Free People, Sydney Dress
Price: $148
freepeople.com

\"PHOTO:
Free People
PHOTO: Free People, Sydney Dress, $148.
>



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

\"PHOTO:
Revolve
PHOTO: Sorel, Ainsley Conquest Shoe, $170
>



Free People, Rare Feelings Maxi Dress
Price: $148
freepeople.com

\"PHOTO:Free
Free People
PHOTO:Free People, Rare Feelings Maxi Dress, $148.
>



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

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



Free People, Modern Femme Vegan Suede Mini Skirt
Price: $60
freepeople.com

\"PHOTO:
Free People
PHOTO: Modern Femme Vegan Suede Mini Skirt, $60
>



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

\"PHOTO:
Revolve
PHOTO: Steve Madden, Rein Bootie, $150
>



The Reformation, Alma Dress
Price: $218
thereformation.com

\"PHOTO:
The Reformation
PHOTO: The Reformation, Alma Dress, $218
>



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

\"PHOTO:
Mango
PHOTO: Mango, Leather Ankle Boots, $149
>



Mango, Flight Button Skirt
Price: $49.99
mango.com

\"PHOTO:
Mango
PHOTO: Mango, Flight Button Skirt, $49.99
>



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

\"PHOTO:
Urban Outfitters
PHOTO: Dr. Martens, Jadon Platform 8-Eyed Boot, $170
>



Free People, Loveless Printed Midi Dress
Price: $168
freepeople.com

\"PHOTO:
Free People
PHOTO: Free People, Loveless Printed Midi Dress, $168
>



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

\"PHOTO:
Nordstrom
PHOTO: Topshop, Arizona 2 Western Bootie, $125
>



Mango, Wool Boots Skirt
Price: $99
mango.com

\"PHOTO:
Mango
PHOTO: Mango, Wool Boots Skirt, $99
>



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