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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
- Your go-to, tailored, Charcoal Suit Jacket. You’ll pack the trousers. Suit options here:
-
Performance Polo: Rhone Delta Pique Anti-Odor Hidden Button Down Collar Polo in Black – $76.50*
*price per polo when you buy a black & navy 2-pack. Wear one on the plane, pack the other. Choice is yours. - Sunglasses: goodr back-9 53mm unisex “blackout” no-slip sunglasses – $25
- Tech Pants: Target All in Motion Performance Pants – $40
-
Briefcase: Fossil Haskell Leather Double Zip Briefcase – $178.50 ($250ish)
Nice leather bag, but the shoulder strap is cheap. Get a pad. Also get a cheap luggage strap. - Watch: Invicta 31290 Auto – $109 (review here)
-
Dress Shoes: Allen Edmonds Park Avenue with Dainite Rubber Soles – $425
Shoes should be well broken in. Not new. - Medium or Lightweight Wool Socks: Darn Tough Cushioned Lightweight Work Socks – $24
- Reversible Belt: Nordstrom Reversible Leather Belt – $49.50
- Performance Traveler Underwear: Ex-Officio Give-n-Go Boxer Brief or Briefs – $20 – $25
Notes:
- 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
- Two Pairs Performance Traveler Underwear: Ex-Officio Give-n-Go Boxer Briefs or Briefs – $20 – $26
- Three Pairs Mid/Lightweight Merino-Blend Socks:
- Hybrid Shorts/Swimsuit: Ten Thousand Foundation Short w/ Boxer-Brief Liner – $39 FINAL ($68)
-
Two Merino Tees or Henleys: PROOF 72 Hour Henley in Black and Navy – $98 per
72 Hour collection = can wear 3 days straight, stink free.
Size up. A Large fits my 5’10″/185 perfectly after first machine wash/dry. - White Dress Shirt: The Tie Bar Pinpoint Solid White Non-Iron Dress Shirt – $55
- Merino Sweater: Amazon Goodthreads Merino Cardigan – $40ish
-
Polo: Rhone Delta Pique Anti-Odor Hidden Button Down Collar Polo in Navy – $76.50*
*price per polo when you buy a black & navy 2-pack. - Chinos/Tech Pants: Target All in Motion Performance Pants in Stone – $40.
-
Dopp Kit: Vorspack Toiletry Bag – $9.99
remember to have any liquids/gels in a separate clear baggie for TSA inspection. -
Necktie: Tie Bar Black Grenlaux – $22
Or navy, or light blue, or gray, or whatever tie matches well with the suit and occasion you’re wearing it for. - Suit Trousers: Spier and Mackay Charcoal Suit – $378
- Athletic Sneakers: asics Gel-Kayano 29 Running Shoes – $109.95
- Dark Brown Suede Chukkas – Clarks Desert Boot Evo – $140
-
The Carry On: Samsonite Freeform Hardside Carry-On 21-Inch – $139.99* ($199)
4.6/5 stars on Amazon after 9,000+ reviews
Review from Travel & Leisure, here
*on sale direct through Samsonite
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.)
Notes:
- 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
- PROOF 72 Hour Henley – $98
- Invicta 31290 Auto – $109
- goodr back-9 53mm unisex “blackout” no-slip sunglasses – $25
- Ten Thousand Foundation Short w/ Boxer-Brief Liner – $39 FINAL ($68)
- Darn Tough Number 2 Micro Crew Midweight Hiking Sock – $25
- asics Gel-Kayano 29 Running Shoes – $109.95
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
- goodr back-9 53mm unisex “blackout” no-slip sunglasses – $25
-
Rhone Delta Pique Anti-Odor Hidden Button Down Collar Polo in Navy – $76.50*
*price per polo when you buy a navy & black 2-pack. - Target All in Motion Performance Pants in Stone – $40.
- Invicta 31290 Auto – $109
- Darn Tough Scout Boot Midweight Hiking Sock – $29
- Clarks Desert Boot Evo – $140
- Nordstrom Reversible Leather Belt – $49.50
The event you came all this way for
- Spier and Mackay Core Line Charcoal Suit – $378
- The Tie Bar Pinpoint Solid White Non-Iron Dress Shirt – $55
- Tie Bar Black Grenlaux – $22
- Invicta 31290 Auto – $109
- Allen Edmonds Park Avenue with Dainite Rubber Soles – $425.
- Bombas Knee High Dress Socks – $24
- Nordstrom Reversible Leather Belt – $49.50
Next Day’s Brunch
- Amazon Goodthreads Merino Cardigan – $40ish
-
Rhone Delta Pique Anti-Odor Hidden Button Down Collar Polo in Navy – $76.50*
*price per polo when you buy a navy & black 2-pack. - Target All in Motion Performance Pants – $40
- goodr back-9 53mm unisex “blackout” no-slip sunglasses – $25
- Invicta 31290 Auto – $109
- Clarks Desert Boot Evo – $140
- Darn Tough Cushioned Lightweight Work Socks – $24
- Nordstrom Reversible Leather Belt – $49.50
Easy, Comfortable Afternoon/Feet are Tired
- PROOF 72 Hour Henley – $98
- Target All in Motion Performance Pants in Stone – $40
- Invicta 31290 Auto – $109
- asics Gel-Kayano 29 Running Shoes – $109.95
- Darn Tough Number 2 Micro Crew Midweight Hiking Sock – $25
- goodr back-9 53mm unisex “blackout” no-slip sunglasses – $25
Night out
- Spier and Mackay Core Line Charcoal Suit – $378
-
Rhone Delta Pique Anti-Odor Hidden Button Down Collar Polo in Black – $76.50*
*price per polo when you buy a black & navy 2-pack. - Invicta 31290 Auto – $109 (review here)
- Allen Edmonds Park Avenue with Dainite Rubber Soles – $425.
- Bombas Knee High Dress Socks – $24
- Nordstrom Reversible Leather Belt – $49.50
Headed Home
- Spier and Mackay Core Line Charcoal Suit Jacket – $378
-
Rhone Delta Pique Anti-Odor Hidden Button Down Collar Polo in Navy – $76.50*
*price per polo when you buy a navy & black 2-pack. - goodr back-9 53mm unisex “blackout” no-slip sunglasses – $25
- Target All in Motion Performance Pants – $40
- Fossil Haskell Leather Double Zip Briefcase – $250ish
- Invicta 31290 Auto – $109
- Clarks Desert Boot Evo – $140
- Darn Tough Cushioned Lightweight Work Socks – $24
- Nordstrom Reversible Leather Belt – $49.50
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.
