Go with a Patterned Shirt
A subtle plaid looks great on its own, with a jacket, or layered under a sweater. Shirt ($345) by Ermenegildo Zegna.
Get a Navy Suit
This three-season wool two-button is a multipurpose workhorse on the road. Wear it as a full suit or pair the pants with a cardigan or the jacket with jeans—you can't go wrong. Suit ($1,980) by Prada.
Choose a Versatile Shoe
These elegant double-monks go with anything, and the straps are a hell of a lot more TSA-friendly than laces. Shoes ($345) by Allen Edmonds.
Try a Neutral Tie
Dark, understated options will sync with any shirt you pack, regardless of color or pattern. Tie ($140) by Alexander Olch.
Stay Secure With Sturdy Luggage
Unlike a typical soft wheelie, a hard case lets you pack even your most precious cargo without worry. Get one in durable polycarbonate for the most protection. Trunk ($475) by Rimowa.
Don't Skimp on Storage
Stow small, easily misplaced items—passport, iPad, cords, chargers—in handsome leather cases that are as stylish as they are functional. Pack them into a luxe leather tote, which is ideal as an all-purpose carry-on (and rests perfectly on top of your hard case). 1. Tote ($795) by WANT Les Essentiels de la Vie. 2. Document holder ($325) by Tod's. 3. Travel wallet ($405) by Smythson. 4. Pouch ($215) by Comme des Garçons. 5. Key fob ($145) by Tumi.
Bring Lightweight Workout Gear
All you need are simple running shoes, a comfy tee, mid-thigh-length shorts, and an anorak in case of rain. 6. Sneakers ($105) by Nike. 7. Anorak ($3,688) by Louis Vuitton. 8. T-shirt ($350) by Dior Homme. 9. Shorts ($150) by Nike.
Pack an All-Purpose Casual Outfit
For a change of clothes, bring a simple dress shirt, crisp dark jeans, and a cardigan. 10. Cardigan ($595) by Dunhill. 11. Shirt ($195) by Diesel. 12. Jeans ($620) by Dior Homme.
Build the Perfect Dopp Kit
For your favorite grooming products in travel sizes, head to the well-curated 3floz.com. If you can't find what you need there, try Humangear's GoToobs— convenient silicone containers for your liquids. 13. Dopp kit ($155) by Jack Spade. 14. From left: Malin + Goetz Vitamin B6 Hand Treatment ($20 for 1.7 ounces). Container ($25 for three) by Humangear. Air Repair Rescue Balm ($10). Boticario de Havana Body Wash ($25 for full travel set). Cutler Specialist Molding Putty ($21).
Three Travel Products to Keep Your Clothes Fresh
Just because you're living out of a suitcase doesn't mean you can't take care of your garments. Pack two TSA-friendly items—a 3 ounce version of Downy Wrinkle Releaser and a mini lint roller—to keep your clothes both smooth and clean. And once your trip's done, keep your dirty clothes separate from the fresh ones with the Tide odor-absorbing laundry bag. Sure, they might not be as essential to your trip as, say, your boarding pass and passport—but they're pretty damn close.