In-between-seasons weather has always had its advantages for me, especially that much-anticipated transition from summer to fall. As someone who hates being too hot, it’s a relief when the heat and humidity are less oppressive, but the tree leaves are still lush, and daylight continues to extend to 7 p.m. Still, despite the benefits, I find this time of year to be a total pain to dress for. The erratic fluctuation of day-to-day temperature, the occasional rainstorm, and inconsistent wind patterns make early fall fashion choices laborious and often ending in low-grade remorse (as in, the now-stained white jeans I wore last week during an unexpected downpour). It’s undeniably a tricky time to navigate on the wardrobe front, but I’ve been relying on a few staples lately that have made this time around much easier.
The key to mastering early fall dressing, I’ve found, is rotating in staples that toe the line between warm and cool weather. I start to incorporate the colors and textures of fall but keep the styling light so as not to get overheated. It’s the time of year when layering comes in handy, and having a sweater thrown over your shoulders at the ready can make all the difference. While this list is by no means exhaustive, the four wardrobe heroes below are godsends during this ambiguous time of year. They all check off the boxes required of fall transition pieces while also holding the capability to become full-time fall and winter items, too. Ahead, shop the edit so you don’t find yourself in a sartorial pickle in the weeks ahead.
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I have always been on team trench coat, and one that has a slightly relaxed, drape-y silhouette is nice for tossing over an outfit without feeling like you’re committing to full-blown outerwear. Weather permitting, I love a denim-on-denim combination with a camel trench polished off with some classic loafers. Lastly, I add a pair of mismatched earrings to finish!
Satin Midi Skirt
A slip skirt is by no means revolutionary, but if you’ve yet to invest in one, trust me when I say — it’s worth it. While it’s still slightly warm, I recommend wearing it with a cotton black t-shirt and gold jewelry to contrast all black. If the temperatures dip, I think a light sweater or festive top is perfect. Plus, it makes a great holiday season staple so I’ll be holding onto it for many months to come. Right now, I’m wearing it with a cheery pullover sweater and flatform sandals.
If you’re like me, an easy-to-throw-on floral dress is the star of summer style — my favorites have been on repeat for months. But, because of this repetition, I’m ready to retire warm-weather frocks for something more seasonal. The best piece to replace with that is a dress in a fall-adjacent pattern (plaid, patchwork, or polka-dot prints are all strong choices). At the moment, I’m wearing mine with strappy sandals and bare legs to keep cool, but once it gets colder I’ll layer a pair of tights underneath.
Oversized Button-Down Shirt
A crisp, oversized button-down shirt has all that I’d want out of a closet classic: It goes with everything, can be layered with anything, and works every season of the year. And as a bonus, it really gives an outfit that feeling of I just threw this on, which is infamously tough to achieve. For transitioning to autumn, I’m wearing mine with a pair of knit pants and heeled loafers.