How to Wear Slouchy Boots

Co-authored by Jordan Stolch and Sophia Latorre

Last Updated: January 25, 2023 References

Slouchy boots are a hot trend right now, and you may be wondering how you should style them. Luckily, you can easily create tons of different outfits that look great with slouchy boots, no matter your personal style.

Method 1

Method 1 of 3:

Choosing Boots

1
Opt for short slouchy boots for everyday wear. Mid-calf slouchy boots are great for everything from going to work to running errands. Pair them with jeans or leggings to keep your look casual.
- You could even go for slouchy ankle boots if you want a shorter pair.
2
Select tall slouchy boots if you like to dress up. Tall slouchy boots can be paired with skinny trousers, skirts, and dresses, so you can wear them for meetings, dates, and other formal affairs. Pick a pair that hits just below the knee or higher.

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3
Stick with neutral colors if you want a versatile boot. Slouchy boots in black, brown, or gray will look great with practically any outfit! You can go for a monochromatic look by matching your pants or dress to your boot color, or wear bold colors or prints with a neutral-colored boot.^{[1]
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4
Pick embellished slouchy boots for a dramatic look. Slouchy boots don’t have to be boring! Look for a pair with embellishments like crystals, buckles, ties, or bows that make them stand out. Keep the rest of your look chic and streamlined so it doesn’t get too busy.^{[2]
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- Slouchy boots studded with crystals would look dynamite paired with a little black dress and understated jewelry.
5
Go for flat slouchy boots if you want a super comfy style. If you’re planning to wear your slouchy boots often, especially through the winter, opt for a pair without heels. The boots will be comfortable enough to wear all the time while still looking chic and trendy.^{[3]
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Choose slouchy boots with heels to make your legs look longer. Slouchy boots come in a variety of heel sizes. If you want to lengthen the look of your legs and pair the boots with dressy outfits, choose boots that have a 2 in (5.1 cm) heel or higher.^{[4]
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- Pointed-toe slouchy boots with stiletto heels are a great statement piece.
7
Pick leather or suede boots if you prefer a matte look. Slouchy boots are available in all types of fabrics and materials. Though leather is the most common, you can also find slouchy boots in many different colors of suede. These boots will be less glossy than those made from synthetic materials.
8
Opt for patent leather or vinyl boots for a super shiny finish. If you like a high-drama, glossy look, choose boots made from patent leather or vinyl. They’ll reflect more light than boots made of real leather or suede, making these boots a statement piece.

Method 2

Method 2 of 3:

Styling the Boots

1
Pull the boots up for a streamlined silhouette. One of the great things about slouchy boots is their versatility! If you prefer a semi-slouchy boot, simply tug the top of the boot up to reduce the slouch.^{[5]
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- Focus on making the boots less slouchy on the widest part of your leg to create a slimmer silhouette.
- If your boots won’t stay up, use a boot band or adhesive tape to keep them in place.
2
Push the boots down to create a more substantial slouch. If you love the slouchy look of this trend, you can embrace it by pushing the boots down. Tug the boots down to create additional folds and wrinkles for a super slouchy look.^{[6]
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3
Pair shiny boots with matte fabrics. If your boots are leather or suede, you can pair them with either shiny or matte fabrics. However, if your boots are patent leather, vinyl, or another shiny material, you’ll want to wear them with matte fabrics to keep your look from becoming too costume-like.^{[7]
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- For instance, shiny black slouchy boots would look great with dark-wash skinny jeans and a floral-patterned blouse.
- A vinyl bodycon dress paired with vinyl slouchy boots, on the other hand, takes the look over the top.

