How to Wear Boots With Skinny Jeans: Outfits for Men

The fall/winter uniform.

Wearing boots with skinny jeans is one of my favorite looks for the colder seasons. Dark-wash denim with desert boots is pretty much my fall uniform, while in winter it’s easy to switch in a pair of heavier work boots to survive the cold and icy streets.

That’s not to say wearing boots with skinny jeans isn’t without risk. The biggest of which is thicker boots causing a loss of balance in your outfit and making it look like you have giant feet. I’m especially tuned in to this fear due to wearing size 12.

Nonetheless, there are plenty of ways men can wear boots with skinny jeans and look great throughout the year. Here are some of my favorites.

Outfit One: Skinny Jeans and Desert Boots

Skinny Jeans and Desert Boots

Wearing skinny jeans with a pair of desert boots is an easy look to pull off. As the boots sit low on the ankle it isn’t that different to wearing them with shoes or sneakers. Additionally, the more casual stylings of desert boots means they have a similar level of formality as jeans making them easy to pair together. I wear mine with pretty much any color, form lighter hues all the way through to black.

Outfit Two: With Chelsea Boots

Skinny Jeans and Chelsea Boots

Skinny jeans with Chelsea boots is a strong look and one that works especially well in less casual settings. Think about wearing them when there is no formal dress code but you want to avoid looking too casual. I typically wear Chelsea boots with black or dark blue jeans as these shades are a bit smarter.

Outfit Three: With Suede Chelsea Boots

If you like the shape of Chelsea boots but want something less formal, consider getting a suede pair. These go great with casual outfits, while providing the same silhouette as their leather counterpart. Pairing boots with light blue jeans and a casual t-shirt as per the image above is a cool look that is easy to pull off.

Outfit Four: With Worker Boots

Skinny Jeans and Black Boots Outfit

I love my worker boots as they do such a great job of keeping my feet warm and dry in winter and late fall. The boots in the image above are a casual style but the black color means I don’t mind wearing them to the office when I have to. As these boots are higher and chunkier than the others on the list, I’ll typically turn up the bottom of the denim a few times when wearing them. You could even pull them all the way to the top to show off the boot in its entirety.

Skinny Jeans and Work Boots

Outfit Five: With Brogue Boots

Brogue boots are a brilliant type of boot to wear with skinny jeans. Despite them typically going quite high, they stay thin around the ankle which reduces the chance of them bunching up. They go well well with casual outfits as per the image above, or you can choose a darker pair for more formal outfits.

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Duncan Elder

Duncan is the founder and editor-in-chief of The Boardwalk. He's a menswear writer who has spent the last 15 years developing his own sense of style, which lies at the cross-section of mid-noughties indie and Uniqlo-inspired minimalism.

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