Jeans and Boots: 20 Stylish Ways to Wear Them

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Jeans and Boots: 20 Stylish Ways to Wear Them

I don’t know about you all, but when it comes to winter fashion I start to lose inspiration very quickly.

Sure, in December it’s all about festive outfits and holiday parties but by the time January and February roll around I am tired.

The seemingly endless cold and dark winter months always put a damper on the “creative outfits” corner of my brain and I often default to the following outfit formula:

Jeans + boots + sweater = outfit!

But I decided to take a scroll back through my camera roll (the benefits of documenting outfits since I was 18!) to find plenty of examples of different ways to style jeans and boots together.

These 20 outfits are proof that even on the coldest winter days in NYC I can take my outfit formula and run in a bunch of different directions with it.

From understated silhouettes to dramatic faux fur coats, these outfits will provide tons of inspiration for how to pair boots and your favorite jeans this winter.

20 Ways to Style Jeans and Boots

Ankle length jeans

Cropped jeans work especially well with boots for the everyday vibe. The shorter hem keeps the outfit feeling light and balanced and draws more attention to your footwear. You can also wear them with low top sneakers once the weather warms up.

Black boots

Classic black boots ground this outfit and make the jeans feel instantly more polished. Some people don’t like mixing black and blue but I always find them to be super chic. I added a green sequin top and a color block purse to create an unexpected color story.

Black mom jeans

There’s always something comforting to me about mom jeans. Maybe it’s the name or the silhouette but I find that I reach for this style quite a lot. For this outfit, I started with my black jeans and I kept the rest of the look to whites and creams to create a monochrome vibe that will have you set for a day of exploring a new city or running errands.

Black skinny jeans

I know relaxed silhouettes have become increasingly popular, but this is reason number 293 why I will always have skinny jeans in my wardrobe. Black skinny jeans tuck seamlessly into boots of all shapes and sizes, making them a go-to option for me during the winter months. You get the added benefit of a snug fit making sure there are no lumps or gaps in your boots.

Brown suede boots

I didn’t expect to fall as in love with these boots as I did, but brown suede boots add warmth and texture to this simple denim look. Paired with classic jeans in a medium blue wash, they bring the earthy vibes. I also added a brown belt to tie in with the boots and this oatmeal colored oversized cardigan for extra warmth.

Cropped blue jeans

Cropped blue jeans let the boots be the star of the outfit. I find they pair especially well with boots at a mid-calf height, but the right pair of ankle boots could also create a seamless silhouette. I especially love the heel of these boots and how it fades from black to brown, picking up some of the warmer yellow tones in the jacket. Tell me I’m not giving Clueless here!

Cuffed jeans

Not to be confused with cropped jeans, cuffed jeans add a relaxed vibe to any outfit and make it easy to highlight your boots. Rolling the hem slightly gives the outfit more interesting layers and is a great way to BYOT (be your own tailor) and make sure your jeans are the perfect length. I especially love them paired with these studded, biker boots.

Distressed hem jeans

I’m always nostalgic for my edgy era where the jeans were distressed, the t-shirts were oversized and the beanies were ever-present. To bring the distressed denim look into the 2020’s, I recommend keeping the rest of the outfit simple (like this cream cropped sweater) and pairing them with chic accessories like this pair of leopard ankle boots and even a beret.

Leopard boots

Leopard boots instantly turn any outfit into a statement, but I find pairing them with denim to be one of my favorite ways to style them. Keeping the denim simple (a true blue denim or black for example) allows the bold print to shine without overwhelming the look. From there you can keep things neutral or add some color like with this red wrap top.

Light wash jeans

There’s just something about ultra light wash jeans that always makes an outfit feel lighter, even when it’s dark or raining out. I personally love styling these jeans with high contrast pieces like the black studded boots and red sweater shown here. But if you want more of an airy spring look, you may prefer styling them with a pink or cream sweater and some neutral sandals. It’s totally up to you!

Medium wash jeans

These are the jeans I think of whenever I think of Blue Jeans (capital B, capital J). They are super versatile meaning that you can style them with pretty much anything. I chose to keep my outfit base simple here but then throw on this dramatic ombre cardigan to match the fall foliage in Central Park.

