InStyle September - Lena Dunham - Lead - 1
Credit: Noam Galai/Getty Images

I peaked at the age of 6.

Thirteen was awkward — I was shiny-faced, with bottom braces and bad highlights. But then again so was 30, with the misshapen news-anchor bob and tea-stained teeth. Thirty-two yielded some upsetting red-carpet shots of my braless nipples peering through a $49 Zara dress.

But 6 — with my blond hair, tanned skin, and purple leggings with matching bedazzled headband — was perfect. I was everything I’d ever wanted to be (formidably adorable), everywhere I ever wanted to go (my bedroom), and hanging with the hottest company in town (my parents). So, like the high school quarterback who can’t stop milling around the football field well into middle age, I have just continued to dress like a full-scale baby.

Rompers? Check. I’ve got dozens. Saggy-crotch harem pants? Those too. Blouses with Peter Pan collars and loose baby-doll shifts? I can’t buy enough. No matter how many times red-carpet blogs eviscerate my cutesy, well-meaning but ill-fitting outfits, I continue to draw from the same well. I just like how my body feels, knock-kneed and flat-footed, when I’m in clothes that might be more at home on a playground than at an actual play.

It started when my body changed from a skinny minnie to a buxom (to put it warmly) teen. My form suddenly made no sense to me, and the pulling at the waistband of my jeans felt distinctly wrong. Rather than shop for some new clothing that fit, I simply rotated the same three items: a giant floral sack dress, pink cotton pants, and a striped boatneck top.

They were all exactly right for a 7-year-old’s birthday party, but I wore them to my high school dances. My mother, elegant and lean, tried to help, supplying me with black trousers, sheer blouses, and draped slate jersey. But I could not be convinced that I didn’t already look my best. I felt good in the outfits I’d chosen, despite the fact that even Chicago West would probably turn her nose up at them.

It was about more than comfort, though comfort was key. It was also about the power of subverting expectations. I could be sexy in a frilly white communionesque prom dress. I could critique a novel in a striped onesie. Nobody could tell me shit about politics when I was wearing my six-tiered minidress. I was the biggest, smartest baby on the block.

InStyle September - Lena Dunham - Lead - 2
Credit: Jutta Klee/Getty Images

When my career began to take off, I felt enormous pressure from parents, publicists, and pundits to start looking and acting like a real, live grown-up. The same thing I was celebrated for — my honesty and sense of self — was lambasted by those who felt celebrity (especially for women) meant a duty to appear camera-ready and probably sex-ready too.

I’ve always zigged when told to zag, which is a habit that’s not as quirky and fun as it sounds. So I made a Z-line straight for the clothes that made me giggle. Lord, when pressed, I could even get Prada to put me in what was essentially a giant lace T-shirt for the Emmys. Everyone was complicit in my sick game.

Occasionally, I would dip into adult style. I’d binge-shop deeply discounted items from The Row that were too tight but created a new narrative. Slowly, methodically, I’d sneak back into the sacks of yesteryear, the frilly floral shirts and stretch pants and flat sneakers. Heck, if I could ride to work on a tricycle, I would.

Through massive personal shifts, like my body’s betrayal and a desperately public breakup, my baby clothes stood by me. Before my hysterectomy, I wandered the halls of the hospital in a frilled purple lounge set. I spent my first night alone in stretch mustard shorts and a T-shirt that read, “I’m a very complicated child.” I plunged into early menopause in stars and stripes.

Recently, a close friend, who happens to be an ultra-fashionable queer man of style (he’s even been on the actual House of Style), confronted me about fit.

“You can’t think that looks good,” he chided, pulling on the sleeve of my minidress adorned with rickrack trim. “You have a waist and a butt, and they’re hidden under all this polyester!”

He explained that if I were to fit my clothes thoughtfully and in a manner appropriate for a well-earning single woman in her 30s, I could focus the conversation on my art and my interests and leave some of the snark behind.

“Just explain to me why you want to wear this,” he said.

I hemmed. I hawed. I changed from penny loafers into neon heels as a quick fix. But all that came out of my mouth was a hushed, defiant phrase: “Maybe looking good just isn’t my thing.”

The next morning I dressed hurriedly in the dark but with purpose in a mustard sweater, slim black pants, and shiny pilgrim boots. At work I got several compliments of the sort that usually elude me in reference to my general snazziness. But by noon my ass felt as if it were being stuffed into a wicker basket, and my feet hurt like sin. I barely recognized myself in the bathroom mirror, and for the first time ever, I didn’t want to dance to the Kelly Clarkson song blaring on the radio. I was single and mopey and desperate to return to my body.

So I went to Creatures of Comfort and bought — on sale for 60 percent off — a pair of Pepto pink Mary Janes, a matching purse, and a waistless prairie dress with ditzy blue flowers. I changed into my new purchases right there in the store, pinned my hair into two tiny buns, and walked down the street to buy a sack of gummy candy.

Being an adult is hard. Might as well go back to when your look soared as high as your youthful heart.

For more stories like this, pick up the September issue of InStyle, available on newsstands, on Amazon, and for digital download now.