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Somehow as I inched closer towards 40, my hemlines inched closer towards my ankles. I turned 39 in November and couldn’t remember the last time I wore a dress or skirt that showed my knees. In the summer I wear flowy A-line cotton dresses that graze mid-calf, in the fall and winter pencil skirts hit my knee or below. I have shorter skirts in my closet, was there a reason I never wore them anymore? Age is certainly a factor. I am categorically an elder millennial and I never want people to think I woke up one morning intent on cosplaying a Gracie Abrams-loving Gen-Z queen. And yet, why can’t an almost 40 year-old wear a short skirt?
I considered this when asking a fashion editor friend whether my mid-calf houndstooth skirt worked with kitten heels. She looked down dubiously, then definitive: “No. The longer the hem the higher the heel needs to be.” I really don’t like wearing high heels for more than a few hours, so I wondered if the inverse would be true: the shorter the skirt, the lower the heel? I figured it was worth a try. And why not experiment with a different silhouette? For some reason, a shorter hem channeled festive to me and felt holiday party appropriate. Off we went.
In 2013 I snapped up a Marc Jacobs mini dress from his fall 2012 goth victoriana collection, one of my favorites, on sale on Moda Operandi. Even then, it grazed too high on my thigh for comfort, especially on sticky bare-legged days. But for an evening with two holiday stops I braved the velvet and pom pom trimmed, tropical print shift with a pair of opaque black tights and Tabitha Simmons pointy toe Mary Janes for two seasonal fétes: Derek Blasberg’s wreath-making extravaganza at Banana Republic and Kaitlin Phillips’ Chinatown bacchanal. The trial began though with pre-school drop-off where I was harshly reminded that bending over needed to be a thoughtful affair. The cardboard gingerbread men they were making in my son Artthur’s classroom were displayed on the floor—I almost surely flashed more than my hem to poor Lenka, Arthur’s unsuspecting teacher. Once at the office I was reminded of a few short skirt concerns: stocking quality is of the utmost importance. Tights move from an ensemble cast member to near top billing, there is just so much more stocking visible with a higher hemline. I tend towards inexpensive tights because I get runs in them so often, but my opaque J.Crew pair were a tad too shiny for this occasion and I regretted not wearing my more matte Wolford or Swedish Stockings ones. I also realized you cannot wear tights with a darker girdle section (as many pairs have) as this gradation can peek out when you sit. Sitting in a short skirt was an extra consideration that I did not appreciate. I am in a lot of meetings seated next to colleagues and the constant fear of showing them too much of my thighs was a distraction.
For the Vogue holiday party I wore a red and navy crewel work Tory Burch skirt that has hibernated in my closet for several years. This attempt was more successful because the skirt is slightly longer than the Marc mini dress and that extra inch or two meant I wasn’t constantly fussing with the hem when seated. But proportions feel important with a mini skirt. The equation that worked for me was: small earring, small heel, large sweater. With the Tory Burch skirt I wore a moss-colored v-neck sweater long ago borrowed from my stepfather. The looseness of it felt right with the narrow, short silhouette of the skirt. I broke my flats rule by wearing a chunky heeled loafer and felt like that worked in this rare scenario but if tried again I may revert to a flat loafer.
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