Fashionable Travel For Men: A Dapper Dude’s Packing List

Shawn Forno

Everything you need to look fresh as hell can be packed in a carry on bag, and when the luggage itself adds to your look, that’s a bonus. All it takes is a few quality pieces of gear, and some style. The rest is just TSA liquid restrictions and not wearing a fedora.

Here’s our full list of packing tips and tricks, and some super fashionable men’s travel gear to help you look like you just stepped off the good kind of runway (get it). Size matters, guys. Keep your packing list to a carry on and be ready for wherever adventure takes you.

Fashionable Travel for Men

No matter where you’re headed or for how long, your carry on packing list should revolve around a few basic pieces of quality gear that you can wear everyday—like travel chinos and a comfy henley shirt.

You just don’t need that much stuff. These items let you dress up (or down) for the occasion with a few simple accessories (or a shower), freeing up your bag for work stuff like your laptop, and souvenirs to make everyone at home jealous.

Head to Toe: The Stylish Man’s Packing List

This is all you need to take on the world:

Add to your clothing a basic travel dopp kit including: 

  • Pomade
  • Gold toothbrush
  • SPF 50 Lip Balm
  • Travel razor
  • Solid cologne
  • Condoms

Trust me, less is more. If you pack too much, no number of stylish shirts will make you look like anything other than what you are—a tourist. Keep reading for some of my favorite stylish men’s travel clothing and gear:

Paper Braid Travel Hats ($33 – $45)

Personally I don’t even think Sinatra pulled off a fedora, but if you like a challenge…

Hats in the Belfry has a range of travel-friendly crushable paper braid fedoras ($45) and pork pie hats ($33) that don’t look too terrible. They keep the sun off your face at the beach and you can smoosh your hat into a ball and shove it in your pocket the minute you see a person you want to impress. Or anyone really.

Filson Watch Wool Knit Cap ($35)

Travel hats, typically, suck. Avoid the hiker look with a well-made wool knit cap. Wool beanies are great for chilly wet mornings on the trail and nights out in the city. Plus, they fold down to nothing, and you can just tuck them behind your belt if they get too warm. I’m a huge fan of the Filson Watch Cap. They’ve been making virgin wool hats for over 100 years, and that craftsmanship never goes out of style.

Mr. Natty’s Pomade ($18)

If a hat isn’t your speed (congratulations), make sure you don’t look like you just got off a plane all the time. Mr. Natty’s pomade is fantastic for that whatever hairstyle you’re going for. Providing long-lasting hold without making your hair look like Ross from Friends, you don’t need to use much to get the look you want.

The best part—each screw top jar is exactly 100mL (the exact TSA liquid limit), so you won’t have to worry about carry on restrictions or scooping this gel into another less reliable container. Just apply a little in the morning and you’re good to go.

For fashionable men’s grooming tips including solid cologne and beard oil, check out our Dopp Kit Essentials packing list for all of your dapper grooming travel items.

Arcade Minimal Adventure Belt ($26)

The stretchy, weather-proof material, lightweight polymer buckle, and seriously slick patterns make all of Arcade’s Adventure Belts a no-brainer for stylish men’s travel.

For a more austere print, try the more professional looking Smartweave belts, or the super slick Crossover Belts ($36), for a look that works in the boardroom and on the road.

Bluffworks Gramercy Travel Blazer $295

This wrinkle-free travel blazer fits great, looks awesome, and has all the right stretch and give to take everything from airport lounges to after hour raves. Machine washable (a bonus on the road) and super comfortable, the Bluffworks travel blazer features 10 pockets, many with zippered enclosures, to keep your stuff safe and organized while in transit.

Wear it to your next meeting or just on your next flight. Either way, you’ll impress someone.

Old Navy Soft-Washed Short Sleeve Henley Shirt $16

Fashionable travel clothes don’t have to cost $100. Case in point, the soft-washed short sleeved henley shirt from Old Navy. I wear this thing everywhere because it’s comfortable, fits great, and the stretch and durability of the fabric makes it perfect for exploring a city in style. Seriously—first thing I wear out of the wash.

Bluffworks Tailor Fit Travel Chinos $125

I’ve written about these awesome travel pants a few times, and I’ve tried other travel pants, but the Bluffworks Travel Chino is still my favorite pair of travel pants. They look fantastic, feel great, weigh next to nothing, and they have travel-friendly features that I love like deep pockets and internal zippered compartments to keep things like cash and my passport safe and organized. The best part is that these pants can take a beating. I bike everywhere in them, dance in them, and I’ve been caught in the rain a few times only to dry out soon after.

I rock the Harvest Gold travel chinos, and I get compliments every time I wear them.

Onia Calder 7” Swim Shorts ($130)

It doesn’t matter if you’re in the middle of the desert or the peak of a snowy mountaintop—always pack a swimsuit. Always. The Calder Swim Trunks from Onia is a great way to look fresh around the poolside bar or around town. The super soft mesh material and chlorine-proof fabric look great in and out of the water. Stylish hybrid shorts and swimsuits are a great way to double your travel wardrobe without packing any extra gear.

