This Is How to Create the Perfect Work Wardrobe

Spoiler alert: Comfort is key.

Clothing, Jeans, White, Street fashion, Denim, Fashion, Waist, Footwear, Outerwear, Trousers,
(Image credit: Kelsey Cherry)

For Kathyrn Condon, a junior strategist at Brand Bureau—a hospitality, design, and strategy firm in New York City—having plenty of comfortable and practical staple pieces in her closet is essential. "While I want to look good and feel good at work, I don't want to be fiddling with my clothes or be in an uncomfortable pair of shoes that don't make me feel like my best self," she says.

That's why nailing down a shoe that's as sturdy as it is fashionable is so important for Condon. Take the Joan of Arctic Wedge II Chelsea Boot, for example. They're the kind of shoes that the California native—whose personal style lands "somewhere between a little preppy, a little bit California-cool, and a little bit practical"—can easily fit into her work wardrobe.

Condon says that being in a client-facing industry, dressing the part is about "putting our best foot forward and looking professional, but also creative and cool, like the creatives we are."

So what does that look like in practice? Check out Condon's styling tricks for filling your closet with items that you'll feel comfortable and stylish in at work.

Invest in Blazers. Lots of Them.

Clothing, Jeans, Denim, Footwear, Street fashion, Shoulder, Fashion, Outerwear, Shoe, Leg,

(Image credit: Kelsey Cherry)

"I'm all about outerwear," Condon says. "Being in New York, [my wardrobe] revolves around a set of really great investment staple outerwear pieces." You'll often find Condon in a white tee and jeans with a blazer on top to dress it up. Then, when meeting friends after work for drinks, she can easily ditch the blazer for a more casual look.

A blazer works with many types of footwear, too, and choosing the right pair of shoes is essential for Condon, who walks all over the Lower East Side. "What I wear to work needs to be super functional," she says. The Sorel boots are an ideal choice—they're chic enough to be paired with the blazer, but comfortable enough to get Condon from work to the wine bar afterwards.

Sorel boots; L’Agence blazerJungmaven topLevi's jeansLuz Ortiz ringLegier ringAmanda Pearl ringsMaslo Jewelry earringsEnki sunglasses

Find a Pair of Boots You'll Wear Into the Ground.

As soon as October hits, Condon has several pair of booties that she wears literally every day. From client meetings to going out after work, she leans toward a low heel and sturdy, supportive shoe—bonus points if it's weather-resistant, like the Sorel boots.

The added few inches on heeled boots is empowering at work, too. "I feel taller, I feel confident—all that jazz," she says. With a versatile pair of boots, you can wear them with basically any outfit. Try them with a skirt for that perfect balance of comfort and style.

White, Clothing, Street fashion, Fashion, Snapshot, Leg, Footwear, Human leg, Waist, Shoulder,

(Image credit: Kelsey Cherry)

Sorel boots; Serrano top& Other Stories skirtAnni Lu necklace; Enki sunglassesCarolina Santo Domingo bag

Don't Underestimate Denim

Clothing, Footwear, Street fashion, Fashion, Shoe, Tights, Ankle, Brown, Leggings, Snapshot,

(Image credit: Kelsey Cherry)

"I pretty much wear jeans all the time," Condon says. "I'm rotating some version of four to six pairs of blue or black denim most of the week." Jeans are a work staple—you can dress them up, like Condon does with this statement blazer, or incorporate them into a simpler look with a white tee.

Consider black jeans when opting to add denim into your work wardrobe. They appear less casual than blue, and there's plenty of freedom to style them. Add a pop of color to the outfit with a brighter shoe, like the red Sorel boots Condon is wearing here.

Sorel boots; Veronica Beard jacketKallmeyer sweaterCitizens of Humanity jeansLuz Ortiz ringLegier ringAmanda Pearl ringsMachete earringsCarolina Santo Domingo bag

Maya McDowell

Maya McDowell is an Assistant Editor at HearstMade.