What to Wear with Leggings for Casual, Work, and Weekend Looks

TL;DR: Wondering what to wear with leggings for different occasions? This blog breaks down how to style leggings for casual days, business casual settings, and relaxed weekend looks so you can feel confident anywhere you go.

Here’s what you’ll learn:

• Easy casual outfits with leggings, including oversized sweaters, ballet flats, and ankle boots
• How to style black leggings for polished business casual looks
• Ways to wear a dress with leggings or a skirt with leggings to elevate your outfit
• How leggings with boots, including knee high boots, create effortless weekend style
• Simple styling tips to build versatile outfits to wear with leggings year-round

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If you’ve ever stood in front of your closet wondering what to wear with leggings, you’re not alone. Leggings are one of the most versatile pieces you can own, but knowing how to style them for different settings makes all the difference.

The right pair of leggings can take you from a coffee run to the office to weekend plans without missing a beat. It all comes down to smart layering, thoughtful footwear, and a few simple styling tips.

Let’s break down the best outfits to wear with leggings for casual days, business casual settings, and laid-back weekends.

Casual Everyday Looks That Always Work

When it comes to casual style, comfort is king. Still, that doesn’t mean you can’t look put together. Classic black leggings are the easiest place to start. They’re flattering, timeless, and pair effortlessly with almost anything.

Oversized Layers for Effortless Style

One of the easiest outfits with leggings is pairing them with oversized sweaters. The contrast between fitted bottoms and relaxed tops creates balance and keeps the look intentional instead of sloppy.

Try:

• A chunky knit sweater and black leggings
• A graphic sweatshirt layered over a longer tank
• A slouchy cardigan over a fitted tee

Finish the look with clean sneakers for a sporty vibe or swap them for ankle boots to elevate the outfit slightly.

Casual Chic with Flats

If you want something softer and more polished, add ballet flats. A longline tunic or lightweight sweater paired with leggings and flats creates an easy, everyday look that still feels feminine and styled.

This combination works especially well for errands, school pickups, or casual meetups. It’s comfortable but doesn’t feel like you just left the gym.

Work and Business Casual Outfit Ideas

Yes, you can wear leggings to work when styled correctly. The key to pulling off business casual looks with leggings is structure.

Think polished layers, longer silhouettes, and elevated footwear.

Structured Tops Make the Difference

To make leggings office-appropriate, pair them with longer blouses, tailored tunics, or even a blazer layered over a fitted top.

A structured jacket instantly transforms a basic pair of leggings into something more professional. Stick with neutral shades like black, navy, or deep burgundy for a clean, cohesive look.

Dress with Leggings for a Polished Finish

Wearing a dress with leggings is one of the easiest ways to create a business casual outfit. Choose a knee-length or midi dress and layer it over sleek black leggings for added coverage and comfort.

This works especially well in cooler months when you want warmth without sacrificing style.

Add ankle boots for a modern touch, or opt for pointed ballet flats for a more classic feel. Keep accessories minimal and polished to maintain that professional edge.

Skirt with Leggings for Transitional Style

A skirt with leggings is another underrated office option. Choose a structured skirt in a thicker fabric and pair it with fitted leggings underneath.

This combination works well with:

• Knee-length pencil skirts
• A-line skirts
• Sweater skirts

Complete the look with knee-high boots in colder weather or sleek flats during transitional seasons.

The result is comfortable enough for long workdays but polished enough to fit into most business casual environments.

Weekend Looks That Feel Effortless

Weekends are when you can have fun with texture, layering, and personality. Leggings shine here because they’re built for movement and comfort.

Leggings with Boots for Instant Style

One of the most reliable combinations is leggings with boots. Whether you’re heading to brunch or browsing local shops, boots add structure and elevate the entire outfit.

• Ankle boots create a modern, casual vibe.
• Knee high boots add drama and polish.
• Chunky boots bring a slightly edgy feel.

Pair black leggings with a long sweater or flannel and finish with boots for an easy, go-to weekend look.

Layered Athleisure

For a more athletic-inspired outfit, pair leggings with a cropped hoodie or fitted long-sleeve top. Layer a lightweight jacket over it for dimension.

This is one of the most comfortable outfits to wear with leggings, especially if your weekend plans include walking, traveling, or light workouts.

Finish the look with sneakers for all-day comfort.

Seasonal Outfit Inspiration

Leggings adapt easily across seasons, which is why they’re such a staple.

Fall and Winter

Cooler weather is perfect for layering. Pair your leggings with oversized sweaters, long coats, and knee high boots for a cozy yet polished outfit.

You can also layer a dress with leggings and add a scarf for warmth and style.

Spring

Spring calls for lighter fabrics and softer layers. A flowy skirt with leggings and flats creates a breezy look that works for casual outings.

Swap heavier boots for ballet flats or lightweight ankle boots.

Summer Evenings

Even in warmer months, leggings work for cooler evenings. Pair them with a loose tank and a lightweight cardigan for balance.

Stick with breathable fabrics and lighter colors if you’re stepping away from classic black leggings.

Choosing the Right Pair of Leggings

Not all leggings are created equal. The right pair of leggings should feel supportive, stay in place, and provide enough coverage for bending and movement.

When building outfits with leggings, consider:

• Fit and waistband support
• Fabric thickness and opacity
• Overall silhouette

A quality pair gives you more flexibility in how you style them. If you’re wearing them to work, you’ll want a smoother, structured look. For casual days, a slightly more relaxed style works well.

Styling Tips to Elevate Your Leggings

If you’re unsure about what to wear with leggings, keep these simple styling tips in mind:

1. Balance proportions. Pair fitted leggings with longer or looser tops for a flattering silhouette.
2. Choose intentional footwear. Boots, flats, or sneakers can completely change the tone of the outfit.
3. Layer strategically. Jackets, cardigans, and blazers instantly elevate simple outfits with leggings.
4. Stick with versatile colors. Black leggings are the easiest to style across settings.
5. Pay attention to length. Tops that hit mid-thigh often create the most balanced look.

Small adjustments can transform basic leggings into a polished, put-together outfit.

Why Leggings Work for Every Setting

The beauty of leggings is their adaptability. They’re comfortable enough for lounging but structured enough for public settings when styled correctly.

From running errands to navigating a full workday, the right outfits with leggings can carry you through it all.

Whether you’re pairing them with oversized sweaters for a cozy feel, styling a dress with leggings for business casual, or rocking leggings with boots for weekend plans, they remain one of the most practical and versatile pieces in your closet.

So the next time you’re wondering what to wear with leggings, remember this: with the right layers and footwear, they can take you almost anywhere. Shop our workout leggings today!