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If you have vacation plans on the books, we think you should spend less time thinking about what to wear and more time basking in the excitement of getting out of here. To help, we’ve put together a few outfit formulas to take the guesswork out of packing. Whether you’re headed to the beach, the mountains, or a far-flung city, here’s how to dress for a successful (and stress-free) trip.
Looking for more affordable, stylish clothes? Here’s what to wear when working, traveling, and playing — and picks for your kids, too.
Tropical Getaway

A maxi dress will go very, very far here. This one from Abercrombie & Fitch can be dressed up with beachy statement earrings and the right handbag, or dressed down with flats or sneakers. Don’t forget a pair of trendy sunnies and a highlighting balm (thank you, Merit) to keep the glow going.
Dipped-Waist Smocked Midi Dress ($110, Abercrombie & Fitch)
Tenly Toe Strap Sandal ($49.99+, Sam Edelman)
FEISEDY Vintage Square 70s Flat Aviator Sunglasses ($13.58+, Amazon)
Large Handknotted Packable Tote Bag ($128, JCrew)
Solana Gold Earrings ($38, Baublebar)
Merit Day Glow Dewy Highlighting Balm ($32, Sephora)
European City

No matter which city you’re headed to, a solid pair of jeans and a high-quality blazer will never steer you wrong. Short booties are a little more elevated than sneakers, but this pair won’t cause blisters after walking all day. Finish it off with a chic and roomy crossbody and classic (but not flashy) watch. Trés chic.
Bella Stretch Barrel Jeans ($50, Quince)
Naturalizer Jada Bootie ($175, Nordstrom)
100% Leather Blazer ($250, Quince)
SoSoft Cropped Cardigan Sweater ($32.99+, Old Navy)
Dagne Dover Mara Phone Sling Crossbody Bag ($75, Nordstrom)
Breda Jane Watch ($156, Revolve)
Outdoor Adventure

Just because you’re hiking, doesn’t mean you can’t look stylish. FP Movement’s trendy jacket is water-resistent and lightweight, but cute enough to wear out. Throw it on over versatile hiking pants and a sweat-wicking basic long-sleeve shirt. When it comes to footwear, we’re going with a pair of waterproof and slip-proof sneakers that are equal parts functional and fashionable, so you can hit the bar for a celebratory post-hike drink without having to do a full wardrobe change.
Dance Studio Mid-Rise Jogger Full Length ($98, Lululemon)
Cloudhorizon Waterproof ($200, On)
Crossbody Bag ($24.90, Uniqlo)
Lightweight Long-Sleeve Crew Base Layer Top ($39.95, REI)
Happy Camper Pullover ($148, FP Movement)
Aprés-Ski

Even if you’ve never touched a ski in your life, you can still have a great time with the aprés-ski crowd. Keep cozy in this oversized turtleneck from Everlane, warm leggings, and these under-$30 cashmere gloves from Quince. Throw your Kindle into a faux-fur tote, and don’t forget to accessorize with a beanie and standout earrings. Spiked cocoa in the jacuzzi, anyone?
The Boxy Turtleneck in Everyday Cotton ($138, Everlane)
Women's Capilene® Midweight Bottoms ($89, Patagonia)
Dôme Huggies ($58, Mejuri)
Sorel Explorer™ III Slip-On Cozy Waterproof ($108+, Zappos)
LAMARQUE Zoey Tote ($145, Revolve)
Mongolian Cashmere Gloves ($29.90, Quince)
The Cabin Beanie ($58, Everlane)
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