What are you going to wear? Sometimes it’s good to look at a few suggestions then add your own tweaks and ideas. That’s what these are for. Travel in 2021 is even weirder than it was last year. In 2020, it was null and void. In 2021, it’s Delta variants and all around travel uncertainties. One way to take control is to indulge in the great American road trip, or at least a long drive for a weekend getaway. And it is possible to stay both stylish AND comfortable in the car. Stay ready for whatever the road brings with a single outfit to last you 4-8 hours in the car, plus snacks, beverages, and entertainment. And whatever you do, don’t be in a rush. Be safe to yourself and everyone else on the road. You’ll get there eventually – enjoy the ride.
The Shirt: Goodthreads Men’s Standard-Fit Short-Sleeve Printed Poplin Shirt in Vintage Ivy – $25. What says summer fun more than an on-trend printed short sleeve button down? This is the vacation-dad shirt for the modern man. Amazon’s Goodthreads offering packs a punch in value and style. Tons of great prints to choose from, but this ivy-green shirt is a great, yet not overwhelming print on a rich color.
The Shorts: J.Crew 9″ Garment Dyed Cotton Short in “Cove Blue” – $24.49 FINAL w/ SALEONSALE ($69.50). J. Crew nails the basics, and their stretch chino shorts are no different. A great fit, classic color, and comfortable stretch – what more could you ask for? This classic Navy plays well with the ivy green for a cool, subdued color combo to let the bold print stand out. When you’re wearing a bold print, pattern, or accessory, the key to pulling it off with success is keeping the rest of the outfit.
The Sunglasses: Warby Parker Barkley in Matte Black – $95. Dark as hell. I actually have to take these off to use my backup camera because the polarization is so intense. But for the time I’m driving forwards into the sun, these are tried and true. Dark black frames with matte black frames are 1 part badass, two parts sharp. Warby Parker knows what they’re doing when it comes to sunglasses under a Benjamin. Luxury-shade quality materials and build with great bang for buck.
The Watch: Dan Henry 1962 Racing Chrono – $270. Cars have traditionally meant chronos. Seiko caliber VK63 meca-quartz movement. 39mm case diameter so not some enormous hulking thing. Classy. Even comes with a second, tan leather strap if you want to go with a higher contrast look. If that’s too expensive, consider Armogan’s E.N.B. for $88. Although with the Armogan, it appears those are final sale and you’d be on your own in terms of any repairs that might need to happen (wait for it) down the road.
The Belt: Banana Republic Italian Leather Belt in Burgundy – $60. Pattern up top, garment dyed on the bottom – shoot for something basic in between. Basic, but refined. Nice leather for the price point. Durable construction. No need to be all “matchy matchy” with your watch strap for such a casual look. But keep it darker with the burgundy for an easy blending of all the shades.
The Shoes: Adidas Stan Smith in White/Off White/Green – $100. You’re driving all day, so comfort and cushion are key. But, gym shoes won’t cut it when you hop out of the car and grab a bite to eat on the way – or when you reach your destination. A perfect in-between is the Adidas Stan Smith, and this color is the one to own.
The Socks: Lululemon Power Stride Socks – 3 for $38. You’re driving all day, or at least for a long time. It’s a strain on your feet. Don’t overthink this one – get the Dappered approved best of the best.
For Drinking: Bodyarmor Lyte 8 pack – $6.39. Nobody wants to take frequent stops on a roadtrip. Stay hydrated without taking in too much fluid. Body Armor Lyte is a favored drink amoung athletes for a reason – all natural flavors, no artificial sweeteners, and low calories and minimal sugar.
The Snack: Seapoint Farms Dry Roasted Edamame – $1.49. Filling, healthy, and easy to eat with one hand while driving.
For Listening: Stuff You Should Know Podcast on Spotify. Use the time on the road to expand your education with an engaging, often humorous medium. The Stuff You Should Know podcast is a reliable, fun back and forth deep dive into topics both niche and mainstream. One of my favorites? An explanation on how inflation works, and why not to panic about all the chatter on the topic today.
The Luggage: Filson Rugged Twill Rolling Bag in Green – $650. Carry on/wheeled bags have no right to be this handsome. Expensive, yes, but Filson makes goods to last, and it’s damn good looking compared to most rolly-bags. If you’re a frequent traveler, put this at the top of your splurge list. With some artful packing, you can squeeze 5-6 days worth of clothes, toiletries, and other needed items for your travels and toss it in the back of your car. For something cheaper and suited for shorter trips check the WP Standard Leather Weekender Duffel. It’s arguably even more beautiful a bag.
About the Author: Jason P. spends his days working in the creative marketing department of a big telecom company. He also does a bit of real estate investing on the side. He believes in curating a timeless, classic wardrobe with subtle modern touches for today. He and his wife love hiking with their dog and shopping at local small businesses and antique stores when they travel. Jason is a practitioner of muay thai and traditional boxing, and his favorite drink is a hoppy New England IPA.