Though I’ve pompously rolled my eyes at every TrRanSiTiOnAl dReSsInG headline I’ve ever read (that, and day-to-night outfits, whatever those are), when the first day of Real Fall Weather hits, I find myself Googling something along the lines of “cool transitional fashion for summer to fall weather.”
Because going from tear-your-clothes-off heat straight into cozy soup season is enough to make anyone question not only their wardrobe, but their entire existence. Should I dress for the season or the actual temperature? Which is more important, the fall trends or the muggy forecast? And what about the days when it’s fall in the morning, but summer by lunch? I’ll admit, it’s confusing—which is why stories like this exist by the dozen.
But while most of those stories will tell you to just throw on a cardigan, I’m here to give you stylish outfit ideas you’ll actually want to wear. Outfits that will bring your warm-weather favorites squarely into the fall season and vice versa (read: fall trends you can wear even when the weather hasn’t quite caught up yet, and summer trends that you can style well into autumn). With help from fashion’s most stylish—and Cosmo‘s own fashion director, Brandon Tan—I’m laying out all the ways to slay the season’s most annoying weather.
A Rugby Shirt and a Short Skirt
I’ve been itching to break out my beloved rugby shirt collection all summer long, and finally, the time has come. Paired with a flippy skirt or Bermudas and boots, the oversized staple is perfect for those in-between days.
A Slutty Little Cardigan (Complimentary)
Okay, I take back what I said about the cardigan. I am going to tell you to wear one, after all, but I’ll say what those other writers won’t tell you—and that’s to embrace it as a way of showing a little skin. Give your look just a liiittle bit of coverage by buttoning only one or two buttons, and then wear a bra underneath or nothing at all.
Capri Pants and a Blazer
Bring summer’s favorite half-pants into the fall season, by styling your capris with a boxy blazer. The added volume will balance out their slinky fit. From there, you can finish with pumps, a statement belt, and a crossbody bag for an office-ready fall ‘fit.
A Breezy Top and Leather Pants
Leather pants are the single most beloved item in my wardrobe, because they truly do it all. And trust me, they can make even the barest of summer blouses feel autumnal.
A Dress Over Pants
Ashley Tisdale was right all along! And, frankly, we owe her an apology. Because wearing a dress over pants can be surprisingly chic—plus, it’s a great way to wear your favorite sundress during the fall season.
Socks and Sling-Backs
Cosmo Fashion Director Brandon Tan says, “Hosiery and socks are a great way to get some more shelf life out of your warm-weather wardrobe.” Sling-backs and socks are a classic combo, but if you’re feeling a bit chaotic (again, complimentary) he adds that “socks with peep toe heels [are] a styling note we saw a lot throughout FW25 runways.”
A Sweater and Jorts
There’s precisely one (1) week per year when it’s appropriate to wear shorts with a sweater, so you had best be prepared to take full advantage when that day finally comes. My best estimate would put it somewhere between October 6 to 8. (Bookmark this for later.)
A Button-Down and Cargos
File this under: fall season, summer temps. Leaving your button-down open, crop-top-style, will give off that full-coverage look, but with a breezy aspect that will still keep you cool.
A Sweater and Swimsuit Cover-Up
That long, mesh maxi you wore down the shore all summer? Give it one last hurrah by styling it under a chunky sweater with a pair of cowboy boots. It’s the perfect casual fall look.
A Barn Jacket and Pleated Skirt
I know, I know—barn jackets are typically done with jeans and riding jackets. But consider this your sign to branch out beyond the royal-approved styling. Wear yours with a micro-mini skirt and loafers for days when the weather can’t quite make up its mind.
A Slip Dress and Blazer
This silky little dress got you through summer’s hottest days. You can’t abandon it just because the temperatures rose a few degrees! Stay loyal to your day-one with a simple fall styling trick—i.e. a posh blazer and sling-back pumps.
A Leather Jacket and Micro Shorts
A leather jacket can make even the most summery items (booty shorts, a bra top, an actual bikini, etc) feel appropriate for fall. Style yours with a pair of your tiniest shorts and matching moto boots for the ultimate Hot Girl look.
A Summer Scarf and Jacket
The girlies were positively obsessed with scarves over the summer and, according to Tan, you can continue that energy into the fall. “During transitional seasons, I like to keep a silk scarf in my bag, if not around my neck. The light fabric makes it perfect for in-between weather. Silk is breathable and extremely packable. They’re also one of the most versatile accessories, able to serve as a headwrap, waist belt, or even a top,” he says.
A Sweater and Midi Skirt
“There are many ways to make your summer pieces work for fall with smart layering and intuitive styling,” says Tan. “A fool-proof recipe is mixing pieces from different seasons into the same look—for example, a baby tee you’d tend to wear in the summer with a heavy pleated skirt you save for the winter could actually make for the perfect fall outfit. You could alternatively go the opposite route and pair a chunky sweater with a mini skirt and boots.”
A Bra Top and Blazer
Most of fall’s dressing woes can be solved simply by throwing on a blazer or leather jacket—and this logic can be applied to your underwear drawer, as well. Pop said jacket over your hottest bra and a mesh top combo for a weather-appropriate nighttime look.
Kelsey (she/her) is a freelance digital fashion editor and writer with a knack for turning top-performing content into top-selling content. She has extensive experience in editorial and e-commerce strategy, having worked in both divisions during her years at Seventeen and Bustle. With more than a decade of experience in digital media, she also offers creative and social media consulting, as well as copywriting services. She enjoys cheeseburgers, traveling, and vintage hauls. Follow her on Instagram at @klstieg.
→ Continue reading at Cosmopolitan
