What to Wear With Desert Boots – 10 Cute Outfit Ideas

Thalita Ferraz // Last Update: September 17, 2022 // 0 Comments

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Are you familiar with desert boots? If your answer isn’t, “yes,” immediately, I bet you’ve probably seen these but aren’t aware of the name―which is misleading, by the way.

Desert boots, are a woman’s version of a Chukka boots, which is a men’s boot. Men get both Chukka’s and Deserts, and the difference is the sole and laces. Desert boots have a rubber sole and 2 holes on each side for the laces whereas Chukka boots have a harder sole and 3 holes on each side for the laces. 

They’re called desert boots because of their history as British military footwear. They’re much more prominent in Europe than they are here, but they’re making their way here in the U.S. 

I’ve been asked about Desert boots. Things like, how do you wear them, what do you wear them with, are they comfortable? Are they dress shoes? All valid questions since they’re typically men’s footwear.

I actually love my husband’s Chukka boots, and sometimes wished that I had them in my size because I’d love to wear them with leggings or skinny jeans. 

Anyone else love their man’s shoe so much but can’t wear it? He only wears his when we go somewhere nice, like for a dinner or event. I definitely would wear them more often and in casual settings. 

So you know what? I want to show you 10 cute outfit ideas on how you can wear desert boots and not look like a guy doing so!

1) Desert Boots With a Denim Skirt

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I wouldn’t say this is quite the summer look since she’s wearing a chunky sweater, but true, desert boots aren’t summer shoes. They’re more a fall and winter shoe, just like how riding boots are more prominent then.

But, I do love the mixture of colors she’s got going on here. Gray and a golden yellow look really good together. It’s a very fall combination, I’d love to even see an eggplant colored sweater with gray, desert boots like these!

Check out my Mustard Sweater outfit, where I’m wearing almost an identical look with a yellow sweater and a denim skirt.

2) Desert Boots With a Black Sweater and Boyfriend Jeans

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Here’s where the men’s fashion inspiration really translates to women’s. It’s like… she took this straight off of her guy and put it on, and it’s super European and cute.  Especially since boyfriend jeans are a thing again.

In men’s style with these types of shoes, it is really common to show off cool patterned socks, so I really love that she added these chunky green socks to be scrunched down. 

Of course, rolling the bottom of the pant legs up is a must to show socks, but you’ll see in some of the next outfits that I’m going to show you that cuffed pant legs is the ultimate way to go when wearing desert boots!

Oh, and we can’t ignore that she’s wearing suspenders over the sweater. This has got to be one of the most comfortable outfits ever.

3) Desert Boots With Khaki Trousers

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I’m loving this palette here. These earth tones are super neutral, plus I’m excited she’s basically wearing fitted slacks. Notice the scrunched chunky socks above the boot and below her cuffed pants.

Her socks and sweater match just like her shoes and pants. It doesn’t look like she’s going anywhere fancy, but she’s going with intention. This is more than just a casual day out look, but it is definitely a casual day out look―if that makes sense.

I’d love to see a collared shirt beneath her sweater with the collar exposed. Maybe with the sleeves rolled up too, it would be a great opportunity to add some color into the outfit although it certainly doesn’t need it.

4) Desert Boots With a Denim Jacket

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There are a lot of layers happening in this outfit. It’s a ton of fun. 

She’s wearing gray, skinny jeans with her desert boots―and they’re not cuffed. This alone changes the vibe of the look. 

You see a plaid shirt beneath a light wash denim jacket and she’s even wearing a thin scarf! So many layers. Her crossbody bag is just about the same color as her shoes and even though I prefer my shoes and bags to match when I can, I don’t dislike this slightly different hue of brown.

5) ​Suede Navy Blue Desert Boots With Tassels

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What is the first thing you noticed when you looked at this outfit? 

For me, it was 100% these awesome navy blue suede desert boots. They are the focal point of this outfit, even though the rest of it is super cute too.

She’s got her jeans cuffed up, so it really draws the eye down to the shoes―and hello! Tassels! I can’t get enough of these. 

Navy blue and camel look really great together, I even like the chunky gray sweater beneath the jacket.  I think it would have been fun to go a little more nautical here and wear a black and white thin striped shirt beneath!

6) Desert Boots With Jeans and T-Shirt

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I fully support and understand wearing a flannel or plaid shirt around the waist. It gives a look of extra oomph of pattern and color without looking like you’re trying. 

Here, you see she’s wearing a darker blue desert boot with her skinny jeans. They’re cuffed, but cuffed low, so you can’t see as much of the leg as you can in the outfit before. Both are totally okay either way, too.

I like that she’s just wearing a plain, gray t-shirt. These shoes don’t need flashy or jaw dropping statement clothing with them. But the addition of the hat is fun because it really takes on that European men’s fashion aspect. 

This is just a cute and casual outfit that you cannot butcher. Anyone can wear it.

7) ​Desert Boots With a White Dress

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A change from the pants, here is a cute way to wear patterned desert boots with a dress and denim jacket! 

Her addition of the denim jacket is perfect because of the blue we see in the boot. The same applies for the dress, she did a great job selecting to wear a white dress with it. 

This is one of those situations where you fall in love with the shoe and you make an outfit to wear with them.  I think they’d be super cute with white pants and a blue blouse, too!

8) Desert Boots With a Vest

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Here’s a cute and casual spring, summer, or even early fall look that anyone could pull off. 

All she did was put a green vest over a white, sleeveless blouse, picked some denim skinny jeans, and added the desert boots. It’s really the opposite of a complex or complicated outfit, although the addition of the vest gives it some depth.

In the event that it is too chilly for a sleeveless, it would be really easy to wear a long sleeve instead, add a scarf, or even wear a different type of vest, like a teddy bear or puffy one!

9) Desert Boots With a Graphic Tee and Blazer

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You’ll hear me time and time again say this: I love blazers. Especially when they’re worn casually. Check out my Plaid Blazer with Jeans outfit, I’m even wearing a graphic tee with it. Gray or even colored desert boots would actually be super cute with it!

So, this outfit alone is mega cute. Like, it would be perfect with pretty much any shoe you own. Heels? Yes. Sneakers? Yes. Flats? Yes. Desert boots? Absolutely.

And how easy is it to put on a graphic tee and jeans, throw a blazer over it and then add boots. Cuff the pant leg bottoms and call it a day!  I’d love to see some striped socks or even a pop of color added to it via socks… or from a purse.

10) Desert Boots With a Dress and Tights

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There is a possibility that these are Chukka boots because of how many times they lace up, but they’re in the same family, so we’re going to run with it.

I wanted to show you that you can wear one of your favorite summer dresses with tights beneath, add a coat, boots, and look cute doing it.

A popular go-to for an outfit like this would be riding boots or even knee high boots, so I love that she’s wearing desert (or Chukkas) with hers. I also think that she could have gone a step farther and added some chunky socks at the bottom, but to each their own!

I wanted to make something known, also. 

The reason I show you guys outfits that are a combination of super fashion focused and a bit more toned down is because not everyone wants that straight-out-of-a-magazine look. Sometimes, that is expensive, or not your taste. Not everyone wants bold outfits. All of it is okay.

What isn’t okay is when you don’t love how you look or when you don’t know how to wear something in your closet that you love. I’m here to help. 

Remember that you’re all beautiful and shoes are our best friends. Please, get yourselves a pair of desert boots if you don’t have one yet. Fall will be here before we know it, and you will not be disappointed with them!

So! I want to hear from you! Which outfit was your favorite? How do/would you wear desert boots? Tell me in the comments below!

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