Dear Winona,
Yesterday I tried on an outfit I used to love — a crop top and a tight mini skirt — and I felt kind of awkward in it. I’m 31, about to turn 32, and I’m wondering if there are certain things I can’t wear anymore now that I’m in my 30s. Do I need to rethink my style? How do I dress my age?
Signed,
What’s My Age Again?
Dear WMAA,
Ever since I was in high school, I’ve been obsessed with miniskirts. Denim miniskirts, sequined miniskirts, vintage miniskirts, trendy miniskirts, flared miniskirts, Spandex mini skirts — I loved them all. And the shorter, the better. I’ve always loved my legs, so showing them off was a no-brainer. I scoffed at the idea of any skirt that approached my knee area, as I deemed this length “old-ladyish,” and even when I was working more professional jobs, I always pushed the dress code limit when it came to appropriate skirt length.
But recently, something weird happened. I also entered my 30s (that’s not the weird part, I swear), and I’ve noticed my style has started to evolve. I don’t really feel comfortable in miniskirts anymore. I’m drawn to garments with slightly more coverage, and I’m choosier about quality over quantity.
Sometimes I worry that my current clothing preferences are proof that I’m subconsciously bowing to societal pressure to cover up and look more “mature,” but the preference feels much more personal than that. I just don’t feel comfortable showing as much skin as I did in my early 20s. It’s not because of body image issues or shame or anything like that; it’s simply a change in personal preference, in what I feel comfortable in (both physically and emotionally), and how I want to present myself. Would my high school/college-age self be shocked that my closet is now home to a few fabulous pencil skirts of decidedly “old-ladyish” length? Absolutely, but I love them just as much as I used to love my miniskirts, so my younger self will just have to deal with it.
The moral of this story? Dressing your age is much more complicated and personal than it might seem. Only you can decide if that “awkward” feeling about your revealing outfit came from a place within yourself or from outer pressure to look or dress a certain way.
If you’re unsure where the feeling came from, here’s a good way to figure it out: Put on the outfit in question, and don’t look in the mirror. Wear it around your house for a bit. Don’t look at yourself in any reflective surface, dispose of any ideas about if you “should” wear it, and resist the urge to assess your outward appearance in any way. Instead, focus on your inner state. How do you actually feel in it? Are you uncomfortable? Do you find yourself tugging and pulling at it? Do you feel like “you,” or do you feel like you’re wearing a costume?
If you still feel awkward in this outfit, it probably means your style has evolved and this look doesn’t mesh with your current preferences. That’s totally fine. If you love how this outfit feels once you’ve banished the idea that you “shouldn’t” wear it, that’s totally fine, too.
Obviously, certain clothing items project a more mature image than others, so it does pay to be mindful of “dressing your age” in professional settings, but in most other contexts, ignore the “shoulds” and focus on your own preferences. If you feel like you’ve aged out of an outfit, that might be true for you, but don’t think you automatically have to retire half your wardrobe when you turn 30. Or 40 or 50 or 60, for that matter.
