A woman’s view of cowboy boots. And how to wear ’em.

Ask A Woman: Pulling off the Cowboy Boot

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Hi Beth

I’d love to know your opinions on cowboy boots.  I’ve been considering getting some for years, but can never bring myself to drop the money on a pair due to my conflicted feelings regarding them.  On the one hand, I think cowboy boots are an American icon, right up there with baseball and apple pie and the like.  Men like Clint Eastwood, James Dean, even Slash, showcase how cool they can be.  However, it seems for every badass cowboy boot-wearer out there, there’s ten others that manage to make them look lame, unstylish, or downright silly.

What’s your stance regarding cowboy boots?  Is it possible to wear them in a cool and attractive way without looking like you’re playing dress-up, or heading to a Billy Ray Cyrus concert?

– Andrew
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Howdy Andrew,

I like cowboy boots.  When worn well, they can be part of a trim, even sleek look.  The operative part of that sentence is “when worn well.”  Andrew, I’m sorry to break it to you…but Slash does NOT wear his cowboy boots well.  He pairs them with skinny jeans (or skinny leather pants) and tucks the pants into the boot.  I realize that the top of most cowboy boots has exquisite leather tooling and stitching…but on men, I don’t like the look of a skinny pant tucked into a boot.  The silhouette is too feminine.  If you think Slash looks cool that way…well, it’s Slash.  He also wears a top hat and leather vests without shirts underneath and his hair is in need of some serious conditioner, but he gets away with all of it because he’s a rock star.  I suspect, Andrew, that you are not a rock star…mmm?

Ted’s Boots from How I Met Your Mother:  1. Don’t tuck in the jeans.  2. Even Slash wouldn’t be able to pull off lipstick red cowboy boots.  But the confidence is commendable. 

So, how does one wear the cowboy boot without making an ass of one’s self?  A question for the ages.  Cowboy boots look best when worn with a slim bootcut pant that is neither too long nor too short.  And now, a few good and not so good cowboy boot looks:

• See how Hugh Jackman’s jeans have the bootcut at the bottom, and the hem just rests on the top of the boot with scarcely a break, but the top of the pant is still fairly close fitting?  See that nice silhouette of solid thigh and straight leg?  That’s golden.  That’s what you want.
• James Dean’s look is harder to analyze since he’s sitting down with his feet up, but it looks like his jeans have a nice bootcut, and the smallest hint of a break.
• Tim McGraw looks pretty good (love the tight fit around the thighs), but I would have liked to see him in shorter jeans–they’re bunching up at the bottom from the excess length, and the bootcut looks too narrow as well.
• Matthew McConaughey is less successful at this look (although the camera angle makes it hard to tell), because his jeans are so baggy.  He’d look much sleeker and more modern with a slimmer fit jean over those boots.
• And then…there’s Benicio Del Toro who–let’s face it–is always a hot mess.  Dude is wearing some nicely textured boots with a pair of baggy, saggy sweatpants.  Um.  Okay.  Hey, at least it’s the fancy sweatpants with the stripes going up the sides.  It’s like the tuxedo of sweatpants.

As for what occasion to where cowboy boots?  Casually with jeans, or more formally with black, brown, or gray slacks.  Please for the love of all that is holy, do not think that you have to go to a Billy Ray Cyrus concert in order to wear your cowboy boots.  Style should be fun, not caterwauling painful.  And, since we’re talking footwear, I’ll make a couple picks.  For those who cringe at spending more than $100 on footwear, if you want to wear decent, real-deal cowboy boots you need to get over it.  Cowboy boots–when done right–are going to be very expensive.  They’re made to last through extreme temperatures, through mud and horse manure, through years of kicking up dust on the prairie.  So you get what you pay for.

This pair of chocolate-toned boats has an awesome name–Mad Dog Goat–and interesting texture on the top of the foot, plus beautiful detailing on the shaft of the boot.  This pair is cheaper by almost $100 and is a good option if you want something a bit showier–the detailing from the shaft goes all the way down to the toe.  Cheaper still, this pair of tan boots with a black heel is simple and constructed for comfort.  And the most economical of the bunch, this pair of short, all black boots with a rounded toe might be the way to start off if you’re not sure whether cowboy boots are for you.  Actually, I take back what I said about needing to spend a lot of money on boots.  If you’re short the dough, try a good thrift store.  You can probably rustle up some decent boots–especially if you live in the southwest part of the country–relatively cheaply.  Double plus bonus?  My Texas cowboy father says they’ll look more authentic if they’re worn in a bit, like you’ve been out on the plains lassoing, um…whatever it is that cowboys lasso.

Andrew, if you’re still nervous about wearing cowboy boots out, it may help to practice wearing them in private…like this guy.

-Beth

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