For most 23-year-olds, operating a fashion line is a pipe dream—but business savvy runs in Kendall Reynolds’s blood. The daughter of local finance titans Jim and Sandy Reynolds, this Hyde Park native has made a name for herself with high-end heels that she designs and has handcrafted in Italy. Reynolds’s glamorous pumps are sold locally at the exclusive Oak Street boutique Ikram and in California at Beverly Hills’ Madison. (She calls her label Kendall Miles Designs, a nod to her younger brother, Miles Reynolds, a former basketball standout at Whitney Young.) As she prepares to preview her fall and winter line at a trunk show July 13, Reynolds shares her favorite things.

My signature style

Elegant and edgy with a refined sensuality. I always have on a stick-skinny stiletto.

Best Chicago meal

Harold’s Chicken. I get five pieces, fried hard, with mild and hot sauce, salt and pepper, and a blue Mistic.

Accessory I’ll never retire

My vintage red leather Chanel bag. It’s great for travel—soft but durable, and big enough for all my stuff.

Hidden local gem

The Garden of the Phoenix at Jackson Park. I went to Lab Schools across the street, and we’d go there to do homework and gossip.

Favorite restaurant

I go to Roka Akor once a week for filet mignon and sushi.

Beauty secret

I use olive oil on my skin, hair, and eyelashes.

Skill I’m dying to learn

I’m teaching myself color theory, and next I’m diving into art history.

What I surround myself with at home

My Maltipoo puppy, Milo. I’m obsessed.

Style icon

Rihanna. She’s never worn a bad outfit.