September 23, 2022

Let’s Find This Reader a First-Day-of-School Outfit!

Recently, a Cup of Jo reader reached out for help finding a first-day-of-school outfit…

“This year, I’m turning 40 and making a career shift,” wrote Anne. “I start law school in the fall, just as my oldest child starts kindergarten (we get to buy school supplies together!). I’m excited but nervous, so on the first day, I want to appear confident and interesting to eat lunch with. Please share advice!”

First, congratulations! We are rooting for you. Remember this comment from a reader named Libby? “The most amazing woman I have ever known retired from a journalism career at 62 and promptly enrolled in law school. She practiced law until she was 94.” For first-day-of-school outfits, here are eight great pieces (that would also work well for the office)…

The oversized blazer: An academic setting begs for a blazer, so give the people what they want! This modern version is polished enough for visiting professor office hours, but casual enough for grabbing drinks with classmates.

The denim shirt: If you’re looking for a fresher take on the white-shirt-with-slacks uniform, swap in a fitted denim shirt. With a dark wash and crisp feel, this top is the cool cousin of button-down shirts. I’d tuck it into these drapey pants.

Wide-legged trousers: I wish everyone could own a pair of wide-legged trousers. They instantly elevate any outfit and have character without looking costume-y. (Plus, they create the ultimate weekend look with white sneakers.)

The statement sweater: When you’re heading to the law library (quiet, please!), add a pop of color to liven things up. This red polo sweater gives a cheery impression and would pair beautifully with a favorite pair of jeans. This other red sweater is just as fun and only $22.

The slip skirt: This midi is a closet staple. The sheen and subtle flip make it both elegant and playful, which are two attitudes we could all channel more of in our lives.

The sweater dress: To feel confident, comfort is key. This calf-skimming sweater dress strikes the perfect balance between flattering and cozy. It’s giving “look gorgeous while wearing a blanket” vibes. This size-inclusive line also has the dreamiest jewel tones.

The low-heeled bootie: The last thing you need to deal with after a day of lectures, commuting and parenting are pinched feet. So, keep the feeling in your toes with low-heeled booties (they also come in warm brown).

The sturdy tote: Law school requires walking from class to class with heavy books. To save yourself from a Home Alone situation, invest in a sturdy bag. These nylon totes have a cult following for a reason: they’re sleek, durable, and have enough room for a laptop, books and snacks.

Thoughts? What would you wear on your first-day-of law school? Or when returning to office?

P.S. Pants we wear to work and a criminal defense attorney’s week of outfits.

(Graphic layout by Miss Moss. Photo by Simone Anne/Stocksy.)

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