10 Rules for the Best Men’s Travel Outfits

As someone who recently traveled to Indonesia, Vietnam, India, England, Ireland, Thailand, Canada, and Ohio, I have thoughts on how to dress for long flights.

This article is not about dressing LiKe a GeNtLeMaN when traveling, it’s more a reaction to all the people I see traveling in sweatpants. I’m here to say there are a ton of lessons I’ve learned over the years that can let you be both comfortable and well dressed (and less stinky) while you travel, whether that’s casually or business casually.

Here are my 10 best tips for better travel outfits.

Our Criteria for Best Travel Outfits

• Style: I’m not saying you can’t wear jeans and a t-shirt, I’m saying there are ways to be stylish and casual while also having extra travel functionality.
• Comfort: Whether you prefer stretch, insulation, or breathability, there are multiple ways to dress for your use case.
• Performance: Where possible I look for a beneficial element like breathability, stretch, stink resistance, stain resistance, and/or packability.

Our top picks hit these criteria: style, comfort, and performance. I simply want clothes that are comfortable and make you look just a level of “put together” higher than sweatpants.

Following these tips will leave you well-equipped, well-dressed, and well-prepared for whatever you want to do, from sightseeing in the rain to a quick business meeting on the way to the airport.

Rule 1. Look for Anti-Stink Clothing

• Wool is naturally antimicrobial
• Natural fibers usually stink less than most polyester
• Some workout shirts have anti-stink tech and can pass for regular t-shirts

You will stink after a long journey, but fortunately, there are a lot of anti-stink fabrics out there.

Wool is the best natural option for fighting stink as it’s naturally antimicrobial. Polyester has some pros — it dries quickly, doesn’t wrinkle, and packs well — but cotton stinks less if you’re picking between the two.

3 Solid Anti-Stink T-Shirts

But my main tip is to find a workout shirt that doesn’t look like one and has anti-stink tech. Ten Thousands’s Durable Shirt is a decent option that has ionic silver in the fabric, which is antibacterial.

My favorite anti-stink t-shirt right now is Wellen’s Sol Performance shirt that is made with a tech called Freshguard that suppresses bacteria growth.

I also often wear Teddy Stratford’s Tedra t-shirt, which is made with a bizarre tech that infuses fish scales with the modal in the fabric to make it stink resistant.

Anti-Stink Travel Pants

For travel pants, I’m enjoying Proof’s 72-hour pants because they’re about 50% wool, so they’re antimicrobial. They’re also super stretchy from elastane and super durable because they mixed wool with a bit of nylon, and they’re water-repellent to help manage spills.

They also have multiple fits: straight, slim, and athletic tapered, which is what I got.

Most of these products are available at Huckberry.com — not the Teddy Stratford one, but the other ones are.

Fun fact: Before I started Stridewise I worked as a fitness writer, so I have tried all the workout shirts in the entire world, and I sincerely think that Wellen is the best right now for combining the elements of being a workout shirt, looking like a normal shirt, and having anti-stink properties.

Tip 2. Embrace Stretch Fabrics

• Look for anything with 2% or more of elastane, spandex, Lycra, or polyurethane
• Find stretch fabrics that predominantly use natural fabrics like wool and cotton instead of synthetics
• I like 4-way stretch denim from Hiroshi Kato

I usually avoid stretch and synthetic fabrics because I don’t love how they drape and how insubstantial they tend to feel. But a stretchy, insubstantial feel is just what you want when you’re 12 hours into your flight and trying to contort yourself into any position that won’t put your butt back to sleep.

I don’t really look for stretchy tops, but stretchy pants do make a difference. Just look at the material on the product page: anything with 2% or more of elastane, spandex, Lycra, or polyurethane will do the trick.

Those Proof Merino pants I mentioned earlier have 6%, which is very stretchy.

