Here’s Exactly How to Style Cowboy Boots and Still Look Chic

There are so many cute trends happening right now in the fashion space, and one that I have fallen for in particular is the cowboy boot look. These shoes have come in and out of style countless times, but I think they’ve always been a fun way to add some personality and visual interest to an ordinary outfit.

Another perk to cowboy boots is that they offer a practical and warm shoe option during the winter. With these shoes, there’s no need to wear clunky snow boots or ankle booties everyday. They offer variety and can give you an elevated, put-together look for a handful of occasions.

Also, as this post proves, you can wear cowboy boots with so many different outfits. To ensure that I could get the most wear out of them as possible, I went with boots that had more of a “western” feel rather than a straight up cowboy look.

You can achieve a similar vibe by opting for a pair that looks fairly minimalist—boots without embroidery and those that come in a neutral color are best.

To give you some inspiration on how to style cowboy boots, I’m sharing four cute and simple outfit ideas below.

How to Style Cowboy Boots

Watch Here: Styling Western Boots Four Ways

Outfit #1: Chunky Knit Sweater + Ruffle Skirt

One of the best ways to style cowboy boots is, of course, with a skirt. In my opinion, few things are more fun, flirty, and girly than a skirt with ruffles. The contrast of a dark and tall western boot with frilly smocked material is always a great look.

On cooler days, pair a skirt and boots with a chunky, oversized sweater. A sweater draped over a mini skirt (ruffled or not) always looks adorable. Bonus: Showing your bare legs with a pair of western boots will make your legs look extra long!

I like to add a crossbody bag (like this one) as a final touch, since it can help bring some structure to this outfit and ensure that it doesn’t look too frumpy. Regardless, the boots will serve as the main attraction!

Moano Cotton Voile Skirt

Maje Short Skirt with Smocking & Ruffles

ANINE BING Sydney Sweater

Jacquemus Le Chiquito Moyen Mini Bag

Heartbeat Earrings

Outfit #2: Blazer and Boots

Simply put, this look is chic. Throw on your favorite pair of black leggings, grab an oversized blazer, and finish the outfit with tall black boots. This look is so simple and so easy to recreate with items you likely have in your closet.

I recommend using a simple t-shirt as your base layer—anything in a neutral color is great. I went with a tan ribbed bodysuit to really keep things tailored and clean.

I love the way the velvet material on my blazer mixes different fabrics. Plus, although I’m wearing almost all black, the contrast between the leggings, leather boots, knit top, and velvet jacket creates such a fun look!

Opal Velveteen Tuxedo Jacket

REVOLVE Sandra Top

Evereve Marx Front Slit Legging

Celine Oval Sunglasses

Outfit #3: Mini Dress + Cowboy Boots

Similar to the first outfit, showing off some leg with your cowboy boots will always be a win. Keep in mind that using contrasting styles can create a fun and interesting outfit, as shown here.

For this look, I’ve paired my cowboy boots with a houndstooth mini dress that is fitted but has a little bit of fun flare. This outfit is perfect for a work holiday party (or any party this season!)

I accessorized with a small handbag that won’t draw attention away from the two main characters of this look—the boots and the dress!

Alice + Olivia Velia Mini Dress

YSL Hobo Bag

Outfit #4: Western Look with Cowboy Boots

If any of these outfits really hit on the western theme, it’s this one.

The other three looks use other wardrobe staples to contrast the cowboy boots, but this look is purely cool, cowboy style. To pull this outfit off, grab your trusted pair of jeans, your favorite graphic tee, and an oversized jacket or blazer. To finish things off, add a fun mini handbag or a pair of gold hoop earrings.

This look encompasses all things winter and compliments the cowboys boots the best. You’re sure to be warm and comfy—the ideal combo this season.

ANINE BING Quinn Blazer

ANINE BING Kate Moss Tee

Isabel Marant Brindi Belt

Bottega Veneta Teen Jodie

Which cowboy boot outfit idea is your favorite? Let me know in the comment section below!