Fashionistas: Help me choose the perfect hat for year-long world travel

May 6, 2022 2:51 PM

I am clueless to fashion and I need some help. I am a 44-year-old American male who next month is going to be leaving the U.S. to work as a remote nomad for at least a year, in Africa, Europe, and Asia. I have worn baseball caps as my primary head gear since I was a teenager. But I would like to level up, make a lifestyle change, ditch the baseball cap, and choose another type of hat as my sole head protection for my time abroad. Any suggestions?

This is a big decision as this is something I will wear almost every day. I need it to be both fashionable and functional, for sun protection, in hot and cold weather, rain or shine, in both big cities and in tiny villages and the outback. I am fairly tall and slim — 6’1, 165 pounds, caucasian, straight, with short, light brown hair, and my travel wardrobe that it will complement will consist mostly of t-shirts and jeans. Before someone answers and says “don’t worry about fashion — just pick what you like,” well, I would but I am mostly clueless and I don’t want to pick something that the world would find ridiculous. I’d like something a bit more cosmopolitan and less stereotypically American than a baseball cap. I'm kind of considering an Indiana Jones-style fedora but I would love for some more interesting suggestions that I haven't considered. Can anyone make some suggestions for this fashion-challenged dude?

posted by fenwaydirtdog to Clothing, Beauty, & Fashion (35 answers total)

Stick with the baseball cap.
posted by dianeF at 2:54 PM on May 6, 2022 [14 favorites]

You can’t wear headgear that’s more than one 'tick' more or less formal than your clothes without looking kind of dumb. In T-shirts and jeans, baseball and other caps are your likely options. Also farmers’ straws.

Everything looks ridiculous on some heads, and probably everything looks good on someone. I’m afraid you need to go to a hat place and try the other caps on.
posted by clew at 2:59 PM on May 6, 2022 [9 favorites]

The men's hat that's most in style right now is a flat-brimmed wool fedora, like a Smokey-The-Bear hat, but they're pretty fashion-forward and you don't sound like they'd quite suit your vibe. You need to really have fashion confidence to wear them, otherwise they will look horribly dorky. It's a fine line between Pharrell and m'Lady.

I would suggest a cabbie hat for slightly more formal outfits or cooler weather.

A sports-branded baseball cap or whatever you usually like for casual.

A very clean unbranded baseball cap for nice-casual. J Crew has cotton ones for summery outfits, but for most outfits a 9Fifty type hat made of thicker material will look better. Make sure the baseball cap has a deep enough cap, on some of them the cap looks look too shallow and it looks sloppy and cheap. A deeper cap made of thicker material looks way better.

Note that nothing you wear every single day will ever look upscale, because looking new is part of looking upscale. And hats get DISGUSTING. So please have a few and rotate between them and for pete's sake wash them every month or so, omg the oil-sweat-mildew smell that comes off of most men's hats is truly shocking!
posted by nouvelle-personne at 3:00 PM on May 6, 2022 [8 favorites]

I can't speak to the fashionable aspects, but when I traveled to the sunny Mediterranean I was very happy to have a Columbia Bora Bora II Booney. It keeps the sun off, is lightweight, cool, and dries quickly when it gets wet.
posted by Winnie the Proust at 3:00 PM on May 6, 2022 [4 favorites]

Since the rest of your outfit is t-shirts and jeans, a baseball hat is probably going to match the best. You might also be able to pull off a bucket hat although those might skew a little more zoomer than you want.
posted by TurnKey at 3:07 PM on May 6, 2022 [2 favorites]

Somewhat older than you and currently on a year plus trip through Central and South America and my Tilley Airflo has been serving me well.
posted by doctord at 3:08 PM on May 6, 2022 [11 favorites]

Tilley hat
posted by crocomancer at 3:09 PM on May 6, 2022 [8 favorites]

Camping hats are very practical for days when heatstroke is a possibility - like if you're on a hike or exploring a canyon or something. But you did mention wanting to look fashionable, levelled-up, put-together, and that's... not what those are for.
A baseball hat is 1000% more likely to look fashionable than a camping hat.
posted by nouvelle-personne at 3:21 PM on May 6, 2022 [1 favorite]

I think a baseball cap is inappropriate in locations where the ears and neck should be protected. I don't think you have to go full Crocodile Dundee, but something with a bit more ledge to it seems in order.
posted by rhizome at 3:33 PM on May 6, 2022 [6 favorites]

Hats can vary so much. I highly recommend finding somewhere you can try on some hats to see what works with your face. For a step up from a baseball cap, maybe look at a Gatsby cap, newsboy cap, or maybe a Castro hat.
posted by hydra77 at 3:35 PM on May 6, 2022 [2 favorites]

If you want protection from the sun and a light rain, a Tilley or Bora Bora as others have mentioned is perfect. They're definitely function over fashion, but they function very well. They breathe (much more than a wool Stetson or an oiled cotton "outback hat"), and you can wash and dry them quickly and easily.

