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

How to build your 9-to-5 wardrobe without going broke.

A model wearing a purple suit
Photo: Club Monaco

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.)

Buy one that you can tell is built well instead of making money the deciding factor — especially if you also wear the pieces separately. Look for heavier fabrics like wool (or tropical wool, if you live somewhere warm), and try bunching it in your hand to see if it wrinkles easily (it shouldn’t). Try Hugo Boss, Elie Tahari, Calvin Klein, Argent, or Theory.

A model wearing ankle pants and a blazer
Ann Taylor jacket ($169) and pants ($98)

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, at places like J.Crew, Michael Kors, Banana Republic, Talbots, and White House/Black Market.

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. Try Ann Taylor first — you’ll be surprised at how good some of them are.

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. “It’s not as important to wear expensive brands as it is to find quality clothes that fit well,” says Raimondi, who gets a lot of her separates at Zara.

A model wearing a black sheath dress and black heels

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 (try brands like Cole Haan, Loeffler Randall, or M. Gemi). That way, they won’t wear out within a couple of months.

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. Find understated options in modern shapes at Vince, Everlane, and Aritzia.

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. Often, pricier brands like Wolford are worth it — the fabric is higher quality, so with proper care, they’ll last longer. For less expensive options, try Hue or Talbots.

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. A great pair from Margaux, Newbark, or Tod’s will last you for years.

If Your Dress Code Is Business Casual

If your employee handbook tells you to dress business casual, congratulations! That means you don’t have to wear a suit, pumps, and stockings every day. Still, it doesn’t necessarily mean that anything goes. So think about how you want to be perceived by the people around you, and dress accordingly. “I work in tech. So when I walk into a room full of CMOs who are usually men aged 40 to 60, I need to look and seem older than I am,” says Alexa Driscoll, an account executive at Pan Communications.

Business casual means different things in different workplaces, though. “Working for a menswear company, the office is pretty laid-back when it comes to attire. I like to call it fashionably casual,” says Erin Grant, who handles PR for Bonobos. “But if I’m at a meeting out of the office, I dress depending on who I’m meeting and where.” Here’s what you need to cover all your bases:

Invest in these pieces

A great black or navy blazer. Wear it with black pants, a dress, or a skirt when you need to look dressy, or throw it over nice jeans and a blouse on more casual days. J.Crew, Club Monaco, and Margaux Lonnberg all offer modern, high-quality options that won’t eat your entire paycheck.

Button-down shirts and blouses. Nice tops are essential, but you don’t need to drop tons of cash on them. “You wear them every day, so they get beat up quickly. There’s no reason to spend more than $50 on a shirt that’ll be gone in six months,” Driscoll says. Try the men’s department for simple, slightly oversized button-downs, too, recommends Grant. Find cool, inexpensive blouses at Mango, and men’s shirts at Gant.

A model wearing Everlane’s cropped navy trousers and a gray sweater
Everlane The GoWeave Crop Trouser ($115)

Dressy pants. Wide-leg, pleated, skinny, and cropped all work, as long as the lines are clean and the material doesn’t look like it belongs at the beach or gym. (So, no linen or lycra.) “Interesting pants have a great flair without being too crazy. And they’re easy to style with simple tops,” says Grant. Just remember the seam rule: If your pants don’t have real seams, you’re dealing with a pair of leggings, says Driscoll. Find trousers at Everlane, Aritzia, and Topshop. Find grown-up slim cut or wide-leg pants at Eileen Fisher.

A pair of grown-up jeans. If it’s a dark wash, mid-rise, and a skinny or boot cut leg, it’ll work with a blazer and ankle boots, loafers, or heels. Find inexpensive options at Levi’s, and mid-price ones from AYR, Industry Standard, and J Brand.

Clean, simple dresses. Unlike in the corporate world, colors and patterns are usually fine. Just stick to clean shapes — like sheaths, shifts, or A-lines — that don’t hit higher than an inch or two above the knee. COS and & Other Stories offer cool, modern ones that are office-appropriate.

A model wearing dark denim mid rise jeans and a white shirt
Industry Standard Simone Mid-Rise Jeans ($115)

Cool flats or ankle boots. They’re more comfortable than heels for running around, and you can have fun with them. “I have a great pair of white oxfords — they brighten up any look and make it feel more me,” says Driscoll. Black ankle boots from Sam Edelman, Sigerson Morrison, and Loeffler Randall always work, too.

Then, add these

Knit shirts and tank tops. Don’t spend a fortune on layering pieces like these. “I try to bulk up at J.Crew or Gap when they have sales,” says Driscoll.

A pair of heels. You might not need them every day, but they’re essential for times when you need something dressier. Pumps are appropriate, but they’re not your only option. “I wear block heels or mules for days that I need something more formal, but also need comfort,” says Grant. Try Jeffrey Campbell, Marais, or Intentionally Blank.

If Your Dress Code Is Creative

Working in a creative space often means having work clothes and weekend clothes that blend together. “I don’t have a strict work look. I’ve been fortunate to always work in environments with unique personalities, and there’s not really a dress code,” says Rebecca Lysen, creative director at Phear Creative.

That doesn’t necessarily mean ripped jeans or a paint-splattered jumpsuit, though. “The women that I work with are put together, and they look good. I want to feel like I’m not falling short of what a woman who works at a magazine should look like, in terms of polish and creativity,” says Redbook senior editor Andra Chantim.

A model in a red leather jacket, light denim, and white ankle boots
Veda Grand Leather Jacket in Red ($498)

One way to do that is by starting with a foundation of business-casual pieces, and then finding ways to loosen them up a little bit. Like this:

Find fun third pieces. Think long vests that can be belted over pants or a dress, or blazers that go beyond the basic navy or black. “I have a green Marc Jacobs blazer and a boxy, buttonless J.Crew blazer that I wear over sleeveless dresses. It looks so much different than a cardigan,” Chantim says.

Or, swap your blazer for a cropped leather jacket. Whether you pair it with a feminine dress or high-waisted jeans, it’ll always make you look like you have your shit together. “It’s what I’d wear to a meeting. It’s like a power jacket,” Lysen says. Try Veda or Ganni.

Add interesting denim. You don’t need to save those amazing vintage 501s for Saturday if you pair them with a dressier top and great shoes — like heels or ankle boots. Try AMO, 3x1, or Re/Done.

Go crazy with your accessories. Chantim wears belts with fun details and whimsical jewelry, like a bedazzled pretzel necklace. Lysen favors a wide-brimmed black hat, and pulls out a furry purple muff to keep her hands warm in the winter. “I’ll wear it instead of gloves. It was probably $10 from ASOS, and I get so many comments,” she says.

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