Lookbook

There are so many different denim styles available right now and there is definitely something for every person’s preference. Regardless of trends, always go with the type of denim you feel the most comfortable in and will wear the most. I have a variety of different denim styles in my closet that I rotate between though I am really enjoying the resurgence of wide leg denim because they are SO comfortable! LOL But if you need some ideas of what jeans to wear with the boots in your closet or possibly how to style your boots with jeans, hopefully this post will help give you some great ideas.

8 Jeans to Wear with Boots

Barrel leg jeans

These are the trendiest pair out of all the styles of jeans I shared, but this particular pair is not as barrel shaped and the dark wash makes them look super chic. They look great with a fitted boot style or a chelsea style boot.

Kick flare jeans

A kick flare is similar to a boot cut style jean in that they are slim through the leg with a bit of a kick out at the hem. My preference for boots to wear with denim is a pointy toe style because it always elongates and looks very flattering. A pointy toe boot with a bit of a kitten heel would be perfect for this style of denim.

Skinny jeans

I have held on to a few pairs of my skinny jeans because they work great with knee high boots. You can easily tuck them to show off the boot nicely.

Wide leg cropped jeans

This is one of my favorite styles of jeans to wear and I find them so versatile with any pair of boots. They look good with a round toe boot, a pointy toe boot, a flat boot or heeled boot – all boot styles look great!

High rise flare jeans

With a high rise flare style of denim, I would keep it simple and go for a slim pointy toe boot to continue the long line that the denim gives you.

Straight leg jeans

Straight leg jeans have become on the most classic styles to wear and much like a cropped high rise, they also look great with almost any style of boot you pair with them.

Boot cut jeans

Boot cut jeans have the same type of look as high rise flare jeans so once again I would go with a slim pointy toe boot either in suede or leather.

Trouser jeans

While a wide leg cropped jean has more options when it comes to boot styles, a trouser jean often follows the line of a boot cut or high waisted flare jean. A round toe could work but it often doesn’t look as flattering to the voluminous hem as a pointed toe. A pointy toe is a great complement to balance out the fullness of a wide leg jean.

How to Wear Boots With Jeans

Cardigan | Jeans | Boots (similar) | Sunglasses | Bag (similar)

Trouser Jeans with Pointy Toe Boots

A long trouser style jean can look so chic and polished so I like to dress it up with pointy toe boots. Trouser jeans really help to elongate your legs so its best to continue that long line with a pointed toe. Also the slimmer tip of the boot will balance out the proportions perfectly.

Cardigan (similar) | Jeans (similar) | Boots | Bag | Sunglasses

Wide Leg Jeans with Pointy Toe Ankle Boots

This is a similar style to the trouser jeans, but a wide leg jean is often a tad shorter and not as exaggerated. I definitely prefer a pointy toe boot with a wide leg style but a slim round toe could work just as well.

Sweater (similar) | Jeans | Boots | Bag | Sunglasses

Flare Jeans with Pointy Toe Ankle Boots

While these are technically a slit hem instead of a true flare, they definitely give the same look a pair of flare jeans. They are slim through the legs and flare out at the hem. Much like a trouser style jean, I like flare jeans worn with pointy toe boots. You can choose a higher heel if you need the added height if the jeans are long, or a kitten heel if you are taller and don’t need the added inches.

Coat (similar) | Sweater (similar) | Jeans (similar) | Boots | Bag | Sunglasses

Skinny Jeans with Knee High Suede Pointy Toe Boots

No other denim style will ever work tucked in to a pair of knee high boots like a skinny jean. It’s truly the best fit for a knee high boots outfit like this and really allows the boots to be shown completely. It’s best to opt for a non-distressed pair of skinny jeans to keep the look modern and fresh.

Sweater | Jeans | Boots | Bag | Sunglasses

Straight Leg Jeans with Pointy Toe Boots

The closest style of denim to a pair of skinny jeans are straight jeans. They are still slightly fitted through the leg but don’t cling to the ankle like a skinny jean. It’s a more updated and modern take if you want something only slightly different from your favorite skinny jeans. My first choice will always be a pointy toe boot but if you have a round toe or square toe, it would also work well with a straight leg jean. An ankle bootie is a must with a style like this because a knee high boot style is too bulky to fit under a straight leg jean. For more ideas of how to wear ankle boots with jeans, check out this post.

Cardigan (similar) | Jeans (similar) | Boots | Bag | Sunglasses

Cropped Wide Leg Jeans with Pointy Toe Boots

I’ve been wearing cropped wide leg jeans for almost 10 years and they are still one of my favorite styles. They are perfect for me specifically because I am on the shorter side so cropped jeans are always full length for me. I love that they allow me to really show off the boots or shoes I’m wearing in a nice way because of the slightly shorter length. Cropped wide leg jeans much like straight leg jeans really look great with a wide variety of boot styles.

