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Here Are The New Dresses To Wear With Your Favorite Pair Of Boots

Start shopping for your fall uniform.

Aug. 18, 2021

For some people, the thought of putting together fall ensembles brings an unspoken rush of excitement. Experts in layering will love the idea of styling a turtleneck underneath a chunky knit sweater while coat lovers can’t wait to break out their many transitional trenches. Before you fully dive into these categories, however, there is one key summer item you can wear well into fall (and even into winter): dresses. In particular, fall dresses styled with boots is a combination worth trying. Celebrities such as Emma Roberts and Cardi B are already embracing this outfit with their Chelsea boots. Meanwhile, Zoë Kravitz likes to style combat boots with her knit dresses for a casual, but edgy feel.

You might think that a dress for fall has to automatically be on the longer end, but that’s not true. No matter how short it is, you can easily throw on a shrunken cardigan or thick outerwear for that coveted fall-layered look. However, if you’re cold averse and can’t stand the thought of exposing your legs to the autumn breeze, there are certain dress styles to look for like knitted long-sleeve options or a maxi number you can tuck a pair of knee-high boots under. (Add in tights if you want extra warmth.) If you’re in need of some new dress options for fall, which you can pair with any boot in your closet, shop the new styles for the season ahead. Give your jeans and sweaters a break this autumn and test drive the dress with boots combo.

We only include products that have been independently selected by TZR’s editorial team. However, we may receive a portion of sales if you purchase a product through a link in this article.

ULLA JOHNSON

Winsor Floral Mini Dress

$475

$190

For a night out with friends, try this flirty floral number with over-the-knee black suede boots. This boot popped up everywhere during Paris Fashion Week.

Ganni

Seersucker Check Smocked Dress in Black

$265

$133

Yes, you can still wear gingham apparel for fall. Make it autumn-appropriate with a pair of black tights and chunky black combat boots. Layer on a cropped leather jacket of your choice.

Derma Department

Else Shirt Dress Taupe

$260

This stunning sandy number can be casually styled with cowboy boots or with a knee-high python print boot for an elegant touch.

McQ Alexander McQueen

Zebra Tube Dress

$385

$115

The zebra print trend isn’t going anywhere and this sleeveless dress is a statement piece. Keep your outfit simple with black heeled boots and minimal jewelry.

Lost + Wander

Staycation Mini Dress

$108

A long-sleeve knit dress is a classic for fall, as you can wear it on its own or with oversized outerwear when the temperatures dip. Style this look with the Bottega Veneta boots Cardi B recently wore.

Onalaja

Naddie Jacquard Shirt Dress

$430

This shiny floral dress has long sleeves and a midi length that make it suitable for fall weather.

If you’re going back into the office and want to keep that comfort-first mentality from your WFH days, slip into a shirtdress. Style with riding boots and tights for an extra layer.

ULLA JOHNSON

Winsor Floral Mini Dress

$475

$190

When in doubt, wear your autumnal botanical pattern dress with knee-high black boots.

Choux 3/4 Sleeve Mini Floral Dress: image 1

La Double J

Choux 3/4 Sleeve Mini Taffeta Dress

$760

$304

This flouncy dress looks great with slides for the end of summer or with ankle boots come fall.

Balmain

Balmain Polo-style Knitted Mini Dress

$1,457

A LBD is versatile for any occasion and can be worn year round with any footwear. This Balmain number would look great when worn with a chunky boot.

1 People

Calabar Silk Slip Dress

$199

For outdoor fall concerts and events where you want to dress up a little, wear a slip with a leather jacket and ankle boots.

See Rose Go

Go-To Dress

$128

A comfortable everyday dress you can easily slip on when you go apple picking season or cider tasting. To jazz up the look, wear pointed ankle booties that have a slight heel to them.

As you can see, this statement dress pairs perfectly with black heeled boots. Keep the accessories simple to let the colors and patterns in this dress shine.

rag & bone

Stephanie Floral Mini Dress

$495

$347

Don’t hesitate in bringing color into your fall wardrobe by way of this multicolored dress.

Ditch your jeans in favor of a denim dress. Just like your favorite pair of skinnies, this dress will go with any boot you have in your closet.

Off White

Off-white Bold Knit Dress

$358.80

Unlike the Balmain LBD above, this Off-White one is more for a GNO with a deep V-neckline and fitted appearance. White wedged booties look great, but for a snazzier appearance you can wear red crocodile-printed boots.

ZIMMERMANN

Viscose Swing Mini Dress in Pink/Purple Stripe

$550

$275

This ZIMMERMANN number would pair well with knee-high riding boots, dainty droplet earrings, and a high ponytail.

Kirna Zabete

The Tiernan Slip Dress

$395

Similar to the dress that Amal Clooney wore for the Fourth of July, this slip dress is on the longer end. For fall you can layer it with an oversized blazer or cropped jacket, plus ankle booties.

En Saison

Aria Knit Midi Dress

$98

A summer dress you can wear well into fall with the switch of a shoe. Style with your favorite pair of white or black booties.