If It Hurts To Get Rid Of Your Old Clothes, Read This

I did a major overhaul of my wardrobe recently and it was a much more wrenching experience than I thought it would be. I got confronted by all the clothes that 2007 Gwen used to love. Like the $6 thrift store chiffon dress I wore the first time I went to a gay club. I remember this guy yelled “Nice dress, bitch!” and I was like huh? But then I realized that where I was, bitch was a helluva compliment.

I swore I’d wear that dress again. But I never did. And now a lot of those clothes don’t quite feel like me anymore anyway. There are things I wore all the time that feel costumey now. And there’s things I only wore once in a while (like button-down shirts) that I’ve rediscovered and feel completely at home in.

If you’re looking to clean out your closet, you’re probably at least as concerned with what your evolved style says about you as you are with what’s “appropriate.” And I don’t know about you, but the thought of dressing appropriately has always been nerve-wracking. All these dire articles telling me what I should and should not wear at my advanced age of 28 are making me feel like I have to give a part of myself up.

But the process is really a lot more organic. You have the right to retain your style, and it will mature as you do. Good style is like good writing. It’s presenting yourself as uniquely as you are while not being inscrutable to other people. Here’s some questions to ask yourself while sorting through our wardrobes:

Who Am I?

A cool thing about the world is that a lot of people are willing to see you the way you want to be seen. The necessary ingredient here is confidence. Blind confidence. Cockiness even. I’m not saying you can pull off anything, but people who have that air of certainty about them seem to get away with a lot more.

That being said, you probably aren’t dressing to adhere to some exaggerated category of human like you did back when you had a MySpace. If you’re still a “type” though (and a lot of people are,) you can just tweak your style to suit whatever you’re doing now.

Are you a prep who wants everyone to know how preppy you are? Lacoste is still cool in my eyes. So are those vertical striped button-down shirts that have spiffy colors like chartreuse and lavender. On the higher end of prep, as in you probably did go to prep school and have good reason to peacock at work, I’d definitely chat up a guy who wears those bright ties from Ralph Lauren.

If you’re a hippie you can make all kinds of jewelry out of fairly cheap semiprecious stones. Lapis lazuli and tourmaline are my favorites. Match your homemade necklace with a relaxed maxi dress and you’ll come out looking like you’re dressed to meet the owner of an art gallery instead of a shroom dealer behind a portapotty at Burning Man.

So basically, who are you now is the operative question. And it can hurt. Never again will you be the person who is completely self-actualized in a halter top with a hamburger emblazoned across the chest that says “well done.” Now you can stop traffic in a loose silk top and skinny jeans. You have to own what you wear. Because if you don’t own your outfit, you don’t own your first impression.

Where Do I Go?

If you’re sexy but you work in an office then some tailored wear from a place like Express would be a good investment. You can wear a hot top under a fitted blazer. You can wear leather too. A leather pencil skirt looks like business in a PG-rated way with a silk blouse or a button-down.

You can repurpose your old clothes for special occasions. Maybe you realized that those punk tights you bought when you were nineteen really do make you look like Ronald McDonald. But that’s a killer Halloween costume right there. Sexy Ronald McDonald. You’ll be the only one in town.

I have a designated drawer for clothes I only wear to these monthly rave/BDSM parties I go to in Bushwick. Heart sunglasses, Hot Topic, cat ear headbands, polka-dotted ‘50s style dresses: let it rip. Alternative culture is usually a lot more timeless than the buttoned-up culture we’re usually stuck in.

How Can I Look Richer Than I Am?

If you’re in sales, you’re always answering this question. Either your customers ask it directly or you insinuate that by following your judgment your client will come out looking like she inherited North Dakota.

If you have one great piece, like a classic wool peacoat or a pearl necklace with matching earrings, you can just wear it with everything. There’s something inherently classy about pieces like that. I think Breakfast at Tiffany’s had a lot to do with it. You can’t imagine Holly Golightly on Page Six, can you? Even though she was selling it just like Holly Madison?

You don’t have to fall into the pearls/peacoat/clutch cliché though. I wear cowboy boots. They look just as rich. Along with cashmere sweaters (Uniqlo you guys), silk midi skirts, and a killer velvet jacket from the consignment shop I worked in that makes me look like a million bucks for about $50. Upscale consignment shops are your friend. So is eBay.

What Is Your Signature Item?

To cultivate a recognizable style you want to follow a pattern. This is your thing. You collect corduroy pants or flimsy, colorful silk scarves. Everyone will expect you to wear them. Getting a reputation for dressing uniquely takes more consistency than most people realize.

Personally, I like hats. I have a loose cotton porkpie hat for summer and a wool one for winter. I’ll be the girl with the hats when I’m forty.

What to Get Rid Of?

Is there anything so out of style that you’ll die before it comes back? Is this item boring? It has to go. If it isn’t boring you should keep it to amuse your future children. Tell them how cool Mommy was when she wore this. They’ll laugh at you and tell their friends. You’ve made them happy.

If it hurts you to admit that you’ll never fit into it, give it up.

If it falls open when you bend down or the straps don’t stay up, give it up. Screw double-sided tape and safety pins. You want to exist comfortably for at least five hours in whatever you put on.

If you have negative connotations with it, like somebody dumped you while you were wearing it, give it up. You’ll always have a nasty thud in your chest when you see it.

What to Keep?

Keep anything you once loved. I pull out my old clothes, now in a box called “memories,” and I remember the awesome things I did when I was wearing them. It makes me happy.

If you’re not a hoarder like I am then all the more power to you. But I think that when you get old you and your kids are going to have less fun. My mom’s like me: she keeps everything. Including her awesome clothes from the 1970s. You all have to purchase those throwback long skirts with the buttons down the front while I get to wear the real thing. There’s nothing like enjoying something now that your parents enjoyed when they were your age.

And clothing is art after all. Like a novel that speaks more to you during a certain period of your life: clothes do that too. You’ll see things you bought way back when that you wonder why you haven’t worn more often. Buy more things like that. Gradually stop wearing things as they stop suiting you. I know we’ve all seen those alarmist pieces in Cosmopolitan and stuff about how we have to purge ourselves of everything we used to love in order to usher in a new era. But it’s just not that dramatic. You don’t have to forget who you were to become who you are.