Midlife Style: My Search for a More Flattering Look

I like to think I appear cool and retro, when in fact I probably look like I'm in grandpa drag

On Fridays, at my workplace, they have 15-minute massages you can sign up for, and if you're thinking, "Well, hey, that doesn't sound too shabby," you're absolutely right. The point is, the massage therapist hovers around my age range. I'd put her at early 40s, although it's sort of hard to tell. She's one of those women who let her hair go gray and has it cut sensibly short, and she's quite thin because she probably seeks kale with the same eagerness that I seek nachos from Hardee's. What I mean is, the no-fuss gray hair may make her seem older than she is; the good diet and meditation may make her seem younger.

I went in there last Friday for my 15 minutes of feign, where I pretend I am relaxing when really that 29-piece, free jazz, all-tuba-and-cymbals band plays in my head at all times.

"Is that another vintage find?" she asked me as I plunked myself facedown in that massage-table hole I always assume is teeming with Ebola.

"It is," I said, my voice empty and shallow as it made its way out the hole of disease and onto her FiveFingers foot shoes. I had on a large teal-blue cardigan that had clearly once belonged to someone's granddad, acrylic and sensible and purchased by me at the local resale shop for 20 dollars. I wear it all the time.

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"God, you find the best clothes," she told me. "I really miss oversize sweaters being in style." Which I guess was a way of telling me my sweater isn't that fashionable, but I already knew that and have ceased to care. I like to think I look cool and '60s-ish, when really I probably look like I'm in grandpa drag.

"I hate sweaters now," she continued as she worked on the boulders of stress that I call my shoulder blades. "They're all see-through, and too short. And I only buy men's pants. Women's pants are too low now. I don't wanna spend my whole day chasing my pants. I really need to find a look to settle into for middle age."

That statement has haunted me ever since. Because what I hadn't really noticed is—I've been doing the same thing.

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Back when I wasn't, you know, zaftig, I wore black miniskirts and big sweaters all the time. With tights in winter, without in summer. If I was feeling bohemian, I'd wear a long skirt with a sleeveless T. If I did that now I'd look like some sort of 1800s washerwoman.

And she's completely right about clothes today. I am over having to enter the southern hemisphere to button my jeans. On who is that look flattering? Because it sure isn't me. What I wouldn't give to get in the car and not have the back of me get intimate with the leather seat. And I know high-waisted jeans are back sort of ironically, but that's the highway to the danger zone when you're middle-aged. You try to do a devilishly ironic look and end up with people thinking you're Delta Dawn, and all the folks 'round Brownsville say you're crazy. Remember when Parker Posey tried to have a big trendy afro? She's 47 and her daddy still calls her "Baby."

I need to have a little dignity in my dress these days. I'm too curvy to pull off a classic Jackie O sheath dress/sleeveless oxford look. I love vintage clothes, but I don't want to teeter into someone you see on BuzzFeed: "This goofy granny tries to be rockabilly. Click here—you won't BELIEVE what happens next."

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My statuesque friend Marianne has embraced flowing shirts and billowy pants with lots of ethnic jewelry, but I have blond hair and blue eyes, so who am I kidding. Plus, on me, that always ends up looking like I had to escape my house with all my belongings on my back.

I could be one of those artsy all-black-all-the-time women, but I really enjoy pink too much for that look. I could go all pink, but see above, re: BuzzFeed. "This sad menopause mama thinks she's the Good Witch of the East. Photo number 8 will make you cry!"

The Real Housewives are around my age, and they wear these tight, short dresses and 97-inch heels all the time. Granted, they're all thin and fit. But recently, "Real Housewives of Beverly Hills" (The best one, really. Go, Lisa!) traveled to Dubai, where they had to wear long, flowing cover-y dresses—and they looked SO MUCH BETTER in those dresses than they do teetering across town in platform pumps. There was a dignity there, a look that said "I've still got it, but I don't have to show you every inch of it." Maybe I could start wearing saris all over town, but see above, re: blond hair and blue eyes and who am I kidding.

Sensible people will say wear whatever makes you feel great, but what would make me feel great is to be a size 5 again with my 23-year-old gams. All I know for sure is, I do not want to totter around in thigh-high boots, nor do I want to succumb to elastic-waist jeans.

I just want to look good, and feel confident, but so far my middle-aged look makes me look frumpy and feel frumpier. But I won't give up. I plan to chase my look the way I chase my pants.

Tags: lifestyle