42 Stylish Things That Have Stretchy Waistbands So You're Always Comfortable

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I consider two things when I buy something new for myself: how stylish is this? And quickly after, how comfortable is this? While style still unusually wins out, when I find a piece with a winning combination of both, it is a must-buy. If you’re comfort-focused like me, you understand there is nothing worse than wearing an outfit that makes you feel great about yourself — for about four hours — and then you’re so uncomfortable, the confidence gets sucked right out of your day. That’s why I rounded up this list of 42 stylish things that have stretchy waistbands — so you’re always comfortable.

First up, I included plenty of casual looks to wear while running errands, hanging out with friends, or grabbing a bite to eat. From high-waisted jean shorts that you can actually sit down in to a casual V-neck maxi that is begging to be taken on vacation — you’ll find plenty of fashion-forward picks that are equally as comfortable.

Now onto work. There’s something about work clothes that makes us think we should be uncomfortable in them all day. But I’ve packed this list with professional wrap dresses and elegant paper bag pants that are work-appropriate and without any uncomfortable buttons or tight-fitting fabrics.

Pajamas shouldn’t be the only clothing in your closet with an elastic waist. Now your favorite looks can be as comfortable as your PJs. Happy shopping!


These Work-Appropriate Paper Bag Pants

Command attention in these fashion-forward paper bag pants that are astonishingly comfortable. They’re cropped just above the ankle and have a unique cinched, elastic high waist and a tie belt. The pant legs are slightly tapered and feature roomy side pockets. They’ve earned more than 14,000 reviews and a 4.2-star rating.

•Available Sizes: X-Small — 3X-Large

•Available Colors: 27


A Button-Up Dress That Ties At The Waist

This casual button-up dress has everything you could want in a comfy, yet stylish dress. It has a side split to keep you cool, a cinched waist and belt to give you shape, and a small polka dot pattern that will turn heads. The short-sleeve dress has a midi length and is breezy and whimsical for so many occasions, from work to play. It’s also available in long-sleeve options.

• Available Sizes: Small — X-Large

• Available Colors: 19


The Stylish Peplum Blouse With A Tie Belt

This peplum blouse can be dressed up for work or kept more casual with jeans — either way, it’s comfy. It buttons down and has short kimono sleeves and a flat collar. It’s loose-fitting, yet the drawstring waist detail and self-tie create a beautiful shape and design detail. The chiffon material is lightweight, breathable, and feels good on your skin. This top is also available in long sleeves.

• Available Sizes: Small — X-Large

• Available Colors: 16


A Wide Leg Pair Of Pants That Are Ultra Cozy

These wide-leg pants are so comfortable and paired with a tank and wedges — a total fashion-forward look. The linen material is soft and lightweight, plus the wide leg and drawstring closure make them the perfect option for laid-back days. They have two roomy side pockets and come in a variety of colors from white to fluorescent green. These pajama-like pants are perfect for dinner dates, shopping trips, or lounging at home.

•Available Sizes: Small — 5X-Large

•Available Colors: 20


A Sophisticated And Stretchy Wrap Pencil Skirt

This pencil skirt is the picture of sophistication — plus it’s ultra-comfy. The spandex skirt has an asymmetrical wrap front and zips in the back, and it’s made from a stretchy material that hugs your hips and moves with you so you never feel restricted. The skirt is lined and hits at the knee so it’s more than appropriate for work, weddings, or a date. It comes in a variety of patterns and solid colors.

•Available Sizes: Small — 3X-Large

Available Colors: 45


An Off-The-Shoulder Trending Maxi With A Slit

This off-the-shoulder dress is so comfortable and breezy, you’ll want to wear it every day. The stretchy dress features a minimal floral pattern and ribbed bodice, short sleeves, and side slits. It makes a great wedding guest dress or pick to wear when snapping those family photos (since the lightweight material will flow beautifully in the wind). Choose from a variety of colors and patterns.

•Available Sizes: X-Small — 3X-Large Plus

•Available Colors: 22


These Sensible And Stylish Cargo Pants

You’ll be the most stylish one on the trail (and comfy, to boot) in these lightweight cargo pants. They’re made of a soft, breathable, and quick-drying material that moves with you. This pair sits at your ankle and features four pockets: two slit pockets and two side cargo pockets. These comfy pants are perfect for traveling, hiking, or running errands.

