Let’s find this reader a first-school outfit! | Cup of Jo

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

“This year I turn 40 and make a career change,” wrote Anne. “I’m starting law school this fall, just as my oldest child is starting kindergarten (we can buy school supplies together!). I’m excited but nervous about being pegged as ‘the old lady,’ so on the first day I want to appear confident and interesting to have lunch with. Feel free to share advice!”

First, congratulations! We care about you. Second, 40 is young and cool! Remember this comment from a reader named Libby? “The most amazing woman I’ve ever known retired from a journalism career at 62 and immediately enrolled in law school. She practiced law until she was 94. It’s NEVER too late.” For first-school outfits, here are eight great pieces (that would also work well for the office)…

first day of school outfit

The oversized blazer: An academic setting is begging for a blazer, so give the people what they want! This modern version is polished enough for the visiting professor’s office hours, but relaxed enough to grab drinks with classmates.

dark washed denim shirt

The denim shirt: If you’re looking for a fresher take on the white shirt-and-pants uniform, switch one up fitted denim shirt. With a dark wash and crisp feel, this top is the cool cousin of button-down shirts. I would put it in these draped trousers.

wide leg pants

Wide leg trousers: I wish everyone could own a pair wide trousers. They instantly lift any outfit and have character without looking costumey. (Plus they create the ultimate weekend look with white sneakers.)

statement sweater

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

slip midi skirt

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

sweater dress

The sweater dress: To feel confident, comfort is key. This calf foam sweater dress creates the perfect balance between flattering and cosy. It gives off “look beautiful while wearing a blanket” vibes. This line including size also has the dreamy jewel tones.

autumn boots

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

black nylon tote

The robust bag: Law school requires you to go from class to class with heavy books. To save yourself from one Home alone situationinvest in a sturdy bag. These nylon totes have a cult following for a reason: they’re slim, 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 you return to the office?

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

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

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