The Softer Side of Style: What to Wear for the Great Return, Part Two

In our WFH lives, we've become accustomed to comfort. Here are our clothing picks for venturing softly, and stylishly, back into the world.

Like many of you, I’ve been thinking about some sort of return. To life. To work. To dinner and dancing and wheeling and dealing. And with that comes a bit of anxiety. I’d be lying if I said the thought of drinking office coffee again and kissing my beloved Nespresso machine goodbye in the mornings was not panic producing. Like so many, I’ve embraced working from home and love the space and freedom it provides. Plus, good coffee. And time with my beloved dog son, Khan.

And no rentrée conversation would be complete without a thorough discussion on what to wear. I’ve written about post-pandemic style here before but consider this an evolution. I wrote about this before right here, but as summer begins its sweet crescendo, I’ve done more thinking on the matter.

I visited the local boutique Meg in my Brooklyn neighborhood to chat with an expert, and I talked with the owner about what’s next when it comes to dress. As the conversation unfolded, I realized that many of us felt a bit shook from a less than soft landing back to reality. It seems like there was minimal transition as people jumped on planes for summer vacations past due and ran out to see live music, and yes, many have returned to offices at least a few days a week.

We will all continue to crave comfort as we get up and go. I’m imagining workwear having a softer side

I’m going with the following for this fashion observer — we will all continue to crave comfort as we get up and go. I’m imagining workwear having a softer side. Think materials that feel fabulous against your skin, loose silhouettes, and easygoing basics that are simple and stress-free, even down to our bras and undies. I can’t be the only one who’s noticed a boob rebellion of sorts against bras with wires.  We are all leaving home again, but we still want what we want.

So let’s go shopping. I have a few ideas on how to go softly back to life in style. If you favor a caftan (and why wouldn’t you, really), think about a great dress for the office.


I’m a big fan of a do-it-all dress, and I was intrigued when I got served this dress by Australian brand ever by X. Sourced from upcycled Japanese remnant fabric, this dress can be worn as a caftan or cinched or sheathed and then some. The idea of only one dress is a cool one, and I love its versatility that could go from home to office in a snap. Layer with a blazer or with a pair of tall boots for the fall. So good and comes in a bunch of fab colors, though I might break my no more black dresses rule and go for it. And this top from Cuyana is lovely and so perfect for work with a trouser or skirt.


If you are troubled by losing your sweats, I feel you. But these sustainable Tencel Lyocell Rag and Bone silk-like pants may button up like jeans but feel like pj’s. I’m obsessed with them and think if you work in a more creative or casual environment, these could work with a nice sweater or blazer come fall.

Rag and Bone

I’m calling it now that this fall will be BIG for knitwear due to my theory that comfort will still be queen

And speaking of sweaters, I’m calling it now that this fall will be BIG for knitwear due to my theory that comfort will still be queen. I love everything on offer from Jenni Kayne. A cocoon cotton sweater to sit cubicle side may be just the thing to ease the Sunday scaries. And these knit trousers from Proenza Schouler are so chic with just about anything. And though their prices are premium, nobody makes a better sweater dress. So comfortable and so good to go anywhere, at all. This one has a bit of lurex for a bit of glam goodness.

Jenni Kayne

Proenza Schouler

And this cardi from J.Crew is soft and stylish. I love the way they’ve paired it with a menswear-inspired button-down and pearls. Great with jeans but could look great with a slim trouser, too.

J Crew

If you’re like me and love a lingerie look at home, this inky Vince slip dress can go back to work when layered with a chunky knit turtleneck. Textures are a big part of the picture for fall, and I love the silky feel of this dress paired with something a bit more substantial like this Cloud turtleneck from Everlane.



I also love a bodysuit paired with a skirt or pants and a blazer. My fav comes from Reformation, and I love the button-down Henley look that somehow feels like Elsa Peretti if you rock it with some great necklaces.


A shirtdress is always a fabulous option. This white take from minimalist masters COS is stylish, and I like it paired with pants for a modern take on two-piece dressing, a look I have loved since spending a lot of time in Amsterdam in my late 20s. All the cool chicks in the ‘dam wore dresses with pants so they could ride their bikes in style and be practical all at once.


Suiting can feel relaxed if you get the proportions right

Suiting can feel relaxed if you get the proportions right. I’m still obsessed with a more oversized vibe, so I can’t get enough of Paris brand The Frankie Shop’s take on workwear. I love this suit. Both comfy and chic and can take you from desk to din-din.


Frankies Shop

This set from MM LaFleur is so up the right alley. Look how buttoned-up and professional a track pant and blazer can be. As for shoes, these slingbacks from Zara are a legit mood lifter due to their snappy color and Balenciaga vibes for a fraction of the price. And if you can get away with sandals at work, these from Gucci are super splurgy but so good.

MM La Fleur



So as I sit here on my annual beach vacation, still under the duvet, I permit you to go softly back to life. Think skin-loving fabrics, loosened up silhouettes, and whatever you need to get to it and get through it. Because, as Glennon Doyle says on her podcast, “we can do hard things.” Particularly when tempered with a side of softness and a heaping helping of style.


  1. If I see one more website that caters to older women using millennial models I’m going to scream. What don’t you get? I work with models over 50. They are out there. Don’t be lazy. Be supportive and hire real models over 50.

  2. Although I agree it would be nice to see models our age, I also understand that the Ageist cannot produce (and pay for) fashion shoots every time they want to talk about fashion. So they rely on images provided by the brands… and the brands use yound people as models. If anything, contact the brands themselves to ask them to feature a more diverse cast 🙂

    • As long as we promote the brands that continuously ignore our demographic we are part of the problem not the solution. How about promoting brands that do use older models? They exist.
      When Lesley Jane Seymour, former editor of More Magazine (fired due to ageism) hired me to write a product review for her online magazine that caters to women 40+, I asked the company to send me the product and used my 67 year old self to illustrate the story. Using an iPhone and the great outdoors the cost? Nothing.

  3. While you probably got the images from the manufacturers…asking that they provide imagery with older models will put some market demand on them to hire more than just young. While you’re at it, consider adding some folks of color as well.
    As a curvy gal, I would probably look like a big lump in many of these…how about soft, comfy and yet still a bit tailored.

  4. Agree with the comments above. Feature mature models and encourage clothing companies to do the same! I want to see women in MY age group.


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Sheri Radel Rosenberghttp://sherimavenblog.com/
Sheri Radel Rosenberg has spent a life in advertising. Currently she's a freelance writer focusing on women at midlife and the power of reinvention. She regularly writes on her own blog and also works with brands to develop content in the areas of women's health, wellness, fashion, and beauty .She lives in Brooklyn with her husband and a ten pound ball of doggie fluff called Khan.


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