What to Wear as 30-Year-Old You

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About six months ago, at 29, I decided my look was all wrong. I was once again pulling on a gray sweatshirt and jeans to go to work. I took the path of least resistance when it came to makeup, too — a swipe of mascara, a cheek pinch in lieu of blush — and I often wore my hair in a bun because that was easiest. I favored sneakers and a frayed denim jacket I’d had since middle school. The finishing touch was always the same leather bag I’d been carrying since freshman year of college, chosen because it was large enough to easily fit my laptop.

I looked fine. I looked like a human who had sort of gotten dressed for the day and had made all necessary decisions to be warm enough and not naked. I’d done the minimum to get myself out the door, and more than the fact that it showed, what mattered was how it felt. I didn’t feel like an almost-30-year-old woman ready to tackle whatever obstacle came her way; I felt like a person who had merely slid into her present form. Someone whose physical make-up was not about conscious choices but rather about what fabric was closest to her reaching hand. I looked (and felt) like someone shrouded in pieces from her past, perhaps out of laziness, perhaps out of fear, stumbling sulkily out into the morning.

I can tell you what I thought I’d look like. I thought that by 30 I’d be polished. I thought I’d have a rotation of classic-yet-flattering work dresses. I thought I’d wear subtle eyeliner and have a perfect trench coat for rain. I thought I’d really know what style of jeans worked for my body type and how to wear a blazer without it feeling like dress-up. I thought my closet would brim with fashionable staples and be accented with accessories that gave me individuality, flair. I thought I’d wear heels on the regular and have a signature scent. More than anything, I thought I’d have it together.

There have been moments along the way where what was in my closet felt right, where the vision I had of myself was the very same one I presented to the world. I can remember the end of high school when my flared jeans and lacy tank tops perfectly complemented the me that I had in my mind — girly but cool, or at least the 12th grade version of it. I can remember late nights in college when motorcycle boots and mini dresses were exactly what I wanted to wear, and exactly what I did. And even post-college, during a few years spent living in Thailand, I cultivated an expat look that felt like me in that moment (a traveler, an American girl in an environment without many) — genie pants of every color and graphic tees that reminded me of home.

Perhaps the biggest problem with me at almost 30 was that I didn’t quite know who I was, and because of that I had no idea what to wear.

My 20s have been confusing. Many jobs, many bad dates, stints living at home and stints living with friends, forays into freelance and startup positions with 100-hour work weeks. I’ve dabbled in many versions of myself, and in the quest to discover who I want to be, it seems I may have lost sight of who I want to present. That’s all fashion is, anyway: It’s the version of you that you want others to see first. It’s a hard thing to nail down when you’re still entirely unsure.

I decided that since getting my life together and then finding the wardrobe to match wasn’t working, this time I would curate from the outside in. I’d cultivate a closet of Marie Kondo-esque simplicity — only keeping the wardrobe items that bring me joy. I would spend a little more time dressing for the day, every day, and doing what I could to feel like the best version of myself.

I scheduled a Saturday for it, emptying my closet and organizing it into those four foolproof piles: to donate, to sell, to keep, to give away. I needed to find the things from my previous lives that still fit with my current, and I needed to purge all of the items that made me feel too young, or too old. Too un-me.

Here’s what I learned and here’s the wisdom I can pass on:

• It’s shockingly easy to get rid of an ex’s old sweats. Though you may still wear them, they likely do nothing but make you feel scorn and spite and sadness. Donate them.
• I bought an excessive amount of vintage slips in high school, and since then they’ve occupied the bottom drawer of every dresser. We all have our version of high school slips, the item that was for whatever reason cool among your teenage crowd. Keep the ones that don’t have cigarette burns and party stains. Keep the ones that somehow still look good, and donate the rest.
• In college, “going out clothes” were crucial, and being trendy was, too; enter H&M and Forever21. If you’re like me, you still have those trend-first items hanging in your closet: baby doll dresses, bubble dresses, cap-sleeved crop tops. Give them away.
• There are dresses I bought that are still lovely but now serve no purpose. You know the ones, you have them too. They were dresses for me at 17, not me at 29. At 29 my hips are ready for a baby, and slinky items I bought as a teenager no longer fit. Odds are yours don’t either. Sell them.
• There are a few things in my closet that I love completely. Sweaters that belonged to my dad, a pair of entirely impractical blue suede wedges that make me feel like Dolly Parton, a purse that I’ve used 10,000 times and still channels the motorcycle chic look that we all need every now and again, a top that my mother bought me years ago on a family trip to Paris (the first blouse that ever made me feel like a lady). You have those items, too — don’t ever get rid of them.

After the clean out, my room was filled with bags. I’d peek inside and see a glimpse of a former self — me at my birthday party and wearing a denim dress that no longer fit; studying in the library in a sweater that was half-eaten by moths way before I ever wore it; a T-shirt I once loved but accidentally turned pink in the wash; jeans that I wanted to work but never actually wore. It felt dangerous to shed those pieces of myself, those good and bad bits that had made up my armor through job interviews and breakups and travels with people who I didn’t even know anymore. But it was also liberating, a molting of sorts, and a necessary one at that.

It’s six months later now, and I can’t say in earnest that I know entirely who I am or what to wear. Those movie scenes of people getting new wardrobes and undergoing enviable makeovers aren’t a reality when you’re minding your bank account and figuring out how to live as a writer. What that means is that my post-purge closet is a hodgepodge of beloved and ancient items. Every now and again, when the sales are great or the money is right, a new staple makes its way in. In those moments, I try to choose something that reflects who I am now, and who I want to be — an oversized gray sweater that makes me feel like a writer of note, a flower-printed wrap skirt that works for both weddings and meetings, good bras always.

Though my vision of 30 — polished, pristine — may not be a reality, there is something to piecing together a new vision and making it work. There’s something to realizing that while the grown-up version of you might not be what you once expected, this new one is an even better fit.