Ex Officio Sport Mesh Travel Underwear ($28)

These travel underwear are the latest edition in an already fantastic line. Ex-officio won the top spot in my latest travel underwear comparison guide, and this latest edition is even better. The ultralight mesh material feels fantastic while wicking away moisture and any odor causing bacteria, and the fit is unparalleled.

Pack two pairs of these underwear and you’re good to go.

Gold Cup Authentic Original Sperry Top Sider Boat Shoes ($159)

These boat shoes are as good as it gets. 24 karat gold eyelets, lambskin lining, memory foam insole, hand sewn leather—Sperry Gold Cup shoes are the cadillac of stylish travel footwear.

Boat shoes are comfy, versatile, and perfect for so many occasions. Walking around town, happy hour, or a meeting with investors—you’re always dressed just right in boat shoes. Especially these. Seriously, they have gold in them. Don’t gloss over that fact.

Tom’s Shoes ($55)

I’m slowly coming around to these versatile travel friendly shoes. It’s not always easy to pack an extra pair of shoes in a carry on bag, but Tom’s espadrille style slip on shoes pack flat to make adding an extra comfy, relaxed pair of shoes easier than ever. Make sure you wear them in for a few days (Toms shoes stretch a little), but enjoy the freedom and comfort of an extra pair of stylish loafers in your carry on bag without the extra weight.

The Frost Grey Chambray Toms are one of my favorites.

Darn Tough Coolmax Hiking Socks ($19)

Is $19 too much to spend on comfortable feet? Of course not. Investing in a good pair of merino socks that will last for years is well worth the upfront investment—especially when you’re trying to save space in your carry on bag. Coolmax fabric reduces friction in your boots or shoes, so you’ll never get blisters, and keeps your sweaty feet from stinking up your new boat shoes.

If hi-tech socks aren’t your thing, stick with the material that’s worked for centuries—merino wool. Darn Tough Merino Wool Switchback Microcrew Socks ($20) are engineered from a blend of the finest fibers to keep your feet cool, comfy, and stink free. Merino wool really is magic, and if you haven’t tried it out, it’s worth a test run. Darn Tough socks are family owned and operated, customer loved, and produce top quality socks. You’ll be glad you got the best.

Travel Sunglasses

Warby Parker Sunglasses ($95+)

Picking a pair of sunglasses that actually fit your face is kind of hard. Unless you’re one of those “symmetrical” people, in which case you’re already good. Luckily Warby Parker has a ton of hyper fashionable frames to choose from and you can have five pairs sent to your house for a real world test. Even cooler, you can put your prescription lenses in the frames and look rad without bumping into a bunch of blurry stuff.

I’m a fan of the throwback Ames frames, but hey, that’s just me.

Ray-Ban Wayfarer Foldable Sunglasses 

For $150, get the classic Ray-Ban look without the worry that your shades will break in your pocket. These folding sunglasses look just like the originals, but take up half the space. 

ROAV Folding Brushed Gold Frame 

The ROAV folding brush gold sunglasses for $195 are about as fashionable as it gets. Seriously. These things are sleek and sexy. You will wear these a lot, and people will talk about it.

REI Lightweight Eye Mask & Earplugs ($13)

Nothing makes you look worse than a bad night’s sleep. Get off the redeye looking fresh and ready to take on the day by packing an eye mask that will let you sleep in practically any situation. I tried this eye mask on in the store, and almost fell asleep in the aisle. Plush, soft, and lightweight, this eye mask completely blacks out the light thanks to a little padded ridge that seals the mask at the bottom (where light usually gets in).

The coolest part is that the mask features a little storage pocket on the top for your corkscrew ear plugs. Never lose your earplugs again.

Beteran KZ-ATE Dynamic Balanced Headphones ($13)

My buddy, Jason Finkle, is one of the best music producers in Brooklyn. He recommended these earbuds, in large part, for their ability to deliver quality sound in such a small, insanely affordable package. I love these bad boys.

While it’s true that these earbuds don’t have a mic like the Apple headphones you’re used to, they more than make up for it with rich dynamic sound, actual bass, and overall sonic quality. You need these $13 headphones.

TL;DR

Minimal fashion is all the rage, and not just this year. Pack travel clothing and gear that looks great, but that also get the job done. Function is stylish—especially on the road. The right pair of travel pants, shoes, or underwear will not only keep your carry on bag light—they’ll make you look and feel confident enough to take on whatever life throws your way.

Style is about more than just looking good. It’s about being ready.

  • Pack it all in the Outbreaker travel backpack
  • Merino wool is amazing
  • One great pair of travel pants is key
  • Zippers are a must for travel clothing
  • Save space: Find a pair of swim trunks you can wear outside of the pool
  • Two good pairs of travel underwear are worth their weight in gold