Every fall, I inevitably find myself saving new outfit inspiration and making mental lists of everything I suddenly need for the season. But when I look back at the outfits I’ve actually loved wearing over the years, I’m reminded that my favorites are rarely the trendiest ones.

There is something about the first hint of fall that makes me want to completely rethink my closet. Suddenly, the linen and raffia I couldn’t get enough of in July are making way for richer colors, softer textures, and all the layers I’ve been missing since spring.

There is always that slightly awkward stretch between summer and fall when I am more than ready to start dressing for a new season, but the weather has other plans. September can still be surprisingly warm, especially here in Connecticut and New York, which means the pieces I’ve been eyeing aren’t practical just yet.