Best 5 Shoe Types to Wear with Leggings: Outfit Ideas and Styling Tips
Leggings are a wardrobe staple that never goes out of style. They’re versatile, comfortable, and can be dressed up or down for just about any occasion. But the real magic of leggings lies in how you style them, and that includes choosing the right shoes. From my own personal experience, pairing the right shoes with leggings can elevate your outfit, making you look polished and stylish rather than underdressed or too casual. Whether you’re running errands, heading to brunch, or going out for a night on the town, there’s a shoe-legging combo that will work for you.
In this post, I’ll walk you through outfit ideas with styling tips for different occasions and explore the best types of shoes to wear with leggings. We’ll talk about everything from sneakers to stilettos and how they can transform your look. Let me jump in. This post may contain affiliate links, meaning I earn a small commission at no extra cost to you.
1. Casual Chic: Sneakers with Leggings
When you think of leggings, sneakers are probably the first type of footwear that comes to mind. Sneakers and leggings are a match made in heaven, especially for casual settings. This combination is not only comfortable but also effortlessly stylish.
For a laid-back, everyday look, opt for classic white sneakers. These work particularly well with black or dark gray leggings. White sneakers provide a clean, fresh vibe that’s perfect for running errands or grabbing coffee with friends. Brands like Nike Air Force 1s or Adidas Superstars are great options. Pair them with a slightly oversized sweatshirt or a cropped hoodie for a sporty yet put-together vibe.
For example:
Black high-waisted leggings + white cropped hoodie + white sneakers + black crossbody bag + gold hoop earrings.
Go Shop this Example Outfit Now:
If you’re feeling adventurous, try colorful or patterned sneakers. These can add a fun pop of personality to an otherwise simple outfit. For instance, bright neon sneakers with a matching tank top can create a coordinated and playful look.
Tip: Stick to neutral-colored leggings if your sneakers are bold. This keeps the outfit balanced and prevents it from looking too busy.
On cooler days, you can layer a puffer jacket or longline coat over your outfit. From my own personal experience, this layering trick not only keeps you warm but also adds an elevated touch to your casual look.
2. Sophisticated Vibes: Flats and Ballet Shoes with Leggings
Flats and ballet shoes are an understated but incredibly chic choice for styling with leggings. They strike a perfect balance between casual and dressy, making them a great option for brunch dates, work-from-home days, or casual office settings. The key here is choosing leggings that look more polished, such as faux leather or ponte leggings.
For a classic Parisian-inspired look, go for black leggings, black ballet flats, and a striped top. Add a trench coat for an elegant finish. Ballet flats with pointed toes can elongate your legs, making the outfit look even more refined. Brands like Rothy’s and Margaux offer comfortable and stylish options.
Example Outfit:
Black faux leather leggings + white button-up shirt + camel trench coat + black pointed-toe ballet flats + structured tote bag.
Go Shop this Example Outfit Now:
> Black pointed-toe ballet flats
If ballet flats feel too traditional for you, loafers or mules can be a great alternative. These shoes add a touch of sophistication and work well with leggings for semi-formal settings. For instance, pair tan loafers with brown leggings and a cream sweater for a cozy yet chic autumn outfit.
Tip: When wearing flats, ensure your leggings are the right length. Ankle-length leggings work best as they prevent any awkward bunching and keep the outfit sleek.
3. Dressy and Daring: Boots and Heels with Leggings
If you’re looking to dress up your leggings, boots and heels are the way to go. This combination is perfect for evenings out, date nights, or even semi-formal gatherings. From my own personal experience, this is one of the easiest ways to transform leggings from casual to glamorous.
For a night out, pair faux leather or velvet leggings with heeled ankle boots. Choose boots with a pointed toe for a sleek and polished look. Black on black is always a winner, but don’t shy away from experimenting with textures or metallic accents.
Example Outfit:
Black faux leather leggings + black fitted turtleneck + black heeled ankle boots + gold statement necklace + clutch bag.
Go Shop this Example Outfit Now:
Tall boots, like knee-high or over-the-knee styles, are another excellent choice for colder months. These boots look stunning with leggings and a long sweater or tunic. Over-the-knee boots, in particular, add a touch of drama and sophistication. Go for neutral shades like tan or taupe for a softer look, or stick with classic black for maximum impact.
Example Outfit:
Dark brown leggings + cream oversized sweater + tan over-the-knee boots + brown crossbody bag + pearl earrings.
