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7 ways to wear fall's best boots: Shop these looks

3:41
How to wear some of this fall's hottest fashion trends
Free People
hinted logo
ByFrancesca Castagnoli of Hinted
October 02, 2018, 8:24 AM

This fall, hems are up, down and everywhere in between, making it the perfect time to show off autumn’s most-wanted boots. Here, we’ve rounded up the trendiest styles and paired them with the season’s hottest looks to create the go-to outfits you’ll wear again and again.

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(MORE: 15 ways stripes can pull your look together)

These products were curated by the Hinted editorial team. Hinted is the social shopping platform that lets you create lists of what you want to buy, and discover what’s new and trending. Use Hinted to keep track of anything you want to buy from anywhere online, including fashion, trips, and experiences. "Good Morning America" has affiliate partnerships, so we will get a small share of revenue from your purchases through these links. All product prices are determined by the retailer and subject to change. By visiting these websites, you will leave GoodMorningAmerica.com and any information you share with the retailer will be governed by its website's terms and conditions and privacy policies.

1. Flouncy + Slouchy

The bohemian’s best bet.

Style Hint: Pair a short, breezy dress with a tall slouchy boot. The combination feels carefree with a touch of edginess. We love these slouchy boots because you can wear them relaxed, or pull them up over your knee to lengthen your legs even more.

Free People, Day-by-Day Slouch Boot

Price: $248

freepeople.com

Day-by-Day Slouch Boot, $248
Free People

Free People, Sydney Dress

Price: $148

freepeople.com

Free People, Sydney Dress, $148.
Free People

2. Maxi + Hiking

Discover the season’s most high-contrast combination.

Style Hint: Fashion’s obsession with the humble hiking boot paired with maxi dresses, proof that beauty and comfort rule this fall. Slip into a long, flowing dress and this go-anywhere boot for an outfit that looks as good as it feels.

Sorel, Ainsley Conquest Shoe

Price: $170

revolve.com

Sorel, Ainsley Conquest Shoe, $170
Revolve

Free People, Rare Feelings Maxi Dress

Price: $148

freepeople.com

Free People, Rare Feelings Maxi Dress, $148.
Free People

3. Sleek Mini + Tall Skinny

The long and short of it.

Style Hint: While a low bootie is the obvious choice with a mini, a tall, a lean boot creates a sophisticated silhouette that lengthens your legs. Here’s proof that showing less can do more.

Sam Edelman, Hai Knee High Boot

Price: $199.95

samedelman.com

While a low bootie is the obvious choice with a mini, a tall, lean boot creates a sophisticated silhouette that lengthens your legs.
Sam Edelman

Free People, Modern Femme Vegan Suede Mini Skirt

Price: $60

freepeople.com

Modern Femme Vegan Suede Mini Skirt, $60
Free People

4. Slit Skirt + Tall Ankle

Strut your stuff.

Style Hint: Diffuse a slit skirt by skipping high heels in favor of a pair of tall ankle boots. When you do, you transform a date night dress into a daytime look that is polished and work-friendly.

Steve Madden, Rein Bootie

Price: $150

revolve.com

Steve Madden, Rein Bootie, $150
Revolve

The Reformation, Alma Dress

Price: $218

thereformation.com

The Reformation, Alma Dress, $218
The Reformation

5. Subtle Suit + Bold Boots

Rethink the power suit.

Style Hint: Up the ante on your work uniform by adding a pair of eye-catching bold booties. We love pairing these stacked turquoise zip-ons with a soft grey skirt to turn a quiet outfit into a fearless style statement.

Mango, Leather Ankle Boots

Price: $149

mango.com

Mango, Leather Ankle Boots, $149
Mango

Mango, Flight Button Skirt

Price: $49.99

mango.com

Mango, Flight Button Skirt, $49.99
Mango

6. Silky Midi + Cool Combats

The new uniform.

Style Hint: Everywhere we look we see delicate dresses paired with chunky combat boots. The stark contrast is part of the new femininity that defines what’s trending: Sophisticated, feminine dressing that shows she is as tough as she is sweet.

Dr. Martens, Jadon Platform 8-Eyed Boot

Price: $170

urbanoutfitters.com

Dr. Martens, Jadon Platform 8-Eyed Boot, $170
Urban Outfitters

Free People, Loveless Printed Midi Dress

Price: $168

freepeople.com

Free People, Loveless Printed Midi Dress, $168
Free People

7. Prairie Plaid + Cowboy Boots

Cowgirl cool.

Style Hint: The way to make the western trend look natural (not like a Halloween costume) is to keep the boots sleek and chic, like these in matte black. Pair them with another fall trend: the plaid midi-skirt worn with a chunky knit.

Topshop, Arizona 2 Western Bootie

Price: $125

nordstrom.com

Topshop, Arizona 2 Western Bootie, $125
Nordstrom

Mango, Wool Boots Skirt

Price: $99

mango.com

Mango, Wool Boots Skirt, $99
Mango

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