I’ve always said that no matter how old we get, September has that “back to school” feeling. This year more than any other it feels that. In some capacity, most of my clients are heading back to work. Some are going back to the office full-time, others will be working in a hybrid manner while a few are continuing to work from home except for times when they are on the road. We’re nowhere near what our work lives looked like pre-pandemic and I don’t think they will for a long time, if ever.

With that, the way we dress for work has fundamentally changed. First of all, there are things we’re not willing to give up, the primary being comfort. Has there ever been a time that we’ve been more excited about elastic waistbands than now? I can’t help but think about my post from last week where I talked about how I am achieving the same goals but in a simpler manner in order to not stress myself out. That’s what we’re also doing with our work clothes. We’re looking to get dressed for work but in ways that are easier, more comfortable, and take less time. We want to look good but we just don’t want to work as hard as we once did.


I have put together five business comfortable looks for the workplace that don’t require you to give up the comfort you have become accustomed to while also looking professional and pulled together.

Outfit #1

business comfortable

This stretch pant style from M.M. Lafleur is an updated pair of leggings that allow you to feel like you are still wearing yoga pants while looking appropriate for work. With these pants, I added this duster cardigan from Eileen Fisher and an ivory shell from Theory. I finished the look with these flats from Marc Fisher and this statement wood necklace, available on Etsy.

Outfit #2

business comfortable

Maybe you’re completely over elastic waists and yoga pants and you’re looking for tailored pieces that are comfortable. Well, the good news is, fashion has gotten more relaxed in general. There is a much wider variety of pants styles, many of which have wider legs and pleats. These washable wool pants from M.M. Lafleur have a more relaxed leg shape and an easier fit that won’t make returning to tailored pants so jarring. I styled them with a cozy beige cropped wool sweater from COS, a burgundy belt, brown booties with a decorative heel from Aquatalia, and simple stud earrings from Lela Horn.

Outfit #3

business comfortable

The Dream Pant from Everlane is a favorite pant among many women for the simple fact that it looks like a trouser but feels like a jogger. If you are old enough, you remember the song, “looks like a pump, feels like a sneaker.” That’s what I think about when I look at these pants. This is what so many of us are going for right now, cleverly disguised comfortable work clothes.

We’re also mixing. We’re pairing super casual with tailored to achieve that mid-point between not looking too dressed up but not too dressed down. It’s a balancing act but also one that allows us to not have an overly compartmentalized wardrobe.

I styled these pants with a dark rose basic t-shirt from Theory and a grey blazer from J.Crew. I finished the look with a pair of grey sneakers from Cole Haan and simple silver hoops.

Outfit #4

business comfortable

While I was working on this post, I realized that not everybody’s idea of comfortable is pants, or after nearly two years of exclusively wearing pants, there may be a large group of women out there who are actually excited about wearing dresses again. Wearing dresses comfortably can be tricky because they often involve so much work, like special undergarments, tights, or finding the right arm coverage. Even knit dresses, which should be cozy and easy, can show off every lump and bump.

What I like about this dress from The Fold is it is a sweater dress but it’s a style that has enough ease not to require pouring yourself into shapewear. It’s also a style that can be dressed up and down. So a style like this could be paired with heels and dressier elements but for a more comfortable look, I styled it down with low heeled tall boots in olive and a stone pendant necklace.

Outfit #5

business comfortable

This has been such a strong look among my clients, an easy pair of narrow pull-on pants and an untucked crisp white shirt. Just simple, effortless, and chic. The shirts usually are more than just a classic button-down and the style is longer to tunic length. Clients are wearing the look with low block heels or flats. It’s unfussy, uncomplicated, and sleek. I styled this tuxed-inspired shirt from Vince with washable tapered silk pull-on pants from Eileen Fisher. I finished the look with the same Marc Fisher flats as in look one and ornate teardrop earrings from Knotty.

We’re still living in unsettled times and we’re still craving comfort and have realized that we don’t need to be uncomfortable to be productive. We can look good and be comfortable, we don’t have to compromise, and as you return to work, I hope these outfit ideas get you inspired.