Go Shop this Example Outfit Now:
For more daring styles, consider pairing leggings with stiletto heels. This is ideal for party settings or upscale dinners. Velvet or suede leggings work beautifully with stilettos, as they’re luxurious and eye-catching. Opt for a flowy blouse or structured blazer to complete the look.
Tip: If you’re wearing stilettos, pay attention to the fit of your leggings. They should be snug and free of wrinkles or sagging to maintain a sleek silhouette.
4. Edgy Street Style: Combat Boots with Leggings
Combat boots bring an edgy and cool vibe to your leggings outfit. They’re perfect for casual outings or concerts, especially in cooler months. Pair your leggings with chunky combat boots like Dr. Martens for a bold statement. These boots work well with both plain black leggings and patterned ones, such as camo or plaid.
For a balanced street-style look, wear your leggings with an oversized graphic tee and a leather or denim jacket. Add a beanie or a crossbody bag for a complete urban aesthetic.
Example Outfit:
Black leggings + oversized graphic tee + black combat boots + leather jacket + silver hoop earrings.
Go Shop this Example Outfit Now:
If you want to soften the look, opt for leggings in neutral shades like gray or beige and pair them with light brown combat boots. A cozy cardigan or a longline shacket can add a touch of femininity while keeping the outfit on-trend.
Tip: Ensure your combat boots are laced properly to avoid a messy look. Rolling the hem of your leggings slightly can also add an extra style detail.
5. Effortless Summer Look: Sandals with Leggings
Leggings and sandals might seem unconventional, but with the right styling, they can create an easy and breezy summer outfit. Opt for simple slide sandals or strappy ones with embellishments. These pair beautifully with cropped or capri-length leggings.
For a casual daytime look, pair black leggings with flat slide sandals and a lightweight tunic or tank top. Add a sun hat and a tote bag for a chic summer vibe. Brands like Birkenstock and Steve Madden offer stylish and comfortable sandal options.
Example Outfit:
Cropped black leggings + white linen tunic + tan slide sandals + straw tote bag + aviator sunglasses.
Go Shop this Example Outfit Now:
If you’re heading out for an evening summer event, swap the flat sandals for heeled ones. Wedge sandals or block heels can add a dressier touch to your leggings. Pair them with a flowy off-shoulder blouse for a feminine and flirty vibe.
Tip: Stick to neutral sandal colors like tan, white, or metallics to keep the look cohesive and polished.
Bonus Tips for Styling Leggings
Colors and Textures
When styling leggings, pay attention to colors and textures. Black and neutral leggings are the most versatile, but don’t be afraid to explore other colors like burgundy, navy, or olive green. These shades are perfect for autumn and winter.
Textured leggings, such as ribbed or jacquard patterns, can add interest to your outfit without being too bold. Just make sure to balance the texture with simple tops and shoes.
Accessories Matter
Accessories can make or break your legging outfit. From my own personal experience, adding a statement bag, scarf, or jewelry can instantly elevate your look. For casual outfits, stick to minimal accessories, like a baseball cap or stud earrings. For dressier occasions, opt for bold necklaces, oversized sunglasses, or chic handbags.
Tops That Work Well
The right top can dramatically change the vibe of your leggings outfit. For casual looks, go for oversized sweatshirts, hoodies, or graphic tees. For something more polished, try tunics, long cardigans, or tailored blazers. Crop tops also pair well with high-waisted leggings for a sporty-chic look.
Seasonal Styling
Leggings are great for all seasons, but your styling should reflect the weather. In summer, pair leggings with breathable fabrics like cotton or linen and opt for open-toed shoes like slides or sandals. In winter, layer up with chunky sweaters, scarves, and boots.
Why Leggings and Shoes Matter
The right shoe can elevate your leggings outfit, making it look intentional rather than rushed. From my own personal experience, it’s all about balance. Sneakers create a relaxed and casual vibe, flats add a touch of sophistication, and boots or heels bring the drama and elegance.
Leggings are versatile and can adapt to various occasions and personal styles. With the right shoes and styling, they can become a go-to option for any event on your calendar.
Share Your Favorites!
I hope these outfit ideas and styling tips inspire you to mix and match your leggings and shoes with confidence. From my own personal experience, experimenting with different combinations can lead to some surprisingly stylish results. What are your favorite ways to style leggings? Do you prefer sneakers, flats, or heels? Share your thoughts and outfit ideas in the comments below. I’d love to hear from you!
I’m Gemma, a passionate lifestyle blogger sharing my creative world with you. Gemitaliano.com is my little corner of the internet, glad you’re here.
