How To Wear Cowboy Boots

September 21st, 2009 by crystal

I went through a serious western-wear phase when I was about 13. I had recently moved to Texas and became quite taken with the whole cowgirl look. It’s embarrassing to admit this, but my favorite outfit was a pair of purple Rockies (you know, the pants with no back pockets…), a very western shirt and tall white boots with–get this–fringe down the sides. I was a sight. To say the least…

I’ve come a long way since then. Thank goodness. But, because of that awkward time, cowboy boots have always made me cringe a bit. Until recently.

Cowboy Boots are quite trendy this season, and not just for rodeo attendees. Depending on how you wear them, they can appear ultra-feminine, super edgy, good girl preppy or country chic. Style cowboy boots they way you would any other item–with your own style and comfort in mind. Assemble an ensemble that is creative and unique, using cowboy boots to highlight your personal flair.

Here is a guide on types, trends and ways to wear cowboy boots this Fall.

Types of Cowboy Boots for Fall 2009

Traditional

Wear With: Traditional cowboy boots can be worn in many different ways as I’ll demonstrate below. For a very Western look, pair with boot-cut jeans and a plaid shirt. For something still Western, but a little more Rodeo Drive than Rodeo, wear that plaid shirt over a pair of ripped leggings.

Ankle

Ankle cowboy boots are a super cute option that we haven’t seen much of in previous seasons. Wear With: Wear ankle cowboy boots the same way you would other ankle boots. Skinnies, dresses and leggings are all great outfits to wear with ankle cowboy boots.

Heeled

Wear With: Wear heeled cowboy boots over a pair of skinny jeans to lengthen the leg.

Slouchy

Slouchy boots are a nice in-between option if you don’t want to look too Western. Wear With: Slouchy boots look great with skinny jeans or leggings, but they are particularly fetching when worn with dresses and skirts.

How To Wear Cowboy Boots

Cowboy boots can be worn a variety of ways. In the past, we’ve seen them worn under jeans, with denim skirts, with sundresses and with full skirts. While it’s not a fashion faux pas to wear cowboy boots any of those ways this Fall, those are no longer the most fashionable ways to wear them.

This Fall, we’re seeing cowboy boots worn in ways that are much more appealing to a wide range of styles.

With Skinny Jeans

Shown: Stetson Boots, Victoria’s Secret Top, Gap Always skinny Jeans, Nordstrom Four Strand Long Necklace

With a Dress

Shown: Stetson Boots, JCrew Paisley Dress, Banana Republic Cardigan, Nordstrom Glass Pearl Necklace

With Tights or Leggings

Shown: Stetson Boots, Nordstrom ‘Denim’ Leggings, Victoria’s Secret Tunic

Quality Cowboy Boots Under $100

Will you be wearing cowboy boots this Fall?

I’m a big fan of all of these looks and will be donning cowboy boots for the first time since my kicker teen days. Will you be wearing them?
If so, how will you wear them?

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5 Responses

myvogue Says:
September 23rd, 2009 at 5:18 pm
to me the best match for cowboy boots are the boyfriend jeans as they are more loose on the legs and will fit perfectly that type of boots which are too wide on top for leggings or skinnies.
crystal Says:
September 25th, 2009 at 9:38 am

Hmmm…that may be. I think most cowboy boots for this season have the styles in mind. The pair I just purchased would be too skinny on top to fit over boyfriend jeans. They work SO well with skinnies, bare legs and leggings!
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Allyson Says:
February 7th, 2010 at 9:52 am
Just got the cutest pair of gray distressed cowboy ankle boots at ALDO..they are SO comfy and CUTE!! I wore them with gray skinnies and a navy tunic….got lots of compliments! The ankle cowboy boot is a great alternative to ballet flats too! Will definitely be wearing these a lot!