As Carrie Bradshaw once wrote, "There is a time of year in New York when, even before the first leaf falls, you can feel the seasons click. The air is crisp, the summer is gone.” That time is upon us now: The unmistakable chilly nights leading to cooler days are here, and it’s time to say goodbye to the less-is-more approach to dressing and start reacquainting ourselves with how to layer. For some, the practice of piling on clothes is no small feat in itself. Perfecting that je nais se quoi attitude can take a lot of trial and error, but that’s half the fun.
“Layering allows you to add depth to your style while still remaining true to your sartorial narrative,” Sarah Brody, brand style director of Tibi, tells TZR. “It’s a small, yet effective way to experiment with different combinations — texture, color, silhouette — without losing myself.”
Playing with these different elements can offer some seriously chic results, perhaps shifting your entire mood and aura. “I love how fall layering in particular can transform your energy,” Daniella Kallmeyer, founder and creative director of namesake label Kallmeyer, says. “Like how a delicious cashmere scarf wrapped and tucked into your jacket can make you stand taller, or how a long cuff sticking out of a blazer might subconsciously cause you to gesture bigger.”
Speaking of scarves: This group unanimously sung the praises of the somewhat simple accessory as a cold-weather styling go-to. “The unsung hero of my fall wardrobe is without a doubt an oversized wool scarf in a neutral hue,” Brody proclaims. “A multi-hyphenate accessory, it transitions from a windbreaker/babushka hybrid outside to a laidback-meets-luxury wrap indoors. Its ability to shape-shift makes it an inflight essential when traveling, too.”
Wanyi Jiang, global creative director of Amyris, adds, “I’m also fond of a gigantic scarf, so that will definitely be something you’ll see me throwing on. It doubles as an umbrella sometimes during NY showers.”
Layering, of course, is all form and function. “Since I’m always cold, I love wearing sweaters upon sweaters upon sweaters,” Jiang states. Still, each piece must serve a specific purpose. “Don’t overdo it — layer intentionally and functionally,” advises Kallmeyer. “Layering doesn’t have to be just for the purpose of making an outfit unsimple. You can emphasize the simple beauty of a garment by layering it with others, like a sweater that's cropped or sleeves that are long, a plunging neckline.”
And as for the aesthetic end of things? “My approach to layering is to not sacrifice modernity for the sake of functionality,” notes Brody. “I like creating thoughtful combinations with intent that highlights this duality.” Indeed, preservation of one’s own unique style and taste is what layering is all about: It’s an expression of self.
“Wear as many layers as you like and don’t care what anyone else says,” Jiang states. “I quite fancy that scene where Joey [from Friends] wears all of Chandler’s clothes and does lunges in them.” OK, so maybe you don’t want to go that literal, but having fun with styling is all part of the layering game.
A few tips worth noting? “Start with a thin layer and go bigger. A heavy top portion can be balanced with cigarette pants or straight jeans with boots,” Jiang explains. “Also, always bring a long camel wrap coat. It goes with everything.” Shopping for pieces that have long-lasting appeal will prove helpful in making endless outfit combinations down the line. Kallmeyer emphasizes the importance of adding in purposeful extras. “I don’t discredit accessories as layers,” she says. “A good blazer with layered chains or ear cuffs, a leather glove, a good belt! There's so much to play with.”
Keep scrolling for these experts’ personal layering tips and tricks — and an edit of pieces to get the looks now.
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Checked Blazer + Thin Long-Sleeve
Plaids and checks always feel right for fall, so a blazer in menswear motifs is an indispensable addition to every closet. When it comes to texture, keep things simple. “I often layer a cotton long-sleeve, followed by a sweater, then a blazer,” Wanyi Jiang says. “The softness of the sweater will keep it cozy and a blazer gives structure.” For bottoms, try an equally tailored, cropped trouser with loafers. A visible ankle on a cold day is the perfect opportunity to play with a fun pair of socks, like a colorful, sparkly style to add a little interest to the generally classic mood.
Oversized Scarf + Chunky Sweater
A cozy and comfy godsend of a scarf can also be a fashion-forward addition when creating an overall lewk. “Experiment with layering knitwear in unconventional ways to create added points of interest,” Brody says. “But set parameters so you don’t stray too far from what makes your style uniquely your own.” Since this combination is about the right mix, keep things interesting with various textures. Pro tip: A more sumptuous scarf from brands like Acne Studios and Loewe will give you major street-style cred, without breaking the bank. After all, investment dressing is always in season.
Shacket + Carpenter Pant
Nothing pulls an outfit together in between seasons like a shacket (for the unacquainted: shirt + jacket = shacket). Whether thrown over a favorite tee or tank, or paired with a cashmere turtleneck and coat, it’s the silhouette that keeps on giving. And when styled with carpenter pants, it is a match made in fashion heaven. Break the old-school rulebook (no white after Labor Day is so passé) and go for a monochrome look, styling cream tones together. For now, keep wearing those strappy sandals, but invest in a chunky Chelsea boot for the days ahead, when it is too chilly for toes to be out.
Cozy Knitwear + Mini Skirt
Transitional dressing is all about having pieces of different thickness and weights. “I typically always carry a thin knit on me — around my neck as a pseudo-scarf or through the belt loops of my pants — for extra warmth without added bulk,” Brody says. “Always bring the sweater; you’ll be glad you did.” Tie yours around the neck over a tank now for an undone approach, and then wear the knit normally when necessary. And play with proportions! A micro mini on bottom will keep things up to date, while pointy black booties (with just a little bit of heel height) bring a polished feel to the outfit. And when the time comes, just add black tights for another layer of warmth and style.
Turtleneck + Sweater Vest
“I love turtlenecks under everything,” Daniella Kallmeyer says. And in clean white or black, the piece really takes a thicker knit to the next level — particularly if you are leaning into this season’s sweater vest moment. Look for quirky knitwear to layer your rollneck piece with, like a Fair Isle or crochet patchwork silhouette, and top everything off with a classic trench coat. Don’t forget to complete your ‘fit with an updated loafer heel for peak prepster-meets-downtown-cool-kid vibes.
Shirt Dress + Tailoring
Keep things minimal in black and white for an unbeatable combo that can be mixed and matched with the rest of your wardrobe a million times over. Take notes from designer Kallmeyer above: She’s reimagined a crisp, white shirtdress by unbuttoning it to show a bra peeking out — and has layered in trousers for some added visual interest (the key is staggered hemlines). Look for Oxford lace-ups in shiny leather to add another element of texture and provide the finishing touch.