How To Wear Jeans with Boots

You already know that fall is boot season. And you’ve done your due diligence by studying up with our Fall Boot Guide. But let’s say you’re more of a jeans guy. How do you wear jeans with boots?

Here are eight of our favorite fall looks that pair jeans with boots.

1. Suede Ankle Boots – Coffee Date

How To Wear Jeans with Boots - He Spoke Style

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Suede boots aren’t your everyday boots, but they’re perfect when you want to make a stylish first impression. We’ve learned recently that women are fine judges of your footwear, and a solid boot game shows that you’ve put some quality thought into your style. Suede boots take it to the next level.

2. Brown Chelsea Boots – Everyday Style

How To Wear Jeans with Boots - He Spoke Style

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Chelsea boots are the loafers of the boots world. They’re comfortable, easy to slip on and are super versatile. My brown leather chelseas are the first pair I reach for in the fall, especially when I’m in a hurry. No fuss and always stylish. Adding a waistcoat to a simple jeans and button-up combo is an easy way to make a good outfit great.

3. Wingtip Dress Boots – Creative Layering

How To Wear Jeans with Boots - He Spoke Style

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Wingtip leather dress boots are the quintessential “dressing up denim” boots. Even if your jeans are a little worn in, a good wingtip dress boot can help tie together an outfit that’s more creative and well-thought out up top.

4. Black Chelsea Boots – Casual Friday

How To Wear Jeans with Boots - He Spoke Style

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Black chelsea boots are your more dressed-up alternative to brown chelseas. If your office indulges in Casual Fridays, that’s a great opportunity to break these out. Paired with black denim (your “in-between dress pant), a crisp white button-down and a sharp leather jacket you’ll transition seamlessly from work to happy hour.

5. Wingtip Dress Boots – Classic Sharp Casual

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Wingtip dress boots are also the perfect pair for a classic sharp casual look – blazer, button-up and jeans. Add in some pattern play, like a nice plaid blazer and brown gingham shirt, for some easy fall style.

6. Desert Boots – Office Apropos

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It’s easy to get stuck in a rut when it comes to dressing for work. That’s why it’s important to think seasonally when it comes to footwear. Swap out your usual shoes for a light suede desert boot to make a subtly stylish seasonal statement at the office.

7. Wingtip Dress Boots – Well-Appointed

How To Wear Jeans with Boots - He Spoke Style

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Like the third look, this one is all about a few well-appointed accessories balancing the wingtip dress boots. As the temperatures start to drop, add a waistcoat, a lightweight silk scarf and wool newsboy cap for warmth.

8. Casual Boots – Easy Weekend

How To Wear Jeans with Boots - He Spoke Style

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Don’t forget your casual boots! If they’re newer and still in decent shape, you can still wear them with dark denim. A good way to add a touch of ruggedness to a fall weekend look.

Search the Style Guide for more fall outfit inspiration.

Thanks for reading.

Stylishly Yours,

Brian Sacawa
He Spoke Style

Photography by Rob McIver Photo

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