For something that feels less tech-y but is still stretchy, Flint and Tinder’s 365 pants have 2% stretch, which is enough to feel almost like sweats but not so much stretch that they look and feel synthetic. The collection include chinos that look pretty smart if you’re dressing nicer for your flight.

That brand also makes stretch jeans, but my favorite ones I wear the most are from Hiroshi Kato. They are unique for being old-fashioned selvedge denim with four-way stretch, so they stretch vertically and horizontally, which is rare for this kind of denim.

Tip 3. Loose and/or Pleated Pants

• Pleated pants give your thighs a lot of room while looking dressy
• Just getting a slightly looser pair of pants will work wonders

If you don’t have or like stretch fabrics, I sympathize.. You should know that pleats are a surprisingly effective alternative to stretch fabrics if you want some freedom of movement when you’re sitting all day.

As a guy who likes menswear and has huge thighs, I took way too long to learn about pleats. When you sit down, the pleats expand, and your pants aren’t as tight on your thighs. Total game-changer — I’m a big Team Pleat guy now.

I’ve picked up a few custom made pairs in Southeast Asia, but for a recommendation that’s actually useful for you, I like Proper Cloth’s pleated pants. Mine aremerino wool, so they’re naturally anti-stink to boot.

On a related note: just buy looser pants. As a millennial I’m part of the generation that grew up wearing slim jeans but lately I’ve been doing looser pants and shocking myself at how much better they feel, especially when sitting down.

A good, super casual, lightweight but all-natural option that I like is cotton sateen fatigue pants. The ones I’m wearing are discontinued ones from Taylor Stitch (sorry) but a lot of brands make them. Fatigues have a nice high rise and loose thighs, and they’re traditionally made of cotton sateen, which is very breathable and quick drying so they don’t feel too stuffy. (That’s why fatigues are also my pants of choice when I’m in tropical climes but I still want to wear boots.)

Tip 4. Dress to Resist Stains

• Patterns and dark colors hide stains well
• Textures like raw or distressed denim, chambray, or a featered t-shirt also hide stains
• Some technical garments have waterproof finishes that help with stains too

Next tip: you will spill stuff on yourself, so think about stain management. One option is to just wear a patterned shirt or darker fabrics.

Another good option is wearing more textured clothes, such as a heathered t-shirt, chambray, or distressed denim.

Tip 5. Choose the Right Jacket for Travel

• Pick a lightweight jacket with secure pockets for valuables
• A good option that’s dressier is an unlined wool chore coat
• Don’t wear military inspired field jackets — they often make airport security jumpy

Next tip: travel with a lightweight jacket with secure pockets. Keeps you warm in cold planes, bundles up into a pillow, and keeps your passport and tickets safe.

The Best Casual Jackets for Travel

I know everyone likes leather jacket looks in these kinds of articles, but leather jackets take up more room when you’re crammed into your airline seat or when you stuff it into your bag.

So personally, I just like denim jackets or anything with pockets you can secure your passport and ticket in, like button or zipper closure pockets. Baracuta’s Harrington is a good option here for like one that’s a bit more modern looking.

The Best Business Casual Jacket for Travel

Now if you’re flying in a more business casual outfit, a really good option here for a light coat is a wool chore coat. I think this is a better option than a sports jacket because chore jackets are unstructured and unlined, so you get more of the breathability and anti-stink benefits of wool plus it’s easier to stuff into a bag.

The Worst Jacket for Travel

While we’re on the topic of jackets, don’t travel in military-inspired green field jackets.

They have many secure pockets, which is great, but these kinds of jackets make airport security jumpy, especially in ports of countries with a history of military or paramilitary tensions. Which is probably most countries on earth. That does include Ireland, and yes, I know from experience.

Tip 6. Know Your Wrinkle-Free Fabrics

• Synthetic fabrics like polyester and nylon wrinkle less than 100% cotton, but they can also stink
• For natural materials that are wrinkle resistant, look for burlier fabrics like denim and Oxford cloth

Next tip: wear stuff that doesn’t need ironing. While I’ve talked smack about synthetic fabrics tending to stink more than natural ones, it’s true that technical fabrics usually wrinkle less. Maybe something with polyester in it will be your pick if it’s a shorter flight and looking unrumpled is more important than not stinking.

