The Best Fall Clothing Staples, According to Fashion Insiders

“I’ve always loved a pleated skirt, but when I saw this Simone Rocha in her FW21 collection, I pretty much became next-level obsessed. I ended up pulling it for a campaign later in the season, but when it came time to wrap, I couldn’t seem to let it go—simply too good a piece not to add it to the personal collection.

“I love that it’s actually quite versatile. You can wear it tied up, of course, but I prefer the stunning imperfection of its silhouette when worn undone—it adds a bit of unexpected drama! I also tend to wear a lot of black, so I love a piece like this that gives you that perfect dusty pop of color. I styled it here over a short wool dress with boots and a wool trench to make sure I stayed nice and warm. With a delicate piece like this worn in fall/winter, it’s really all about creative complimentary layers that can carry it through the colder seasons.” —@shibonleigh

“My fall wardrobe and my summer wardrobe are essentially the same, with an added layer or two, so I’m most looking forward to experimenting with accessories. I’m always holding my breath waiting for the next Telfar bag drop—it’s so exciting to see what colors they come up with. For Season 5 of Insecure on HBO, we got to debut an extremely exclusive, never-before-seen colorway, and I can’t wait to add that to my Telfar bag collection.” —@shionat

“Anyone who knows me knows that my fall essentials consist of a great sweatshirt and sweatpants. There’s so many ways you can dress them up or dress down. You’ll see me layering my sweatshirt with a long coat and accessorizing with a gold pair of hoops. If I want a more relaxed look, I pair it with some high-top sneakers and a fun bag. Recently, I’ve been living in my The Local Love Club Varsity Crew and Pant set.” —@stylememaeve

“The Puma Classics are my go-to fall staple. The retro-classic style sets the stage and foundation for the rest of my look. They’re perfect for running around the city in all weather. I wear my Classics to the office paired with Yohji Yamamoto pants or to dinner with a Prabal Gurung skirt. I even wore them to the Met after-party paired with a Gucci gown! They’re so versatile, so timeless.” —@juneambrose

“As a girl on the go, I always dress for comfort first. Layering is key for me as I may be running from set to the airport at a last-minute’s notice. A staple trench is key for me for fall. I would style it with a hoodie under and leggings and some cool sneakers. Effortless but yet still super stylish.” —@mollyddickson

“I intend to remain in a chic cocoon this winter so hyper comfort is key. I love this cashmere Commission sweater for the pillow-soft texture and whisper-pink color. Something about the soft palette makes me less fearful of being cold. I’ve actually already worn this around my shoulders with the chocolate turtleneck version and a lipstick-red pleated skirt. Next, I’ll wear it with some gray, wide-leg cashmere trousers. And then, again with my patchwork, wide-leg denim.” —@solangefranklin

“My favorite fall wardrobe essential is a really nice leather trench. I typically like to shop them vintage or faux leather. This Bottega Veneta option is a showstopper! I really appreciate trenches in pops of colors, as it really sets my fall looks apart. This Bottega jacket can be worn as either a dress or with a sheer top and trouser. I also love to layer leathers creating a full leather look by pairing it with a knee-high boot, a leather bag, and simple accessories.” —@meccajw

“For fall, I am craving oversized everything and a heavyweight utility shirt is the perfect antidote. I especially love this GOTS-certified organic cotton version from SlowCo, my new favorite conscious-fashion hub. I love dressing up a shacket with ribbed flares and lots of jewelry or dressing it down by tossing it over a hoodie and pairing with well-worn Levi’s and Chillbies.” —@rachaelwangstudio