How to Wear Men's Boots with Jeans

Co-authored by Susan Kim

Last Updated: October 20, 2020

Jeans are versatile enough to match with many different kinds of footwear, including boots. There are a number of ways to wear men's boots with jeans, and the styling varies based on what kind of boots and jeans you have. Depending on what's in your closet, you can tuck, cuff, or stack your jeans so that they go perfectly with your boots.

Method 1

Method 1 of 3:

Tucking Your Jeans into Your Boots

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Fit your jeans into your boots on days with bad weather. Go with slim-fit jeans for this look, as they'll be more cooperative with your winter boots.^{[1]
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Susan Kim
Professional Stylist

Expert Interview. 30 April 2019.} This look is perfect for days where there is slush and snow on the ground because your jeans will be protected from the elements by your boots and will stay clean.^{[2]
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- Make sure the boots you wear for this specific look go up near your quads. This lets you cover a good portion of your jeans and keeps them away from grimy weather conditions.
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Tuck your denim into boots that end below your calf. Try this look in the fall, when you won't need bigger boots to shield your jeans from snow and slush. Work boots that end just before your calf are still big enough to fit the bottom of your jeans. This means that the jeans won't be flopping around outside of your boots, which is a bit of a sloppy look.^{[3]
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- Tucking your jeans into your boots also helps lessen the wear and tear that comes with walking around all day. Not only will your jeans look great because of tucking, they'll last longer as well!
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Grab the fabric right below your knee to see if the fit works. While seated, place your hand below one of your knees and grab a piece of your jeans. You should be grabbing about 1.5 inches (3.8 cm) of fabric or fewer. If you grab more material than that, the bottom of the jeans won't stay tucked and you'll lose that coveted streamlined look.^{[4]
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- Do this before going out. You don't want to spend your day constantly re-tucking your jeans back into your boots.

Method 2

Method 2 of 3:

Cuffing Your Jeans to Complement Your Boots

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Fold up looser-fitting jeans for a more stylish look. To make this cuff, pinch 1–2 inches (2.5–5.1 cm) of your jeans away from the either side of your leg. Then, fold the excess fabric back against your ankle to cuff your jeans. Smooth around the rest of the cuff while keeping your pinched fabric pinned to complete the look. This is called a pin roll.^{[5]
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- The inside of your jeans should be facing outward when this is done. Usually, the inside of your jeans is a lighter shade of blue than the outside.
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Use a double cuff to pair the look with your boots. While a single cuff goes well with shoes that barely reach your ankle, a double cuff is better for boots because it lets you show off the entirety of the boot. All you have to do to get a double cuff is flip the hemline (the bottom of your jeans) back a second time.^{[6]
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- Pinch off 1 inch (2.5 cm) of fabric both times you flip the hemline.
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Stop at a double cuff to maintain a polished look. Rolling up your jeans too many times can create an awkward, unflattering shape. Cuffing is a great way to adjust jeans that are a bit too big or wide around the bottom of your leg, but rolling them up more than twice is excessive.^{[7]
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- Making more than two cuffs can also expose your ankle and create a gap between your jeans and boots. The best cuffing look involves having your jeans end right where your boots begin.

Method 3

Method 3 of 3:

Stacking Your Jeans

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Pair this style with an ankle or mid-calf boot. Stacking jeans means scrunching them up so the fall just above your boots. It's a more casual look than tucking or cuffing and gives you the chance to show off your footwear.^{[8]
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- How much fabric you need to stack depends on the cut of the boot. Ankle boots are smaller than mid-calf boots, so you don't have to scrunch up as much fabric to make the look work.
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Choose slim-fit jeans to make this option work best. Jeans that are narrow around and below the knee are best. The less fabric you have to scrunch up against your boots, the better you'll look. Stacking is meant to be a more effortless look, but too much fabric will make everything look sloppy.^{[9]
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- Avoid jeans that are too tight, as skinny jeans will look disproportionate with a bigger style of shoe.
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Pull the bottom of your pants up around the top of your boots. This is a much simpler process than cuffing because all you have to do is move the hemline of your jeans up to the top of the boot. If a little bit of fabric gets tucked into the boot, that's okay! Just make sure most of it is scrunched up above the footwear.^{[10]
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- If you're serious about this look, buy stiffer jeans that are 100 percent cotton next time you go shopping. Looser fabrics will not hold the scrunch.