Mom jeans

Mom jeans paired with boots create a cool, effortless silhouette. The slightly looser fit adds a relaxed feel while the boots keep the outfit grounded. For this particular look I added a black belt and sunnies to match the boots but threw in a colorful purse that also pulls color from the denim. It’s a great everyday combination to reach for when you don’t know what to wear.

Over-the-knee boots

Over-the-knee boots pair beautifully with skinny jeans for a sleek, elongated look. The longer boot style adds drama while keeping the outfit streamlined. This is a perfect example of how boots can completely define an outfit—just make sure to keep the proportions of the top half in mind so that things feel balanced.

Pointed toe boots

Pointed toe boots instantly make this jeans outfit feel more elevated. The sharp toe elongates the leg and if you choose a boot in a contrasting color like this pair of bright white ankle boots, it will pop even more. I decided to make this outfit a (mostly) monochrome, mod moment but the jeans definitely ground it and make it feel more wearable.

Studded boots

Studded boots bring an edgy twist to any pair of classic jeans. Letting the boots stand out keeps the rest of the outfit feeling balanced and wearable. This is a great way to experiment with trendier footwear without committing to a full statement look. If you want to commit even more to the edgy bit, mix in a pattern like leopard or plaid.

Tan suede boots

Tan suede boots provide some natural colors that can often soften (haha, rhymes!) the vibe of an overall look. For example, I could have styled this outfit with some black ankle boots but it may have felt too harsh. Instead, the tan color softens the other black leather accessories and picks up on the warmth of the top.

Tucked in mid calf boots

Okay, this one requires extra attention to getting the proportions right, but when it hits, it hits. Tucking jeans into mid-calf boots is another great way to get that clean silhouette. This style combo works best with slim or straight-leg jeans to avoid bulk. It’s functional, stylish, and ideal for cooler weather.

White straight leg jeans

This is the newest pair of denim that I’ve added to my rotation and I’m here to tell you, white straight leg jeans paired with boots feels fresh and modern. I personally love white denim all year round (sorry to any Labor Day rule followers) and in this case pairing it with the martini puffer jacket and red purse makes it feel wintery and festive.

White wide leg jeans

There are so many different ways you could style these pants, but I personally opted for some patterns (leopard, again!) and color with the red faux fur coat. White wide leg jeans make a bold statement when paired with boots, since the eye is drawn towards the ground with this silhouette. This look feels fashion-forward while still being very wearable—jeans, coat, boots and you’re out the door!

Wide leg jeans

Wide leg jeans with a relaxed fit and boots can absolutely work together when styled intentionally. The key is choosing boots with enough structure to balance the volume of the denim. In this case, I opted for a Chelsea boot with a very low heel and a slim fit around the ankle. This outfit proves that looser silhouettes can still feel polished, especially when grounded with some pretty accessories.

Which jeans + boots combinations work best?

After trying and testing several different combinations, these are the top three pairings that I’d recommend.

Skinny jeans and over-the-knee boots

This combination is a match made in heaven—or at least your favorite department store. The skinny jeans tuck perfectly into over-the-knee boots and provide extra warmth during colder months.

Straight leg jeans and ankle boots

If you’re looking for a super versatile and classic combo, look no further than ankle boots and straight leg jeans. Start out simple with classic blue denim and black ankle boots and then you can always mix in other colors later on.

Wide leg jeans and mid-calf boots

I personally find this pairing to be so flattering! The wide leg style leaves plenty of room for a mid-calf boot to slip underneath so if you wanted to add more height with a heel or warmth during the colder months, this is a great option.

What type of socks should I wear with my boots?

You definitely want to make sure that you’re comfortable in your boots, so finding the perfect socks to wear with each style is key.

For an ankle boot, I’d recommend a sock in a similar color that comes just above the ankle. This way it won’t overshadow the boots. Just make sure the leather of your boots isn’t rubbing against your ankle.

For a mid-calf boot I’d recommend crew socks. They come up about mid-way on your leg just where a mid-calf boot would.

If your boots are poking out from underneath your jeans, you could even go a little higher and no one would notice.

And finally, for an over-the-knee boot, you can go as high as you want! You may find a crew sock is perfect especially since you’re tucking in your jeans.

For added warmth, you could always do a taller knee-high sock.