I had an assignment in college that began as a burden and ended up being one of the most thought-provoking experiences of my life. Studying Anthropology, I was required to take a number of cultural anthropology courses despite a focus in archaeology. One of my professors set us an assignment—to keep track of everything we wore for a month. We had to create a spreadsheet and write how/where we acquired what we wore, how much we spent, where it was made, how often we wore the items, what we were doing when we wore that outfit—and at the end of the month, submit an analysis of our style, our shopping patterns, and what our clothing said about us. I’ve never been able to get dressed the same way again.
This assignment shaped a good deal of my life. Instead of applying anthropological thinking to other cultures, I started thinking about my own life and culture through that lens. Why do we dress the way we do? Why is there such pressure on our culture to constantly be consuming, to be searching for the next thing, to feel like we’re missing out if we don’t have the latest fashions? Why does a sale seem to equal a compulsion to purchase something, because otherwise we’re missing out? (Hint: 99% of the time, we’re not–and that’s why the item is on sale to begin with!)
So this is why I write this particular column (and a previous one, “What Do I Really Wear?”) I’m fascinated by the why of it all. In this column, I share three favorite outfits from the previous week, what I wore, and why I chose them. I hope you find this process interesting just as I do!
In the city for more casual meetings
Jacket | Tee | Jeans | Shoes | Bag | Sunglasses | Watch (c/o; 20% off with FEWERBETTER20) | Cashmere wrap (similar)
Why am I wearing this outfit?
I had a meeting at a restaurant near Julliard for a concert we’re sponsoring for work, and I was really looking forward to learning more about the program! It was a chilly morning and warmed up slightly in the afternoon, so layering was crucial and making sure I had a cashmere wrap was crucial. I wore jeans for this meeting as it was a casual event, but also because I was starting to clean up my new office after the contractors finished. The expression on my face, model’s own, is courtesy of yet MORE construction work rerouting my lovely little walk through the Upper West Side.
In the city for formal meetings
Cardigan (c/o) | Tee | Pants | Shoes | Watch (c/o; 20% off with FEWERBETTER20) | Scarf (c/o) | Sunglasses
Why am I wearing this outfit?
Another day, another meeting! This one was at a private club to review the details for our upcoming dinner dance. I met with my colleague at one of my favorite coffee shops for work before our meeting (Via Quadronno, if you aren’t absolutely obsessed with their paninis, I have serious cause for concern). Later, we went back to our office on the Upper West Side and did more cleaning. This outfit was great because I had a tee underneath my cardigan, so I could take off the cardigan and scarf and still be dressed without worrying about ruining the nice pieces of my outfit. These trousers are my favorite ever work pants from Everlane—they recently brought them back and I’m so glad, as my previous pairs had been retired after a decade of heavy use. These are trousers that break my “natural fibers only” rule for my wardrobe—they have a good deal of stretch and really suck you in, which is perfect. They’re extremely comfortable and move with you. Unlike the ever-popular kick flare pants, these have a slim leg (cigarette style, as they were once called), so I feel like Laura Petrie or Audrey Hepburn in Funny Face. Highly recommend. (They’re also currently $23!!!!) I love these so much I own multiple pairs in multiple colors.
In the city (and Governor’s Island) for a work event
Shirt | Belt | Pants | Shoes | Watch (c/o; 20% off with FEWERBETTER20) | Bag (c/o)
Why am I wearing this outfit?
I was speaking at an event organized on Governor’s Island on Saturday on one of the hottest September days. It was a hike from the ferry terminal, so I wore comfortable shoes (should have worn these, though!), and clothes that would still look professional despite the train, subway, ferry, and walking it took to get there!
I love this bag (c/o Parker Thatch) because it really holds everything without being super heavy. It’s been the bag I’ve carried the most this fall and I’m so glad to have it in my rotation! As well, it goes with my watch band, belt, and shoes, so it’s nice to have that cohesion to ground an otherwise standard outfit.
I’ve been reaching for these chinos more and more lately—they’re truly excellent, with a slim straight leg and no flare. They’re almost identical in cut to these Nantucket Red trousers I’ve had for twelve-ish years. The chinos are a perfect way to get a little more dressed up without being overdressed or uncomfortable. I did feel very “Official Preppy Handbook” with this outfit (and the following day’s outfit, when I wore a blue oxford with the same chinos and shoes). But that’s fine! The point is: they are comfortable, polished, and easy.
It’s also a lesson in great pieces being found in unexpected places. I snagged these when we were in California and stopped by J. Crew Factory to browse while passing the time. I was delighted to find such a fantastic preppy staple in a typically bohemian area. The quality is also GREAT, particularly for the price—they’ve already been in constant rotation in my wardrobe and they’re holding up and washing beautifully. Highly recommend stopping by your local J. Crew Factory store to take a browse, particularly as seasons switch over—it’s a wonderful time to find pieces you’ll hang onto.
My local J. Crew Factory store (in Garden City, NY) is having a great event next Saturday the 28th from 12 to 4pm. “The Classics Rewind” is a throwback to the year J. Crew first started. I can’t wait to stop by and enjoy all the fun activities (and also shopping!) that the store is hosting.
Great stuff… sorry I missed you at the governors island event….