How to Pack a Hat for Travel

Shawn Forno

Hats. Love ’em or hate ’em, they’re a pain to travel with. Especially fedoras. Don’t pack a fedora. But if you’re a hat person, or you just need that extra protection from the sun, you have more options than ever for packing a great travel hat.

Foldable travel hats, rollable travel caps, non-goofy trail hats, and surprising innovations are coming to your dome piece. And if you don’t want one of those new-fangled travel hats, we’ve got a few simple packing tips for traveling with that massive hat on your next beach vacay.

How to Pick a Good Travel Hat

The most important packing tip for a hat is—pick a hat that travels well. A hat that can handle being stuffed into your travel backpack or soaked by a sudden downpour is far superior than the most stylish hat on earth if it needs its own special case and meticulous care. You don’t need more luggage. And while you can pack a hat without folding it (more on that below), it’s nice not to have to worry about it.

It sounds obvious, but picking a hat for the road (that you actually want to wear) is harder than you think. Here are a few great travel hat options including: sun hats, rolling travel hats, crush down caps, trail hats, and of course biking caps (my personal favorite).

Best Travel-Friendly Cycling Caps

The hard and fast rule for a great travel hat is simple—if you can stuff it in your back pocket, you’re good. If portability, ease of use, and style are your top concerns, cycling caps are the perfect travel hat for you.

These little devils, with their small bills, are built for the rigors of travel. They can handle sweat (you bike in ’em). They look awesome (if you’re the kind of hip dude that can pull these hats off). And they weigh next to nothing. Bikers routinely roll bike caps up and stuff them in their back pockets. And you can too!

Cycling Cap 101: Biking hats are designed so you can tuck your ears in when it’s cold. Don’t be afraid to tuck up your ears on a windy day.

Ministry of Culture Cycling Cap ($42)

Handmade in Vermont (buy local!) Ministry of Culture cycling caps are works of art you can wear. Made from waxed canvas and organic cotton, they can also stand up to heavy use and abuse. Even better, each cap is one of a kind, so snag yours and wow those smug Europeans with your flashy-ass American made travel hat game.

Sportful Giara Cycling Cap ($20)

The lightweight polyester blend, featherweight feel, and quick dry performance means it’s actually built for hard riding. Which means it’s built for travel. This performance cycling cap works on your bike, the trail, or just around town. Flip that bill up and you’re ready for happy hour.

Bianchi Reparto Corse Celeste Cycling Cap ($20)

Warning: You can really only rock this fashion icon if you’re a real cyclist (seriously, you better back this hat up with some pics of your Bianchi). An icon that works for travel or when you’re back home and reunited with your faithful Italian steed.

Rapha Thriver Cycling Cap ($4)

The best part about a cycling cap is that it’s always budget friendly. Packed with performance features, generous fit options, and all the swag you can handle. Never spend more than $20 for a cycling cap.

Best Trail-Friendly Travel Hat

Personally I think all “trail hats” are a waste of money. They make you look like an idiot tourist, don’t actually perform that well, cost an arm and a leg, and don’t work in all environments. You will not want to wear a “trail hat” in the big city, and yet, odds are that’s where you’ll be outside the most—exploring the city during the day in the hot sun of summer.

You don’t want to pack a floppy safari hat complete with neck scarf, mosquito net, and cork dongles straight out of Crocodile Dundee. A trail hat is only good if you use it. That’s where the Buff Pack and Run Cap comes in.

Buff Pack and Run Trail Cap ($32)

These hats seem a little skimpy at first glance, but they’re more than up to the task of protecting your face and head on the trail. With UPF 50 protection, 4-way stretch, and adjustable sizing to fit practically everyone, the fast wick lining will keep the sweat out of your eyes on the trail or the sweaty, summer-packed streets of Rome.

