If you purchase one of the products recommended in this article, I might receive a small affiliate commission. Thank you for your support!
Ankle boots are one of the most sought-after boots for fall and winter because of their easy-to-wear design. When you’re wearing ankle boots, you can wear them with straight leg jeans in light or dark wash. You can choose high waist jeans when you’re wearing your ankle boots with cropped tops and sweaters.
When you want to wear your ankle boots in a more relaxed way, you can wear them with destroyed or frayed denim. Wear cropped jeans when you want to show a little skin. This is the ultimate guide that will give you ideas on how to wear ankle boots with straight leg jeans, from casual to dressy.
Ribbed Sweater, High-Waist Straight Leg Jeans, and Suede Ankle Boots
Try wearing a neutral color sweater with a pair of ankle boots. Your sweater can be ribbed, which is a nice way to add elegance to your outfit. You can also choose a fitted cardigan that buttons in the front. Add a pair of high-waist straight leg jeans in a medium wash.
You can wear your jeans in a cropped style as well. Keeping your sweater a neutral color will create a cool, casual look since your jeans will be a medium wash. You can cuff or roll your sweater sleeves and add a watch for accessories.
Complete your look with a pair of taupe or brown ankle booties in a suede material.
Leopard Print Ankle Boots and Cable-Knit Sweater
If you want to create a look that’s more unexpected, you can choose a pair of stand-out boots. Start your look with a cable-knit sweater in orange or red color.
Add a pair of straight leg jeans in a dark wash or black color. Top off your look with a pair of leopard print ankle boots. The brown color in your boots will compliment the color of your sweater. If your sweater is red, try a look that’s not as “fire engine” red, but more of a red-orange.
You can add a chain strap handbag that you can wear on your shoulder or as a cross-body. Add a pair of oversized sunglasses when the sun is out. You can also cuff your jeans.
Long Winter Coat, Patent Leather Ankle Boots, and Destroyed Denim
Wear a full winter look with a pair of patent leather, chunky heel ankle boots. Choose a turtleneck sweater in grey. This look can be a monochromatic outfit, where you’ll wear a look that’s mainly one color.
You can wear grey or black with this look. You can also choose a cropped sweater when it’s not too cold. Add a pair of high waist cropped, straight leg jeans. You can wear destroyed denim, but be sure your jeans are lightly destroyed, instead of a pair that has more than one tear or open tears that are more for warmer weather.
Add a long coat in a plaid design. This is how to wear ankle boots with straight leg jeans, by creating a focal point with your coat. Your coat can also be in a trench coat style, if you don’t want more of a peacoat. You can even wear a long blazer if you don’t want to wear a coat.
Add a pair of white or black patent leather boots that have a chunky heel. You can wear a cross-body handbag in a leather style or you can wear an envelope clutch.
Denim Jacket, Light-Wash Jeans, and Graphic Tee
When thinking of how to wear straight leg jeans with ankle boots in an edgy way, you can try denim on denim look. Start with a light-wash pair of straight leg jeans.
Add a matching, light-wash jean jacket in a cropped style. Choose a graphic tee that has a retro design, reminiscent of a band t-shirt. These types of tops can easily be found at stores like Hot Topic.
If you want to quickly find a graphic tee, you can find them at thrift or second-hand stores at an extremely affordable price. Complete your look with a pair of leather ankle boots.
With this style of ankle booties, they don’t necessarily have to be in a patent leather style. This way, your shoes will look more grunge, rather glam. Wear a double strap leather handbag or a top handle handbag with buckle closure.
Utilitarian Vest, Color Jeans, and Leather Ankle Boots
Create an all-purpose look that can be worn on virtually any occasion with a utilitarian style vest (think army-chic). Your vest will be the main piece of your outfit and you can build around it. Add a long sleeve shirt underneath. Your shirt can be a button-up, if you’re attending a more serious event or if it’s more of a business-casual type of occasion or environment.
