Most seasoned shoppers will tell you that by September, all the good stuff is gone. When the cold rolls in and you actually feel ready to buy that chunky sweater, your size is likely to be out of stock, picked over, or back on pre-order.
This season, I’m not feeling very trend-driven. I’m craving a return to the basics, which is why my first order of business was refreshing some well-loved sweaters and investing in one good bag and pair of boots for the season.
I’ve done a good job of wardrobe-building over the years, so I don’t need much to fill in the gaps — the fall 2025 vibe is way more rotate, refresh, restyle. Here’s what I’m eyeing and buying.
These boots were made for walking, and I can see myself styling them under trousers in the city or over jeans in California. They’re only going to look better with age, and the stack heel offers a little lift, which I appreciate. I’ve had these in my mental cart since I first saw them come down the runway at Khaite, and this fall I’m going to make them mine. Hashed in with a pair of Phoebe Philo boots from last year, I’ve got good coverage for most daytime outings.
A classic for a reason, The Row’s blockbuster hit sweater has never really been successfully duped because it relishes in the details that make an expensive sweater look… well, expensive. (That would be the proper oversize fit, drop-seam shoulders, the way it drapes to cover your rear, a heavy-ass knit, and those delicious long sleeves.) People try to fake her, but Ophelia forever stands in her own class as the real deal.
A closet fit with Ophelia doesn’t exclude other novelty knits! For example, this fantastic turtleneck from COS in a deep shade of fig. I’d style it over an oversized white Oxford shirt—cuffs and tail peeking out—over my favorite jeans.
If there is one central truth about living in New York City, it is this: your bag is your car. In the winter, your schlepper of choice also has to present one key function: the strap must fit over your shoulder in a coat! The Row’s Marlo 14 is just right because it doesn’t look like luggage, but it’s still plenty roomy. It takes the best parts of the brand’s Margaux bag and Park Tote and combines them into one superbag. I especially like this color, a tawny brown with green undertones that coordinates with my leather boots without matching exactly.
Did you have a Jet 2 Holiday Summer? Was it the Summer You Turned Pretty? For me, it was the summer my eyes started to go. Optometry went from something optional when I felt like wearing readers to Oh shit, the words on the screen are blurry. Since I have to wear glasses sometimes now, I might as well enjoy it. Maybe even get a little weird with it. Can someone ask Alison Bornstein if the wrong shoe theory also applies to glasses? Because I think it kinda works!
Those boots are gorgeous. Added to the list immediately
Jess you nailed the vibe- I’m feeling a big focus on classics this fall too and this got me excited to rewear all my closet faves soon! Also welcome to the eyeglasses club- those are so cool! X