In Which I Thrill You All By Styling Cowboy Boots 5 Different Ways

On a list of the most appealing Wild West-related clothing items, I suppose cowboy boots would land solidly in third place, only after the uber-popular ten-gallon hat and meticulous fringe shirts, and squarely ahead of chaps of any kind. However, on a list of things contained in my closet, boots are the only cowboy regalia that make an appearance.

I went to school down south, so I feel adequately prepared to guide you all through the best ways to style these guys, because I had to watch rednecks mishandle them for four years. The best way to learn a skill is to watch those who don’t have it, I suppose. Shall we?

In a quick apology: sorry for the quality of these photos, the fact that they’re mirror selfies, and for the state that my childhood bedroom is currently in.


The Businesswoman with a Secret

Alternatively titled, “Boots, but who knows?” I decided to go full Laffy Taffy with this one and pair these bad boys with a strawberry polyester suit (and yes, I have tried to get those weird stains out━multiple times. Let’s roll with it). The professional cut of the suit pairs well against the playfulness of the tasseled boots, and no one will even know they’re boots unless you’re feeling particularly Victorian-frisky and wanna show your ankles.

Thrifted homemade (?) suit (similar here and here); Lenni boots

The Southwestern Tuck

Ordinarily, these pants are almost comically flared, measuring 16.5 inches across each pant leg opening. Therefore, they are perfect for what I am hereby dubbing the Southwestern Tuck, black-sheep cousin to the French. Or does Parachute Pants 2.0 sound better? Either way, the striking mushroom shape at the ankle and primary color scheme is working for me.

Edith Young's Reds on the Red Caps in Renaissance Portraits tee; thrifted homemade pants (similar here); Lenni boots

The Austin Powers Bimbo

We’re veering dangerously close to redneck territory with this one, but then again, the finest lines are often the most contrasted. Cowboy boot/dress combos are tricky this way, but the secret is to pick an interesting shape and/or color when choosing a dress. The subtle swirls and sheerness work nicely for offsetting the skater dress-ness of it all, and the purple tights push this look out of country-bumpkin territory and into the eclectic.

Tyler McGillivary early sample dress; generic purple tights; Lenni boots

The Closest to Cowboy We’re Gonna Get

Sometimes you’ve just gotta indulge in the fantasy. This one is cowboy-meets-Romantic-meets-hippie, because in the end, they’re all the same, aren’t they? We’re all just looking for a place to hang our metaphorical spurs. I went with classic denim jeans, flared and rolled to add a bit of texture (not loving the corduroy accents with the radioactive blueberry boots, but live and learn, or whatever). The ruffled Byron-esque shirt is layered under a Woodstock-era vest, and voila. A non-cowboy cowboy, before our very eyes.

Thrifted purple vest (similar here and here); thrifted white shirt (similar here and here); Forenza jeans from denim set); Lenni boots

The Casual Fan

For a more subtle look, just throw on a sweater and some shorts. I picked this one because the bright colors in the sweater complement and accentuate the boots, but don’t think too hard about it. It’s casual, right? Let your boots speak for themselves.

Rafaella sweater; Time and Tru shorts; Lenni boots

Tucking your jeans is now officially reserved for Uggs and Uggs only (although cowboy Ugg boots do exist!). Go forth, be free in your newfound stylistic opportunities. Wild horses, and all that.