The Individualist

As chief media and marketing officer for the lesbian lifestyle company Olivia and a longtime activist in the gay and lesbian community, she is literally shaping the style in which lesbians live: personally, from her posts on the national board of governors for the Human Rights Campaign and the board of directors for SF’s LGBT Community Center; and professionally—Olivia provides lesbians with first-rate vacations, entertainment, media and community support. To see Riddle’s savvy in action, head to Orson, the new SoMa restaurant that she’s cofounding with her partner, chef Elizabeth Falkner, when it opens later this year. What influences your style? I travel a lot, so I like to wander around cities and see what people are wearing. Also art and installations. Jenny Holzer uses public spaces, light and other media to create her thought-provoking artworks. For me, my own personal style can also be a public space to say something or create a conversation. How do you create conversation through your style? One of my favorites was pairing a ruffled white shirt from Anne Fontaine with a black T-shirt from M.A.C. with “Warning: President Bush is hazardous to women’s health” emblazoned across the chest. Proceeds from the shirt went to Planned Parenthood. What’s your favorite item in your closet? I just can’t choose. I have a sensational Gucci long-haired-shearling double-breasted jacket with an exaggerated collar. It’s just so decadent. I also have a custom watch with a classic Cartier roadster face and an incredibly cool H-link band by Chrome Hearts. It combines my two favorite jewelry lines. What’s your fashion pet peeve? This notion that lesbians have no sense of style. There have been plenty of lesbians who’ve inspired great trends. Is there a beauty product you can’t live without? I’d be lost without a great haircut and my Kerastase and Bumble and Bumble hair products. I often mix them together, using my palm like a painter’s palette. What’s the best fashion advice you’ve ever received? To wear what you feel comfortable in. It doesn’t have to be sensible, but it has to fit and you have to carry it well. How would you describe your personal fashion sense? Edgy, with a little feminine flair. Even if I’m wearing a suit, there’s going to be something edgy—I like to use bracelets as cuff links and weave scarves through buttonholes. What I wear alters how I feel, and it’s important for me not to be constrained by someone else’s perception of what I should be wearing.