Editors handpick every product that we feature. We may earn commission from the links on this page.

5 Ways to Style Fall Boots That Actually Look Chic

Now that fall is here, it's time to put away those open-toed sandals in exchange for more seasonally appropriate boots. But now you have to face that eternal fashion struggle: How to style them in a way that looks chic instead of clunky? Here, we've got five perfect solutions, because clunky does *not* cut it.

Product, Brown, Textile, Hat, Denim, White, Style, Fashion, Black, Tan,

Now that fall is here—let's face it, it's nearly October—it's time to put away those open-toed sandals in exchange for more seasonally appropriate boots. But now you have to face the eternal fashion struggle. How to style them in a way that looks chic instead of clunky? Here, we've got the perfect solutions.

Advertisement - Continue Reading Below
1 Saturday Brunching

Venturing outside in the elements to get to that double-bellini weekend meal with your friends? Toss on a pair of durable high-heeled boots to stay warm and look great. Dial up the prep by layering a cashmere sweater over a crisp white button down shirt.

Timberland Glancy Hiker Boot, $129.95, nordstrom.com; Topshop MOTO Mid Blue Ripped Jamie Jeans, $75, topshop.com; Victoria Beckham Denim Stretch Cotton-Blend Poplin Shirt, $355, net-a-porter.com; Givenchy Shark Lock Bracelet in Leather and Palladium-Tone Brass, $575, net-a-porter.com; J.Crew Collection Relaxed Cashmere Pullover Sweater, $228, jcrew.com

2 Leisurely Window Shopping

There's no better weekend activity than strolling past boutiques (and perhaps sneaking in to try a few things on). To make the most of the day, tug on flat boots that go the distance. Be sure you're properly outfitted to slip easily in and out of dressing rooms (read: the more streamlined the attire, the better!) and always layer up in case it gets chilly.

Timberland Whitermore Boot, $239.95, nordstrom.com; H&M Super Skinny Low Jeans, $19.99, hm.com; Saint Laurent Classic Denim Shirt, $850, net-a-porter.com; Burberry Prorsum Wool and Cashmere-Blend Reversible cape, $1,274, matchesfashion.com; Maison Margiela Segmented Ring, $490, farfetch.com

3 Dinner Out

Fabulous but not too fussy is your goal here: Start from the ground up with comfortable and chic black booties; a whimsical skirt paired with a sheer-accented top show just the right amount of skin, while twinkly earrings and a luscious lip make a statements. It's like an LBD, but deconstructed, and way more interesting.

Timberland Glancy Hiker Boot, $129.95, nordstrom.com; Antonio Berardi Silk-Chiffon and Wool-Crepe Blouse, $920, net-a-porter.com; MSGM Heart Panel Wrap Skirt, $186.30, farfetch.com; Ben-Amun Women Crystal Earrings, $260, shopbop.com; NARS Audacious Lipstick, $32, sephora.com

4 Attending an Outdoor Music Festival

To look stylish and perfectly outfitted while enjoying the crisp weather, go for a comfortable daytime dress and knee-high boots. Add a pair of chic sunnies to protect your eyes all day long.

Timberland Savin Hill Tall Boot, $239.95, nordstrom.com; J.W. Anderson Long-Sleeved Corduroy Mini Dress, $1,032, matchesfashion.com; Chloé Cate Simple Bracelet, $441, matchesfashion.com; Tom Ford Marco Aviator-Style Gold-Tone Sunglasses, $440, net-a-porter.com

5 Running Around Town

While it may not be glamorous, spending a day getting all those errands out of the way is an occasional necessity. To keep your pace (and your spirits) up, pull on comfortable military-style boots over flexible leggings and toss a loose t-shirt on beneath an oversized cardigan. Top it all off with a chic fedora to protect your face from the sun as you go!

Shop similar Timberland boots, nordstrom.com; Rag & Bone Leather-Trimmed Wool-Felt Fedora, $195, net-a-porter.com; Michael Michael Kors Panelled Leggings, $134.10, farfetch.com; Jersey Pocket Tee, $25, topshop.com; H&M Long Cardigan, $34.99, hm.com

This content is created and maintained by a third party, and imported onto this page to help users provide their email addresses. You may be able to find more information about this and similar content at piano.io
Advertisement - Continue Reading Below
More From Fashion