Comfortable Workwear You Need Now To Survive Going Back To The Office

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Comfortable workwear is finally de rigueur.

While some employers are fully embracing 100% remote work, others are easing into back-to-the-office plans, either fully or partially. For those of us headed (or already) back at our cubes, the thought of ironing a stiff button-down, pulling on an unyielding pantsuit, and slipping into thin-soled heels may leave you cold. The solution – a new generation of workwear that’s soft, stretchy, cushy, and downright cozy. These five pieces are appropriate for your next executive meeting, but feel like your favorite athleisure. Let’s just say you could take a nap in them and still feel comfortable. (And don’t worry, I have heels covered for you too.)

The Turning Point

I spent all of last year in sweatpants and t-shirts, pulling my mind-of-its-own hair back with one of three headbands on rotation. It was part of the ease and flexibility of working at a marketing agency with a laid back dress code that even took the step of ditching office space and going 100% remote before the end of 2020. Zoom calls made it even easier to be casual since people only saw me from the shoulders up. (If I have earrings in, it looks like I showered, right?)

In January of this year, I did a full 180, accepting an in-house corporate marketing job at a big company with a more formal dress code – and a return to office plan. While dressy jeans are acceptable, if 2020 taught me one thing about my wardrobe it’s that denim is just not that comfortable. I quickly turned to the source of my favorite sweatpants for a solution.

Proof that comfortable workwear can be chic.

The Not-Sweatpants

The Everlane women’s track joggers are on constant rotation when I’m at home, because they’re super soft, fitted, and cropped just a little for an off-duty chic look (size down for the best fit). Meanwhile, I think I bought the entire Everlane Men’s Track collection for my husband. Lucky for me, Everlane worked it’s cozy-sweats magic on their aptly named Dream Pant that look like sleek cropped work pants, but with generous stretch and a hidden drawstring waist to accommodate lunch, bloating, or heck just wanting to feel comfortable at work.

I love the delicate piping detail down the front of these pants, and bonus – they don’t wrinkle or attract my dog’s hair like velcro. While I do wish they had a faux-fly for an extra touch of polish, these are all-around a must-have if you want to feel like you’re wearing sweats at work.

Pictured with my favorite work bag, the Lo & Sons Seville Tote.

The Draped Top

I often wear the Dream Pants pants with an equally lovely, equally forgiving draped top from M. M. LaFleur. (pictured wearing the discontinued Deneuve, but the new Antoinette is almost exactly the same). It’s a faux-wrap, which means you don’t have to worry about gaping, and the wrinkle-resistant knit fabric looks elevated while staying light and airy. Plus the front is just low enough to feel a bit sexy, without being inappropriate.

This draped top from Amour Vert is similar, comes in different colors, and bonus – is crafted in a cooling modal knit that’s comfortable even in summer. (I have it in four colors). The draped wrap style is such a classic, it goes with pants or skirts, flats or heels, and makes it so easy to get dressed in the morning.

The Workhorse Heels

You may be thinking – why are heels on a list of comfortable workwear? These Mia slingbacks from Inez are hands down one of my favorite pairs of shoes ever – I wear them at least once a week if not more often. Not only do they have amazing arch support, they come in three different widths and have an elegant 2.8” heel that doesn’t hold up a quick stride.

The snakeskin print is a great addition to your workwear wardrobe because it effortlessly ties together light and dark colors, but the Mias also come in nude, black, red, and navy. Your other heels may get jealous. Use code VANESSA15 for 15% off.

The Stretchy Skirt

While finding a pair of cozy, stretchy work pants wasn’t too hard, finding an equally comfortable skirt was much tougher. I lucked out by stumbling across the Cortlandt skirt from M. M. LaFleur in their lightweight-yet-substantial Worth fabric that I can only compare to scuba material – but breathable and body-skimming instead of skintight.

Pencil skirts can too easily feel stuffy, but the sassy front slit keeps it fresh. I can see myself styling this just as easily with a blouse for a work presentation, as a strappy top for a night out. You’ll definitely get mileage out of this one!

This top is another favorite from Amour Vert (while the exact style is sold out, this one is somewhat similar). It feels like a sweatshirt but somehow dresses up effortlessly, especially with a classic Ferragamo belt (this one is reversible!) to elevate the workwear look.

The Killer Comfy Pumps

And of course we have to talk about these stiletto heels. While flats fly at my office, I truly love a good heel. The sleek Alta pumps from Inez have a 3.5” heel that’s sexy and leg-lengthening, yet work appropriate. This pair in classic black nappa leather is a go-to on days I want to add some length while keeping it classy.

Like all Inez heels, they have amazingly squishy insoles, arch support, and come in three widths. What’s not to love? You can read my full review of the style here.

Styled with the Senreve Midi Maestra bag in Mimosa Bordeaux – Get $50 off with my link.

Going back to the office shouldn’t require sacrificing the soft, stretchy, clothing we’ve grown accustomed to while working from home. I’ve definitely stocked up on comfortable workwear and have disposed of anything that doesn’t fit the bill or otherwise bring me joy!