Having said that, I wear a cabbie hat most of the time, and it really works for most occasions, from T-shirt and shorts to a night out.

If you can pack a couple hats, it's nice to rotate them not only for variety but to help air them out. If you can't do this, be sure to wash it regularly or at least Febreeze it once in a while. Hats get gross, and it's one of those things where, if you wear it all day every day, when it starts to smell, it'll just be background noise to you, but others will definitely notice.
posted by xedrik at 3:42 PM on May 6, 2022 [3 favorites]

Best answer: I am a fashionista and I encourage you to think about the terms "stylish" and "ridiculous" and how often they intersect.

Most fashion-conscious people are bored by safe choices.

Hats are inherently funny. I think you should go hat shopping and get the most exciting and interesting hat you like. I bet you will receive lots of compliments on it from people who enjoy fashion.
posted by RobinofFrocksley at 3:43 PM on May 6, 2022 [6 favorites]

What's "fashionable" varies a lot country-to-country. How about asking locals when you get to each area/country what kind of hats are popular (or, look in stores, etc). That has the added bonus of probably being the best hat for whatever environment you're in, in terms of protection/practicality.
posted by bearette at 4:12 PM on May 6, 2022 [9 favorites]

It may be because I live in Texas, but a cowboy hat transcends fashion and goes with anything.
posted by a humble nudibranch at 4:53 PM on May 6, 2022 [6 favorites]

I’m a baseball cap guy myself, but allow me to put in a word for the New Radicals-style bucket hat. Someone needs to bring it back, and I nominate you.
posted by kevinbelt at 5:58 PM on May 6, 2022

Both wife and brother wear cowboy hats with everything and look amazing.
posted by joycehealy at 6:20 PM on May 6, 2022 [1 favorite]

Best answer: I can only speak for Europe, but here it is seen as somewhat strange that Americans wear hats all the time. Why??
That said, in general stick with your baseball cap if you love it. Be you. Wear a bucket hat if you need to fit in more, and go hatless in any formal situation, such as if you are going to a fancy restaurant or an indoors party, I can't think of any hat that would work there.
posted by mumimor at 6:38 PM on May 6, 2022 [2 favorites]

I am a bald guy that has lots of hats. I don’t think there is THE ONE HAT that’s going to cover every situation on your journey (hot/cold, rain/sun). If I were you, I would bring 3 hats. 1. Bucket or boonie hat for sun protection. 2. Cap for daily wear (I prefer a 5-panel hat over a baseball cap). 3. Light beanie for colder weather (Neff Daily beanie is great.)

While Tilley hats and the like are great, I am personally not a fan of structured and/or expensive hats for travel. Hard to pack, too much worry about damaging or losing it, and potentially attracting more attention than I want.

Maybe try a flat cap or 5-panel hat if you’re looking for a slightly more stylish upgrade from a baseball cap.
posted by gnutron at 7:37 PM on May 6, 2022 [5 favorites]

For multiple seasons, locations and climates you will definitely need more than one hat.
posted by kinddieserzeit at 8:53 PM on May 6, 2022 [3 favorites]

This 45-year-old wouldn't be caught dead in a baseball cap, simply because it leaves my big dumb ears completely out in the sun and does squat for protecting my neck. I've worn a (...checks label...) "Sun Day Afternoons 'Charter Hat'" - basically a Tilley knock-off from REI - for a few years now, including the better part of a year in Italy, and it's done the job admirably. I even got a compliment on it once.
posted by niicholas at 8:58 PM on May 6, 2022 [2 favorites]

The kind of hat that works on safari -- wide brimmed, ventilated -- isn't going to look quite right in European cities. Also, a hat to keep you cool and warm and keep off the rain? That's asking for a lot!

It's not great for sun protection, but what about something like this for more urban environments? It's a step up from a baseball cap.