Shirt (similar) | Jeans | Boots | Bag (similar) | Sunglasses

Slim Straight Jeans with Pointy Toe Boots

Another style of denim just one small step away from skinny jeans. These are a slight mix between a slim straight and a skinny jean but the ankle one again doesn’t cling quite as tight. I love the lengthening effect of a slim straight jean and often will pair that with a pointy toe ankle boot to continue the long line of the jeans.

Jacket (similar) | Turtleneck | Jeans | Boots | Bag (similar) | Sunglasses

Straight Leg Jeans with Chelsea Boots

Here’s a great casual look with straight leg jeans and a pair of round toe chunky chelsea boots. They are the perfect style to wear with almost any boot that you have!

Coat (similar) | Sweater (similar) | Jeans | Boots | Bag | Sunglasses

Straight Leg Distressed Jeans with Pointy Toe Ankle Boots

These jeans are actually the exact same as the outfit above this one but I wanted to share because it is a good example of the versatility of straight leg jeans!

I have come to love winter and the cold weather because I love to be cozy. Cozy at home or cozy when I go out. I actively seek out clothes that allow me to be super comfortable when I go out but still look cute and put together. My biggest tip when dressing casually for winter is to wear matching sets. There are so many chic athleisure brands and pieces available now and you will instantly look put together when you wear something that matches. Also, I still stick to the basics when it comes to my winter wardrobe. Neutrals and classic shapes allow me to get dressed in an outfit that keeps me warm and cozy but still looks elevated and polished. Here are some examples of past cozy winter outfits that I have worn and love.

Cozy Winter Outfits

Puffer Vest and Matching Sweat Set

Sweatshirt | Sweatpants | Vest | Sneakers | Bag | Sunglasses

I’m well aware that for some places, this out is NOT WARM ENOUGH. Lol But that being said, for many places it is plenty warm for mild winters. A simple puffer vest and a matching athleisure set is one of my go-to looks all fall and winter. To make this outfit a tad warmer, you could add socks and a base layer under the sweatpants and joggers. I love the high collar of this sweatshirt because it keeps my neck warm without feeling like I’m suffocating. I also love wearing a vest because it does add an additional layer without making me feel too overstimulated and weighed down.

Long Puffer Coat and Matching Athleisure Set

Coat | Sweater | Joggers | Sneakers | Bag | Beanie | Mittens

Here is nearly the exact same look with my favorite maxi length puffer coat. An all monochromatic look always looks instantly polished despite that fact that I am literally wearing sweatpants, a knit and sneakers. Adding some fun accessories like these fingerless mittens and a cute beanie will keep you even more cozy and give the outfit some more interest.

Oversized Tunic Sweater and Jeans

Coat | Sweater | Jeans (similar) | Shoes | Bag | Sunglasses

This long puffer coat is a favorite for the winter. It looks great with athleisure and slightly more elevated look as well. I have a few oversized tunics from Amazon that I wear all winter and this is one of them. It has a nice roomy fit and the added length keeps me nice and warm. Simple straight leg dark denim is always a classic any time of year and these fuzzy slides were an impulse purchase yet have proven to be one of my favorite cozy shoes to wear all winter.

Teddy Coat and Knee High Boots

Coat (similar) | Sweater (similar) | Jeans (similar) | Boots | Bag | Sunglasses

Cozy winter outfits don’t have to just be casual. I love a warm sweater, jeans and knee high boots as my one of my go-to winter looks. A fuzzy teddy coat is a great alternative to a puffer coat if you want something you can dress up more often.

Wool Coat and Wide Leg Trousers

Coat | Turtleneck | Trousers | Sneakers | Bag | Sunglasses | Beanie

Trousers made a big comeback a few years as a more casual alternative to denim and I haven’t stopped wearing them since. Trousers were traditionally seen a more professional clothing option for the workplace, but I have loved wearing them with sneakers or boots in the winter. Layer some thick tights underneath for an added layer of warmth!

Cashmere Lounge Set

Coatigan | Sweater (similar) | Pants (similar) | Shoes | Bag

This look is a perfect example of how matching sets are a winter must have. A cozy cashmere or knit set is great for lounging around the house but can easily be worn out because it still looks polished and put together. If you live somewhere that doesn’t get too cold for the winter, a long coatigan is a great alternative to purchasing a big winter coat. It is a great mix between a coat and cardigan, can be super warm and dressed up or down.

Puffer Coat and Black Leggings

Coat | Sweater | Leggings | Boots | Sunglasses

When all else fails, you can always go back to black leggings and a comfy oversized sweater. It’s like my comfort outfit that I know will always work. This is another one of my favorite Amazon tunic sweaters that I have in a few colors and wear all winter long. It’s roomy enough to layer something underneath and just the right length to wear with leggings.