12 Fall Dresses to Pair with Boots and Sweaters

Face the autumnal chill in relaxed silhouettes, just-warm-enough knits and easy layering pieces.

by Laura Jackson

four models wearing dresses in a grassy field
Photographed by Emma Summerton for W Magazine.

We love a good pair of jeans topped with a light jacket more than anyone, but sometimes we crave an alternative to the standard fall outfit formula. On days that fluctuate between summery midday heat and crisp, cool evenings, an easy dress paired with boots and a sweater can be the ideal fashion recipe: It feels relaxed and comfortable, but looks stylish and elevated. For weekdays at the office, a crisp shirtdress is a foolproof base; for weekends or nights out on the town, a flirty knit or an off-the-shoulder number fits the bill. We’ve even got you covered for cocktail parties, festive dinners and cool-weather weddings—which are notoriously hard to nail. Here, our favorite dresses of the season, for every occasion.

An All-In-One Cocktail Dress

Who even needs accessories when a print can do all the work? Just add short black boots and you’re good to go.

The Perfect Daytime Mini

A pair of tall brown suede boots and a light cardigan will keep this ‘60s-inspired mini in the 21st century.

A Foolproof Office Ensemble

This is a true all-season dress: wear it with sandals on warmer days, and add an oversized turtleneck and flats for cooler weather.

An Easy Weekend Look

We love this paired with a bright scarf, delicate jewelry and neutral footwear.

For a Casual Date Night

Throw on something with a heel, and add a belted cardigan for the trip to the restaurant.

For a Night on the Town

We love an all-over leopard moment, but if you want to tone the energy down a little, a black sweater on top will balance things out.

When You Want to Show a Little Skin

Perfect for a party or night out dancing with friends.

For an Afternoon of Apple Picking

Emphasize the cottagecore element with a chunky knit and a pair of lace-up boots.

For Meetings or a Business Lunch

Keep this on hand for days when you want to look chic with zero effort.

An Ideal Fall Wedding Look

Nailing cocktail attire in cool weather can be tricky. Keep things fuss-free with this elegant take on crochet.

For a Holiday Dinner Party

A festive print and subtle ruching looks elegant and feels comfortable.

Another Perfect Date Night Piece

Bare a little shoulder in this otherwise neutral piece.