For some reason, as I approached 40, the hemline started to inch closer to my ankles. I turned 39 in November, and I can’t remember the last time I wore a dress or skirt that showed my knees. In the summer, I wear flowing A-line cotton dresses that hit my mid-calf; in the fall and winter, I wear pencil skirts that hit just below my knees. I have a short skirt in my closet, but is there a reason why I don’t wear it anymore? Age is certainly a factor. I’m definitely a millennial, and I never want anyone to think I woke up one morning and decided to cosplay as a Gracie Abrams-loving Gen Z queen. So why can’t people who are almost 40 years old wear short skirts?
I thought of this when I asked a fashion editor friend if my mid-calf houndstooth skirt would go well with kitten heels. She looked down suspiciously, but then said firmly: The longer the hem, the higher the heel should be. ”I don’t really like wearing high heels for more than a few hours, so I thought the opposite might be true. In other words, the shorter the skirt, the lower the heel? I thought it was worth a try. And why not try a different silhouette? For some reason, a shorter hemline gave it a festive feel and felt appropriate for a holiday party. I left.
In 2013, I purchased a mini dress from Marc Jacobs’ Fall 2012 Goth Victoriana collection. One of my favorites was sold at Moda Operandi. Still, it just skimmed over my thighs for comfort, especially on those sticky barefoot days. But on two holiday nights, I braved the two-season event in a tropical-print shift with velvet and pom-pom trim, opaque black tights and Tabitha Simmons pointy-toed Mary Janes. Went to: Derek Blasberg’s wreath-making extravaganza at Banana Republic and Caitlin. Phillips’ Chinatown Vacation. But the trial began at kindergarten drop-off and pick-up, with a stern reminder that bending over requires thoughtful action. The cardboard gingerbread men they had been making were lined up on the floor in their son Arthur’s classroom – and I was almost certain that poor Lenka, Arthur’s unsuspecting teacher, had his eyes widened beyond the hem. Aimed. When I got to the office, I remembered some of my concerns about the short skirt. That means the quality of the stockings is the most important. Tights move from ensemble cast members to positions near the top, with higher hemlines allowing more of the stockings to show. I tend to prefer cheaper tights because they chafe a lot, but the opaque J.Crew pair were a little too shiny for this occasion and I wish I hadn’t worn the more matte Wolford or Swedish Stockings tights. I regret it. I also found that I couldn’t wear tights with a dark girdle (like many pairs) because this gradient would peek through when I sat down. Sitting in a short skirt was a special consideration that I didn’t appreciate. I often sit next to my co-workers in meetings, but I’m constantly worried about showing too much of my thighs to them, which is distracting.
For the Vogue holiday party, I wore a red and navy Tory Burch crewel work skirt that had been sitting in my closet for a few years. This attempt was more successful. The skirt was slightly longer than Mark’s minidress, and the extra inch or two meant I didn’t have to fiddle with the hem as often while sitting. However, I feel that proportion is important in miniskirts. The formula that worked for me was small earrings, small heels, and a large sweater. With the Tory Burch skirt, I wore a moss-colored V-neck sweater that I had borrowed from my father-in-law a long time ago. The loose fit was just right for the silhouette of the narrow, short skirt. I broke the flat shoe rule by wearing chunky heeled loafers and felt like it worked in this unusual scenario, but I might go back to flat loafers if I tried them again.
