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The Secret to Wearing Boots with Shorts


I have to admit, when I first thought about wearing boots with shorts all I thought about was the cute little starlets I’ve seen sporting  the look in fashion mags. I mean, I can wear boots with a skirt or dress every day of my life, but shorts? And then I realized: I’m a grown woman and I can wear anything I want to. And so can you when you know my secret.

The look I’m going to focus on for this post will feature one of my favorites: cowgirl boots. Whether short or tall, blinged out or laid back, whether you are in the North or the South, cowgirl boots with shorts is a winning look when you do it the right way. The winning looks have nothing to do with how old the wearer is or what size she wears. To successfully wear this look, the only secret you need to know is how to work with balance and proportion.

boots with shorts

First we’ll start with the individual pieces:


Cowgirl boots are a way to elevate any look. Most wearers pick a boot with a slight heel, which of course is very flattering to the line of the leg. Pairing boots with shorts is a great way to flatter your leg and an alternative to wearing heels, which sometimes can feel too dressy. For my leg, I prefer a taller boot. A shorter boot that hits right at my ankle is not at all flattering – the reverse effect of pants length, where I prefer an ankle length pant. (Ankle height boots might work for you if your leg is more of a uniform width or if your legs are shorter – more skin makes them look longer.) A taller boot that hits me mid-calf is so much better for me because it gives my legs the appearance of being a more uniform width.


Because your boots will really highlight your legs, you want to get the length of your shorts right. When trying on shorts I realized very quickly I should never wear 3.5″ length shorts! It couldn’t have been less flattering on me — it made my legs look out of balance. Longer 5″ shorts were so much better. Why? Because of where they hit my leg. They come far enough down to create a flattering line. The shorter shorts emphasized the widest part of my thigh whereas a longer short hit on a more narrow part, creating a leaner line. What works for my leg won’t necessarily work for yours and vice versa, so use a critical eye and try on a couple different lengths.

Now let’s put it all together:


Say you’ve picked a shorter pair of shorts and a taller boot with some embellishments. You can balance these pieces with a longer sleeve, loose fitting shirt in a solid color. Always add accessories for visual interest. Here’s a great example of a balanced, modest look featuring shorts with cowgirl boots that gets balance and proportion right:

boots with shorts
A great modest look, getting the boots with shorts look right. (Image via Country Outfitter)

When I talk about “balance” I am referring to the amount of skin being shown but also to how dramatic (or not) any of the given pieces are. Most of us want a healthy dose of balance in our everyday style. This can be accomplished by showing less skin on your arms if you are showing more on your legs, or choosing a less ornate top if your boots have lots of detail. NOT adding a necklace might make the outfit too plain, but just the simple addition of the necklace balances the look above. Proportionally, this look wouldn’t work as well with longer shorts. It would make her legs look shorter. We can use the lines of our clothes to redirect the eye, remember?


For me, adding boots to an outfit with shorts is something I’d do on a special occasion, not for my weekly grocery store trip. So, where are you going?

Below are a few looks to give you more ideas. A longer, looser peasant-type blouse with denim cutoffs and boots would be a nice look for a date night, and a way to add some drama without adding the skin involved with high heels. A looser tank (to balance the tighter shorts) with the boots would be a great choice for an outdoor concert, especially if you have lawn seats and want to protect your toes and ankles from critters. And if you happen to have a local team you root for, your boots might be apropos for a game-watching-gathering, particularly if your team has a name like my local NFL team’s.

Boot & Shorts

This post is sponsored by Country Outfitter. Images of models wearing boots were provided by them. All opinions are my own.

Here are some of my favorite boots:

11 thoughts on “The Secret to Wearing Boots with Shorts

  1. Your Bio photo is darling. Hey, love the title as it states exactly what I found out by reading your article. I had no idea about most of these balance and proportion concepts. This would be a good article for Country Living magazine. You should write to the editor. That staff is very open and creative. Great !

  2. Love this! I am often so late to trends like this. And I don’t own a pair of cowgirl boots, even though I’ve been wanting a pair for years. Might need to go get a pair now!

    1. They are so fun. And surprisingly comfortable! I know they look all pointy, but they don’t feel that way at all. My favorite trends are the timeless ones (can they even be called trends, then?) – I think cowgirl boots are always a win!

    1. Thanks! I know – this is a look that can go wrong in a hurry if you don’t pay attention to how much skin is showing. Cowgirl boots are so great, though. I really think anybody can wear them. Thanks for stopping by!!

    1. Kara, you might be surprised. It’s all about matching short length and boot height to the shape of your leg. If you have shorts that fit you well and hit at a length you like, I’m sure you can find a boot that makes them work. I totally have chicken legs (thighs are too big in proportion to my ankles) but with the right shorts/boots combo I can create the optical illusion of nice shape and length. In the end, it needs to be a look that makes you *feel* good. That is the most important thing.

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  4. As one who has lived through generations of styles, and a Country style fan, the Boots with Jean Shorts (including shorty shorts, shy of showing extra cheeks) are a wonderful look. They turn heads with or without boots, but knock the guys out with that total ensemble. Even Legs that might be a little chunky, the girls look just darn cute. The Cowgirl Boots are best with the jean shorts, as it emulates Country Values and Innocence. Love It! Never give it up girls,even in the wind, sleet, rain or snow. Run for a warm place and be stylish. Turn Heads while you can. To the girls I know that wear this stylish trendy look, I’m told that it is just a comfy style and easy to maintain/wash and slip into every day, Absolutely no place that this style can not be worn. The boots give the jean shorts a dressy look (the shorter the shorts, the more dressy/to a point) so go comfy. Make a few old guys feel young, and show ’em while you got ’em. You’ll know when it’s time to roll down the boy cuff or finally give-up that sexy trendy fashion all-together; however, always acceptable as for hiking, camping or the beach at almost every age.

    Remember when Hot Pants and boots came on the scene back in the 60’s-70’s. Whatta CLASSY STYLE. Let a girl wear shorts into a fancy nightclub where jeans weren’t even allowed. Even then nice looking new shorty short jeans, rolled discreetly with a Boy Cuff were acceptable. Some teens i know today are trending that rolled up cuffed jean shorty shorts and calling them “HOT PANTS” again. Look up “SAVVY HOT PANTS” I run a Pageant “Miss Country Western Pageant” local to California (but anybody can enter/ages 15-28.) giving away $5,000 to the winner. The primary outfit is the Cuffed Jean Shorty Shorts (No Bathing Suits) and emphasis the country girl look. Cowgirl Hats & Boots Required. LOVE THE STYLE! So girls, go for the five thousand dollar winning look and become a cowgirl.

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