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Winter Essentials: Mastering Boots and Jeans

Writer's picture: Tom GoedhartTom Goedhart

Boots and jeans – the ultimate base for Fall/Winter outfits – have a special place in the hearts of style-conscious guys (my readers included). Pairing these two right instantly nails a casual vibe, making it a breeze to layer in T-shirts, jackets, and more.

But while it sounds easy, mismatching these staples can mess with your proportions – a look no one’s after. I know plenty of guys who admire boots but stick to sneakers all year, fearing boots are harder to pull off 😆.


If that sounds like you, here are some foundational tips to help you rock boots with jeans!


The Basics of Pairing Boots with Jeans


Get the Balance Right

Balance is everything when it comes to making boots and jeans work together. For instance, ankle-high Chelsea boots and wide-leg jeans? Not the best combo. Instead, pick jeans that complement your boots' shape. Slim-fit jeans usually pair well with most boots, while chunkier boots (like those with commando soles) often look better with straight or relaxed fits.

A quick rule of thumb: if the length and width of your jeans don’t hit just right around the top of your boots, rethink the pairing 😁.

Now, there are exceptions. Guys with a slim build and great proportions can sometimes pull off cropped jeans with boots. Lucky them! 😢

To Cuff or Not to Cuff?

Leaving your jeans uncuffed works, but cuffing adds a clean edge to the look.

Rolling up those pant cuffs will give the outfit a more defined touch.

Cuffing draws attention to your legs, creating a nice transition between jeans and boots. It also shows off the boots more.

Just remember: the larger the cuff, the shorter it makes your legs look 🤣. Stick with smaller cuffs for a cleaner line.


Color Coordination Counts

These days, jeans and boots come in just about every shade. But be cautious – not every color combo will look right 😉

The main rule: avoid colors that are almost identical, except when going for a classic black-on-black look.


Tuck In? Hard Pass

A firm no on this one. Tucking jeans into boots doesn’t usually hit the “cool” mark 😅.


Go-To Combos for Boots and Jeans


All black

From head to toe, black jeans and black leather boots give off serious rocker vibes.

To keep an all-black outfit interesting, add a biker jacket to balance the sleekness of Chelsea boots. The zippers and studs will bring in that edge.


Smart Casual

With office wear going more casual, jeans and boots have become fair game for work style too.

A blazer or sport jacket adds polish, while jeans and boots give it a relaxed finish. Chelsea or Derby boots are classic choices here. Opt for darker jeans to keep it professional. And ditch the distressed denim 😉


Basic Style

For men’s style, "less is more" is a mantra that works 😁. A pared-down outfit makes it easy to mix and match.

Basics like T-shirts, sweatshirts, pullovers, and Oxford shirts are all great with jeans and boots. Stick to plain, well-fitted pieces to keep the look clean.

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