But also check out these photos from the men's fashion show in Paris last summer. Lots of baseball caps on display. Maybe the thing to do is get a fresh baseball hat and then bring an old one for hot days when you might get grimy?
posted by bluedaisy at 10:14 PM on May 6, 2022

My dad rocked an Amish straw hat for many years and people loved it. The key is you've got to wear it with confidence.
posted by potrzebie at 10:46 PM on May 6, 2022 [2 favorites]

Honestly in most European cities wearing a hat at all will stick out. In Poland for example you wear a beanie or ski hat etc as long as it's cold (under 5C for guys, that's 41F in US money), and above that is "hiding a bald spot" territory. Plus hats are 100% nope in any situation where there's a roof over your head, not just in church. So it'll be weird anyway and you might as well wear whatever you want.

(Except a cowboy hat, because people might try to give you money for performing country songs and cowboy skits. Unless you have a good cowboy skit.)
posted by I claim sanctuary at 11:41 PM on May 6, 2022 [5 favorites]

Flat cap (plus sunscreen if you'll be out in the sun for a long time) for cities in Europe. Flat caps aren't fashionable in the sense of being super trendy, but they are classic, not uncommon (especially on guys in their 40s and up) , and look fine on most guys. So for blending in in Europe at least it'll do fine. Can't speak for Africa and Asia.

Any wide brimmed hat for when you'll be out in nature and it doesn't matter what you look like. I would have said straw hat, because they can have a certain panache and don't clash with t-shirt and jeans like a fedora would, but you should get something you can cram in a backpack if you're gonna be travelling. Also, I'm not saying not to wear a fedora if that's what you feel like doing, but it isn't going to accomplish the goal of looking cosmopolitan, at least not with t-shirt and jeans.

If you're looking to get more into fashion, keep your eyes open WHILE you travel. What are men your age wearing? Do you want to look like them? The clothes they have are from the local shops, so you can go to a store and get the same kind. Or maybe you don't like how men dress in a certain place and want to dress differently from them. Develop your personal style that is a mixture of how you want to look, how you want to fit in, how you want people to perceive you.

The way fashion works is by people modelling their look on other people. So if everyone in a city is wearing one kind of hat and you are wearing another, you won't necessarily be fashionable. But that doesn't mean you can't be stylish if the hat fits with your personal style. You can also get several hats and experiment with different looks. They're just hats; you can have more than one. In the end, you may also find you just like baseball caps best and that they fit with your t-shirt and jeans American style, who knows!
posted by starfishprime at 11:43 PM on May 6, 2022 [2 favorites]

One hat can't do all of this. You will need at least two. I would go with:
- a tilly hat or boonie hat for sun/rain protection outside the city
- a flat cap / newsboy cap / cabbie hat for inside the city, in a not-too-formal fabric. I'd pick canvas.

But honestly, you are talking about three continents, and all kinds of weather, and all kinds of circumstances. You're going to stand out some of the time. The only way to stand out less is to look around, see what your local peers are doing, and adapt.

I also want to echo the remark made above: in many European countries, wearing a hat all the time, especially indoors, is not at all common.

Straw farmer hats and Amish hats will make you look quite remarkable in most places outside of the US. Whether you care about that is of course up to you.
posted by Too-Ticky at 12:09 AM on May 7, 2022 [2 favorites]

For warm weather, I recommend a good Panama hat. The kind that can be rolled up, folded, and tucked away when inappropriate and then pulled out and opened up none the worse for wear. A lightweight brimmed hat like this is great in the sun or light rain, but not so good when it's windy or very cold. A wool watchcap is also easy to stow in a pocket.
posted by rikschell at 4:47 AM on May 7, 2022

Also, a Panama hat is going to look better with a button down linen or seersucker shirt than with a Tshirt, but if you want to upgrade your style a notch, you could invest in some new shirts too.
posted by rikschell at 4:51 AM on May 7, 2022

The most fashionable hat OP can get is a great haircut and sunscreen. Too-Tacky nailed it:

I also want to echo the remark made above: in many European countries, wearing a hat all the time, especially indoors, is not at all common.

and

The only way to stand out less is to look around, see what your local peers are doing, and adapt.

If you really need a hat, just buy one locally when you see one you like or have a need (e.g. in sun or cold).

But also check out these photos from the men's fashion show in Paris last summer. Lots of baseball caps on display.

