Ankle boots are a wardrobe staple that can elevate any outfit. Whether you’re going for a casual day look or dressing up for a night out, ankle boots add a stylish touch that works in every season.
But knowing how to pair them with different outfits can sometimes be tricky. Do you tuck your jeans into the boots? Should you wear tights with skirts? What about pairing them with dresses?
In this guide, we’ll cover everything you need to know about how to wear ankle boots with jeans, dresses, skirts, leggings, and pants.
Let’s dive in and make ankle boots your go-to footwear choice!
How to Wear Ankle Boots With Jeans
Wearing ankle boots with jeans is probably the most common and versatile pairing. Whether you’re into skinny jeans, mom jeans, or flares, ankle boots can work with them all. Here are a few tips to get you started:
1. Skinny Jeans Skinny jeans and ankle boots are a match made in heaven. To create a sleek, streamlined look, tuck your skinny jeans into your ankle boots or go for a cropped jean that ends just above the boot. This combo works especially well with heeled ankle boots, as it elongates your legs and gives you a bit of height. If you’re feeling extra stylish, opt for a pair of sock boots that hug the ankle for a clean, modern look.
2. Cuffed Jeans If you’re wearing straight-leg or boyfriend jeans, cuffing the hem slightly above the ankle boots creates a relaxed vibe. This look is perfect for casual days when you’re running errands or grabbing coffee with friends. Pair with flat or low-heeled ankle boots for an easy, laid-back style. Darker denim works well for a polished look, while lighter washes make it more playful.
3. Cropped Jeans Cropped jeans are designed to hit right at the ankle, making them an excellent choice for showing off your boots. This style works best with fitted ankle boots that sit snugly around your ankle. A chunkier boot can add some edge to the look, especially if you’re going for a more fashion-forward outfit. Try pairing cropped jeans with suede ankle boots for a softer, more feminine look.
4. Flared or Bootcut Jeans If you’re a fan of flared or bootcut jeans, ankle boots can still work. The trick is to find a pair of boots with a narrow toe and a slight heel. This helps balance the wider leg of the jeans and keeps your proportions in check. Let your jeans fall naturally over the boots for a 70s-inspired vibe, perfect for a casual but chic outfit.
5. Distressed Jeans For a more edgy, street-style look, pair your ankle boots with distressed jeans. Ripped or frayed jeans add texture and interest, while the ankle boots keep things grounded and stylish. This combo works especially well with combat-style or chunky ankle boots, giving you that effortlessly cool vibe.
How to Wear Ankle Boots With a Dress
Ankle boots with a dress is a classic fall and winter look, but it can be worn year-round depending on the dress style. Whether you’re dressing up for a night out or keeping it casual for the day, here’s how to make it work:
1. Casual Dresses For a laid-back, everyday look, pair ankle boots with a casual dress like a t-shirt or sweater dress. A pair of flat ankle boots adds a touch of cool while still being comfortable enough for all-day wear. If it’s chilly out, throw on a pair of tights or leggings to keep warm. Opt for neutral-toned boots like brown or black to keep the look understated.
2. Maxi Dresses Yes, you can totally wear ankle boots with a maxi dress! The key here is balance. Since a maxi dress is long and flowy, pair it with sleek ankle boots that hug the ankle. A slight heel can help elongate your frame and prevent the dress from looking too overwhelming. If you’re going for a boho vibe, try pairing a floral maxi dress with suede ankle boots.
3. Mini Dresses For a fun and flirty look, try ankle boots with a mini dress. Heeled ankle boots, in particular, work great with this pairing, adding some height and making your legs look longer. You can go for a chic monochromatic look by matching the color of your boots to your dress, or mix and match with contrasting shades for more visual interest.
4. Midi Dresses Midi dresses and ankle boots are the perfect transitional outfit for fall or spring. To make this combo work, choose a pair of ankle boots with a sleek, fitted shaft that won’t add bulk under your dress. If you’re wearing a flowy midi, opt for a slightly heeled boot to balance the silhouette. For more structure, pair a bodycon or tailored midi dress with block-heeled boots.
5. Sweater Dresses Sweater dresses and ankle boots are a go-to cozy yet stylish look for colder months. Pairing a chunky sweater dress with heeled ankle boots can add some polish to an otherwise casual outfit. Throw on a long coat or a scarf, and you’re ready for anything from brunch to a weekend stroll.
How to Wear Ankle Boots With Skirts
Skirts and ankle boots can make for an effortlessly stylish pairing, whether you’re dressing up or down. From mini skirts to midis, here’s how to rock ankle boots with skirts:
1. Mini Skirts Pairing a mini skirt with ankle boots creates a fun, youthful vibe. For a polished look, choose heeled ankle boots to give your legs an elongated appearance. This combination works great for nights out or casual daytime outfits, depending on how you style it. Tights can be added in the cooler months, and flat ankle boots can make the look more laid-back.
2. A-Line Skirts Ankle boots work wonderfully with A-line skirts because they help create a balanced silhouette. Choose a boot that hits just above the ankle to show a little skin or wear tights for a more classic look. This combination is perfect for casual outfits with a tucked-in blouse or sweater. Heeled ankle boots will dress up the look, while flat ones keep it more relaxed.
3. Pencil Skirts For a sleek, business-casual outfit, pair ankle boots with a pencil skirt. Ankle boots with a pointed toe can elongate your frame and add a modern edge to the classic pencil skirt. If you’re wearing a longer pencil skirt, make sure the boots hit above the ankle for a more balanced look. Block-heeled boots work particularly well here, adding both height and comfort.
