What to Wear with Leggings (without looking sloppy)

Leggings are a wardrobe staple for many, and for good reason—they’re comfortable, versatile, and flattering. Especially in the dead of winter when the idea of putting on jeans sounds awful. While I typically stick to wearing leggings for my workouts or athleisure (here’s a roundup of my favorite affordable athleisure), I know there are lots of ways to style them so they look polished and intentional– like you’re wearing a “real” outfit. If you’ve ever wondered how to wear leggings without feeling like you’re in loungewear, this post is for you.

How to Style Leggings for Different Occasions

How to Style Leggings for Athleisure 

Athleisure is where leggings truly shine. As I mentioned above, I usually wear leggings for my workouts or with athleisure/loungewear. My favorite pair of leggings for working out and athleisure are the HeyNuts Workout Pro leggings that I ordered from Amazon (I reviewed all the best Amazon leggings in this post). I wear a size XS for size reference. Or if you want something that’s truly comfortable, you can shop my favorite loungewear in this post. Here are some tips for making your leggings look intentional (but still relaxed) rather than like you’re heading straight to the gym:

• Pair with Layers: A longline hoodie or sweatshirt layered under a tailored coat can elevate your look instantly. Even a sweater thrown over a white t-shirt works well for athleisure when paired with leggings. I’m wearing the Rhodes Shearling Quarter Zip below. I shared my 10 favorite affordable sweaters (that don’t feel cheap) in this blog post.
• Add Accessories: White sneakers, a structured bag, a hat, jewelry and oversized sunglasses add a polished touch. My puffer bag is the small Porter tote by Vee.
• Stick to Neutrals: Black, gray, or navy leggings are versatile and look more sophisticated than neon workout gear. When I’m working out, I’ll wear pink leggings with a pink workout top, but not for athleisure. The goal when I wear athleisure is sleek and neutral.
• Wear fashion sneakers: Opt for Vejas, New Balance 327s, or retro sneakers rather than your true running shoes. Running or workout shoes tend to look worn out and old, but a pair of sneakers that’s made for fashion rather than workouts is the perfect shoe for athleisure outfits. When it’s super cold, I’ll even wear short Ugg boots. The sneakers I’m wearing below are the white New Balance 327s.

How to Style Leggings for Casual Errands or School Drop-Off

Leggings are a lifesaver for busy mornings when I’m running Thomas to school or headed to a doctor’s appointment. While I don’t need a full-blown outfit for those tasks, I still want to look put-together. Here’s how to style your leggings for casual errands or school drop-off so that they’re a bit more elevated than athleisure:

• Choose the Right Top: Cropped sweaters are on-trend and pair perfectly with high-waisted leggings, creating a balanced silhouette that feels modern and fresh. Cropped styles paired with modern outerwear like puffers or sleek coats make leggings outfits feel intentional and current vs. sloppy if everything is long and oversized.
• Layer Thoughtfully: Add a puffer jacket or tailored coat for a stylish, weather-appropriate finishing touch. Here’s a round-up of my favorite cool puffer jackets for the winter.
• Pick the Right Shoes: Ankle boots are perfect for cooler weather. I recommend choosing a pair without a heel like Chelsea boots (see how to style Chelsea boots in this post). Clean sneakers are also a perfect shoe pairing. They add comfort without looking too sporty as I mentioned in the athleisure section.
• Accessorize Thoughtfully: A structured bag like a crossbody or tote instantly elevates your outfit, making it look intentional. I love pairing a puffer tote with leggings (as long as I’m not wearing a puffy coat). Add a scarf, sunglasses, or a simple hat to complete the look while staying practical for busy days. My favorite puffer tote these days is this Porter style by Vee Collective.

With these styling tips, your leggings can transition effortlessly from school drop-off to errands, proving they’re both functional and chic.

How to Style Leggings for Date Night or Polished Look

Leggings can also be dressed up for a polished, put-together outfit or even for a night out—if styled intentionally. Here’s how to take them from casual to elevated:

• Go Leather or Faux Leather: Leather or faux-leather leggings (try these from SPANX) are a wardrobe game-changer. Pair them with a tailored blazer and heeled boots for a sophisticated look that works for everything from date night to dinner with friends. In cooler months, suede or velvet leggings add a luxe, seasonal touch.
• Embrace Monochrome: A monochrome outfit is effortlessly chic and elongates your silhouette. Pair black leggings with an oversized black sweater or silky blouse, and complete the look with sleek boots or heels. (These Sam Edelman boots are perfect). Layer on a long blazer to tie the look together for extra polish.
• Add Texture: Incorporating interesting textures elevates your leggings outfit instantly. Chunky knit sweaters, silky blouses, or tops with lace or velvet accents add dimension and sophistication. I absolutely love this House of Harlow 1960 faux fur coat to add a bit of interest to a very monochrome look.
• Accessorize Wisely: The right accessories can take your leggings outfit to the next level. A bold clutch, statement jewelry, or a sleek belt can add just the right amount of flair to make your look feel intentional and elevated.
• Pair with Boots: Knee-high boots work really well with leggings when paired with oversized sweaters or an oversized blazer. I always prefer black boots for a streamlined effect, and this pair from Sam Edelman is the best overall.

Whether you’re heading out for a night on the town or just want a polished vibe for an evening dinner, these styling tips prove that leggings can be both comfortable and chic.

