The Dress Trend Everyone Will Wear With Boots in a Matter of Days

Just because summer has abandoned us, that doesn't mean you must resign yourself to months of wearing only pants. In fact, there's a new casual dress trend the fashion crowd has wholeheartedly embraced, and it happens to look amazing with boots. If those oversize (often baby doll) dresses that were all over the streets of fashion month come to mind, you're correct. As the month progressed, more and more show attendees started pairing them with boots. 

Now that temperatures have finally started to drop and October is in full swing, you too might want to consider wearing one of these comfortable dresses with boots. It's the perfect outfit combination for this time of year, and if you want to hang on to it through winter, simply add a pair of tights and a coat of your choosing and be on your way. 

Keep scrolling for a hefty dose of styling inspiration, and shop a few oversize dress–and-boot pairings we love.


(Image credit: The Style Stalker)

Western boots and baby doll dresses look surprisingly cool together.


(Image credit: The Style Stalker)

Love the contrast of this boho dress with patent-leather knee boots.


(Image credit: The Style Stalker)

Wearing a long oversize dress with chunky boots feels unexpected in the best way possible.


(Image credit: The Style Stalker)

Between the lug-sole boots and the hot-pink oversize dress, there are a lot of trends happening here, and it works.


(Image credit: The Style Stalker)

Layering an oversize sheer dress over a sweater is the perfect way to combat the fall chill.


(Image credit: The Style Stalker)

White boots look so fresh in this instance.


(Image credit: The Style Stalker)

Scandinavian girls have really perfected this look.


(Image credit: The Style Stalker)

If your dress is particularly long, consider platform boots.


(Image credit: Edward Berthelot/Getty Images)

This is basically the perfect fall outfit, if you ask us.


(Image credit: The Style Stalker)

Bonus points if your dress has puff sleeves.

Shop the Look

Baby Doll Minidress + White Ankle Boots

Puff-Sleeve Dress + Kitten-Heel Boots

White Dress + Western Boots

Oversize Midi Dress + Knee Boots

Tiered Maxi Dress + Western Knee Boots

Sheer Babydoll Dress + Combat Boots

Next up, 21 affordable ankle boots that are even better than designer.

Allyson Payer
Senior Editor

Allyson is a senior editor for Who What Wear. She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories for Who What Wear. Prior to her career in fashion, Allyson worked in the entertainment industry at companies such as Sony Pictures Television. Allyson is now based in Raleigh, North Carolina, and is originally from Baton Rouge, Louisiana. She holds a BFA in theater. Her path to fashion may not have been linear, but based on the number of fashion magazines she collected as a child and young adult, it was meant to be.