Another good tip for looking less rumpled is to just wear burlier fabrics like denim shirts for casual wear or Oxford cloth for smarter looks.

Tip 7. Wear Easy Slip-On Footwear

• Loafers, sneakers, and slip on boots like Chelseas are the best

Next, an obvious tip: opt for footwear that’s easy to slip on and off.

Loafers, of course, are great. For boots, Chelsea boots really shine when you have a long trip. My favorite boot for traveling and my pick for the most underrated boot is Red Wing’s Weekender Chelsea boots.

Most of Red Wing’s boots are made like classic work boots (ie. stiff and heavy) but these ones are made on a thin crepe rubber sole and a flexible kind of stitchdown construction. These two elements make it much lighter, more cushy, and more flexible than your typical heritage boots, even though it’s still resoleable. I wear it a lot when I travel.

As for loafer recommendations, here I’m wearing the Randolph ones from Allen Edmonds for the business casual look.

But a famous loafer that is specifically made for travel is the Patnoflex from Astorflex. Made in Italy with an unusual kind of resoleable construction called ideal stitch, it manages to be resoleable but ultra light and flexible.

One more category of shoes is the sneaker, of course. Obviously they’re comfy in their own way, but for traveling I recommend an unstructured canvas sneaker like Chuck Taylor or Nothing New. I opt for these over fancy leather sneakers just because these ones don’t take up much room when you take them off and stuff them under the seat in front of you. 

Tip 8. Wear Socks

• Wearing shoes without socks won’t be comfortable on hour 20 of walking around airports
• No show socks always slip down when you’re walking this much
• If you’re wearing loafers, match your socks to your pants

Whether you’re in sneakers or loafers, I know it’s considered very cool to not wear socks or to wear no-show socks, but I strongly advise against that.

You’re doing a lot of walking when you’re traveling and no-show socks always slip down even if they promise they won’t. Wear long socks with your loafers and make them match your pants.

Tip 9. Consider a GMT Watch

• GMT watches let you track the time in two timezones at once

Next tip: If you’re a watch guy, look into a GMT watch. They help you keep track of your time at your destination and your origin at the same time.

You can also just get a digital watch that does that, of course. But GMT watches are considered like the travel watch for the watch guys.

Tip 10. Get a Backpack, Not a Shoulder Bag

• Backpacks are the best for storage, and comfort
• Leather backpacks are my recemendation for “adult looking” backpacks
• Messenger bags and briefcases will hurt your back and shoulder after extended use

You will need a bag, and do not use a briefcase or a messenger bag. I know they are very cool, they’re basically all I wear, but when you have a lot of walking and standing ahead of you, you will get a sore back, neck, and shoulder from carrying a bag on your shoulder or across your body.

My go-to backpack for casual stuff is the canvas Filson Journeyman. If I’m dressed a bit more modern or street wear-y, I like Goruck’s Slick Bag because it’s very sleek, so it’s easy to stuff into tight spots, and because the front pocket is recessed it’s relatively pickpocket-proof.

But you might be saying there’s no way to wear a backpack and look like a grown-up, especially if you’re doing the business casual thing. And to that I say: get a minimalist leather backpack.

I have a very, very premium one from Satchel and Page with Italian vegetable-tanned leather and lined with suede — or you can get this one from Thursday Boot Co that costs about $250 less.

Final Tips

All right, those are my travel tips — all very hard won from personal experience.

One more tip that I didn’t want to make a big deal out of: I don’t think you should fly in shorts. Just because there’s no way to avoid bumping your leg into the leg of the person sitting next to you at some point, and they don’t want to bump against your legs. Plus, planes get cold.

Let me know in the comments if I missed anything!