Recently, I became convinced that the time was right for a floor-length, sheer black caftan dress split to the upper thigh. I had an intoxicating image of myself as the Stevie Nicks of the Midwest, swooping from the zoo to a kindergarten birthday party in a flutter of witchy black gauze.

The trouble is that I am not witchy and gauzy, and neither are my clothes. I'm a devotee of tall, flat brown leather boots; dark jeans; tweedy blazers; and V-necks. I like a pendant necklace or a chunky cuff bracelet. My image of myself in this core outfit is of someone polished but not fussy, purposeful and effective. Someone who speaks her mind and doesn’t whisper and has no patience for jeweled necklines or puffy sleeves.

But it's hard to find the line between knowing thyself and falling into a big, fat rut. I'm getting older, I have a young child, I work at home—and my "signature" jeans are usually the same old pair, my beloved V-necks all in varying subdued shades. Have I focused my style, or have I just given up?

It’s this conundrum that leaves me susceptible to the siren song of the caftan. Or a clingy orange cocktail dress with cutouts, because I’m attempting to remember to be sexy. I go through several Burning Men’s worth of flowing peasant blouses in an effort to appear carefree. I buy a short, bright Aztec-print dress in the hopes that owning it will force me out to the kinds of places that demand a short, bright Aztec-print dress—um, dancing, maybe?

The terrifying thing about these makeovers is that they leave me wondering if I have any clue at all how I really look: my age, my body, what flatters me, where I should even shop. I knew I was too old for whatever store I was in last spring when the first ten things I grabbed turned out to be rompers. I am 42, and there will be no romping.

Not long ago, I finally realized these fraught shopping trips are less an attempt to look different than an attempt to imagine living differently. The woman who wears that caftan is obviously someone who goes to the theater more than I do, who entertains more effortlessly than I do, and who is unafraid to set herself apart from everyone else at a backyard barbecue. Someone who still pays attention to herself and hasn’t forgotten how to command attention from others.

Because unless I'm delusional—for the sake of argument, let's assume I'm semilucid—I have commanded some attention in my day, for looks or talent or wit, and sometimes I miss that feeling. I miss the days when I would work a party and count up the eyes that followed me around the room. I no longer do that, because I’ve been married for years and all those eyes now belong to good friends who are also married. The point is that I never intended to blend in. Even though 99 percent of the time my life is just what I want it to be, I need these fashion crises to help me test whether I can still be extraordinary.

Fine, so it's not a perfect system. I return a lot of my aspirational purchases or watch them languish in my closet until they hit the donation box. But some of them become new staples—the formfitting wrap dresses, the floaty scarves, the bold-print tunics. My very favorites are two big cocktail rings I bought, each for a professional milestone: one has an emerald-cut citrine, the other an oval lemon quartz. They look amazing with jeans or with dresses, with stilettos—or even with flat brown boots. They’re flashy and unusual, their tawny brightness reminding me that I’ve accomplished some singular things. And no one I know wears anything like them.

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