Jennifer Aniston Proves Flip-Flops Can (and Should) Stay in Rotation Throughout Fall 2025

It is clear to me that I will be wearing my flip-flops like Jennifer Aniston from September onwards.

September is a month of change. The return to routine and reality after the holidays always brings with it new things in our lives, as well as a (necessary) drop in temperature. It’s contradictory: Changing our wardrobe is not necessarily essential at that time, but you can feel in the air how styles are moving further and further away from summer.

It’s that in-between time of year when clothes and accessories are shuffled halfway between one season and the next. And, without being sure how my style will evolve next month, I have to say that Jennifer Aniston’s latest look has solved my lack of inspiration and is already part of my mood board for those first days of uncertainty.

To begin with, I will say that it’s not that I’m going to follow the styling to the letter. Although it works for the Friends star, I would look a little weird in a fedora at this point in my life. If I wore it, I think I’d feel like a teenager spending hours on Tumblr—because yes, I was one of those who wore these hats to death in 2015. Putting my past aside, I will copy Aniston’s decision to style sandals beyond pairing them with shorts and dresses in the middle of summer.

While leaving a Manhattan store on August 8, Aniston paired her brown flip-flops with beige ankle pants and a black top. Two basics to which she added a gray scarf on top, a chocolate maxi bag, several pendants and bracelets and two (two!) pairs of aviator glasses, her favorite silhouette and the absolute winning style of 2025.

Far from being out of place, the flip-flops here provided a casual touch, balanced by the sobriety of her neutral pieces. What Jennifer Aniston always does to succeed is, basically, rely on basics and the minimalism that characterizes her style. And, like her, I imagine myself styling my flip-flops like this in the middle of September, and even adding a jacket to the mix when it gets cooler.

Weather permitting, flip-flops can be that little bit of summer we can cling to when the pace picks up and we need a little calm amidst the chaos. And I’m not just saying that. I’m sure that, in this golden moment for flip-flops, many more celebrities will follow suit, and we’ll continue to hear the soft clicks of them for at least a few more weeks.