How to Pack for a Very Stylish Summer Weekend

By Liza Corsillo

Maybe you’re very organized and have been planning your trip for the long Memorial day weekend since December. Or maybe you love a last-minute deal and literally bought a plane ticket this morning. Either way, weekend getaways are your chance to indulge in comfortable clothes and experiment with a new style vibe. The second you step out of your house and onto new territory—be it beach, trailhead, or city sidewalk—you get to be a new man, one who’s unafraid of aviators, bold swim trunks, or wearing a pair of white jeans while eating at a taco stand. No matter where you go, as long as you stay within the bounds of good style and fit (that’s where we come in), the world is your fashion oyster. So, as the first long summer weekend approaches, we put together three helpful packing guides for three very different kinds of trips. Each one is aimed to deliver vacation-level comfort without sacrificing style. Think of these as packing cheat sheets that you can shop with the click of a mouse—suitcase and sunscreen not included.

If you’re planning to…

GET THE LOOK: Bandana Print Short Sleeve Shirt, Black Browline Sunglasses, Canvas Flip Flops

Get ready to chill. You’re headed for healthy dose of rest and relaxation, dozing seaside in between drinks and massage appointments. Because you’ll spend most of your time partially dressed, you can pack extra light. In fact, everything you need should fit in a duffel or a backpack. Our expert advice? Embrace the tropical nature of this trip with classic vacation prints. Our vintage inspired Hawaiian print swimsuit, wave-pattern slip-on sneakers, and island print button down will help you transition from workaholic bro to nap-taking pro. Fill in the outfit gaps with stylish basics like bright white denim and a gray tank for layering or grabbing a quick lunch (shirt, shoes, etc). Make sure to protect your eyes with a pair of handsome shades and your feet from burning hot sand with some grown up flip flops. Just remember sandals are for the beach, but slip-ons are for everywhere else.

SHOP: Wave Print Slip-On Sneakers, Reflective Nylon Backpack, Hawaiian Print Swim Trunks, Slim White Comfort Jeans, Island Floral Short Sleeve Shirt, Jersey Pocket Tank

GET THE LOOK: Washed Canvas Lion Baseball Hat, Charcoal Rim Aviators

Whether you’re a New Yorker, an L.A. diehard, or a small town guy for life, exploring a brand new city will jumpstart your creative brain. Places like Austin, Philadelphia, Minneapolis, Nashville, New Orleans, and Boulder are jam packed with local delicacies, craft beers, museums, and live music to get your juices flowing. But that means you’re going to do a lot of walking—so start by packing a comfortable and stylish pair of sneakers. Next fill your bag with essentials you can wear day or night like an elevated striped tee, a handsome pair of , tailored chino shorts and slim dark denim. Lastly, to keep blisters and stinky feet at bay, pack a few pairs of no-show socks.

SHOP:Striped Popover ShirtDark Wash Stretch Jeans, Flat Front Stretch Shorts, Loafer Socks, Striped Crew Neck Tee, Perforated Low Top Sneakers

GET THE LOOK: Water-Resistant Windbreaker

You could use a break from your computer and phone screens. So if you’re planning a trip off the grid, we salute you—and look forward to the pics you’ll post on social when you get back. Camping, sailing, and hiking may be casual activities, but they don’t have to lack in style. Our advice might seem silly, but believe us, it will reward you in likes: pack two kinds of henley one short sleeve and one soft long sleeve sweater. The sexiest shirt known to man makes a perfect dating app profile pic even more so when it’s taken on the trail or while floating peacefully in the middle of a lake. Everything else you bring should help you enjoy the great outdoors in all of its sunny, windy, or rainy splendor. You’ll need shades to combat glare, thick socks to ward off ticks, a windbreaker for summer storms, a swimsuit for cliff jumping, and a watch to keep time without looking at your phone.

SHOP: Long Sleeve Striped Henley, Slim Fit Chino Pant, Leaf Print Board Shorts, Short Sleeve Henley, Marled Socks, Classic Fit Cargo Shorts