In my grand plan to overhaul my life and get more comfortable with, well, everything, I knew one important step would require a hard, in-depth look at my closet. And not because it’s overflowing. More for the opposite reason: I hate the thing. And most of the things in it. (See, I can’t even refer to my clothes as “clothes.” They’re “things.”)
Those who know me well can tell you my style without hesitation: simple and with lots of gray. For decades, I’ve lived in jeans, tanks and flip-flops or easy flats. I rarely leave the house without my heather gray American Apparel sweatshirt. (Without fail, I’m cold; so what if I’m nearly barefoot and without sleeves.) Accessories? Beyond a nice handbag, I couldn’t care less about earrings and those things women having hanging around their necks. What’s the point?
I realized, once I really thought about it, that it isn’t so much that I don’t like clothes or jewelry or fun, girly outfits. I mean, I do love to dress up for those rare nights on the town. I throw on a pair of skinny jeans, nice heels and a sleek top. I’ll curl my hair. On occasion, I’ll even experiment with eyeshadow, throw on some mascara and a little lip gloss. Inevitably I get a “Wow, you should dress up more often” comment, which is sweet, but always feels staged.
But why don’t I try more often? Why not on a daily basis? Where did this hostility toward looking good come from, and how could I squash it once and for all?
Growing up, I never got into makeup and hair like a lot of little girls. I was rough and tumble, albeit with My Little Ponies. I rode my bike with my friends, which wasn’t conducive to pretty hair and glossy lips. At least not to me. And besides, no one in my life modeled that behavior — the primping and prettying. And that’s when it hit…I’m practical largely because the glamour of it all is so foreign to me. Like cooking (and that’s a WHOLE other story for another day), the luxury of looking good was a concept that seemed only to apply to others, not to me. And that’s how I got through my teenage years never wearing makeup to high school.
So as I traced my resistance to dressing nicely to my early days of “Who cares, since I’m just gonna get dirty anyway,” I instantly decided how I’d tackle this hurdle: I’d invite over a couple friends whose styles I admired (and not for the sake of copying, but for knowledgeable guidance) and I’d try on every. last. piece. of clothing. Goal being figuring out what to keep or toss.
I had fun with it. I made signs for each one of them: trendy Erica, artsy Michelle and Michelle’s ridiculously astute six-year-old clothes horse son. We had wine, cheese and chocolate — but not too much — and I tried on each and every item of my wardrobe, except for undergarments. Coats? Check. Formal dresses? Check. Jewelry, scarves, shoes and handbags? Check.
Three hours later, I had a rack (yep, you read that right. One single hanging rack.) of clothing to keep, and a mound of unwanted threads on the ground. And as I looked at the rack, I got excited. I loved every last piece on it. For the first time in my life, I wouldn’t mind opening my closet doors and picking anything to throw on. Wow. How liberating.
What also helped was the $1,000 I had saved to make up for the tossed clothes. I mentally divided it among the two friends (sadly the five-year-old and I have yet to shop together) and I spent an afternoon with each of them, getting advice and having fun in dressing rooms across Austin. With Erica’s prodding, I splurged on a luscious caramel-colored Tory Birch clutch, which I carry religiously and with such pride. I found the perfect skinny jeans and some trendy suede booties that were both high-end and on sale! Michelle helped me discover my inner accessorizer and prompted me to purchase that perfectly art deco necklace at J. Crew. And yep, that too was on sale.
The cool thing is that through this reflection on all these experiences, I realize I’ve discovered my own physical identity. My own fashion-related likes and dislikes. My own style. Just like that. And it doesn’t hurt as much as I thought it would — to throw out memory-filled outfits I never liked wearing, shoes that are sexy but hurt like hell, gifted jewelry that you hate but keep due to that damn guilty conscience. And it’s actually FUN to shop sometimes. And it feels amazing to be dressed beautifully and be simultaneously comfortable. And some items are worth the hefty price tag. And no matter what, I still get that addictive giddy high when I find that amazing piece at an amazing price. Now I just know better what to look for.