There are plenty of tried-and-true ways to stay stylish when you’re flying, whether you’re on your way to a conference for work or escaping your city for a much-needed vacation. But packing for a road trip is a different animal altogether. How can you dress for hours in the car, and still look classic and stylish when you stop for lunch or to stretch your legs? While questions like who to take on your road trip, what route you should take, which snacks you should prepare, and how you need to ready the car are all important — the question of which clothes are true road trip essentials is the one that leaves many guys baffled.
But there’s no reason to stress about what you should wear on the road trips you’re planning for the summer (and likewise, no reason to default to gym wear or the worn-out tees and shorts that look like they’d be the only thing left in your dresser after weeks of procrastinating about doing the laundry). Fortunately though, figuring out what to wear on a road trip isn’t all that difficult. All you need to do is pack a duffel bag with a few classic road trip essentials and you’ll be on your way in style. Here are 10 pieces you should throw in your bag if you want to look well-dressed and well-groomed — despite what days packed into the car with your friends can do to your sanity and personal hygiene.
We’re all about finding the right sunglasses to change up otherwise basic outfits. So a great pair of sunglasses is right at the top of our list of road trip essentials. If you’re looking to make an investment in a pair that will last you for many road trips and summers to come, we’d recommend a style like the Gregory Peck 47 from Oliver Peoples. They’re handmade of high-quality acetate, not the cheap plastic you’d get if you picked up a pair of sunglasses at a gas station, and are offered in a variety of different colorways so that you can choose the pair that best matches what you’ve packed for the trip.
2. Cotton tees
While some guys love synthetics for the gym, we’d advocate for soft cotton tees for wearing on the road. Choose a few dark ones and a few light ones (we like staples like white, navy blue, and heather grey), and don’t forget a striped tee or two. Check out this handy cheatsheet to the most classic styles of t-shirts and how to style them, or you can opt for one or more of a few perennial basics, like Club Monaco’s garment-dyed tee, J.Crew’s striped field-knit tee, or Rag & bone’s garment-washed white tee.
3. Lightweight jacket
Another of the road trip essentials we’d recommend stashing in your trunk is a lightweight jacket. One like Our Legacy’s cotton-jersey jacket will be just as comfortable as a sweatshirt, but will keep you looking polished on pit stops. When choosing an outer layer, think carefully about the color scheme you want the rest of your clothes to adhere to. Selecting just a few colors, and ensuring that each piece looks good with just about everything you’re packing, will make things easy to mix and match, and ensure that when you’re getting dressed in a dark motel room, you won’t end up grabbing a combination that you’ll regret.
4. Button-front shirt
While you might not think of a button-front shirt as the best choice for hours of driving or co-piloting, the right one can actually be a very comfortable road trip choice, especially if you’re prone to getting chilly thanks to the AC in the car or at roadside diners. The white button-front is a classic, and works particularly well for summer in a light linen. Our favorite is J.Crew’s slim-fit linen shirt. Or, if you’re too prone to spills to trust yourself with a white shirt on the road, opt for a lightweight chambray shirt if you want something that’ll wear wrinkles well.
5. Comfortable chinos
While you might be tempted to wear sweatpants in the car, and just change into something more classic when a photo opportunity presents itself, you’ll quickly learn that road trips are unpredictable, and that taking the time to change is pretty inconvenient. Instead of the sweatpants, choose a more stylish pair of pants like a pair of chinos. They’re light and breathable, not to mention they’ll look a lot better in the inevitable Instagram photos rather than a pair of sweatpants or gym shorts. If you need a new pair, we’d recommend you add NN07’s slim-fit chinos to your wardrobe and your packing list. Even after hours of sitting in the car, they’ll still look neat and tailored. Plus, a classic army green is a neutral that’s easy to pair with anything else you want to wear this summer.
Unless you’re planning on going to a semi-formal dinner when you arrive at your destination, then there may not be much need for anything more than one pair of shoes. When it comes to sneakers, we’d aim for the right combination of lightweight and classic and choose a pair of canvas sneakers, like Converse’s signature Jack Purcell. If you want to leave your options open and pack an extra pair of shoes that will enable you to dress up a little, we’d recommend one of these great pairs of American-made shoes. A penny loafer, a derby shoe, a moccasin, or even a boat shoe will work with all of your casual outfits, but can also dress up a pair of chinos and a button-front shirt.
7. Swim trunks
Whether it’s the hotel pool or a lake in the middle of nowhere, the best road trips often present opportunities that you’ll only be able to take advantage of if you pack a pair of swim trunks. And because they’ll take up so little space in your bag, this is an area where we’d recommend always being prepared. We’re a fan of a classic navy blue pair, like Saturdays NYC’s mid-length swim shorts. They’re short enough to be much more flattering than the knee-covering pairs that too many guys wear to the beach, but not short enough to raise eyebrows at the hotel pool.
8. Baseball cap
Whether you want to protect your scalp from getting sunburnt or hide hair that’s a little greasier than would be ideal, a hat is definitely a good addition to your packing list. A baseball cap is easy to throw in your duffel or stuff in the glove box, but will add some sporty style to even the most basic of outfits. Ralph Lauren’s cotton-chino baseball cap, for instance, is a must-have for any road trip, since it’ll look great on sunny or rainy days and have any ensemble looking like the perfect laid-back summer outfit.
While you don’t need to fill up a dopp kit with all of the products you have in your shower or around your bathroom sink, there are at least a few that we’d consider road trip essentials. The first is a good sunscreen, which you should really be wearing all day, even when you’re in the car with the windows rolled up. We’d also recommend a good cleanser and a small bottle of shampoo, since even (or perhaps especially) if you’re only showering at a truck stop, you’ll want to feel as clean as possible. If you want everything all in one place, we’d recommend a starter kit of skincare essentials, like Mr. Porter’s grooming kit stocked with Aesop essentials.
10. Water bottle
A water bottle is a must-have on the road, and instead of buying and discarding countless water bottles along the way, we’d recommend packing your own, like this stylish stainless steel bottle from S’well. Speaking of water? There are a few other essentials that you’ve likely already accounted for, but your mom would appreciate us reminding you anyway. Make sure you have some cash, your AAA card, a spare tire and jack, a paper map, a small first aid kit, paper towels, duct tape, a spare car key, plus a car charger and battery case for your smartphone.