How To Look Stylish In Leggings, Stretchy Pants, and Capris

Posted by Stella Carakasi on

The model shows how to look stylish in pants.

If Covid has taught us anything, whether for work, play, or anything in-between, we want to be comfortable. And leggings are one of those styles that almost every woman has in their closet yet sometimes question if they are appropriate outside of yoga class! While leggings and stretchy pants may seem inappropriate or intimidating to style at first, they’re one of the most versatile garments and can be worn to the office, dinner dates, and beyond! In some circles, they are even considered the new jeans! If you’re stuck on how to style these ubiquitous and sometimes controversial bottoms, keep reading. Today, we’re breaking down our favorite stretchy pants and leggings and how to style them for any occasion.

The model shows how to look stylish in pants.

The pant that feels like a legging

Searching for the perfect work outfit to transition from summer to fall? Look no further! The star of this outfit is our Slimming Ankle Pants because they’re designed to flatter most body shapes and sizes! These super comfortable stretchy pants feature slimming style lines that show off your curves. They hit right at the ankles so you can accentuate your shoe or boot of choice! We love Stuart Weitzman Gala Studs Mary Jane Flats and Franky Lift Bootie.

The best part? Our Slimming Ankle Pants are made from a Tencel® blended Ponte knit so it feels like you’re wearing leggings! We love pairing the Slimming Ankle Pants with our Illusion Tunic for a classy, yet fun look for the office. This top comes in a fashionable graphic print that spices up your workwear but isn’t too loud. And it’s made with 100% recycled polyester georgette. You can choose to wear the Illusion Tunic alone or wear it with our Go-To Cardigan on top during the cooler months or if your office is chilly!

For date night

Keep it simple, yet classy for date night by wearing our Slimming Ankle Pants with the Favorite Thing Top in Black! Flattering enough to dress up for a night on the town, be creative and pop this stylish look with the right accessoriesJohn Hardy has some stunning statement pieces that are modern and updated but have a classic heirloom appeal, like the classic chain round necklace with diamonds. The Favorite Thing Top has a flattering V-neck and its unique pleated front gives this top a chic flare and will keep you comfortable throughout your night of dinner, dancing, and fun. Try pairing it with a statement jacket or cardigan for those colder nights as the season starts to shift. To upgrade this look, rock these bottoms with a pair of Steven Madden black leather boots to elevate the look for nighttime.

The model shows how to look stylish in pants.

For work

Every woman should own a great pair of dress pants to wear to work, interviews, and beyond! Our Lounge Dress Pants not only look good on everyone, but they feel good too. They actually look like you’re wearing dress pants, but feel like you’re rocking yoga pants (yes, we’re serious!) They’re the best of both worlds and can be dressed up or down.

All in the details

Leggings to live in. A playful legging in soft Tencel® Ponte knit, the Criss Cross Leggings feature a delightful criss-cross ankle design detail at the ankle. These Ponte leggings are that go-to style in your wardrobe and are the one piece of clothing that will always make it into your suitcase.

The model shows how to look stylish in pants.

These playful, eco-friendly leggings are also available in sustainable, soft denim knit made from organic cotton and are offered in dark– and vintage wash finishes.

For lunch with the girls

While we love dressing leggings up for the office or date night, we also love styling them for more casual settings like lunch with your girlfriends! Our Ready to Wear Leggings are made from stretchy organic cotton to keep you comfortable and chic! And while these may seem like your traditional leggings at first, the shirred ankle detail adds that extra flare of style that takes the look up a notch!

Our Raise the Bar Top complements the Ready to Wear Leggings perfectly, especially in this gorgeous White/ Sunshine color combination! This top features a splash of color with a unique dip-dyed design in a soft Modal® jersey fabric. It has a slight high-low hem which makes it the ideal pairing style with leggings! The Steve Madden Hadyn White Leather Sandals finish this casual lunch look off perfectly because they are comfortable yet put together!

For Sunday errands

Speaking of casual outfits, we love this look featuring our Second Nature Capris. And trust us, there’s more than meets the eye with these flattering bottoms! The Second Nature Capris are made from eco-friendly organic cotton and feel buttery soft on your skin. The button hem gives these cropped leggings added style and class. The Second Nature Capris have an easy flattering fit and a full elastic waistband for comfort. If you’re into cropped leggings, these bottoms are the perfect alternative to our full-length Ready to Wear Leggings!

For days filled with errands, try pairing the Second Nature Capris with our Can’t Resist Tunic for style and functionality. This tunic features front pockets and is made from a sustainable, yet durable Tencel® denim. It has an A-line shape with a longer hem which pairs great with leggings. This top can be worn year-round and even layered with cardigans or jackets during the winter months. A practical tote bag is a must for busy days and one of our favorites is the Banana Republic Leather Mini Crossbody Tote in Silver. It has the functionality of a tote bag but can be worn crossbody so your hands can be free while running around! Talk about a win-win.  

For picnics in the park

Ready for a pop of color? So are we! Our best-selling Tiburon Tunic Icon paired with our Second Nature Capris makes the perfect outfit for casual days but it can also be dressed up for a perfectly comfortable office-friendly look. The crisp cotton poplin keeps you cool and comfortable throughout the day no matter what your plans are. It’s also wrinkle-resistant which makes it the best option for those with a busy schedule. The deep front pockets allow for practicality and the easy A-line shape makes this top flattering for all body shapes and sizes. This tunic is long enough to cover your bottom so it’s great to pair with tighter leggings such as the Second Nature Capris, or the longer Ready To Wear Leggings. Stay cool, breezy, and stylish with the combination of the Tiburon Tunic Icon and Second Nature Capris. To finish off this look, we love wearing a simple yet dazzling pair of sandals such as the Stuart Weitzman Sierra Slip On Sandals.

Looking for more outfit ideas to pair with your new leggings? Make sure to check out our Looks We Love page for even more wardrobe inspiration featuring all of your Stella Carakasi favorites!

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