How to Style Cowboy Boots for Women This Fall and Winter

Cowboy boots have moved well beyond the ranch and the concert crowd. Today they show up with flare jeans, slip dresses, oversized sweaters and long wool coats, and they make simple outfits look more interesting. If you have been wondering how to style cowboy boots for women without looking like you are wearing a costume, the good news is that it is easier than it seems.

Here is how to choose a pair and wear them through fall and winter.

Start with the right pair

Western boots come in many shapes, and the style you pick changes how you will wear them. Think about three things: height, toe shape and detail.

Height

• Ankle height: the easiest to style, especially with cropped jeans and dresses. The Embroidered Suede Cowboy Ankle Boots with Stacked Heel are a good first pair if you are new to the look.
• Mid-calf: the classic cowboy boot height. It works with flare and straight leg jeans worn over the boot or tucked in.
• Knee high: a bolder choice that looks great with dresses and skirts. Try the Knee High Western Boots with Floral Embroidery.

Toe and heel

Pointed toes look sleek and elongate the leg, while slightly rounded toes feel more relaxed. Stacked heels give you a little height and are generally comfortable for walking.

Detail

Plain leather is the most versatile. Embroidery, studs, rivets and rhinestones add personality and work best when the rest of the outfit is simple. If you are only buying one pair, a brown or tan leather boot like the Genuine Leather Cowboy Boots with Embroidered Shaft will go with almost everything.

Outfit 1: Cowboy boots with flare or bootcut jeans

This is the classic pairing for a reason. Flare jeans fall over the boot shaft and leave just the toe and heel showing, which creates a long, balanced line.

• Flare jeans, like our Vintage-Inspired Flare Jeans
• A fitted knit or tucked-in blouse
• Mid-calf cowboy boots in brown or black
• A denim jacket or a cropped trench on top

Keep the top half fitted to balance the flare. A belt with a simple buckle ties it together.

Outfit 2: Cowboy boots with straight leg jeans tucked in

Tucking slimmer jeans into your boots shows off the shaft, which is ideal if your boots have embroidery or stitching worth seeing. Straight or skinny jeans work best here because they sit neatly inside the boot.

Pair with an oversized sweater, like our Oversized Crew Neck Knit Sweater, and a long wool coat for a fall weekend look. Find more denim in our jeans for women.

Outfit 3: Cowboy boots with a midi dress

A midi dress and cowboy boots is one of the easiest fall outfits you can put together. The boots add weight and texture to a soft dress, and the dress makes the boots feel less rugged.

• A denim midi dress, like the Denim Midi Dress with Pockets, or a knit midi
• Mid-calf or knee high western boots
• A cropped jacket or long cardigan

For colder days, add opaque tights. Knee high boots like the Knee High Cowboy Boots with Silver-Tone Rivets cover most of the leg and keep you warmer.

Outfit 4: Cowboy boots with a sweater dress

Sweater dresses and western boots are a cozy winter combination. Choose a ribbed or cable knit dress that hits at or just above the knee, then add mid-calf boots so a little leg or tights shows between the hem and the boot. Finish with a long coat and a beanie for a relaxed cold-weather outfit.

Outfit 5: Cowboy boots with a long coat

Western boots look surprisingly polished with tailored outerwear. A long wool-blend or teddy coat over jeans and a turtleneck, finished with black cowboy boots, has a modern, slightly unexpected feel. Explore coat options in our winter coats for women.

Outfit 6: Dressing up for the holidays

Cowboy boots can absolutely work for holiday parties. Rhinestone or metallic styles, such as the Rhinestone Cowboy Boots, Mid-Calf in Black, add sparkle to a simple black dress or a velvet midi. Keep accessories minimal so the boots stand out. Find party pieces in our holiday party outfits.

Common styling mistakes to avoid

• Going head-to-toe western: one or two western pieces is plenty. Pair boots with modern basics rather than fringe, bandanas and a hat all at once.
• Jeans that bunch at the top of the boot: either tuck slim jeans fully in or choose a flare that falls cleanly over the shaft.
• Ignoring proportion: with knee high boots, shorter hemlines and midi dresses work better than mid-length skirts that end at the same point as the boot.

How to care for your cowboy boots

A little care keeps your boots looking good for many seasons.

• Wipe off dirt and salt after wet or snowy days.
• Let boots dry naturally, away from direct heat.
• Condition leather pairs from time to time to keep them supple.
• Use a suede brush on suede styles and avoid soaking them.
• Store them upright, ideally with boot shapers, so the shaft keeps its form.

Shop cowboy boots at ONORA

Whether you want a classic brown leather pair, bright red cowboy boots or a studded knee high style like the Studded Knee High Western Boots, you will find plenty of options in our cowboy boots for women collection. For more styles, browse knee high boots and fall boots.

Many styles are on sale right now for Early Black Friday. Every order ships free within the US, and you have 30 days to return anything that does not work for you.