A Week of Outfits: Kim Anderson


Kim Anderson

Kim Anderson, a senior VP at the cannabis-infused beverage company Cann, gets style inspiration from Tracee Ellis Ross and Solange. “Solange is always a little different,” Kim says. “I’ve definitely gotten comments like, ‘Only you could wear that.’ I don’t know if it’s meant as a compliment! But to me, that means you have the confidence to play around.” Here, she shares five outfits she wore in a week…

Kim Anderson

Plaid set: Derek Lam 10 Crosby (skirt, top), via Rent the Runway. Sandals: Target, similar. Hat: thrifted, similar. Bracelet: flea market, similar. Rings: heirlooms from Kim’s grandmother.

“I try to be cost effective while still having fun with clothes. I used to work at Rent the Runway and still rent a lot of my clothes, which makes it easier to experiment with trends. Matching sets are a big thing right now. I also like showing off my body, like how this crop reveals my waist. It’s especially nice to see skin this summer, after two years of ‘inside dressing.’”

Kim Anderson

“This outfit makes me feel like Anne of Green Gables — with a touch of Gen Z.”

Kim Anderson

Dress: Nike. Jacket: Adidas. Sneakers: Target, similar. Fanny pack: Target.

“Because of my body shape — a small waist with thicker, shorter legs — I’ve always preferred dresses over shorts. The athleisure dress is a vibe, and I love that something so genuinely comfortable is currently in fashion. It’s easy to dress up or down — I wear it while running errands and for going out at night. Since the jacket has red details, I pair it with my favorite lipstick. Red lipstick is like a power tool; I keep it in my purse for whenever I need a pick-me-up.”

Kim Anderson

Necklace: thrifted, similar.

“My husband found this evil eye necklace at a market, and I wear it every day. Before meeting my dad, my mother traveled by herself all over the world and spent time in Africa. She brought back beautiful art, including a tapestry with a big eye, which she hung above my crib when I was a baby. The evil eye represents protection, and it was one of the first things I ever drew with crayons. When I was 12, I even asked my parents if I could get an evil eye tattoo. They made me wait until I was 18.”

Kim Anderson

Dress: R. Vivimos. Sandals: Funky Monkey. Bag: Target, similar.

“As you can see, Bridgerton has been a big influence! This dress is ethereal and light and gets so many compliments. I bought it in both white and green, and I wear it at least once a week.”

Kim Anderson

“Wearing white seems to make people nervous. But I just put it in the washing machine with a bit of bleach, and it’s fine.”

Kim Anderson

Tank: Nordstrom Rack. Joggers: Target. Boots: Steve Madden. Sunglasses: Amazon. Necklace: Kenneth Jay Lane, similar.

“This is my ultimate airplane outfit: black joggers, black tank, no bra.”

Kim Anderson

“The guy on the sweatshirt is my dad! He paid his way through Harvard Law School by modeling. So, now we have all these hilarious old modeling photos of him. For his 60th birthday, one of his coworkers made sweatshirts with them, as a prank. I found the shirts when I was home a few years ago. My dad was taking them to Goodwill, and I said, ‘Absolutely not.’”

Kim Anderson

Top: Farm Rio and pants: Farm Rio, via Rent the Runway. Sandals: Target, similar. Sunglasses: thrifted.

“When I was growing up, I got a lot of shit for my freckles. I mean, I’m mixed race and grew up in Georgia, so people took issue with my skin in general. But I’ve always liked my freckles. For my wedding, I told the makeup artist, ‘Whatever you do, my freckles need to show.’”

Kim Anderson

Thank you so much, Kim!

P.S. More women share their weeks of outfits, including a Toronto professor and a writer in the English countryside.

(Photos by Christine Han for Cup of Jo.)

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