| October 16, 2013

Outfitted & Equipped, Style & Grooming, Visual Guides

Outfitted and Equipped: Weekend Road Trip

what to bring wear on a weekend road trip

This post is brought to you by Timberland.
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With summer behind us, the days of epic cross-country road trips have come to a close. But fall ushers in the perfect time for taking a shorter weekend trek with friends (or a special someone). With the leaves beginning to change colors in many places in the country, the scenery along the way can’t be beat. It almost makes the destination superfluous.

If you’ve never taken a road trip of any length, it can be intimidating to try to think of everything you need. You don’t just want a mass of stuff, you want the right things to help you get to the other side happily and not screaming at each other from being cramped in a car for too long.

Here are our recommendations for a relaxing and memorable weekend road trip with your buddies:

1. The Shades. J.Crew Factory Aviators. The sun can be brutal on the open road. Protect your eyes with these great-looking and affordable aviators.

2. The Camera. FujiFilm FinePix S4200. This is my other camera besides my point and shoot, and I love it. You get robust features for a great price including 24x zoom, image stabilization, and a great 3-inch screen. It also has a viewfinder in case there’s glare on the screen, which I appreciate and not all cameras have these days.

3. The Boots. Timberland Earthkeepers® Rugged Waterproof Moc Toe Boot. These boots are like the holy grail of road trip footwear: comfortable enough for long stretches in the car, rugged enough for taking jaunts into the woods, and good looking enough for going out in the city. They’re breathable with a moccasin-like feel, waterproof for braving autumnal weather, and pair perfectly with jeans. Incredibly versatile.

4. The Tunes. Lost And Gone Forever by Guster. What makes for the perfect road trip music? It’s kind of an ineffable quality: not so up-tempo and bombastic that it jars the smooth vibe of your four wheels turning round and round, but not so mellow that it puts you to sleep. It fits the rhythm of the road perfectly. One candidate I’d recommend for your road trip playlist: Guster. Try Lost and Gone Forever and cruise the highway to their smooth melodies and bongo’d beats.

5. The Tech. Mediabridge Aux Cable. If you’re renting a car (I recommend it for road trips), you’re almost guaranteed to have an iPod/smartphone port, so don’t forget to bring your aux cable. Also don’t forget your car charger for your phone; using the GPS feature tends to drain the battery.

6. The Beverage. Nothing goes better with salty snacks (see below) than an ice cold can of soda. Instead of reaching for the same old Coke or Pepsi, try to pick up a unique variety available only in certain regions of the country. For example, if you’re traveling through New England, keep your eye out for Moxie, a weirdly delicious, medicinal-tasting, old-time soda made with gentian root extract. Plus it contains caffeine to keep you alert.

7. The Jacket. Timberland Woodhick Hoodie. On a road trip, you usually get warm in the car, and then get chilled when you stop and get out for gas, and then warm back up when you get going again. You need something that’s super comfortable and easy to take off and on, which makes the hoodie your perfect road trip wear. Plus, with the seasons changing, you want to be prepared for any kind of weather. This fleece-lined hoodie will keep you warm and cozy wherever the open road takes you.

8. The Tee. Gap Striped Henley Tee. You definitely want a comfy shirt for your travels. A good-looking henley classes it up a bit.

9. The Jeans. Charles Regular Selvage. With storage space at a premium on road trips with friends, you don’t want to have to pack too much. This pair of jeans will you get you through a whole long weekend of not only sitting in a car for long periods of time, but also whatever other adventures may come along. They’re handmade in San Francisco, reasonably priced (for selvage denim), and will last you a lifetime.

10. The Cooler. Igloo Soft Cooler. You’ll definitely want some cold beverages on your road trip (see “The Beverage” above), but traditional coolers can be big and unwieldy, and you don’t want to stop at a gas station every time you’re needing something to wet your whistle. This small cooler is made with soft material, so you can shove it into any nook or cranny of the car you can find. Remember to keep this with you and not in the trunk!

11. The Snacks. Sweetwood Beef Jerky. There’s no better road trip snack than beef jerky. That’s a scientific fact. It’s mighty tasty and will keep you satisfied far longer than a can of Pringles.

12. The Bigger Picture. Rand McNally Road Atlas. While your phone can give you turn-by-turn navigation, a paper atlas gives you the bigger picture of where you are and where you’re going. You can study the atlas to find off-road diversions, as well as chart your route ahead if you’re like me and still have a slight distrust of GPS and Google Maps.

13. The Reading Material, Part 1. Kindle Paperwhite. For the times you aren’t driving, and the car has exhausted its fantasy football conversation, the Paperwhite is your perfect companion. I bought this as soon as it came out a couple years ago, and couldn’t go back if I tried. With the built-in light, you can read in the dark and not disturb your driver/companions with needing a light on. It also doesn’t glare in the sunlight like tablets do. Zen and the Art of Motorcycle Maintenance (only $2.99 this month for Kindle) is the perfect book for your road trip for two reasons: 1) It’s our selection for the AoM book club for October, and 2) the main plot features a road trip between father and son and several philosophical discussions.

14. The Reading Material, Part 2. Make Magazine. Road trips are a great time to catch up on lighter reading material like magazines. Make Magazine focuses on things you can do with your hands — everything from woodworking, to electronics, to homemade yogurt. We caught up with founder Mark Frauenfelder in a recent AoM podcast.

Last updated: October 7, 2017

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