Method 3

Method 3 of 3:

Creating Outfits

1
Pair slouchy boots with skinny jeans for any occasion. Slouchy boots are best paired with skinny jeans, as they fit neatly under the boots and create a streamlined look.^{[8]
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Jordan Stolch
Image Consultant & Style Advisor
Expert Interview. 25 September 2020.} You can dress up the look for work or other formal affairs by adding a blazer and sleek handbag. Or, you can keep it casual by throwing on an oversized sweater on the weekends.^{[9]
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- Short red slouchy boots would pair well with light-wash skinny jeans and a rose-printed sweater.
2
Wear a midi dress with slouchy boots for an understated look. A midi dress has a hemline between the knee and the ankle, so pairing it with slouchy boots keeps you from showing too much skin. You can choose a dress in a color that complements or contrasts your boots, depending on how much you want them to stand out.^{[10]
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- Pair silver slouchy boots with a raspberry midi dress for dinner and drinks with friends. Finish off the look with silver jewelry and a black clutch.
- Black slouchy boots and a midi dress in a contrasting color, like white, create a polished look. Add a pop of color with your handbag or jewelry.
3
Wear a T-shirt dress with slouchy boots for informal affairs. If you’re late for brunch and don’t know what to wear, throw on your favorite T-shirt dress or sweater dress and slouchy boots. Add an oversized handbag and a cute pair of sunglasses, and you’re ready to go!^{[11]
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- T-shirt dresses and sweater dresses are loose and unstructured, without a seam at the waist. If you want to define your waist, add a cute belt to the outfit.
4
Put on leggings underneath your slouchy boots for a casual vibe. Leggings also pair well with slouchy boots since they are fitted and slip right under the boots. Keep in mind that leggings have a casual feel, so this look is best for after-work hours.
- Black slouchy boots, tribal-printed leggings, a white sweater, and a black scarf would be a comfy and casual outfit that’s perfect for brunch or shopping.
- Black leggings, black slouchy boots, and a black tank underneath a flannel shirt make a great outfit for running errands.
5
Pair a mini skirt and slouchy boots for a sleek look. You don’t have to just wear pants with your slouchy boots! You can pair tall slouchy boots with a skirt that hits above the knee to lengthen the look of your legs. Choose a skirt in the same color as your boots for an understated look, or pick a contrasting color for added flair.
- Over-the-knee slouchy boots in a rich color like caramel or red would look great paired with a denim mini-skirt and a sheer black blouse.
6
Match your boot color to your pants for a monochromatic look. Skinny trousers look great with slouchy boots. If you prefer a monochromatic style, match the shade of your trousers and the shade of your boots. Choose a top in a contrasting color to make your legs look a mile long.^{[12]
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- Skinny black trousers underneath tall black slouchy boots and a printed blouse would be the perfect outfit for dinner and drinks.
7
Wear a long, flowing skirt or dress with slouchy boots for a boho vibe. If you’re a fan of maxi dresses or skirts, don’t be afraid to pair them with slouchy boots!^{[13]
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Expert Source

Jordan Stolch
Image Consultant & Style Advisor
Expert Interview. 25 September 2020.} The hemline should end just above the top of your foot so your boots are visible underneath. Pick a dress or skirt with a slit in the side if you want to show off your boots—and some skin!
- A tan maxi dress and olive green slouchy boots creates a beautiful, boho-chic look. Add some oversized sunglasses and a slouchy handbag to complete the outfit.

Expert Q&A

Question

What do I wear with mid-calf slouch boots?

Jordan Stolch
Image Consultant & Style Advisor
Jordan Stolch is an Image Strategist, Style Advisor, and the Founder of MiKADO - a concierge personal styling firm. With over a decade of experience, Jordan specializes in helping people eliminate the confusion and insecurities associated with how to dress in order to build a powerful image and use clothing to their strategic advantage. Jordan trains entrepreneurs, business leaders, and corporate executives in the foundations of "power dressing", from some of the country's preeminent companies such as Morgan Stanley, Deloitte, Berkshire Hathaway, Universal Music Group, Starbucks, and Disney. She works with clients both in-person and virtually, teaching them how to take the confusion out of style so they can operate at a higher level. Jordan earned her BA in Psychology from the University of Waterloo and studied Merchandise Marketing at the Fashion Institute of Technology (FIDM).

Jordan Stolch

Image Consultant & Style Advisor

Expert Answer

Put on a pair of skinny jeans and wear your boots over them for a sleek outfit.