I spend a lot of time agonizing over what to wear. Starting law school was no exception. Before law school, I was a business casual reporter. But a couple of weeks before law school started, I was told I’d need a suit for orientation. So, there I was: 30 years old , in school again and completely weird about having to wear a suit for more than just a job interview.

Up until that point, I owned one suit that i bought when i was 22. It was a black, off-the-rack, size six Le Suit. The jacket was too tight in the shoulders and puckered when I buttoned it. The skirt fit perfectly around my hips but was uncomfortably snug around the waist. Going up a size, meant the skirt would sag, but the jacket would fit. At the time, I thought who needs shoulder movement anyway?

After wearing the suit for two hours at an internship interview, I wanted to set fire to it. I didn’t wear Le Suit once after that. It wasn’t comfortable and I felt lame and frumpy. But years later, post-layoff, I decided to go to law school. Since you’re expected to wear a suit to all types of events in law school, I had to learn how to dress myself appropriately very quickly.

Sizing Woes

I’ve learned a lot about the shape of my body by trying on dozens of suits. Sizing conventions for women tend to be woefully inaccurate when you’re working with a 2, 4, 6, 8, 10, etc., numbering scheme. Rare is the woman whose torso is the same size as her lower body, and I’m no exception. I ended up with two skirt suits before orientation. This time both jackets fit me in the shoulders, but the sleeves were way too long, making the outfit look super frumpy. For one suit, the skirt was way too big and long on me, and the other one was uncomfortably tight around the waist. The store wouldn’t let me mix and match sizes, because the suits came in sets. At the time, I thought I couldn’t afford to purchase the clothing that fit me better because they were sold as separates, and even then everything was sill too long. When I bought the suits, the sales attendant suggested I get the clothes tailored, which ended up defeating the purpose of buying the suit as a set since nothing fit me quite right.

Since I’m short to begin with, the sleeves on my jackets, legs on my pants, and length of my skirts are always too long. After a long conversation about suits with Maria Evangelista, my supervising attorney at the Office of the San Francisco Public Defender, I discovered I should probably be wearing petite sizes. Although alterations, Evangelista said, are also part of the cost of buying a suit, a jacket’s sleeves should rarely be altered. Pants are always going to have to get hemmed. You’re almost always going to have to take this in or let that out, but there are some things that rarely need altering.

Get comfortable with a tailor

“A suit is supposed to make you feel good. It’s not supposed to be too tight, but, at the same time, it’s not supposed to be baggy,” Evangelista said. “In my opinion, a good suit should make your body look the best it can. I think it’s better than a black dress. A well-fitted, well-tailored suit should hide all of your flaws.”

Evangelista pointed to men’s suiting to illustrate her point. “If you ever look at a man, he has a multitude of physical imperfections,” she said. “But if he’s wearing a good suit that’s well-cut and fits properly, he looks handsome. It doesn’t matter how overweight he is or how off he is physically.

For my fellow-intern, Tiffany Malcolm, knowing what to buy isn’t the problem. It’s finding flattering suits in her size. “What surprised me about suit shopping is how little of a selection there is for larger sizes,” Malcolm said. “Most women are not a size 2, 4 or 6, yet the selection and styles of suits for larger sizes is very minimal. What I look for when buying a suit off the rack is comfort and style. I like a suit that is comfortable and stylish. I like a little stretch in the waist and a nice cut that shows off the curves of my body.”

So, what have I learned in all of this? I prefer to buy separates because I’m a dress size or two bigger on the top than the bottom, and I was happy to hear Evangelista echo my feelings when we talked about how to go suit shopping and getting the most bang for my buck.

But Evangelista gets the most out of her suiting by making sure she can get the matching skirt, jacket and pants. “It took me a while to figure this out, but if I had to redo everything, I would never buy a suit unless I could buy all three pieces. I’m maximizing the use out of my blazers. You’re really getting two suits with three pieces.”

The fun comes with picking out the jewelry, shells, accessories and shoes, she said. “You don’t have to struggle. There’s no ‘oh, what’s the weather like today. It’s fall, I want to wear brown. Oh, but too bad, I got it in a skirt, but not in a pant.’ There are too many issues in your head. When you get the three pieces it’s so easy.”