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The Work Clothes That Feel Like Pajamas

Woman wearing beige tunic sweater/blonde woman wearing white t-shirt and blush maxi skirt/woman wearing beige wide-leg trousers

Remember when you were in school and you would have “pajama day” once in a while? What if we told you you can wear pajamas to work as an adult? Okay, not actual pajamas, but you can wear work clothes that feel like pajamas.

Thankfully, if you know where to look, these fashionable and comfy pieces are findable. The best part? They fit the dressy-casual attire most offices are looking for, and you’ll stay comfortable all day, no matter what tough tasks you have to tackle.

Not sure where to start looking for work clothes that feel like pajamas? We’ve got you covered.

Wide-Leg Trousers

Woman wearing high-waisted wide-leg beige trousers

Wide-leg trousers are extremely popular at the moment. They offer a vintage vibe and can be made dressy-casual by pairing them with a fitted blouse and a pair of heels.

But, the best part is that they’re extremely comfortable. Most are made of thin, flowing fabric so you don’t have to worry about any tight, ill-fitting pants that cause you to stretch and twist throughout the day just to find some relief.

Tronjori Women High Waist Casual Wide Leg Long Palazzo Pants

Wide-leg pants are dressy enough for the office and will leave you feeling free and breezy all day.

Linen Pants

Woman in high-waisted linen pants

It’s not easy to find pants that feel like pajamas, but linen comes close. Linen pants can be dressed up or down, and the fabric is so light and breathable that you might find yourself wearing these pants on the weekend as well as in the office. While you might not be able to wear linen as much in the fall and winter, it’s the perfect option for staying cool at work in the summer or in climates that are warm year-round.

heipeiwa Women's Linen Casual High Waist Wide Leg Straight Dress Pants

Linen pants that are breathable and perfect for work and play---in a variety of colors.

Swing Dresses

Woman wearing a purple swing t-shirt dress

A knit swing dress can be considered dressy-casual attire for the office, but most are comfortable enough to wear just about anywhere. Need a post-work nap? You can fall asleep in a t-shirt swing dress and be just as comfortable as you are in your jammies.

If you’re worried a knit swing dress is a little too casual, dress it up with jewelry and heels.

DUSDIMON Women's Summer Casual Tshirt Dresses

A swing dress that's casual enough to fall asleep in---just not at your desk!

Loose and Flowy Jumpsuits

Woman wearing olive green loose jumpsuit

Remember when you used to wear onesie pajamas as a kid? While you probably can’t get away with wearing them to work, a light and loose jumpsuit is the next best thing when it comes to work clothes that feel like pajamas.

Jumpsuits are very much in style right now, and they’re a perfect transition piece from summer to fall—you can add a cardigan or jacket, and dress yours up with jewelry and heels for an office-appropriate ensemble.

Prinbara Womens Casual Sleeveless Strap Loose Adjustable Jumpsuits

A casual and flowy jumpsuit that's easy to dress up or down for any occasion.

Cozy Cardigans

Woman in jeans and chunky cardigan sweater

You might not be able to wear a robe to the office, but a cozy, blanket-soft cardigan is the next best thing. Plus, let’s be honest—office spaces are notoriously chilly! Stay comfortable and warm in a chunky knit cardigan that can be considered both dressy-casual attire and comfortable loungewear for hanging out at home on the weekend.

MEROKEETY Women's 2023 Winter Long Sleeve Soft Chunky Knit Sweater

Comfortable, cozy, and perfect for chilly offices!

Maxi Skirts

Blonde woman wearing blush-colored maxi skirt and white crop top

Some dresses and skirts can be uncomfortable because you feel the need to tug them down all day. Maxi skirts are the solution for the office.

Not only are maxi skirts floor-length, but most of them are made with light, flowy material that is extremely comfortable and not confining at all. Plus, maxi skirts (and maxi dresses) are great seasonal transition pieces that you can wear into the cooler months of the year since your legs are fully covered.

ebossy Women's High Waist Flowy Pleated Chiffon Maxi Skirt

Flowy, fabulous, and totally comfortable enough to feel like pajamas.


Woman looking at phone on workout bench/woman wearing t-shirt and leggings smiling with her dog

Looking for pants that feel like pajamas? With cooler weather approaching, you might already have a few leggings in your wardrobe. They’re great for pairing with oversized sweaters and tunics, and you might even wear them to the gym. But, the right kind of leggings can also be worn to work—not necessarily as standalone slacks, but underneath skirts and dresses to keep you cozy and comfortable all day.

High Waisted Leggings for Women

These leggings provide comfort and flexibility, and they're buttery-soft to make your workday feel just a little bit more relaxing.

Sheer Shawls

Woman wearing a white tank top and a flowy floral cardigan

If a cozy, warm cardigan feels like a winter robe, a flowy, sheer shawl will make you feel like you’re wearing a silk robe to the office. Comfort meets class when you don one of these sleeved shawls. It’s a great transition piece for the cooler months, and you can even get away with wearing a thin-strapped dress or top underneath it since it provides plenty of coverage.

Women's Floral Print Puff Sleeve Kimono Cardigan

A flowing floral cardigan can add a touch of elegance to any outfit, but the best part is how soft and comfortable it feels!

Plush Socks

Variety of plus slipper socks

There’s no rule when it comes to dressy-casual attire that you have to wear high heels to work every day. In the fall and winter, wearing a pair of sensible shoes or boots can keep your feet warm—and they’re far more comfortable.

You can give that comfort level a boost and make your feet feel like you’re wearing cozy slippers with a pair of plush socks. Often called “slipper socks,” you can experience toasty feet and pretend you’re binging your favorite Netflix series on the couch while crunching numbers or taking calls at work.

Womens Super Soft Fuzzy Plush Warm Winter Home Sleeping Slipper Socks

Comfortable, cozy slipper socks that are perfect for home or the office.

Tunic Sweaters

Woman wearing oversized beige tunic sweater

Have you ever thought about curling up in a blanket at your desk and taking a mid-afternoon nap? It’s okay, we won’t tell your boss. While you might not be able to sneak in a snooze with a throw blanket, you can feel just as warm and comfortable with a long, cozy tunic sweater.

These pieces are often made of thick, warm material and naturally loose-fitting, so it can feel like you’re wearing a heavy blanket. Double up the comfort by pairing a longer tunic sweater with leggings!

ANRABESS Women's Turtleneck Oversized Sweaters

An oversized sweater that feels like a blanket.

As you can see, there are plenty of options when it comes to work clothes that feel like pajamas. Consider adding a few of these items to your work wardrobe—the next day you’re feeling a little tired before heading to the office, you’ll be glad to have these comfortable pieces to pull from your closet.

Stacey Koziel Stacey Koziel
Stacey Koziel is a news writer at LifeSavvy. She's worked as a freelance writer for over ten years, focusing on family and lifestyle content. She also has a background in marketing and social media, and is always eager to talk (and write!) about the latest TikTok trends. Read Full Bio »
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