Long Shorts
Photo courtesy of @anoukyve

The Most Stylish Ways To Wear Long Shorts Now & Through Fall

Thanks to Bottega Veneta, CELINE, Givenchy, and more, long shorts are a modern wardrobe staple. Here, your guide to the chicest styles with tips on wearing them with aplomb. Plus, shorts outfit ideas to carry you through the transitional season and into fall.

Shorts outfits are often associated with warm weather, with the hotter seasons seeing us favor the likes of white shorts and denim cut-offs. Then, there are fall and winter iterations crafted in wool blends and sumptuous leather, making the cropped bottom a year-round staple. For 2020, long shorts have become one of the most in-demand looks among the style set, from tailored Bermudas to luxe leather shorts and knee-grazing denim. Gaucho and culotte silhouettes have similarly resurfaced, too. But before you write off this trend as dated or unsightly, the latest versions of long shorts are quite refreshed from decades past (a common occurrence with cyclical style drifts). Though the current buzz is yet another resurfaced nostalgic clothing trend—the look saw much prominence in the ’80s and ’90s—new-season takes come with a fresh feel thanks to modern designs and contemporary styling cues.

Long shorts were noticeably prominent on designer runways for spring/summer 2020, from slouchy leather styles at Bottega Veneta to tailored versions at CELINE, Max Mara and The Row, all the way to denim gauchos at Givenchy. As such, the trend swiftly found its way into the wardrobes of trendsetters, paired with timeless tanks, bodysuits, and classic shirting on top and most favorably, chunky gold jewelry, Bottega Veneta sandals and a designer it bag to finish. 

Once the fall/winter 2020 collections debuted, it became clear that long shorts were all but a fleeting trend. Instead, cool-weather versions abounded from knee-length leather and tailored cuts at Saint Laurent, Victoria Beckham and Alejandra Alonso Rojas to sharp shorts suits at Marc Jacobs and Jonathan Simkhai—tall boots, luxe knits and high-neck tops proved to be key styling pieces. Given that the style set has embraced the trend with such zeal, plenty of outfit inspiration has made its way into our saved folders on Instagram. 

Ahead, we’re sharing with you 15 of our favorite long shorts looks to help you can approach this trend with confidence. We know how tricky it can be to pull off, from nailing the perfect length for you to figuring out the best styles to pair with basics and tailored attire alike. Not to mention, striking the right balance between layers and textures as we enter into the cool-weather season.

Keep reading for your definitive guide with long shorts outfits you can wear now, during the transitional season, and well into fall. 

Long Shorts
Givenchy SS'20/21 | Max Mara SS'20/21 | Bottega Veneta SS'20/21 | The Row SS'20/21 | Celine SS'20/21
Long Shorts
Victoria Beckham AW'20/21 | Jonathan Simkhai AW'20/21 | Saint Laurent AW'20/21 | Marc Jacobs AW'20/21 | Alejandra Alonso Rojas AW'20/21

Tailored Minimalism

One of the easiest ways to wear long shorts is to keep things simple by choosing pieces with clean lines or a neutral color palette. To avoid a too-casual look, a pair of tailored Bermuda shorts, like Anouk Yve’s pristine pair, can span seasons whether you pair yours with a black bodysuit or layer up with a blazer or chunky knit. In warm weather, a woven leather belt and slide sandals are fuss-free and chic, but come fall, swap for a pair of knee-high boots and add a tailored wool coat to the mix. 

Dark Denim Bermudas

Blue jean Bermudas are a failsafe when it comes to long denim shorts, but for a slightly more elevated take, try a darker denim wash in black or charcoal. Then, style yours with an earthy button-down blouse, strappy sandals, and a delicate diamond necklace for a relaxed yet polished effect. We love this look for running errands, a casual lunch or as a chic work-from-home ensemble. 

Long Shorts: Style With Elevated Basics

A pair of long, tailored shorts is inherently polished, making it a versatile option to dress up or down. If the latter is your preference, that doesn’t have to mean sneakers and a T-shirt as your styling go-to’s. Instead, try a slim-fit tank top or bodysuit in white and finish with a sleek black belt, The Row’s cult Bare Sandals, a thick chain-link necklace and a leather Dior Saddle Bag

Long Shorts: A Playful Pop Of Color

When neutral hues aren’t cutting it, long shorts in a colorful shade like banana yellow is a playful look to embrace without teetering into too-bright territory. Whether you opt for a leather, cotton or wool-blend pair, steer yours in a sophisticated direction by styling with an oversize white button-down in crisp cotton poplin  à la London-based stylist, Monikh Dale. For a relaxed-chic finish, add a pair of leather thong sandals and a trendy gold chain anklet

Long Shorts: Graphic Black And White

A pair of trim, black shorts are another versatile approach to the long shorts trend. For a timeless look that packs a significant punch, go for a graphic black and white palette with your look à la Christie Tyler. As you can see, a minimal blouse and on-trend mini handbag flawlessly set off this style of short. A pair of block-heel strappy sandals in supple leather make for a stylish and comfortable finish—a look we’d recommend for dinner or cocktails. 

