3 min readIt’s likely you’ve heard the old adage, “Dress for the job you want, not the job you have.” But in today’s world—where business casual can sometimes lean more casual and what’s considered office-appropriate is often decided on a case-by-case basis—we’re left with the ever-present question: What do I wear to work?
Rather than leaving you to sift through your closet with a pile of clothes in your wake, we tapped some of the coolest women in the workforce to share their go-to outfits that make them feel confident, empowered, and, best of all, like a boss. From trailblazing entrepreneurs to fashion and beauty pioneers, these women are not only good at what they do, but look good doing it. Take a page from their sartorial playbooks as inspiration for your next office outfit, below.
Bozoma Saint John
Marketing Executive, Entrepreneur, and Author
“My go-to work look is all about Black excellence, with every piece designed by Black creators. I’m wearing a striking houndstooth dress by Olivier Rousteing for Balmain, paired with sleek black strappy heels from Arch NYC. I accessorized the look with the Retro Africa Sign Medallion bag by Orijin Culture and earrings from Khoi. Each piece reflects my bold, unapologetic style, ensuring I leave a lasting impression and own every room I walk into.”
Balmain Long-Sleeve Diamond Jacquard Bodycon Mini Dress
Orijin Culture Retro Africa Sign Medallion Round Bag + Stash Necklace
Aya Kanai
Senior Director of Marketing at Target
“A printed dress is an easy go-to for work, but to me, accessories always make the outfit. My jewelry is a mix of special pieces I wear every day and will pass on to my daughter with fun, interchangeable items. I love the Mary Jane trend so much that I have four pairs in different colors.”
Future Collective Long Sleeve Drop Waist Ankle Dress
Rothy’s The Square Mary Jane
Jamie Wolf Hoop with White Topaz Blackened Edge Drop
A New Day Brass Beaded Bracelet 3-Piece Set
Jodi Kahn
Vice President of Luxury Fashion at Neiman Marcus
“I’ve always been a dress girl for work and play—the simplicity of one item makes all the difference to me. I particularly love this understated Jil Sander dress; the sheerness gives just enough drama by revealing a hint of skin, but it still feels like an elegant option for any meeting or appointment. When making investments in my wardrobe, I always consider versatility. Since I often wear black, I like to choose statement accessories that pop. Snakeskin is timeless yet always on trend, especially for fall. I love this iteration from Bottega Veneta.”
Jil Sander Pleated Sheer-Skirt Sleeveless Maxi Dress
Alaïa La Bombe Stud Ankle-Wrap Stiletto Sandals
Bottega Veneta Small Andiamo Bag
Bottega Veneta Knot Python Minaudiere
Lauren Chan
Head of Partnerships at Universal Standard
“My go-to work look is a black suit, because it’s both chic and comfortable. I never understood why women—at least in the offices I worked in—were expected to invest in new trends every season when it was completely acceptable for men to wear the same suits on repeat and be seen as equally put-together. I thought they had a better deal, so I built a wardrobe of easy-to-wear power suits—and I’m never going back.”
Universal Standard Henning x US Warren BlazerBlack
Universal Standard Henning x US Irving Suit PantsBlack
Cuup The Plunge – Mesh
Now 25% Off
Naturalizer Karina Pump
Now 19% Off
Katie Sturino
Founder of Megababe and Body Acceptance Advocate
“One of my principles in life is ABV: always be venting. I love how this dress is flowy and ABV-approved. I also love a high collar for work, because it makes me feel professional and chic, and the shorter length makes it fun and versatile if you’re grabbing drinks after. As always, I have my blue-light glasses on for another professional touch, a.k.a. my work goggles. No outfit is complete without them, in my humble opinion.”
Tuckernuck Faded Roses Tate Dress
Gabriel + Simone Maverick
Journee Collection Jenicca Wide Calf Boot
Rue de Verneuil Parcours XL
Dee Poku
Founder and CEO of The WIE Suite
“Everything about this look is designed to make me feel comfortable, confident, and professional. I’m very partial to a pantsuit. I love the way they look, the message they convey, and the way they make me feel inside. I have a zillion well-cut button-down shirts. They’re my go-to staple. Hoops work with just about everything. And if you want to stride into a meeting with energy and self-assurance, there’s nothing better than a chunky heel.”
La Ligne Elizabeth Blazer
Now 50% Off
La Ligne Elizabeth Trouser
Now 65% Off
Tod’s D’Orsay Pumps in Leather
Jennifer Fisher 1.5” Lilly Baby Hoops
Marianna Hewitt
Co-Founder of Summer Fridays
“The tailored vest paired with classic jeans creates a polished yet relaxed vibe that feels effortlessly chic. I love the balance between comfort and sophistication, which makes it perfect for work. I’m always trying to balance feeling pulled together without sacrificing ease, especially on days when I’m on the go, from meetings to creative sessions.”
The Frankie Shop Fern Vest
Levi’s 501 Straight Jeans
Toteme The Heeled Sock Boot
Now 50% Off
