Fashion Conundrums: Are You Too Old For That Hemline?

The great length debate.

Last week, I went to a wedding. One of the guests was a politician, there with his wife who looked to be in her mid- to late-forties. Halfway through the ceremony, a friend leaned over and whispered to me:

“He won’t ever be president. Look at his wife. She doesn’t have that First Lady look.”

I rolled my eyes, because talking politics — or anything remotely political — with this particular friend is sort of like running a marathon: You begin not knowing why you ever started, you’re dazed, confused and hating life halfway through, and deliriously exhausted at the end. But I stole a peek at the woman a few pews up, and had to agree: It wasn’t a good look.

Let’s get this out of the way: Unless you’re a celebrity, I don’t really care what you wear. If it makes you feel great, go for it. Still, there are certain sartorial offenses that drive me crazy, and they generally fall into the Too Tight/Too Short category. This was the latter. The woman’s body was incredible; her arms had the Gwyneth Paltrow Ripple, that subtle cut in the arm just beneath the shoulder. (Side note: GOOP got it by doing bizarro dance moves like this.) The non-First Lady also had a flat stomach and Jessica Simpson’s new legs. And she was showing it all off in the world’s shortest dress.

The dress itself was fine: a white (is wearing white to weddings okay now?) shift that looked terrific against her tan. I’d even give her a pass on her shoes — a pair of uninspiring cork wedges that, fine, weren’t formal enough for the evening reception. Whatever. Wedges are comfortable. But the length of the dress is what really stopped me. The hem stopped smack-dab in the upper-middle part of her thigh, a good eight inches from her knee. It was — without any room for debate — too. Damn. Short.

I think “dressing your age” is mostly a dated concept. Right now, twentysomethings are wearing caftans better than most octogenarians, and eightysomethings are sporting pink hair and sparkly sunnies better than most twentysomethings. But there is a hemline rule, and unless you’re Kate Moss, that rule is this: If you wonder if you are too old to be wearing a miniskirt (or anything, for that matter), the answer is yes. But what exactly is too short, and when exactly are you too old to wear it?

InStyle’s fashion director Cindy Weber Cleary wrote a blog post about the hemline debate:

I recently saw a picture of a very attractive, 50-something-year-old fashion executive wearing a tight “bandage” mini-dress at a cocktail party and I thought, “Oops! Even style icons slip up on occasion.” Her body looked amazing, but the overall effect was a little Real Housewives, as one of my editors put it—surely not what she was going for.

Personally, as a woman who is over 50, I would not wear a mini. Even if I were a marathon runner or Pilates instructor, I still wouldn’t be wearing a thigh-revealing skirt or dress anywhere except on the tennis court or by the side of a pool. Longer lengths are so much chicer. And they actually create a more youthful, flattering look.

I agree with her, but it’s easy to: I’m not gifted with miniskirt-friendly legs. Mine are tiny little stubs, with muscular calves from years of running and high-heels. Maybe if I had very long, very thin legs, I would be tempted to wear tiny skirts, too. I called a (very stylish) friend who has miniskirt legs and is 33 — just about the age at which the hemline debate begins.

“It’s the first time in my life that I’ve ever thought of whether or not things are age-appropriate. There are certain things that I used to love that, if I wear my hair down and wear sunglasses, I might be able to fake that I’m younger and get away with. But my face is too old, even if my legs are not,” she said. (Ed. note: This isn’t true.) “A lot of it has to do with the shape of the skirt. I don’t mind a short romper, but I used to have these pleated flouncy cute skirts and I feel like, after 28, you just can’t wear them anymore.”

I noted this logic — rompers okay, miniskirts not okay, keep shape in mind — and called my next fashion friend, stylist Lauren Kozakiewicz, to get her take on the hemline debate.

“Even when women have amazing bodies in their fifties or late forties, you still don’t want to see them in a miniskirt,” she said. “There are subtle changes even when you take care of yourself. If you have good knees, then right above the knee is about as mini as you should get. If you’re talking mid-thigh, and you’ve got gorgeous long legs, you can go a couple of inches above the knee. But if you have to tug it down every five minutes just to walk, then you shouldn’t be wearing it.”

Knees, I thought, making a mental note to slather mine with SPF every chance I get so that they don’t get old-looking. (Another thing to worry about!) But dealing with longer lengths has its challenges, too. (A tip: Find the skinniest, most toned part of your leg — a couple of inches above the knee, just grazing the knee, just above the knee, just below the knee, just below the calf muscle — and choose a skirt that hits there.)

Then I started to do the math. I’m 32. That leaves me eight more years of short lengths before I have to give myself and my wrinkly knees over to sophisticated pencils and chaste midis. Even though I never really wanted to wear minis in the first place, I started to sweat. Perhaps I should go out and get a bandage skirt, just in case I am 39 and have a sudden desire to wear one while I still can! While I still have youthful knees!

“It’s a touchy subject. How people dress themselves is a true extension of who they are, and if, when they look in the mirror, they feel good, more power to them,” says Joan Shepp co-owner and buyer Ellen Shepp diplomatically. “But, if we’re talking about how people are judged, then it has more to do with how that short miniskirt is put together. To me, anyone can wear a short skirt with an opaque tight and a boot that comes up to the knee. You put on a blazer and a scarf with that and it doesn’t really have an age.”

A-ha! So it’s the layering that is key, which makes winter the unexpected best season to break out the mini. “Bare legs definitely show your age,” Ellen said. “The huge selection of opaque tights makes much easier to wear shorter skirts.”

I can’t give you a definitive no-minis-past-this-point age; I wish I could. It would make dressing easier, for stylists and politicians’ wives alike. I guess in the end, it’s all sort of like of the great political divide: Some will say to screw it all and wear what makes you happy, others will remind you of pesky things like wrinkly knees. I won’t tell you which side I fall on, but I will leave you with this quote:

“It’s much more graceful to leave it to the kids. You have less to prove,” Lauren says. “Enjoy the sexuality of your wisdom. You just know more, and one of those things you know is to keep your skirt below your knees.”