A Shorts Suit

Shorts tend to come with a casual feel, but the beauty of long shorts is their inherent polish and one of the chicest takes on this trend is the shorts suit, like we saw on many a designer runway—from Givenchy to Max Mara. Whether you opt for this look for work or an event, you can’t go wrong with tailored black coordinates. To lighten things up, style yours with a powder blue tank top and neutral accessories like stylist, Sylvie Mus.

Long Shorts: Combine Luxe Textures

A tonal palette always makes for an ultra-chic outfit, and as Pernille Teisbaek proves, it’s an ingenious approach to the long shorts trend—especially for transitional weather. To start, pluck a pair of leather shorts—Bottega Veneta’s straight-from-the-runway styles are essential for the season—and add in a slightly oversize cashmere knit. Before the weather cools off, finish with a pair of leather mule sandals and a diamond ring for a glimmering accent. 

Long Shorts: Modern With A Twist

When aiming for polish with a pair of long black shorts, a modern white button-shirt ensures a timeless yet directional result. At work, classic pumps or sleek mules would do. But for cocktails, a dinner, or a special event, accessories are the place to play with this outfit formula. Take a cue from Oumayma Elboumeshouli and try a colorful pair of strappy sandals and a multicolored diamond and gemstone necklace. 

A Neutral Shorts Suit

With muted shades of beige and brown continuing to trend into fall, you can’t fail with a neutral shorts suit, whether worn for a meeting or outing with friends. As Amy Julliette Lefévre exemplifies, black accessories make for a sleek and elevated finish to this long shorts look—Bottega Veneta’s padded Cassette bag with a weighty gold chain strap being a prime choice. 

Long Shorts Styled With Tall Boots

The CELINE, Saint Laurent, Victoria Beckham and Alejandra Alonso Rojas runways all made it clear: tall boots and tailored long shorts are a must-try pairing in cold weather. The secret to pulling off this combination with aplomb is proportion; a slim-fitting leather boot that hits just under the knee will break up your line just enough to avoid a swathed-in-fabric feel. We love a continuation of tailoring on top; a tonal high-neck knit and blazer will read seamlessly stylish while a Fendi Baguette will break up the solids. 

Long Shorts: Minimalist All The Way

Another minimalist take on long shorts that works well in transitional weather is to opt for ultra-clean lines all-around like lingerie designer, TyLynn Nguyen, so flawlessly demonstrates. First, start with a pair of tailored white shorts and add a thin and soft-hued cashmere knit on top. Accessories are where you can add some contrast; The Row’s Bare sandals and Alexander Wang’s Scrunchie mini bag appear fresh as ever. 

Long Shorts: Black And Brown Pairings

You may think of black and brown together as a fashion faux-pas, but trendsetters like Chantal Li know that’s anything but the case. The two neutrals pair beautifully together, which can create quite the impact when well-executed. Apply this color theory to the long shorts trend by starting with a pair of black leather shorts and topping with a wrap blazer in inky noir. To finish, Bottega Veneta stretch mules in black will elongate your line. Then, reach for the Italian label’s cult-loved Pouch bag in tawny for distinction. 

Dress Up Your Blue Jeans

Denim Bermudas are among the most popular styles of long shorts and are a style that’s generally reserved for casual, off-duty occasions. Rethink the staple by dressing it up for work, a dinner or warm-weather occasion—Sylvie Mus proves the look can be done and in a fuss-free manner. As evidenced by the stylist, a crisp cotton poplin shirt does wonders for the laid-back bottom with a simple pair of mules and diamond stud earrings to finish.

Double Up On Leather

When it comes to leather this season, there’s no such thing as too much. Apply this rule to the long shorts trend by opting for a tailored pair with a boxy blazer on top à la Nina Sandbech. As a high-impact combo, you’ll want to keep the rest of your look simple, but not boring—i.e., a classic pair of pumps, but in an electric color like hot pink and a retro-inspired chain-link belt. 

Cozy Long Shorts At Home

With increased at-home time as part of our reality, we, of course, had to give you the perfect long shorts look to wear around the house. For the ultimate in serene chic, focus on a frothy palette, and choose comfortable silhouettes like light-and-loose shorts and an oversize cardigan. If the bralette trend has tempted you, there’s no better place to try a cashmere version than the comfort of your own home. 

About the Author
Laura Lajiness is a freelance writer and editor covering fashion, accessories, fine jewelry, and lifestyle topics, including fitness, beauty, home, and travel. You can see her work across various outlets, including ELLE, InStyle, Glamour, Brides, Women's Health, The Zoe Report, Popsugar, Refinery 29, and Well+Good, among other titles and brands. She's held senior fashion editor positions at Popsugar and The Zoe Report, with additional experience as a stylist, brand consultant, copywriter, and fashion publicist.
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