41 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!

1

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

2

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

3

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

4

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

5

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

6

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

7

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

8

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

9

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

10

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

11

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

12

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

13

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

14

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…

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