Fashion is not for the faint of heart. Fortunately, actress and SNL Alum Rachel Dratch has a few tricks up her sleeve when a look needs to become a lewk. 
InStyle May - Rachel Dratch
Credit: Rachel Dratch with her son, Eli. Photographed by Robert Trachtenberg.

I have an on-again, off-again relationship with fashion. OK, mostly off-again. It wasn’t always this way. Growing up, I used to follow the trends of the day. In junior high it was the preppy look — whale turtlenecks and chinos accentuated with ribbon barrettes. In high school and college I moved on to typical ’80s-wear, which meant a lot of baggy blouses, probably with polka dots on them. This actually came in handy when I wanted to camouflage my giant bazooms. OK, I’ll get serious here for a second and stop being so juvenile. My jugs. Since I’m 5 foot 1 with narrow shoulders and a cup size that comes perilously close to the middle of the alphabet, finding clothes was a problem. I’d always opt for bigger shirts, and if they semi-fit, that was all I cared about.

Beyond that, though, I think my disregard for fashion had its roots in an early kid feminism, largely based on listening to the record Free to Be ... You and Me on repeat. There was a predominant message that “it’s what’s inside that counts.” I also had a book called Girls Are Equal Too (which, when you think about it, is inherently sexist, but I digress). I received the positive message that girls and boys were equally smart and capable and I could become anything I wanted. As a girl, I could conquer the world! So who the heck cared what I wore while I was doing it?

Then I got to Saturday Night Live, and aside from it being my comedy dream job, I now had the unforeseen perk of exposure to stylists who showed me the Other Side. The wardrobe supervisor, Tom Broecker, would toss us fun clothes to wear for the “Good nights” portion of the show — clothes that actually fit and were flattering, that I got to wear with fun earrings and cool boots. It was all very Cinderella for me; the clothes may as well have been draped on me by some cartoon mice. Along the way I learned some tricks about how to dress myself and what to avoid. An Empire waist will make me look like a very square pixie. A high-neck knit will make me look as matronly as the old-world peasant women from whom I descended. The most memorable piece from that time was a shiny black jacket made of I don’t know what — plastic? It was very Grace Jones. I may have pilfered that one for my own use, because it 1) fit! 2) was cool, and 3) made me look and feel like a hip New Yorker adult lady person!

I don’t have cartoon mice dressing me anymore, but I did get the tutorial. If you’re as challenged as I was, there are ways to get help. This can come in the form of a savvy and trusted friend whose style you admire (but who will be sensitive to how you dress your body). If you are feeling more spendy, you can splurge on a session with a stylist. They do exist — and not just for TV. You may learn you are wearing the completely wrong size in something, and that can improve how you are presenting yourself by miles. Another option is to find a great salesperson who can open your eyes to things you wouldn’t have tried on your own. I like this method a lot, although it recently backfired when one aggressive saleslady kept bringing things into the changing room that were so not me, saying, “Just try it!” If that’s the case, don’t be afraid to stand your ground like I did. “No, thank you, ma’am, but I don’t think I’ll be wearing these Golden Girls–esque palazzo pants and a black-and-white, um, referee’s jacket to my college reunion.”

The other thing I realized is that I should pay attention to girlie things like jewelry and shoes and purses (oh, my!). I know, with all that’s going on in the world, do we really need to think about this stuff just to put together an outfit? But if you have an important event, these things do help give you a lewk instead of just a look.

Trust me, I don’t always follow the lessons I’ve learned. I still don’t understand how one goes about wearing orange eyeliner or a “statement cape.” And at my son’s school pick-up, I’ll definitely rock the Rachel Dratch I’ve Stopped Caring Collection™. But there are times when it feels good to dress up and have someone ask, “Have you lost weight?” To which I’ll happily respond, “No, I’m just wearing a jacket that isn’t two sizes too big.”

Dratch stars in Wine Country, on Netflix and in select theaters May 10.

For more stories like this, pick up the May issue of InStyle, available on newsstands, on Amazon, and for digital download Apr. 19.