I hate shopping. If a friend somehow talks me into going to a mall, I spend the entire time acting like the husband on a bad sitcom—I sit on a bench by the door, make a lot of impatient huffing noises, and probably say something about how I better be getting some sex later (and we all know how women, especially wives, hate sex).

I would give up shopping altogether, but here’s the rub: While I hate to shop, I really like clothes. This is My Struggle and yes, I’ll be writing a six-part series of novels on the subject. Shopping online is no help to me either because my body—despite serving me well these 28 years—often ends up looking weird in the trends that are most readily available. I like to try before I buy, reason being that—as you’ve probably experienced with your own body—clothing in the wild ends up looking quite differently than it does on a model during a tightly controlled photoshoot.

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But that’s not news to anyone! We all know that shopping can be hard and, on your worst days, maybe even demoralizing. I have cried in changing rooms after trying on seven items that all look equally terrible on me, because, while logically I know that it’s not a personal offense that I don’t look good in American Apparel disco pants, it can sometimes feel like one anyway.

With this in mind, I’ve been coming up with some tricks that have genuinely made the experience of shopping easier for me and now, in the spirit of kindness and generosity, I will share them with you. Please don’t get so hostile. I’m only trying to help.

My first tip is to befriend a stylist who you can constantly hassle with questions. Chances are, however, that that is not an option, in which case, move onto step 2: Turn to Pinterest. No, I’m not being sarcastic. Sometimes I get so overwhelmed by contemporary fashion that I forget what my own style is. Starting a Pinterest board has helped me relocate it and narrow down what I really like. Turns out that my tastes tend to lean towards Teddy Girls (hate their politics, love their androgyny), Kathleen Turner in Body Heat, and the many great outfits of Debbie Harry and Patti Smith.

Might seem a little all over the place, but it’s really helped me realize that my favorite looks tend to combine the typically masculine with the typically feminine, the glam with the grit. And THAT, in turn, has helped me realize what to look for on a clothing rack and what to ignore.

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The third thing I’ve done to make shopping an iota easier is to defining a Seasonal Look for myself. It might sound cheesy and, yes, it definitely is, but it’s also, dare I say, fun?. Like, mine, for example, is “the only divorced mom at a 1976 PTA meeting”—she wears big sunglasses, big hair, and mid-length skirts. She’s cool, a little harried, and probably braless. And best of all, she’s ME and she successfully shopped at Top Shop—WITHOUT CRYING—the other day.

Here, I even asked the Jezebel staff to tell me their Summer Looks and they had a GREAT time.

Jane Marie:

“Backless dresses because everything else is kinda wonky these days?” ...but I still have a back! I’ll always have a back.

Anna Merlan, Office Goth:

I’m really into matching crop tops and skirts.

...which means I have bought several black crop tops.

Bobby Finger:

Linen on linen on linen.

Natasha Vargas-Cooper:

ISIS bride honeymoon resort chic.

Julianne Escobedo Shepherd:

As ever: Bette Midler as Sue Menger.

Mark Shrayber:

I am working from home this summer and my look is also a lot of nudity.

Erin Gloria Ryan:

My summer look goal is to recreate the exact summer wardrobe I wore when I was 5—rompers, jelly shoes, jeans with holes in the knees.

Kate Dries:

To be as stunning as Susan Sarandon is in ‘Bull Durham.’

Kara Brown:

I’m into the bucket hats and lack of matching this summer.

(Note: Kara provided this photo of Lil B with her answer.)

See? FUN. It’s like role play, but not just for nerds!

Chances are that shopping will always sort of suck. But maybe you and I—me as the mid-’70s divorcée who’s trying to get back out there again and you as WHOMEVER you want to be—can make it work for us and stay looking fly.


Contact the author at madeleine@jezebel.com.

Image via Pretty Woman/Touchstone Pictures.