timothyedward6147]

Hi there I so far have a black felt fedora, what should I use for with that?

[@kevinbryan4215]

I’d love to start wearing some hats, but as far as I can tell, there’s no stores that sell flat caps, let alone fedoras or other classic hat shapes, in my state at all. How should I go about finding these hats besides ordering them online?

[@Superbatmanbro]

There a classic vintage hat shop in Seattle and there online hat shops like Herbert johnson Hats and christy hat shop and Agnoulita hats to

[@kartikeya1985]

do a video on cowboy hats, greetings from Texas!

[@justinleemiller]

Panama hat in summer. Great for festivals and being lazy at the beach.

[@n.b.2164]

I wear panel caps. I wish there was a hat store near me.

[@zombieslayer7759]

9:11 Does anyone know where Sven got that black fur overcoat that he was wearing? Please tell me since that coat is magnificent. 🙏🏼

[@Lordrixson5489]

Hey Preston 👋🏻 Please give us your rendition of Fly Me To The Moon 👌🏼

[@insertnamehere001]

Well, before the 60s, daily shampooing wasn't common, wearing a hat would help keep your hair clean from outside air. If you do look, the decline in hats does correlate to the rise in daily shampooing.

[@andrealicciardiello676]

I bought an old Borsalino an an old barbisio from 70s just because they cost 40€ for both but now I can't go out without seeing a hat

[@rikvandijk6904]

Could you guys do a review on "alberth clothing"?

[@Trashloot]

I kinda want a hat now :D.

[@jerbearnone2012]

so, what hats work for a white t and denim?

[@Knux02]

Fantastic Video as always. I am happy to see classical hatwear return and lose that stigma of dorkyness. That being said, i noticed that modern hat sizes of some brands, like Stetson, do not reflect where the hat should be worn. For example, i believe a fedora looks best if there is always half an inch to an inch of space between the tips of your ears and the brim. Yet, when you chose a hat in your size from that brand you'll notice it will slip right down to your ears, sometimes even bend them, which looks not good in most cases but also discourages people from wearing hats, thinking they just dont fit them when in reality all they need to do is choose one size smaller. The same rule is mandatory for top hats, Rafael shows this nicely in some shots.. Nothing looks worse than a too-large top hat touching the ears. If you compare pictures from the 30s or 40s, youll always see that the hats are worn quite high on the head as that compliments natural head shapes the best! Id love if you could cover how a hat should be worn properly in future videos. Preston, unfortunately you also fell victim to this is the past (as did i years ago unfortunately) with your boater hat that is definitely at least one size too large as your ears bend down. Was quite a revelation when i figured this out.

[@kuechenchief]

Can you make a video about winter hats? Especially in these cold days I'm searching for headwear that keeps my ears warm, but I don't know whats appropriate. A normal hat like a Fedora is looking good but it won't keep my ears warm.

[@True_Christian]

Either 1) you can get ear muffs that have no band on them and just sit directly over your ears or, 2) you can wear a scarf and pull it over your ears.

[@marioburgos712]

You can also find flat caps with ear flaps; some even cover partially the neck.

[@mrcvry]

A Mayser winter hat with „fold-out“ ear protection. You only pull it down if needed.

[@oh_scheibe1878]

What about German or Finish Ski Caps?

[@rodorapido]

Oh my God. What a complex materia.

[@dhunter4315]

I only wear a baseball hat at work, and a beanie when it's cold at work. Because I've been listening to GG for

[@christophermartin5742]

Garment brush?