What to pack when traveling light and in style (for Men)

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The Carry-On Wardrobe  – Lots of Style, one Wheelie Bag

  • Get Wicking, Breathable, Anti-Microbial Basics: That means higher quality performance and/or merino wool underwear, socks, polos, and tees. Pricey, but absolutely worth it. They fight stink, dry quick, and you’ll pack half as much… or less.
  • You’ll Do a Little “Laundry” Daily: Each day you’ll hand wash your most recently used pair of underwear with soap in the shower (or w/ detergent in the sink/tub.) Set it out to air-dry. Rotate daily like this and you’ll always have a clean pair. Any sweat-soaked or stinkified casual gear and/or socks will get hand washed too.
  • Adjust Colors for Taste, Occasion, Weather, Etc.: This guide is for those who will require a dark gray suit & black shoes at their destination (for a wedding, funeral, etc.) If brown shoes and a lighter gray, navy, or blue suit is on the menu, you’ll have to adjust some colors and contrast. For example, if the chosen suit is medium or lighter gray, a combination like this would work. Overall: the suit is your anchor. Work off that.


What you’re Wearing on the Plane

What To Pack Travel Light Stylishly Dappered – Wear on the Plane


  • If you’re worried about wrinkling your suit jacket on the plane, you might be able to politely ask one of the flight attendants to hang it up for you if they have room. Big “if” though.
  • Because the odds of misplacing/breaking one’s sunglasses on a trip are higher than normal, go cheap. The goodrs are non-slip, classic in shape, and cheap. They’ve blacked out their logo on that particular model, which is a plus.


What’s going in your Carry-On

What goes in the carry on TOP test

What goes in the carry on BOTTOM test


Roll up your socks and stuff them in your sneakers.
Underwear and the tie gets rolled up and goes in the chukkas.


Proof it all fits. Bag Shown is the Samsonite Freeform 21-inch Carry-On – $139.99 ($199)
(There’s a flap that folds over to separate each section, but…
pack your dress shirt deeper than shown above so the shoes don’t smash into it.)


  • Iron your dress shirt when you get there. Don’t leave it to the last minute. Let it hang up and air out
  • Use the furniture. If your hotel/AirBnB has a dresser, use it to store your clothes in. Don’t leave them smashed in your carry on. Shake them out, re-fold them, let them breathe.
  • Buy a newspaper. Each night when you take off your shoes, stuff them with newspaper. It’ll soak up extra moisture overnight, keeping your shoes fresher.
  • Wash underwear with each use. Underwear like Ex-Officio is built to be hand-washed on the road/air dry overnight. I was skeptical too, until I only packed two pairs for a 5 day trip. The “wear one while the other has been washed/is drying” strategy really does work.
  • You DON’T have to wash your socks with each use, as long as they’re good quality merino wool. Crazy, but true.


The Outfits…

Morning Workout/heading to Pool/Beach

Workout Beach Pool

Tip: When you jump in the shower after your workout, bring your workout clothes in with you. Don’t let your stuff just marinate in your sweat in a ball on the floor. Showers are like washing machines for people. Might as well use it to its full potential (and do some laundry) while you’re in there.


Classic Bond-Style Chinos Chukkas Polo

Chinos Chukkas Polo Classic Bond – What to pack when packing light


The event you came all this way for

Event you came all this way for – What To Pack Travel Light Stylishly Dappered


Next Day’s Brunch

Next Days Brunch – What To Pack Travel Light Stylishly Dappered


Easy, Comfortable Afternoon/Feet are Tired

Easy Afternoon – What to pack when packing light


Night out

Night Out – What To Pack Travel Light Stylishly Dappered


Headed Home

Headed Home – What To Pack Travel Light Stylishly Dappered

And that’s just the start. Clearly there’s more combinations than that, especially if you’re able to keep up on your nightly laundry. You could easily live for a week or significantly more out of that bag, assuming access to laundry facilities for your dress shirt & when your pants need a wash, as well as any necessary dry cleaning for your suit jacket and trousers (only dry clean a suit if you’ve sweated hard in it/or it needs to be freshened up after a significant number of wears). 


Final Tips

  • Don’t overthink any/all of this. Traveling is hard. People understand, and they don’t notice what you’re wearing nearly as much as we’d all like to think.
  • Again and this is important: Choose polos, tees, underwear, and socks that breathe, wick, and have some sort of anti-stink properties (either performance-wear with an anti-microbial finish, or merino wool which is naturally anti-microbial).
  • Splurge on the over-the-calf Darn Tough socks for flying days. They have extra cushioning at the heel and under the foot. They’re amazing.
  • Go with rubber sole dress shoes. Get the grip.
  • Splurge on black and navy Rhone polos. The under-collar buttons help keep the collar points in line and look great with a suit or blazer.
  • Upon arrival, hang your suit jacket up in the bathroom. Steam from the shower should help release those wrinkles.
  • You can always use an iron (carefully) as a steamer. Less is more. Be careful. Don’t scorch your suit.
  • The setup in the above post is best for milder weather. If you’re headed somewhere cold, pack long sleeves instead of short sleeves. If it’s cold/wet where you’re headed, you’ll clearly need a mac (mild) or overcoat (cold). If it’s absurdly hot you’ll probably default to picking lighter-in-color stuff, but don’t be surprised if dark performance-fabric and/or merino clothes outperform even the lightest cotton.
  • Leave/Book your return flight earlier than you have to. If you’re on one of the last planes to land at your home airport at the end of the day, then be prepared to get stuck somewhere overnight. Things happen. Especially if you’re connecting somewhere else. You need wiggle room. Better to get back earlier in the day than to not make it back as planned at all.