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How to Wear Trendy Cowboy Boots

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Considering cowboy boots were just about everywhere during New York Fashion Week for S/S 2019, it only makes sense that we’re watching these classic shoes with renewed interest. Can anyone pull them off, or are they reserved solely for trend-setting models?

The good news: cowboy boots are versatile enough for any aspiring fashion gal to work into her wardrobe. Here’s how to wear this fun Western-inspired style.

How to Style Cowboy Boots


  • Wear cowboy boots with skirts, dresses, jeans and even trousers or leggings.
  • Choose boots with modern styling. Lean towards sleek shapes and understated details.
  • Layer on top with a cardigan or blazer.
  • Keep your boots clean. A muddy boot just isn’t chic.
  • Go monochrome by pairing all-black boots with an all-black outfit.


  • Don’t add lace, fringe or other country-inspired details to your outfit. Let the boots make your Western statement all by themselves.
  • Don’t wear cowboy boots with shorts. Let the celebs have this look. It’s very hard for us non-famous ladies to pull off.
  • Don’t double down on denim. You can pair cowboy boots with jeans — but not jeans and a denim jacket.
  • Don’t bare too much skin unless you’re intentionally channeling Daisy Duke.

4 Cowboy Boots Outfits

1. To Ease In: Cowboy Boots + Maxi Dress

You absolutely can ease into the cowboy boot trend. Translation: don’t feel pressure to go all-out Western with the boots and jeans and belt buckle.

Instead, establish balance by pairing a lower-profile boot with a flirty maxi dress. This combo unites two opposing worlds — which always makes an interesting fashion statement. The leather jacket shown here adds a welcome edge to an already flawless ensemble.

Ariat’s Darlin boots look right at home with your favorite maxi.

2. Cowboy Boots With Casual Duds

If you’re less a jeans-and-tee type and more the kind to wear your casual best even on the most relaxed of days, slip into something like this to pull it off perfectly. The simple black jeans and lean sweater look pulled together with rugged boots and, naturally, a lovely hat to match.

Try Chase & Chloe’s cowboy boots to make this look your own.

3. Blue Jeans, the Classic Pardner

Is there anything more classic than a pair of blue jeans, a white shirt and a pair of cowboy boots? Probably not. This look lets the boots shine and serve as the ensemble’s major statement piece.

All you need is a hat if it’s sunny and a low-slung hobo bag to complete the look. Try SheSole Western Cowgirl Boots.

4. Sassy Style: Cowboy Boots + Short Dress

Just as you can wear them with a maxi, you can easily pair your boots with a shorter silhouette, too.

If you prefer a patterned boot like the style seen here, balance it with a simple, sophisticated dress that allows your footwear to stand out on its own. Definitely avoid wearing a dress that’s country/western in tone — as you might end up with a costume vibe.

Coconuts Pistol Cowboy Boots pair nicely with a shorter hemline.

For more cowboy boot style inspiration, see our Pinterest board below!

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