Confession time. Lean in real close, would you?

I lack the shopping gene.

I never know what’s in style or what’s on sale or where to buy anything. I walk through stores with the same wide-eyed wonder that a third grader might have on a field trip to the Museum of Natural History. “Wow … so this is where it all comes from …” So sure, it’s fair to say that I’m not the most fashion-forward person. Most of my clothing purchases during the past three years have been of the vintage variety … which is a nice way to say that I regularly hit up the Goodwill down the street.

Heck, I don’t even own a full-length mirror.

That makes it all the more bizarre that now, at age 41, I’m working with a fashion stylist. She’s teaching me not only how and where to shop, but how to put together attractive outfits that simultaneously express the essence of my true authentic self and also make me look 10-20 pounds thinner.

My head might explode. This experience so far has been like my personal fashion edition of The Biggest Loser. But instead of a treadmill, I’m facing down a pile of clothes in a dressing room and Elizabeth, my stylist, is going all Jillian Michaels on my ass. “Come on, Trish! You can’t wear those black-and-white prints forever! They totally wash you out! Here, try on this cobalt shirt! No, these jeans are not too tight! Jump and down and if that’s how you need to get them on! Keep telling yourself I am pretty and petite!”

Let’s be honest. The real draw of The Biggest Loser isn’t watching a bunch of people count and burn calories. It’s about the contestants’ histories, their self-esteem, and the way they walk through the world. It’s not about the food.

Turns out, it’s not about the clothes either.

 

The Universe doesn’t like your outfit

I didn’t seek out a stylist. But since I subscribe to the “there are no accidents” school of thought, I suspect that somewhere out in the cosmos some higher beings had grown tired of looking at my thrift store ensembles and so they decided to throw Elizabeth Douglass* into my path.

Elizabeth was the only non-blogger at my lunch table for the Guy Kawasaki keynote at Blogher ’13. She explained that she was a stylist and in the process of building her website.

I’d never met a stylist before. The one thing I really wanted to ask her was “How do I accessorize?” but even a remedial fashion flub like myself knew that was painting with too broad a brush.

Instead I asked her what type of client was her favorite. I expected to hear a story of a budget-be-damned socialite who was on the hunt for a perfect pair of suede boots, but Elizabeth’s answer surprised me. “I love working with someone who wants to learn, so they can dress themselves later,” she said. I pressed her a bit. Surely it was more fun to work with someone who had higher spending limits. “You’d be surprised,” she told me. “Some people want to shop at Target and Kohl’s, so that’s what we do. It’s not about the money. I can work with any budget.”

That knocked me off-kilter. Here was a professional fashion stylist saying that she could build an attractive wardrobe at any budget level? Hmm. If that were possible, did that mean that I didn’t have an excuse for phoning it in, fashion-wise? I chewed on that thought while the conversation continued.

Someone at the table suggested that Elizabeth put before and after photos on her website. She explained that she’d love to, but that her clients were often high-profile executives who didn’t want people to know that they were working with her. “I even told them I’d give them my services for free if they’d let me photograph them. All they’d need to do is buy the clothes.”

Then my mouth formed this sentence before my brain had a chance to intervene: “I would totally do that.”

 

Am I beyond help?

Elizabeth took a good long look at me. I suddenly became extremely self-conscious about my outfit choice for the day: jeans, a black sleeveless shirt, a cardigan with what I thought were some fun details (bell sleeves and a cute collar – I counted it as a thrift store “find”) and animal print sandals. I imagined she was thinking one of two things: “Oh boy. There’s so much room for improvement here. I’m going to look like a genius,” or “This chick is a lost cause. How do I get out of this gracefully?”

“I’m a little dressed down today,” I admitted to her. “It was a long day yesterday so I decided to go casual with today’s outfit.”

“That’s not an outfit,” she said quickly. I busted out laughing, guessing that her idea of an outfit was probably very different from mine.

“Where do you live?” she asked. Turns out, we only live about 45 minutes away from each other – me in the western ‘burbs of Philadelphia and her in Wilmington, DE.  “That’s completely doable,” she said. Then she agreed to style me as well as my conference compadre Stefanie, who lives in Brooklyn.

Elizabeth got down to business right away. She said she’d come to our homes to interview us and look at our clothes. “You’re not even at my house yet and I’m embarrassed for myself already,” I told her as I mentally threw out at least ten things. “Can I clean some stuff out beforehand if I know it’s crap?”

“No! Those things can be the most telling,” she said. “We can talk about what you were thinking when you bought them. Unless there’s blood from a murder scene on it, keep it.”

She asked me and Stefanie if there were any celebrities whose looks we admired. As Stefanie began gushing about Agent Scully’s suits in the later years of The X-Files, I was quiet. I couldn’t think of anybody.

I sat there struggling to recall any outfit that I had ever liked at any time. I came up dry. It occurred to me that perhaps this was more serious than I realized: I was suffering from fashion blindness.

 

Second thoughts

Stefanie and I spent the rest of the conference mercilessly ribbing each other about our clothes.

“Nice cargo pants, Trish. And what’s up with that shirt? That’s the same material as my underwear. Look,” Stefanie said as she yanked up the waistband of her panties.

“I know Elizabeth hasn’t seen your shoes today, but I can feel her hating them,” I hissed back.

We were laughing our heads off, but the truth was that I was starting to second guess every item I put on my body. Even outfits that I had liked before the conference started to seem lame and sad to me.

“I don’t know if I want to go through with this,” I told Stefanie. “I know who I am. I’ve done a lot of work to make peace with my true self. If this is going to chip away at my self esteem then I don’t know if it’s worth it.”

“Fuck that,” Stefanie said. “You are beautiful and an amazing person. This is an opportunity to show that to the rest of the world.”

And then I thought about how my life had been stripped to the bone over the past few years. I had gotten divorced. I went bankrupt. I had to rebuild my career while adapting to life as a single mom and also learning to date again.

Reinventing my life had given me the chance to transform some things that hadn’t been right. Part of that included paying more attention to my appearance. I had made some deliberate strides to make the outer me look more like the inner me – but that was hard for a fashion-blind woman on a thrift store budget.

I remembered something Elizabeth said when we met her. “You pay someone to do your taxes. You pay someone to cut your hair. If you never had anyone take you under their wing and show you how to put together a great outfit, how would you know?”

She was right. If I ever wanted to get Inner Trish and Outer Trish on the same page, I was going to need some help. Little did I know, my fashion makeover was going to turn into one of the most powerful therapy sessions of my life.

 

*Elizabeth is in the process of creating her new website. In the meantime, you can find out more about what she does here.

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