8 Ways to Wear Dresses With Boots

Blonde fashion blogger KatWalkSF wearing a turtleneck dress at the Hotel Yountville.

Dresses with Boots a classic combination in the winter.

For this post, I’ve rounded up a few of my favorite ways to pull off this combination. Below I’m highlighting 8 different ways to wear your favorite dresses with boots. Some work for chilly temps while others are better reserved for slightly warmer wintery weather. Still, no matter what the day may look like outside, you’re guaranteed you’ll find some easy outfit inspiration below.

8 Ways to Wear Dresses With Boots 

KatWalkSF at the Ferry Building in the AE Soft & Sexy Plush Shift Dress

Number One 

A neutral palette and white bootie

This simple sweater dress is down to $12 and has been a nonstop staple in my wardrobe. The soft and sexy plush fabric looks just as good as it feels—proof that style and comfort aren’t mutually exclusive. Pair this sweater dress with a white bootie and some tights so that you don’t look as FREEZING cold as me.

Willow & Clay Floral Print Smocked V-Neck Fit & Flare Dress, Dresses with Boots

Number Two

A 90s floral mini dress  (down to $45.15 from $129)

with a lace-up combat boot

Willow & Clay Floral Print Ruffle Trim Poet Sleeve Mini Wrap Dress, Dresses with Boots

Number Three

Another 90s style floral mini dress (down to $38.15 from $109)

but this time with a faux fur coat and neutral suede bootie

Blonde fashion blogger KatWalkSF at RH Yountville in the WAYF Manor Ruffle Bib Mini Dress.

Number Four

A black floral bib dress (down to $112 from $140)

with THICK tights and chunky boots

Blonde fashion blogger KatWalkSF wearing a turtleneck dress at the Hotel Yountville.

Number Five

LBD (down to $29.99 from $59.00)


 Knee High Boots

Banana Republic Leopard Print Ruffle-Cuff Shift Dress, Dresses with boots

Number Six

A leopard shift dress with white booties and sheer tights

ASOS DESIGN shoulder pad mini dress with seams, Dresses with Boots

Number Seven

A LBD with STATEMENT boots

For the Love of Cables Dress, Free People, OTK Boots, Sole Society

Number Eight

A chunky sweater dress (down to $69.95 from $168)

with OTK boots and a floppy hat (also styled here)


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