What to Wear to Work, From Women Who Have It Figured Out

Sunday Fashion
Mar 4, 2019
3 min read

Whether you’re just starting out or having been doing the daily grind for a while, getting dressed for work can be a struggle. You want to wear something that shows people how awesome you are at your job without actually taking the focus off your work. You also desperately need to find a pair of cool black pants that don’t look like they came from The Limited circa 1995.

Those sound like tall orders, but building (or rebuilding) a functional work wardrobe that you love is completely within the realm of possibility. In fact, it might actually be easier than you think. We asked six women about the pieces they reach for again and again, and how they put it all together to build cool, comfortable outfits that let their bosses, coworkers, and clients know I’ve got this. Here’s how you can do the same. (Hint: All the links will take you directly to the pages you’ll want to hit first on each brand’s website.)

If Your Dress Code Is Conservative

In high-powered fields like law, business, and finance, professionalism is obviously still the name of the game. “You have to be well-dressed and well-groomed to impress corporate clients from big companies and funds. They expect you to look conservative and traditional,” says Shannon Raimondi, a lawyer in New York.

Usually, that means suits and separates in classic colors and shapes. “I try to pick things that won’t become a conversation point. If my boss comments on my outfit, I feel like I’ve failed for the day,” says New York lawyer Ilana Wolk. Here’s what works:

Invest in these pieces

A great suit in a neutral color. Skirt and pant suits are both acceptable, just make sure the fit is impeccable. (Read: If it’s not quite right off the rack, get it tailored. The jacket’s shoulder seams should end at your shoulders, and the lapels should lay flat when the jacket is buttoned.)

Neutral dresses in simple shapes. Black, navy, or wine-colored sheath dresses are easy, one-and-done outfits that you can wear year-round. Find them, along with blazers, pencil skirts, and dress pants.

Blazers. Start with one or two blazers in traditional shapes and colors (like black or tweed). You can add more to your collection over time. “Blazers are my one way to show my personal style,” Raimondi says. “I have ones in white, light pink, seersucker, and a black one with a black lace back.”

Knee-length pencil skirts. Approach these like blazers: Start with one or two in basic colors that you can mix and match with your blazers, and expand from there. T

Black or gray dress pants. If full-length ones feel stuffy, opt for a chic pair of ankle pants instead. “They’re more stylish, so they’re the only dress pants I wear,” Raimondi says. Don’t feel like you need to spend a fortune on fancy separates, though.

Shirts and blouses. Simple button-down shirts always work. But blouses in different colors or with interesting details (like ruffles or bows) can be an easy way to make your outfit feel less cookie-cutter. Non-iron materials like washable cotton or poly blends are your friend here.

Classic pumps. Think two to three inches max in simple colors like black, navy, or maroon. They don’t need to be high-end, but they do need to be comfortable and sturdy.

Then, add these

Sweaters. Crew necks, V-necks, and cardigans in neutral colors all work, and they can be paired with dresses, skirts, or pants.

Sheer stockings. They’re a must in conservative work environments, so stock up. “You should wear black stockings with black dresses and suits, navy with navy, and nude if you’re mixing colors. I always match my shoes to my stockings,” Wolk says.

Comfortable loafers or flats. A dedicated commuting flat extends the life of your heels, and it looks better than sneakers. “Most female lawyers in New York, including myself, have a collection of shoes under our desk that we slip on when we get to the office,” says Raimondi.