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After years of comfortable dressing—think sweatsuits, athleisure, and more—it seemed like the fashion crowd was starting to favor dressing up over down. A feminine aesthetic rose with the help of voluminous midiskirts by Bottega Veneta, nipped waistlines at Khaite, and sweet shoe styles like Mary Janes and ballet flats. This season, however, we’re seeing that the same street style set has returned to a fuss-free fashion formula—one where wardrobe essentials shine and chic comfortability is of the utmost importance. At the most recent London Fashion Week, showgoers exuded effortlessness, sporting comfortable outfits like an overshirt and suit pants to denim midi skirts and tank tops. Also, when it comes to comfy yet chic street style, no one does it better than Hailey Bieber. Her repertoire of oversized outerwear, baggy jeans, and stylish sneakers may be pared back, but it’s never boring.
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The allure of the comfortable outfit is not surprising given how non-trend trends (as we like to call them) are dominating not only our closets this season. It’s also an especially easy fashion formula to replicate, given that you likely have a few of these pieces tucked away in your drawers already. In our opinion, nothing says casual coolness like jeans and a T-shirt—and these street style stars know how to elevate their essentials, whether it’s layering over a transitional trench coat or slipping into a luxe loafer. There are even items traditionally meant for lounging, like a basic black legging, that get revamped enough to sit in the front row.
According to the street style set, dressing down is just as—if not more—impactful than dressing up. This spring, embrace fuss-free fashion and shop the below nine chic yet comfortable outfits.
The Bomber Jacket + Baggy Jeans
When it comes to comfy yet chic street style, no one does it better than Hailey Bieber. Recently in her local Los Angeles, the supermodel stepped out in an oversized bomber jacket, baggy jeans, and stylish sneakers that put any other outfit formula to shame. Get the look courtesy of The Frankie Shop, Agolde, and Adidas.
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The Oversized Overshirt + Suit Pant
British Vogue’s deputy editor and fashion features director, Sarah Harris, is known for her effortlessly elegant style and her wardrobe of minimalist must-haves. To and from shows, Harris kept it polished and classic in a camel overshirt, plain white T-shirt, and loose-fitting trousers. Accessory wise, a Prada pump is the definition of an elevated essential.
The Menswear-Inspired Coat + Mary Jane
A classic overcoat is one style worth borrowing from the boys; just ask this street styler. Underneath, nothing says casual coolness like jeans and a white tee. For an element of sweetness, embellished Mary Janes from Miu Miu are another hero piece.
The Denim Midiskirt + Tank Top
For the non-jean enthusiast, a denim midiskirt is a happy medium. Take inspiration from this showgoer and style with a trendy tank top from Cos and Holzweiler’s padded bomber jacket. Pointed-toe boots from By Far are a sleek addition, as is Gucci’s classic Jackie shoulder bag.
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The Strong-Shouldered Suit
Though a strong-shouldered suit may not first come to mind when crafting a comfortable outfit, let this street style say otherwise. The relaxed tailoring of this Loulou Studio suit is simultaneously easy and elegant. Underneath, Éterne’s ribbed tank top is a consistent wardrobe staple, as are these ivory loafers from Cos. Add a personal element with Oscar de la Renta’s initial gold-plated necklace.
The Simple Sneaker + Relaxed Pant
According to this street styler, all you need to achieve a model-off-duty look is a simple yet stylish sneaker and a relaxed pair of pants. The entire look is masterfully minimal and monochromatic, thanks to additions like an Everlane turtleneck and The Row’s ivory moon bag. Meanwhile, Mango’s wool coat keeps it tailored to perfection.
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The Trench Coat + Plain White Tee
When navigating between seasons, a transitional trench coat should be first on your shopping list. Take this street styler, for example, and style yours atop a well-worn white tee and lived-in pair of denim. Little black boots tie the look together, while a burgundy tote bag pops some welcome color.
The Casual Quilted Coat + Double-Denim
Speaking of transitional outerwear, enter the casual quilted coat. Like this fashion darling, Ganni’s chocolate brown version pairs perfectly with a double-denim look. Put some pep into your step with a Gucci loafer and chunky socks from The Row. To finish, DeMellier’s crossbody bag is both practical and polished.
The Turtleneck + Sleek Black Legging
Sometimes going back to basics is best—and what is more foundational in a wardrobe than a sleek black legging? Traditionally meant for lounging, Skims’ split-hemmed pair is easily dressed up alongside Rixo’s animal print coat and Maison Margiela’s tabi flats. Equally as critical to a closet is a slim-fitting turtleneck–and this one from Wolford oozes sophistication.