The exact same baseball cap will read as fashion forward when worn with the outfits in that article but hopelessly American when worn with OP's jeans and t-shirts, which I'm assuming are more Levi's and less Rick Owens. For what OP wants, baseball caps are just a hard no.
posted by Special Agent Dale Cooper at 7:31 AM on May 7, 2022 [1 favorite]

Bring a nice, unbranded, breathable baseball-style cap. Buy other hats along the way when you inevitably lose the one you brought. As a general rule: long-term travel is not the time to be daring with your style unless you’re a jet setter. You want clothes that are functional and comfortable, and that comfort includes stylistically.

Also, please bring some pants and/or shorts that are not jeans, unless you’ll exclusively be in cool climates. You don’t want to be stuck with only jeans in, say, Southeast Asia.
posted by lunasol at 9:14 AM on May 7, 2022

If your primary concern is to "level up, make a lifestyle change, ditch the baseball cap" and look "less stereotypically American", I suggest you forgo wearing a hat altogether.
posted by Ahmad Khani at 10:59 AM on May 7, 2022 [4 favorites]

Best answer: If you're really insistent on the one hat thing, the best way to thread the needle between a baseball cap's casualness and a full brimmed hat's function is probably a bucket hat.

There's a wide range of those, from fisherperson-ish to athleisure-iffic to tacticool to fashion-y.

You'll want to hit that last category. Or, to put it another way, you want to avoid the first three. No grommets, no snaps on the brim, no MOLLE loops, absolutely no chinstrap, natural fibers preferred.

(Tilley makes many good hats in and around this style, but they're not fashionable.)
posted by box at 1:38 PM on May 7, 2022 [2 favorites]

Here in Spain, structured hats are mosly what old dudes who need to protect themselves from skin cancer wear. My retired dad has a collection of cabbie hats, alpine hats, baseball caps, fedoras and straw hats.

Baseball style caps are not terribly common but mostly unremarkable with causal clothing. If you want to protect ears, neck and face from the sun, try a bucket hat that you can fold and store in your luggage. It's not going to be fashionable because you're not going to be fashionable with hats, but at least it'll be functional.
posted by sukeban at 9:28 AM on May 8, 2022 [1 favorite]

Response by poster: Wow, people. You all gave me so many rich and insightful suggestions. Thank you to everyone who responded to this. Your comments were extremely helpful. AskMeFi never lets me down.

The primary reason I want no more than one hat is that I will be living out of a single carry-on bag all year, so I can't take multiple noggin-protectors.

Based on your input, I have decided to forgo the fedora idea. And I considered the suggestion that many of you had of continuing with my baseball-cap tradition, except that it's really time that I get a hat with some neck and ear protection.

So the bucket hat seems to be the best choice. I may just get a tan one of these. But the suggestion above by box for one of these Aimé Leon Dore blue printed bucket hats really struck a chord with me. The blue floral print looks wonderful and I used to have board shorts with a similar pattern. This hat seems so chill and fun and relaxed and good looking, as well as being packable and functional. It's so "me." And I'll take your word for it that it's fashionable! I think this suggestion struck a bullseye. The only issue is that my hat size is 7 5/8, and the biggest version of this hat that they offer is 7 1/2. But I probably will order one and see if I can make it fit.

I will remember not to wear my hat indoors in Europe (and probably most other places as well).

Thank you, again, for everyone's valuable input. It is greatly appreciated!
posted by fenwaydirtdog at 1:49 PM on May 10, 2022 [1 favorite]

Response by poster: I wanted to give my own humble answer to mumimor's question as to why Americans wear hats so often.

As for me, the primary answer is that I want to protect my skin and eyes from the sun when I go outside. I wonder why Europeans don't wear hats outside too often, for this same reason! Another reason is that the "national pastime" of the U.S. is baseball. Although this sport is not necessarily the most popular one anymore, it is still an essential aspect of American culture. Baseball players have been playing the national pastime while wearing baseball caps since the 19th century, and Americans have been emulating this for so many generations, so wearing ball caps has just become ingrained in our DNA.
posted by fenwaydirtdog at 2:22 PM on May 10, 2022

The remnant of Euro-American hat-wearing culture in the US doesn’t wear hats indoors either, it’s just a small remnant. Much outnumbered by cap wearers who don’t take them off.
posted by clew at 8:05 PM on May 10, 2022