•Available Sizes: XX-Small — X-Large

•Available Colors: 4


A Pencil Dress That’s Polished For Work

If you work in an office or as a teacher, it’s key to find professional wardrobe pieces that you don’t mind spending a lot of time in. This casual pencil dress has all of the sophistication of a suit skirt and blouse, but is 10 times more comfortable. The top of the dress features a rounded neck, three-quarter-length sleeves, and gathers at the waist, while the skirt of the dress is snug, stops just past the knee, and has pockets. There are no zippers or liners to get bunched up or make you uncomfortable.

• Available Sizes: Small — XX-Large

• Available Colors: 13


This Leopard-Print Dress With Elasticized Band And Belt

Make a statement in this belted A-line dress that won’t restrict you and has a bold leopard print. The long-sleeve dress is surprisingly breezy since the material is so lightweight — so you know you’ll always be comfortable. It has a delicate button-closure neckline and cinched elastic waist that allows the dress to lay beautifully. If traditional leopard print isn't your thing, this beauty comes in three other colors: white, red, and green.

• Available Sizes: Small — X-Large

• Available Colors: 4


This Trendy Midi Slip Skirt That’s Soft As Can Be

A silky midi skirt is a staple for any fashion-forward closet, but real silk doesn’t come cheap and can be hard to take care of. This affordable option has the same luxurious look and feel as silk at a fraction of the price, plus it features an elastic waistband. It’s actually made of satin — which is less expensive, easier to care for, and machine washable.

• Available Sizes: XX-Small — 3X

• Available Colors: 17


A Pair Of Paper Bag Shorts With A Removable Belt

Looking for a polished pair of shorts that are still as comfy as your favorite cut-offs? These paper bag shorts are the ideal pick. They have a high-waist, which is elastic and features a removable belt, with two open pockets in the front. This pair has earned nearly 4,000 reviews and a 4.2-star rating. Choose from bold colors like hot pink, royal blue, or yellow, as well as plenty of options for the neutral-lovers.

• Available Sizes: Small — XX-Large

• Available Colors: 30


The High-Waisted Jean Shorts That Stretch

Love the look of high-waisted shorts, but hate having to actually sit in them? Same. That’s why I love these paper bag denim shorts. They have a thick, elastic waistband and two-button closure that’s secure without feeling suffocating. The loose-fitting legs and cuffed hem create an A-line silhouette that is cute with a crop top or tucked-in tee. This pair has earned more than 6,000 reviews and comes in seven washes.

• Available Sizes: X-Small — X-Large

• Available Colors: 7


A Trendy Loungewear Set With Drawstring Shorts

Move over old ratty pajamas, this designer loungewear set is here to take your place. It’s just as comfy and way more stylish. The two-piece set includes an off-the-shoulder knit top and drawstring shorts. The knit material is super soft, lightweight, and stretchy, and the slouchy look is trendy and cozy. This adorable look is for more than just lounging — pair it with simple jewelry and cute shoes for a comfortable and fashionable look.

• Available Sizes: Small — XX-Large

• Available Colors: 18


A Midi Polka Dot Dress For Any Ocassion

Here’s another wedding guest dress that’s surprisingly comfortable. This romantic maxi dress makes a statement with an A-line silhouette, adorable ruffle details, and an elasticized bodice. It has puffy sleeves and a stunning square neckline that carries through to the back of the dress or can even be worn off the shoulder. The polka dot pattern adds a subtle detail that reviewers can’t get enough of.

• Available Sizes: X-Small — X-Large

• Available Colors: 15


This Sporty Drawstring Waist Dress You’ll Love

This sporty dress is ready for brunch, shopping, or “mom-ing” around town. It has long sleeves, a scoop neck, and a drawstring waist. The super-soft terry dress feels like cozy pajamas but looks a lot more stylish. One five-star review noted, “Perfect casual dress. The fabric is good-to-great. Love the knit, drawstring waist as it provides you with shape.”

