What to Wear With Cowboy Boots: 5 Outfits for Women

Cowboy boots go with far more than people expect. The women who come in worried they can't pull them off are almost always picturing a costume, when the boots actually work best as one western piece in an otherwise ordinary outfit. Here are five combinations we see work, and the handful of rules underneath them.

The short version:

• Jeans go over the boot, hemmed long enough to reach the heel.
• With a dress or skirt, keep the hem well above or well below the top of the boot shaft, never level with it.
• One western piece anchors an outfit. Three or more starts to read as a costume.
• A brown or cognac boot goes with more of your closet than a black one.

The mistake is dressing around the boots

The most common thing we see is someone buying a good pair of boots and then feeling like they need the whole outfit to match: fringe, a hat, a concho belt, a bag in the same tooled leather. It rarely looks the way they hoped, because everything is competing.

Boots are a strong piece on their own. Put them with clothes you already own and already wear, and let them be the thing people notice. A pair of cowboy boots with plain jeans and a white tee reads as style. The same boots with four other western pieces reads as an outfit someone assembled for a photo.

Five outfits that work

1. Jeans and a plain tee

The one you'll wear most. Bootcut, straight leg or a relaxed flare, in a length that reaches the top of the heel in back and stays there when you sit down. For most people that's one to two inches longer than the inseam they'd buy for sneakers. Tuck a simple tee in at the front, add a belt, and stop there. If you're not sure about hem length, we wrote a whole guide on how to stack jeans over boots.

2. A midi dress

A dress or skirt that hits mid-calf or just below the knee is the easiest thing to wear with boots after jeans. It gives you a few inches of leg between the hem and the top of the shaft, which is what makes the proportion work. Prairie dresses, shirt dresses and simple knit midis all do this. Browse women's dresses if you're starting from scratch.

3. Shorts or a denim skirt in summer

Shorter hems go better with a shorter boot. A bootie or an ankle-height western boot keeps the whole thing balanced, where a 13-inch shaft under denim shorts leaves very little leg showing. Look at booties for this one.

4. Dark denim, a blazer and a snip toe

This is the version that goes to dinner. Dark, clean jeans with no distressing, a fitted jacket or blazer, and a dressier boot — a snip toe or a narrow round toe in a smooth leather rather than a rough-out or a wide square toe. Add one piece of turquoise and leave it at that.

5. The fall layer

Jeans, a sweater, a jacket, and a tall boot. This is where tall boots earn their keep — a 13-inch or taller shaft under a long coat looks deliberate in a way an ankle boot doesn't. It's also the warmest combination on this list, which matters in a Kansas January.

Shaft height decides what you can wear with them

If there's one rule worth remembering, it's this: never end a hemline at the same height as the top of your boot. A skirt that stops exactly where the shaft stops cuts your leg into two equal pieces and makes both look shorter. Go several inches above the boot top or several inches below it.

Most women's western boots run 11 to 13 inches in the shaft, which lands somewhere around mid-calf. Booties sit at the ankle. Tall boots run 14 inches and up. Knowing which one you own tells you which hems are off the table.

Toe shape and heel change the whole outfit

A square toe or broad square toe is the most casual and gives your toes the most room. A snip toe is the dressiest — it narrows to a point and reads sharp with a skirt or dark denim. A round toe sits in the middle and is hard to get wrong.

Heel height matters more for comfort than for looks. A walking heel of about an inch and a half is what most people want for a day on their feet. A taller fashion heel looks good and wears differently, so buy it knowing that.

What color to buy first

If this is your first pair, buy brown. Cognac, tan, chocolate and distressed brown go with denim, with black, with navy and with almost every dress color. Black boots are sharp and read a little dressier and a little edgier, but they narrow what you can put them with. Save the leopard, the turquoise inlay and the bright stitching for pair two, once you know what you actually reach for.

Brands we stock for women run from Ariat and Dan Post through Corral, Circle G and HYER, and they fit differently from one another, which is the other reason to try a few pairs on.

Keeping them looking right

Leather boots you wear often want a conditioner every few months and a day off between wears so they can dry out. Rotate two pairs if you can. Store them upright with boot shapers so the shaft doesn't fold over at the ankle. Our boot care section has conditioners, brushes and shapers.

What to wear with cowboy boots FAQ

What should you not wear with cowboy boots?

Avoid a hem that ends at the same height as the top of the boot shaft. Beyond that, avoid matching your belt, bag and boots in the same leather and color. One western piece anchors an outfit better than five.

Can you wear cowboy boots with a dress?

Yes. A midi length that hits mid-calf or just below the knee works best, because it leaves a few inches of leg between the hem and the top of the boot.

Do you tuck jeans into cowboy boots?

No. Jeans are worn over the boot shaft. Tucking in is for mud, snow and working cattle.

What color cowboy boots are the most versatile?

Brown. Cognac, tan and chocolate go with denim, black, navy and most dress colors. Black boots read dressier but work with less.

Can you wear cowboy boots every day?

Yes, if the heel is a walking height of around an inch and a half and you give the leather a day to dry out between wears.

Come try a few pairs on in Shawnee

Nigro's Western Store has been fitting boots in Shawnee, Kansas since 1973. Stop in at 10509 Shawnee Mission Parkway and we'll measure your feet and pull a few pairs, or shop women's cowboy boots, women's jeans and everything for women online.