How to Style Leggings for Business Casual/Work Casual

Can You Wear Leggings to Work?

While leggings aren’t traditional workwear, they can work in more relaxed or creative office settings—if styled thoughtfully. Here are some tips for making leggings work-appropriate while maintaining a polished look:

• Pair with a Blazer: A longline or tailored blazer instantly adds structure and professionalism. Choose a length that provides extra coverage for a more balanced look. I love a plaid blazer – this is the most similar to mine. I shared 10 ways to style a blazer in this blog post.
• Choose Dressier Leggings: Opt for ponte or structured leggings with seams, which resemble trousers more than workout wear (try these SPANX Ponte Leggings). Faux leather leggings can also elevate your outfit in the right setting.
• Opt for Tunics: A tailored tunic or shirt-dress adds both length and sophistication, creating a more polished appearance. Covering your behind is important in a work setting, so make sure your top is long enough.
• Stick with Classic Footwear: Loafers, heeled ankle boots, or pointed flats are ideal choices to round out the look with a professional edge. The pointed flats I’m wearing below are sold out, but this Nori pair is similar.

If you’re unsure whether leggings align with your office dress code, err on the side of caution. Professional environments often require tailored, polished pieces, and leggings may not always meet that standard. However, when styled intentionally and paired with elevated pieces, they can bridge the gap between comfort and workplace appropriateness.

Why I Don’t Wear Leggings to Work

If you’re wondering if you can wear leggings to work, let’s start with a disclaimer: I worked in financial services at a Fortune 500 company in the conservative South where professional dress codes were the norm. Leggings were never part of the equation there. However, I know that workplace norms have evolved, and in some industries or more casual offices, leggings might be perfectly acceptable when styled appropriately. That said, knowing your workplace culture is essential before testing the waters. Since I now work from home and work for myself, I definitely wear leggings to work.

My Favorite Leggings

• Affordable Athleisure and Workout Leggings: Amazon HeyNuts Leggings
• High-end Workout Leggings: Align leggings from Lululemon and Set Active Leggings
• Ponte Leggings: SPANXsmooth™ Ponte Zip Legging
• Faux Leather Leggings: SPANX Faux Leather Leggings

How to Style Flare Leggings

Flare leggings (also called yoga pants) are making a comeback, blending comfort with a nostalgic 90s-inspired silhouette. I definitely wore them for my 9th-grade dance concert. Their flared shape is versatile for both casual and slightly elevated looks – and they’re insanely flattering. My favorite pair of flare leggings is this affordable pair from Amazon. Here’s how to style them:

Casual Looks with Flare Leggings

• Pair with a Fitted Top: Since flare leggings have a looser bottom, balance the look with a fitted tank, tee, or bodysuit.
• Add Layers: Throw on an oversized cardigan, long vest, or cropped hoodie for a relaxed yet stylish outfit. The vest I’m wearing in the photos below is from Amazon.
• Sneakers: White sneakers pair effortlessly with flare leggings for a casual but intentional look. I’m wearing Veja Recife sneakers below.

Polished Athleisure with Flare Leggings

• Monochromatic Matching Set: Opt for a matching top and flare leggings in a neutral or muted tone for a sleek athleisure look.
• Add a Long Coat or Duster: A longline coat or cardigan over a fitted top and flare leggings elevate the outfit.
• Neutral Sneakers or Slip-Ons: Stick to clean, simple footwear for a polished finish.

Dressing Up Flare Leggings

Honestly, I’d recommend buying a great pair of jeans rather than dressing up flare leggings! But if you insist…

• Pair with a Blazer: A fitted blazer with flare leggings creates a chic silhouette. Opt for leggings in a thicker fabric, like ponte or knit.
• Heeled Boots or Mules: These will typically look better than traditional heels since they balance casual with elevated. 

What Shoes to Wear with Leggings

The type of shoes you pair with leggings can make or break your outfit, so it’s important to choose footwear that complements the overall look you’re going for. Here are some general do’s and don’ts to keep your leggings outfits polished and intentional:

DO:

• Wear Sleek Sneakers: Neutral-toned sneakers with a slimmer shape work perfectly for polished athleisure looks. Or, opt for an on-trend pair that’s chunky, like the trendy New Balances but be sure to align the rest of your look to that vibe.
• Choose Pointed Flats or Loafers: These instantly elevate leggings for business casual or more professional settings.
• Opt for Ankle or Knee-High Boots: These pair beautifully with oversized sweaters or tunics for a chic, seasonal vibe. Save boots for your most elevated leggings outfits. I love this tall black pair of boots for leggings.

DON’T:

• Wear Flip-Flops or Slides: These casual shoes can make leggings look sloppy and unintentional.
• Default to Workout Sneakers (Outside of the Gym): Unless you’re going for a workout or true athleisure look where you can look cute while walking with a friend, avoid pairing athletic sneakers with everyday outfits.

The right shoes can transform your leggings from a casual staple into a stylish foundation for a range of polished outfits. Always consider the occasion and the overall vibe you’re aiming for!

Final Thoughts

Leggings are undeniably versatile and can be styled in countless ways to suit your lifestyle. Whether you’re wearing them for athleisure, casual outings, or exploring the boundaries of workwear, the key is balance. Pair them with the right pieces, prioritize quality, and avoid common mistakes for a look that’s both comfortable and polished.

What’s your favorite way to style leggings? Let me know in the comments—I’d love to hear your tips and tricks!

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