• Available Sizes: X-Small — XX-Large

• Available Colors: 5


This Halter Maxi Dress With A Tie Waist

Stay comfortable at your next nuptials in this halter neck sundress. The loose-fitting dress is a head-turner with delicate polka dot details, a tiered skirt, ruffled neck, and stylish waist tie. Best of all? It’s made of viscose, a soft fabric that is often used to make bedsheets (so you know it's cozy). It’s available in 29 colors and patterns.

• Available Sizes: Small — XX-Large

• Available Colors: 29


The Professional Wrap Dress With Three-Quarter Sleeves

Everyone needs a wrap dress in their closet and this one is ultra-comfy. It’s made of polyester and a little bit of elastane, so it stretches and looks professional. The collared V-neck is classic and the overall length hits just above the knee. The lightweight material keeps you cool all day and the cuffed three-quarter-length sleeves are perfect for wearing alone or styling under a cardigan or blazer. While the silhouette is classic, this is also a fun and versatile piece that has lots of personality.

• Available Sizes: X-Small — XX-Large

• Available Colors: 6


This On-Trend Tennis Skirt With A Stretchy Waistband

The schoolgirl look is back but this time with a comfy elastic waist. This pleated tennis mini skirt is trendy, whether you wear it with a polo or a chunky sweater. The plaid pattern is subtle and classic, plus it’s easy to pull on and head out the door in style. The skirt is lined and sits comfortably at your natural waist. Choose from more than 20 colors and patterns, including navy, red, and white.

•Available Sizes: Small — XX-Large

Available Colors: 20


This Smocked Ruffled Top That’s Flowy

This smocked ruffled tank top keeps you cool and collected on sunny outdoor excursions without bearing all. The sleeveless crop top has wide ruffled shoulder straps, a smocked bodice, and a flared hem that cuts off at the hip. Offered in a charming floral print (as well as other solid shades and patterns), it looks perfectly cute and flirty at your next picnic.

• Available Sizes: Small — XX-Large

• Available Colors: 16


This Midi Dress With A Unique Wrap Skirt

This unique T-shirt dress has so many stylish details and yet is just as cozy as a traditional, simple T-shirt dress. This one has short, cuffed sleeves and a wrap skirt that’s shorter in the front and maxi-length in the back. It ties at the waist with an elasticized band, as well as a decorative tie. This is a year-round dress since it looks good with flip-flops or boots and a jacket.

• Available Sizes: X-Small — X-Large

• Available Colors: 25


A Cropped Blouse With A Smocked Waistband

If you love the cropped top trend but hate when your shirts ride up too much, snag this blouse with an elasticized waistband pronto. The long-sleeve top has a deep V-neck and ruffled hem, as well as flowy sleeves. The polka dot pattern is fun and flirty for date night, paired with jeans and some heels. The smocked band defines your waist and keeps the top in place without making you feel restricted. It’s available in solid colors, as well.

• Available Sizes: X-Small — X-Large

• Available Colors: 12


These Faux Leather Bike Shorts That Are Stretchy

Bike shorts are the ultimate wardrobe purchase because they’re equally as trendy as they are comfortable. This pair has an edgy, cool look that mimics leather, however, one reviewer mentions that the material is still “breathable and not hot or uncomfortable the way pleather can be.” They are fitted, with a mid-rise and look good paired with an oversized tee and sneakers or a crop top and blazer.

• Available Sizes: XX-Small — XX-Large

• Available Colors: 1


This Floral Mini Dress With A Smocked Waist

It’s hard to find a dress that fits you well without being form-fitting, but this floral, flowy dress fits the bill. It has a smocked waist that cinches in without feeling too tight and a ruffled V-neckline (with ties if you prefer a polished high neckline). Its long sleeves make this the perfect fall look and you can just add tights to make it work for winter, too. The small, dainty pattern is beautiful and complements the romantic flared skirt and tiered hem. It’s partially lined and comes in 17 colors.

• Available Sizes: X-Small — X-Large

• Available Colors: 17


This Casual T-Shirt Dress With Classic Pleats

Toss on this pleated T-shirt dress and head out the door in style. The stretchy material is fitted on top and flows away from the hips with delicate pleats. The lightweight material and scoop-neck make this dress easy to style for any season by adding (or subtracting) layers and accessories. It’s available in fun patterns like camo, florals, and stripes. Best of all? It has pockets.

