The Best Fall Wardrobes for Every Kind of Traveler

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 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

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

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

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

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

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

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

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

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

• Best Fall Boots for Walking
• 7 Must-Have Fashion Accessories for Fall
• 9 Classic Weekend Getaways That Are Better in Fall

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.