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The Best Fall Wardrobes for Every Kind of Traveler

It’s time to get your fall wardrobe ready for another season of color-shifting foliage, cinnamon-spiced everything, and, of course, excellent fashion. There are as many ways to experience the season as there are to dress for it.

The Weekender: Men

Fall is a great time of year to get away for the weekend, whether you’re exploring a new city or escaping to nature. Stay comfortable but casually fashionable with leather boots, slim-fit pants, and a shirt. Top it all off with a hooded sweater that will keep you warm in cooler weather and elevate your style.

Shop the Look: Jacquard Shirt, $30; Plain Toe Chukka Boot, $90; Knit Hooded Sweater, $18; Slim Khakis, $36

The Weekender: Women

The Broadcast Coordinator Dress from ModCloth is a super-versatile dress that’s perfect for switching up your weekend looks. Give the dress an edge with a black bomber jacket and comfortable combat boots or dress it up with a statement necklace. And of course, you’ll need chic a chic weekend bag to complete the look.

Shop the Look: Broadcast Coordinator Dress, $80; Leather Duffle Bag, $350; Sweater Combat Boots, $18; Leather Bomber Jacket, $148

The Leaf-Peeper: Men

For casual strolls through multi-colored forests, you’ll want to don some of fall’s vivid hues. Pair casual jeans and a light earth-toned jacket with the multi-toned Tynedale boot and burnt-orange sweater for breezy fall style.

Shop the Look: Crew Neck Sweater, $80; Straight Fit Jeans, $119; Casual Cotton Jacket, $40; Tynedale Boot, $80

The Leaf-Peeper: Women

Fall is the best time of year for accessories, so begin your day of leaf-peeping with a basic tee and leather skirt. Then, add on a floppy hat and scarf to complete the look—the bigger the better.

Shop the Look: Leather Mini Skirt, $70; Willamette Scarf, $25; Floppy Hat, $12; Side Split Tee, $15

The Euro-Tripper: Men

It’s no secret that fashion in Europe operates on a higher level, so if you’re visiting the continent during fall, make sure to bring a wardrobe that’s comfortable, warm, and on-trend. Pair a neutral-colored Oxford shirt and Banana Republic’s Traveler Jean with a stand-out leather jacket and an understated scarf.

Shop the Look: Oxford Shirt, $30; Scarf, $10; Leather Jacket, $47; Traveler Jean, from $49

The Euro-Tripper: Women

Bring your wardrobe to the European level with a trendy blouse paired with a classic leather skirt. You’ll also need to bundle up against Europe’s colder weather, so stay comfortable with knee-high riding boots and a cozy infinity scarf.

Shop the Look: Riding Boots, $185; Fashionable Blouse, $45; Leather Skirt, $70; Infinity Scarf, $11

The Hiker: Men

If you’re taking a more rugged approach to fall you’ll need sturdy clothes, but that’s no reason to throw fashion out the window. Match a high-performing jacket and all-season pants with a thick beanie for a stylish outfit that will also deliver on the trail.

 Shop the Look: Cardigan Fleece Jacket, $89; Quandary Pants, $79; Burgundy Beanie, $20

The Hiker: Women

Keep it casual but chic on your autumn hike with a long tunic, athletic tights, and light-knit beanie. Danner’s hiking boots will spice up any outfit with their signature red laces,  and are sturdy and comfortable enough for high-difficulty trails.

 Shop the Look: Toad & Co Tunic, $79; Slouchy Beanie, $10; Athletic Tights, $70; Cascade Hiking Boot, $236

The Vacationer: Men

If you’re looking to stretch out your summer vacation by heading somewhere tropical, you can still dress to fit the autumn season. Keep things earth-toned but casual with neutral-colored shorts, a pair of Vans, and a graphic tee. This light bomber jacket from Fabletics is perfect for covering up and transitioning between cool and warm weather.

Shop the Look: Bomber Jacket, $25; Rivington Shorts, $40; Pineapple Tee, $20; Vans Sneakers, $40

The Vacationer: Women

Stay cool in warmer weather with these Salt Water Sandals and lightweight Elephant Pants. Add some classic accessories like the Collar Necklace and a straw hat, perfect for a walk on the beach or brunch in town.

Shop the Look: Elephant Pants, $24; Floppy Wool Hat, $20; Salt Water Sandal, $42; Collar Necklace, $38

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Jamie Ditaranto is a writer and photographer who is always looking for her next adventure. Follow her on Twitter @jamieditaranto.

Editor’s note: This story was originally published in 2016. It has been updated to reflect the most current information.

We hand-pick everything we recommend and select items through testing and reviews. Some products are sent to us free of charge with no incentive to offer a favorable review. We offer our unbiased opinions and do not accept compensation to review products. All items are in stock and prices are accurate at the time of publication. If you buy something through our links, we may earn a commission.

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