• Available Sizes: Small — 3X-Large

• Available Colors: 30


A Cardigan That Ties At The Waist

Who says cardigans have to be oversized? This fitted option is just as cozy and much more stylish. The open-front cardigan has an irregular hem, long sleeves, and tie waist that can be secured in the front or back. When tied, the rest of the stretchy and soft material drapes beautifully. This is the cardigan you want to bring “in case you get cold,” that way you never have to sacrifice style for comfort.

• Available Sizes: Small — 3X-Large

• Available Colors: 16


The Cozy Leggings That Look Like Denim

They look like jeans, but they’ll make you feel like you’re at home in your pajamas. That’s why reviewers can’t stop wearing these jeggings — in fact, they’ve earned more than 13,000 reviews. They have two stitched faux front pockets and fly, plus two functional back pockets. They’re stretchy and made of a soft cotton blend that has a mid-weight thickness.

•Available Sizes: Small — 3X-Large

•Available Colors: 7


A Faux-Wrap Dress With Wide Waistband

If you loved the ruching of the dress above, but want a bit more support, this dress has a similar tulip skirt, but a wider empire waistband. Similarly, it wraps in the front to create a V-neck and has long sleeves. This stretchy drapes beautifully and is available in more extensive sizing.

• Available Sizes: Medium Plus — 5X-Large Plus

• Available Colors: 21


These Faux Leather Leggings With Fleece Lining

Turn heads in these faux leather leggings that feel an awful lot like your workout leggings. They’re stretchy, high-waisted, and have a thin fleece lining so they really are as cozy as can be, but with a trendy leather look. The four-way stretch construction makes these leggings opaque, plus the gusset crotch won’t chafe. Whether you’re headed out for a night on the town or on your way to brunch — these jeggings are the perfect combination of style and comfort.

•Available Sizes: X-Small — 4X-Large

•Available Colors: 4


This Lightweight Jumpsuit That Feels Like PJs

It’s no shock that this lightweight jumpsuit has nearly 37,000 reviews and a 4.4-star rating — it’s just that comfy. It’s made with cotton and polyester so it’s soft and breathable. The off-the-shoulder neckline is stylish and the cuffed ankle creates a more fitted silhouette. It has two side pockets and short sleeves that make it perfect for traveling or running errands.

•Available Sizes: Small — XXX-Large

•Available Colors: 39


The Trendy Bell Buttons That Have An Elastic Waist

These trendy bell bottoms are made of a cotton blend with stretchy elastane so they're equally as comfy as they are stylish. The raw hem gives this pick a distressed look and, in place of zippers or buttons, they have an elastic waistband that will make you feel like you’re slipping into a pair of leggings. They are full length, with two functional pockets on the back and rips at the knee. If you love this silhouette but would prefer them to look less distressed, they're also available in two additional styles without rips.

•Available Sizes: Small — XX-Large

•Available Colors: 15


A Bodycon Dress That You Can Dance All Night In

This is the dress you want to dance in all night long because it’s stretchy yet stylish. The top of the dress fits like a scoop-neck tank top, however, at the waist, the slim bodycon skirt begins. The racerback top is sporty and casual and the lightweight jersey knit material is reminiscent of your favorite loungewear. You can’t go wrong busting a move in this trendy, versatile dress.

• Available Sizes: X-Small — X-Large

• Available Colors: 31


A Sleeveless Maxi Dress With A Classic Empire Waist

This flowy maxi dress is perfect for strolling the beach or wowing at a family gathering, but the reason it's loved by so many reviewers (almost 10,000) is how comfortable it is. It’s made with spandex so it stretches and moves with you. The thick straps and quintessential V-neck, paired with a thick, empire waistband, is a classic silhouette. Dress it up or down depending on where you’re headed. It’s available in solid colors or prints such as florals, tie-dye, or polka dots.

• Available Sizes: Small — XX-Large

• Available Colors: 41


A Tunic-Length Wrap Top That’s Super Soft

Have you ever worn a shirt that feels like a hug? Order this wrap top and you’ll understand. The super-soft material has a faux criss-cross and V-neck, as well as three-quarter-length sleeves. The tunic-length top gathers on the sides creating a ruched detail that’s supportive and cozy. The silky soft material is super stretchy, yet lightweight. Pair it with leggings or jeans for a comfortable look that’s still on-trend.

