10 Transitional-Outerwear Outfits Perfect for Early Fall 2023

Speaking of timeless trench coats, it’s no secret that the style staple reigns supreme season after season. When it comes to styling the wardrobe essential, take a cue from this fashion crowd and wear yours from Toteme and J.Crew with sleek pairs of jeans, cozy knitwear, and even a kitten heel or two. Quilted shell jackets topped our spring shopping carts, beloved for their versatility and understated elegance. For fall we’re eyeing Ganni’s glossy quilted coat, and we’re not the only ones. One street-styler opted to wear hers with a cream-colored crewneck, tailored trousers, and a chic pair of city sneakers to match. Classic menswear-inspired items, like oversized tuxedo jackets and blazers, are also crucial to a transitional-outerwear outfit, with noteworthy options from Khaite and Everlane.

Err on the edgier side with leather jackets from Massimo Dutti and Remain Birger Christensen. From the latter, distressed detailing makes all the difference, particularly when styled with a black knee-high boot and plaid miniskirt, as modeled below. And when it comes to transitional closet mainstays, nothing is as evergreen as a delightful denim jacket. Courtesy of the Copenhagen Fashion Week street style scene, 10 chic ways to style the season’s best transitional-outerwear offerings, below.

The Lightweight Trench Coat With a Sleek Jean

When it comes to timeless closet combinations, a trench-coat-and-jeans pairing is about as classic as it gets. Take a cue from this street-styler, and wear J.Crew’s lightweight ivory trench with Citizens of Humanity’s barely baggy jeans. Kitten heels from Aeyde elevate the look ever so slightly, and the same goes for The Row’s sleek Sienna clutch.

The Quilted Shell Jacket With a City Sneaker

According to this fashion darling, if you buy any outerwear for fall, make it Ganni’s glossy quilted coat. Styling-wise, wear the cool-weather staple with COS’s chunky crewneck, a pair of By Malene Birger trousers, and chic city sneakers from Novesta. Trust us: This is one transitional outfit formula you’ll want to wear on repeat this season (and beyond).

The Oversized Tuxedo Jacket With a Fancy Flat

Perfect for day or for night, Khaite’s oversized tuxedo jacket is a street style sensation. Per Vogue’s very own Madeline Fass, wear the menswear-inspired It item with a pair of baggy jeans from Madewell, Sold Out’s plain but perfect white tee, and Khaite’s navy suede Lotus bag. The pièce de résistance of this transitional-outerwear outfit, you ask? Mango’s crystal-embellished ballet flats, of course.

The Classic Khaki Trench With a Fall Clog

From the cult-favorite, Copenhagen-based brand Toteme, this oversized khaki trench coat is the ultimate wardrobe essential. Like this fashion darling, keep the staple right on trend with Loulou Studio’s denim maxiskirt, a sleeveless turtleneck top from Mango, and dainty jewels from Fallon. Then slip into a pair of Studio Nicholson clogs to finish off the look to perfection.

The Distressed Leather Jacket With a Knee-High Boot

This fall, the devil is in the (distressed) detail, as seen with Remain Birger Christensen’s brown leather jacket. Styling-wise, wear with Nili Lotan’s caramel-colored tank top and Rag & Bone’s plaid miniskirt. Meanwhile, a pair of just-released knee-high boots from Staud takes this transitional-outerwear outfit to another level entirely.

The Biker Jacket With a Wide-Leg White Jean

A high-quality leather jacket, like this biker from Massimo Dutti, makes any outfit look effortlessly cool. Like this showgoer, style the prized piece with slouchy white jeans from Agolde, an Everlane T-shirt, and a pair of metallic heels from Reformation. To hark back to the ’90s, finish the look off with The Row’s little black bag.

The Menswear-Inspired Blazer With a Ballet Pump

It’s officially blazer weather! This season shop Everlane’s oversized offering in gray. Styling-wise, wear with Tibi’s dark-wash cargo jeans and COS’s baby blue turtleneck. Another trend we saw on the Copenhagen streets? Ballet pumps, like this pair from Maison Margiela.

The Jean Jacket With a Leather Midiskirt

A jean jacket is a seasonless star, whether it’s peak heat or just starting to chill. Shop Goldsign’s casual and chic paneled-denim pick this fall. Like this showgoer, style the closet classic with Massimo Dutti’s leather midiskirt and a pair of pointed-toe boots from 3.1 Phillip Lim. & Other Stories’ braided shoulder bag is another seriously chic addition.

The Colorful Trench With a Hero Handbag

For a festive twist on the classics, find Loulou Studio’s colorful leather trench coat. It packs the perfect punch of color, so keep the rest of this transitional-outerwear outfit minimal with white jeans from Frame, Theory’s elongated suit vest, and Toteme’s T-lock clutch. Meanwhile, barely-there sandals from Tony Bianco hold onto what’s left of summer.

The Black Overcoat With a Smoking Loafer

A longline black coat is an effortless and eternally chic way to pull together a look, as modeled above. Styling-wise, rely on similarly stylish essentials, like H&M’s ribbed turtleneck, By Malene Birger’s maxiskirt, and Aesther Ekme’s shoulder bag. And when it comes to defining quiet luxury, look no further than Burberry’s black smoking loafers.