Add a pair of straight leg jeans in an unexpected color like olive green or wine red. These styles of jeans are usually readily available in the fall and winter seasons.
Wear a pair of brown leather ankle boots. With this look, be sure to avoid colored jeans that are in a loud color. Keep your colors on the darker or more muted side. This will make it easier to pair with the green color of your vest.
Moto Jacket, Flat Ankle Boots, and Black Jeans
Straight leg jeans also pair well with moto jackets and ankle boots. Although you’re wearing a motorcycle jacket, you don’t necessarily have to wear an edgy or punk look.
You can wear a more glamorous look by wearing a beige or nude color sweater that has a turtleneck, high neck, or cowl neck, that gives the illusion of a scarf. You can also wear an actual scarf with a scoop neck sweater. This will create a high neckline to your sweater, which will pair well with the open, v-neck style of your jacket.
Add a dark brown moto jacket. Finish your look with a pair of black, straight leg jeans. Your jeans don’t have to be high waist and can be mid-rise.
Wear a pair of brown ankle boots that are in a flat style. They don’t have to have a chunky or high heel. This is how to wear ankle boots with straight leg jeans in a way that’s relaxed but also high-fashion.
Bomber Jacket, Scoop Neck T-Shirt, and Cropped Jeans
For a simple, chic look, try wearing a bomber jacket with your jeans and ankle boots. This look is more for a mild weather day when you need to cover up but it’s not extremely cold.
The base of your outfit can be a solid grey, scoop neck t-shirt. Add a pair of black, cropped, straight leg jeans. You can even cuff a pair of full-length straight leg jeans instead. Wear a bomber jacket in black or green.
You can also wear a blue bomber jacket. Add a pair of black, suede ankle boots that have a high heel, for a model-like look. When the sun is out, wear a pair of aviator sunglasses. Finish your look with a leather-style top-handle handbag.
Off-The-Shoulder Sweater and Dark Wash Jeans
Wear an off-the-shoulder sweater with a pair of western-style ankle boots and dark wash jeans. Your sweater can be a chunky cable knit in a solid color.
Try wearing a pair of jeans that are destroyed on the edgier side. If you want to wear a striped sweater, keep your jeans solid, instead of distressed. Add a pair of ankle boots with suede material and a wooden heel.
Finish your outfit with a western-style fedora or wide-brim hat. When thinking of this look and how to wear straight leg jeans with ankle boots and an off-the-shoulder sweater, you can add to it with a leather-style backpack.
Cardigan, Blouse, and Black Jeans
When you want to cinch your waist, you can wear an oversized cardigan. Choose a sweater that’s in a solid color like grey, black, or tan. Add a ruffle blouse underneath for a girly aesthetic.
Pull in your waist by belting your cardigan and top. You can wear a chunky belt or a slim belt, depending on the look you’re going for. Be sure to choose a belt that has a bold buckle in gold or silver!
Add a pair of black straight leg jeans and brown or black ankle boots. Finish your look with a double strap, leather handbag. This outfit is ideal for wearing necklace jewelry and elegant earrings.
If you’re going out or you need to dress up jeans for work, choose a pair of chandelier earrings and a simple chain necklace. On casual days, try a pair of studded earrings or small hoops.
Wearing ankle boots with straight leg jeans is an easy way to create different looks. Since straight leg jeans are one of the most classic jean styles, they can be found at your favorite clothing stores.
Old Navy and H&M are two retailers that offer the best deals when it comes to straight-leg jeans, allowing you to mix higher-end pieces with them, as well.
When it comes to adding ankle boots to classic straight-leg jeans, choosing a quality pair is important. This is how to wear ankle boots with straight leg jeans, including flat and chunky heel booties so that your wardrobe remains versatile.
Always start with your sweater or shirt type and build upon each look with your jeans, whether cropped or distressed. You can create casual looks by wearing a scoop or v-neck t-shirt. Or, you can dress your jeans and boots up by wearing a chunky sweater!