• Available Sizes: Small — 3X-Large

• Available Colors: 18


This Stretchy Wrap Blouse That You Can Dress Up

The details of this wrap shirt make it look and feel much fancier than it really is — so you can wear it to dressier occasions without compromising comfort. The V-neckline, draped hem, and wrap front are elegant and the smooth, and the buttery-soft fabric is reminiscent of your favorite pajamas. One reviewer cited, “Its almost pajama soft and stretchy all over [...] I was looking for something that would be comfy to travel in and this is it. Plus it looks awesome with jeans or with a skirt for work.”

•Available Sizes: 16 Plus — 32 Plus

•Available Colors: 31


The Ruched Pencil Dress For Cocktail Parties

Headed to a party and want to look fabulous while feeling like you’re curled up on your couch at home? This retro number is the ticket. The long-sleeve ruched dress is dressy enough for a formal wedding, night on the town, or cocktail event. It has a fitted body, faux-wrap front, and an empire waistline. Reviewers say this number is stretchy and so comfortable: “I wore this dress for a holiday dinner and was great for a long day of cooking, cleaning, and eating, was super comfortable but looks classy.”

• Available Sizes: Small — XX-Large

• Available Colors: 39


The Short-Sleeve Romper You’ll Want To Wear 24/7

This short-sleeve romper is oh so cozy. It features a V-neck, elastic high waistband, and two pockets. It has a keyhole back that makes it easy to take it off, but trust me, you won’t want to. The cotton-blend material is breathable, lightweight, and opaque — what more could you ask for?

• Available Sizes: X-Large — 5X-Large

• Available Colors: 5


The Relaxed-Fit Jeans With Side Elastic For Comfort

A pair of jeans without an uncomfortable waistband? Sign me up. This relaxed-fit denim has comfortable elastic on the sides of the waistband that make them the most flexible jeans you’ve probably ever worn. They have a mid-rise and tapered leg that can be dressed up for dinner and drinks or paired with sneakers for errands around town. These cotton jeans come in three washes and reviewers say they love how the elastic band creates a perfect fit. “With the elastic sides, the waist is a perfect fit for me, no gap in the waist at the back and roomy for my hips.”

•Available Sizes: 4 — 20, short, regular, and long inseams available

Available Colors: 3


A High-Waisted Pair Of Joggers That’s On Trend

Joggers are the refined sweatpants of your dreams, and you truly cannot go wrong with this cozy trend. The cuffed ankle keeps the pant legs slim and straight, like a more comfortable pair of skinny jeans, and the drawstring waistband is fully adjustable. This pair has two slit pockets and looks cute with a fitted tee and jean jacket.

•Available Sizes: Small — X-Large

•Available Colors: 11


This Pair Of Stretchy Dress Pants With Functional Pockets

These dress pants are beloved by reviewers because they look professional but are shockingly comfortable. They pull on and have an elastic waistband with a high-rise. They’re made of cotton, polyester, and spandex so they stretch as you move. The skinny fit has functional pockets, unlike many jeggings, for holding your keys, phone, or cards. Pair them with a button-down and flats for a comfortable work outfit you’ll love.

•Available Sizes: X-Small — 4X-Large

•Available Colors: 6


This Belted Vest That’s Chic And Cozy

This belted vest cinches in on your waist without making you feel restricted. Wear it over jeans, leggings, or a dress to add a little cozy flare to your outfit. This sleeveless vest has an optional belt and large lapel. The asymmetrical hem and luxurious material make this a unique must-have that combines comfort and fashion. It’s available in rust brown or black.

•Available Sizes: Large Plus — 4X-Plus

•Available Colors: 2


A Trendy Two-Piece Workout Set That’s Seamless

Even after your workout, you’ll struggle to change out of this super-comfy and stylish seamless workout set. This two-piece set includes a scoop neck bra and high-waisted, full-length leggings. The skin-friendly material wicks moisture to keep you dry during an intense workout or a really hot day. Plus it’s less than $30 — what a steal.

Available Sizes: X-Small — X-Large

•Available Colors: 35