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What to Wear to the Office This Fall

What’s in, what’s out, and a fashion stylist’s “formula” for dressing with confidence.

Photograph by Sarah Heaton.

After months of rotating athleisure wear for long days working from home, many of us have grown accustomed to a much shorter morning routine—one that doesn’t require a lot of time in front of a mirror. And while we may be looking forward to getting back to office-appropriate attire—whenever we may need it—our wardrobes may be so out of date, ill-fitting, or otherwise irrelevant-feeling that the process of getting ready may not be easy.

We asked personal stylist Naina Singla for tips on simplifying a new morning routine.

Do a Purge

As a rule, Singla tells clients to get rid of clothing they haven’t worn in two years. But if you haven’t touched something in that period of time because of the pandemic and you still love it, you might be able to keep or rework it. For example, a blazer you used to wear with pants and heels may be paired now with a T-shirt, jeans, and flats if your office has gotten more casual.

Singla advises getting rid of anything that doesn’t fit your current lifestyle—and that includes uncomfortable clothes: Make sure your closet has only “pieces that feel good and are not super-tight or itchy.”

Create an “Outfit Formula”

An outfit formula, Singla says, is “a recipe for a specific combination of items you can wear in different versions”—for example, the aforementioned jeans/tee/blazer combo with flats or sneakers, or a dress and cardigan with flats if that’s more you. “Not everything in your wardrobe needs to be part of your formula, but think of your outfit formula as your style staples.” Deciding on one or two formulas can make dressing for work a snap.

To start, she suggests assessing what you already have. Think about how you’ve worn your favorite pieces so you get a sense of which combinations you like best. (If you don’t feel confident doing this alone, you can book a session with a stylist.)

Once you’ve found a few looks you like, take photos to refer to later when you’re feeling stuck. Investing the time upfront, Singla advises, will save time in the future.

An edited wardrobe includes fewer but better-quality, more versatile pieces, all of which should make you feel confident. Invest in basics in neutral colors. Getting dressed in something that makes you feel good, Singla says, is a form of self-care: “It’s not just about how you look. It’s also about how you feel.”

Know What’s in Style

Before you purge your closet, it’s worth considering what’s in fashion.

No surprise, officewear is skewing more comfortable and casual, says Singla—in fact, it has been since before the pandemic. But not too casual: “There will always be space for yoga pants, but leave them at home.”

Here’s What Else to Know

Out: Skinny jeans.
In: High-rise straight-leg, slim-cut, or wide-leg jeans. Also, boot-cut (Singla points out these have smaller flares than they used to), cropped jeans, and ’90s-inspired baggy cuts.

Out: Anything too tight or too tailored.
In: Lightly tailored double-breasted blazers, soft jersey materials, and softly fitted, flowy dresses. Skip the pencil skirts, tailored suits, and form-fitting dresses, which Singla says don’t feel quite right at this moment.

Out: Black suit pants.
In: Looser, stretchy silhouettes. Think sleek cigarette pants—M.M.LaFleur’s “Stella” leggings are the perfect example, Singla says—or even wide-leg dress pants.

Out: Fitted white button-ups for women.
In: A more oversize version of the white shirt. “It’s all about how you style it. Half tucked, rolled-up sleeves, top buttons unbuttoned, layered over a dress [or] paired with athleisure. So versatile.”

Out: Traditional button-up shirts for men.
In: Untucked shirts and shorter shirt hems.

Out: Sky-high heels, wedge heels, round-toe pumps, and peep-toes.
In: Block heels or kitten heels, square or pointy toes.


Invest in These Seven Pieces

Shopping for fall? Naina Singla suggests the following wardrobe essentials to her female clients.

1. Classic trench coat: “Timeless layering for cooler days.”

2. White sneakers: “Dress down a look and make it more casual with a statement sneaker.”

3. Black oversize blazer: “Instantly makes any outfit modern and chic.”

4. Jeans: “Invest in one pair that make you feel amazing every time you put them on. Consider tailoring them to make them just right.”

5. Black dress: “One black dress that can be dressed up or down depending on how you accessorize. It’s a clean slate. I like a simple black silk slip dress.”

6. Layering jewelry: “Take your outfit to the next level with some layering gold chains and bracelets.”

7. Cashmere cardigan or sweater: “It can be worn over a silk cami, thrown over the shoulder for cool summer nights, or on its own.”

This article appears in the August 2021 issue of Washingtonian.

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Amy Moeller
Editor, Washingtonian Weddings

Amy leads Washingtonian Weddings and writes Style Setters for Washingtonian. Prior to joining Washingtonian in March 2016, she was the editor of Capitol File magazine in DC and before that, editor of What’s Up? Weddings in Annapolis.