Also, they just look great. Get a colorful design, a bold solid color, or keep it classic with black. (I rock a rusty red color). Each cap features the same lightweight sturdy build (these things only weigh 1oz!), and the ability to just smoosh down into any shape. If you’re on the fence about packing a hat for your next trip this lightweight versatile travel hat is one of the few “just in case” items I ever recommend.

This hat doesn’t take up space, requires zero special treatment, weighs next to nothing, looks and performs great. It’s all upside as far as I’m concerned. And for all you runners out there (you’re nuts), the reflective material on the back adds great visibility for those (ugh) early morning jogs.

Momentum Cap ($28)

If you’re not into the cycling cap aesthetic, but still want something smaller than a snapback that you can stuff into your pocket, go with the Momentum cap. It’s minimal, stylish, lightweight, and the pliable brim means you can use and abuse it.

Best Travel Sun Hats

Sun is a serious issue. A hat should protect your eyes and face at least. It should it also add to your summer look, and of course it needs to be packable. 

J Crew Wide Brim Packable Straw Hat ($55)

J Crew is one of the best under the radar travel brands out there, and their wide brim travel straw hat is no exception. Stylish as hell, the rafia build folds flat and rolls into your backpack, but also holds its shape when you need it to. It says it’s a women’s hat, but I’ll be damned if I don’t look awesome in this bad boy.

Guys, get in on the straw hat game. It’s awesome.

J Crew Panama Hat ($25)

If the wide brim hat is a bit much for you (and you don’t want a fedora, because of course you don’t), the Panama hat is a great substitute and it won’t break the bank. Perfect for summer or the beach. Low investment, high reward.

If you want to roll a regular (non-travel friendly) panama hat, there is a right way to do that. Simply bend the brim down all the way around your hat,

then pinch it in the middle and fold it in half vertically. You now have a cup-shaped hat that you can roll into itself without ruining it. I’ll let the expert show you how to roll a panama hat in this quick video:

Madewell Packable Mesa Straw Hat ($42)

In the same vein as J Crew, Madewell has a solid line of packable straw hats that won’t look ridiculous, or break the bank.

Stylish, simple, and scrunchable, the paper straw construction is lightweight, flexible, and more durable than you’d expect.

A solid way to look good and keep the sun of your face.

Wear It, Don’t Pack It

The easiest way to pack a travel hat is to not pack it. Just wear it all the time. On the plane, around town, on the trail. Every photo will feature you and your cap, like a low-budget Where’s Waldo.

In all seriousness, if you can’t justify wearing your hat on the plane, maybe it’s time to rethink how “vital” that hat really is and how many hoops you’re willing to jump through for a few occasional uses. Realistically, there are only three reasons to pack a hat for a vacation:

  • It looks dope as hell
  • It protects you from the weather (sun, rain, or cold)
  • It doesn’t take up any space (like a trail hat)

That’s it. You need to want to wear your hat all the time, or it’s just not worth bringing.

Travel Hats are Actually Packing Cubes

Depending on the type of hat you’re rocking (I’m a fan of hats that wad up into a ball), you can turn your hat from a packing problem into an organizing solution. Flip your hat upside down and fill it with small items like socks, underwear, or rolled up shirts to keep your hat crisp and your undergarb organized:

  1. Lay down a base of clothes so your hat isn’t on the bottom of your bag
  2. Flip it upside down
  3. Stuff it to the brim (literally!) with clothes or small items to help it hold its shape
  4. Pack around it
  5. Ta-da

TL;DR

Traveling with a hat shouldn’t be hard. Just get a travel hat (*cough* cycling cap *cough* ) that you can wad into a ball. Failing that, you can pack a regular brimmed hat without ruining it.

Best ways to pack a travel hat:

  1. Stuff the inside of the crown with clothing or small items
  2. Pack around the hat so it doesn’t shift in transit
  3. Roll it down like a pro
  4. Or, just wear it all the time and never take it off, even when you sleep, and dream of your beautiful, beautiful travel hat and perfect style

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