4. Pleated Skirts Pleated skirts have a lot of volume, so pairing them with the right ankle boots is essential. Opt for sleek, fitted ankle boots to create balance and avoid adding too much bulk to the outfit. If you’re wearing a midi-length pleated skirt, a heeled ankle boot will give you some height and help elongate the overall silhouette.
5. Denim Skirts For a casual yet trendy look, pair ankle boots with a denim skirt. Whether it’s a mini or midi-length, ankle boots will give your denim skirt a fresh, modern update. Try a pair of chunky or combat-style ankle boots for an edgier vibe, or stick to classic suede or leather ankle boots for a more timeless feel.
How to Wear Ankle Boots With Leggings
Leggings and ankle boots are the ultimate combo when it comes to comfort and style. Whether you’re going for a sporty look or something a bit more polished, here’s how to pair your ankle boots with leggings:
1. Casual Look For an easy, laid-back outfit, pair leggings with flat ankle boots and an oversized sweater or tunic. This look is perfect for running errands or lounging around but can easily be dressed up with a few accessories. Stick to black or neutral-colored leggings to keep things simple, and opt for leather or suede ankle boots for a bit of texture.
2. Sporty Look If you’re a fan of athleisure, you can totally rock ankle boots with sporty leggings. Pair black ankle boots with sleek, high-waisted leggings and a cropped hoodie or jacket. The key here is to keep the color palette simple and let the boots add a bit of edge to your outfit. This look works best with leggings that have a smooth, fitted finish rather than a loose or baggy style.
3. Dressy Look For a more polished outfit, try wearing leggings with heeled ankle boots and a longer blouse or tunic. Add a structured jacket or blazer to pull the whole look together. Leather or faux leather leggings work especially well for dressier occasions, giving your outfit a sleek, modern vibe. Heeled ankle boots with a pointed toe can elevate the entire look, making it perfect for dinner or a night out.
4. Tucked-In Look Tucking your leggings into ankle boots can create a sleek, elongated silhouette. This works best with fitted leggings and slim ankle boots that hug your ankles. Avoid pairing baggy leggings with bulky boots, as this can make the outfit look unbalanced. Instead, go for a streamlined look with a longer top or coat to add some layering and dimension.
How to Wear Ankle Boots With Pants
Finally, let’s talk about how to wear ankle boots with different types of pants. Whether you’re dressing up for work or keeping it casual, ankle boots can complement a variety of pant styles.
1. Trousers For a business-casual look, pair ankle boots with tailored trousers. Opt for slim or straight-leg trousers that hit just above the ankle, so your boots peek through. Heeled ankle boots work best for this look, adding a bit of height and sophistication. Stick to neutral-colored boots like black, brown, or grey for a professional finish.
2. Wide-Leg Pants Wide-leg pants can be tricky to pair with ankle boots, but it can be done if styled correctly. The key is to find ankle boots that balance the volume of wide-leg pants. Go for a boot with a bit of a heel to add height and prevent the pants from overwhelming your frame. Make sure the hem of the pants falls right at the top of the boot or slightly above. Pointed-toe boots can help elongate the legs and create a sleeker silhouette, while round-toe boots will add a softer touch to the outfit.
3. Cropped Pants Cropped pants and ankle boots are a stylish pairing that shows off both your footwear and your ankles. Whether you’re going for a casual or dressy look, cropped pants work best with fitted ankle boots that hug your ankles. The gap between the boots and the hem of the pants creates a flattering, elongated look. For a more polished outfit, choose heeled ankle boots in a sleek leather finish. If you’re going casual, opt for flat boots and rolled-up or cuffed pants to show just the right amount of skin.
4. Leather Pants Leather pants paired with ankle boots make for a bold, edgy outfit that’s perfect for a night out or a trendy daytime look. Whether you’re wearing faux or real leather pants, the shiny texture pairs beautifully with matte or suede ankle boots. Stick to a slim or skinny pant style to keep the outfit balanced, and go for ankle boots with a heel to add some height. For a monochromatic, streamlined look, try black leather pants with black ankle boots.
5. Printed Pants If you’re feeling adventurous and want to wear ankle boots with printed pants, the key is to let the pants take center stage. Opt for simple, neutral-toned ankle boots that won’t compete with the bold print of your pants. Whether you’re wearing florals, stripes, or animal prints, a sleek pair of ankle boots in black, grey, or beige will complement the look without overwhelming it. Heeled ankle boots can dress up the outfit, while flat boots keep it more casual.
Conclusion
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Ankle boots are one of the most versatile and stylish pieces you can have in your wardrobe. Whether you’re pairing them with jeans, dresses, skirts, leggings, or pants, ankle boots add an effortless, chic touch to any outfit. From casual everyday looks to polished, dressy ensembles, ankle boots work for every season and occasion.
The key to pulling off ankle boots is all about balance and proportion. Skinny jeans tucked into boots create a sleek look, while cuffed or cropped jeans add a casual vibe. Dresses and skirts, whether mini, midi, or maxi, pair beautifully with ankle boots, adding a modern twist to a feminine look. Leggings and ankle boots make for the ultimate cozy yet stylish combo, while trousers and wide-leg pants can be dressed up or down with the right boots.
No matter how you choose to wear them, ankle boots offer endless styling possibilities. Play around with different outfits, experiment with various heel heights, and have fun incorporating this fashion staple into your wardrobe!