How To Pull Off Jeans And Boots Outfit

Wearing your winter boots and favorite jeans together can look cool—if you do it right. Here’s how.

There’s something to be said about waking up each day knowing that no matter what the weather brings, a simple jeans and boots combo is all you need (for your lower half, anyway) to leave the house in style and fully prepared.

Here are three of our favorite ways to rock our denim atop a pair of winter boots. 

Related: How To Find The Perfect Jeans


If you’re going to tuck your jeans into your boots—a great look for trekking around slushy city streets—be sure to opt for a slim-fit jean (shown above). 

You should be able to grab an inch and a half or less of fabric right below your knee. If the leg is any wider, the ankles won’t stay tucked and you’ll lose the streamlined look.


A photo posted by UGG® for Men (@uggformen) on Nov 17, 2016 at 11:02am PST

Tucked denim looks best with work boots that end below your calf, like those worn by the model above. 

Related: How To Wear Denim Jacket And Jeans—And Actually Look Cool



A photo posted by Timberland (@timberland) on Nov 20, 2016 at 7:05am PST

Compared with tucking your jeans into your boots, cuffing them creates a more versatile look that will work anywhere, from the office to a first date. 

You can get away with a looser fit here—but pay attention to material. Stick to a stiffer fabric so the fold stays in place.


A photo posted by Denny Balmaceda. (@denny623) on Nov 22, 2016 at 7:23pm PST

Opt for work boots or street-friendly hiking boots, like Timberlands or the L.L. Bean boots shown above. 

Bonus points if you’re cuffing selvedge denim; the signature white and red ID tape is a telltale sign your denim game is strong.

Related: How To Cuff Your Denim Jeans



A photo posted by Daniel (@magic_fox) on Nov 21, 2016 at 9:25am PST

“Stacking” your jeans is just fashion speak for scrunching them up. The finished look is effortless, but not sloppy.

It’s a stylistic choice that’s more casual than cuffing or tucking, and good for showing off an ankle or mid-calf boot (see above). We’re partial to this look with a sand-colored Chelsea boot.

Related: 5 Rules of Denim Jeans

Pull the bottom of your pants up so they scrunch around the top of your boot. You can also catch part of the hem in the boot so the jeans stay up. 

If you’re serious about this look, aim for stiffer, 100-percent cotton blends when looking for your next pair of jeans. Looser fabrics won’t hold the scrunch.

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