The rise of wearability: why 2021 fashion trends are reflecting new values

Wearability in 2021 fashion trends

The sun dipped low and golden over the city of Milan as my friend Val and I navigated the narrow streets of the historic center. Our destination: early evening aperitivo in one of the area’s hippest bars, and we were dressed to kill. Unfortunately, the assassination was already underway, and the first targets were my feet. I’d donned my most comfortable stilettos (is this an oxymoron?), but as we tripped our way across the uneven cobblestones, rendered even more deadly in the fading light, I demanded aloud to know why we had opted for high heels in a city where we walked everywhere.

Val, ever the style devotee, snapped back with the force of a ruler across my metaphorical knuckles.

“Because,” she declared, “we work in fashion! And fashion is pain. You aren’t supposed to be comfortable.”

Now that we live on separate continents, I haven’t had the chance to see Val in years, let alone enjoy nightlife with her in one of the world’s top fashion capitals. But her words stuck with me, this long-standing notion that fashion and comfort should not make plans to interact. If their paths cross by coincidence, enjoy! But don’t go developing expectations.

Conventional fashion wisdom taught us that when aesthetics are prioritized, good style will be the result, and this is the singular goal. A comfort-above-all mindset places you teetering on a precipice. Lying in wait below: frumpiness. But is that idea finally changing?

Comfort & Wearability as Emerging Brand Values

Over the past decade, the rise of streetwear-inspired trends has driven up the value placed on wearability and versatility of use in fashion. The undeniable MVPs of the day are sneakers, of all things (Val would’ve had a stroke). Over the past year, the industry’s trajectory towards wearability accelerated even further, as quarantine measures and working from home had us all turning to our most comfortable attire. Retailers rushed to stock pieces that transition from loungewear to professional Zoomwear without missing a beat. Comfort is back in the game.

Case in point: I recently purchased a pair of draw-string joggers in a crisp and decidedly trending business plaid. What does it want? I mused when I saw the pair of pants folded neatly on a table marked “new collection.” Who is it trying to be? It’s an existential crisis of a garment in very soft cotton and you’ll have to tear it from my cold dead legs. Functional and unfussy for every context and camouflaged in an on-trend print, it exquisitely embodies the concept of wearability for 2021 and beyond.

Once little more than a buzzword, now wearability is a value, a philosophy, a promise to consumers that even luxury labels are willing to make. Dior, for example, now merges sharp tailoring with more functionality than ever before; Chanel brings quality construction to innovative and — dare I say — comfortable designs, while contemporary Scandinavian brands like Ganni and Filippa K embrace wearability alongside democratic price points.

Customers continue to hunger for fashion that feels unique, and styles that tick multiple boxes, blending looks with smarts and proactive wearability, are dominating the trend list.

The Escapism Theory of Wearability in Fashion

Naturally, the question arises as to why fashion has been indifferent to basic, humane levels of physical comfort for so long, and perhaps the query requires retrospection into the semiotics of dress through the ages.

In her book The Language of Clothes, Alison Lurie posits that structured, polished, cosmopolitan clothing echoes the imagery of the cityscape, often in hues that mimic dark wet pavement, sooty pollution and neutral cement. Comfortable attire, on the other hand, speaks the pastoral language of rurality, the bucolic escapism we’ve been chasing in recent months.

“Whereas urban clothes tend to be hard-surfaced, like the worn asphalt of an urban landscape, rural fabrics are usually soft and fuzzy. Tweed and wool and homespun repeat the textures of grass and bark and leaf, while corduroy, the traditional rural fabric, mimics not only the feel of moss but the look of a plowed field.”

There’s plenty of evidence demonstrating that the collective challenges faced in 2020 have translated directly into consumer preferences for idyllic interpretations of rural life. Our yearning for simpler times and comforting escapes are born out in the rise of the cottagecore aesthetic (the hashtag jumped over 150% on Twitter alone last spring), soaring leggings sales, and the hunt for wearable, multi-tasking clothing that prioritizes comfort (all hail the plaid joggers).

If streetwear put wearability back on the table, the trying circumstances of the past year pushed us to become even more demanding for style that marries urban appeal with the sensory rural qualities of functionality and tactile indulgence. Fashionable ideals needn’t be compromised in deference to the practical needs of the wearer anymore, and that’s good for everyone.

As for the best news? They’re dressing this way in Milan, too.


Palazzo Pants 
Palazzo pants in 2021 fashion trends with wearability
via Racked | via Who What Wear

These chic pants are characterized by tailoring at the waist and around the hips that then loosens into roomy, flowy legs. While in past years the palazzo pant has trended in extremely wide legs and avant-garde motifs, current fashion renderings focus on more structured fabrics and solid colors or geometric prints. These pants made a grand entrance into 2021, creating plenty of buzz in Michelle Obama’s Inauguration look. 

Chunky Knits
Chunky knits in 2021 fashion trends with wearability
via The Fashion Tag | via Elle

From cardigans and polos to pullovers and sweaters, it’s all about the chunky knits. They’re warm, they’re layerable, and their organic textures hearken back to an era when women made most of their own clothes by hand. To get it on this trend, fortunately, you don’t have to.

Teddy Coats
Teddy coats in 2021 fashion trends with wearability
via Need Supply Co. | via Timur Emek/GC Images

 This look has been steadily filtering down from the most elevated luxury brands like Giorgio Armani to bring us the winter coat we deserve in plush textures. Cozy and infinitely wearable, the key here is to prioritize a soft hand-feel, thanks to polyester, acrylic and modal blends, and to emphasize total warmth. No more hypothermia in the name of fashion. 

Long Faux-Leather Trenches
Long faux leather trench coat in 2021 fashion trends with wearability
via ENT/splashnews.com | via Azalea

Nothing is chicer this season than a full-length PU (polyurethane) faux-leather trench coat with wide lapels and a relaxed, longline silhouette that’s endlessly versatile. Classic and understated, it can be fastened with buttons, tied at the waist for added definition or left open. Style it as you please, atop as many layers as you wish, through the winter, spring and fall for multi-seasonal wearability in fashion. 

Oversized Boyfriend Blazers
Oversized boyfriend blazer in 2021 fashion trends with wearability
via Walk in Wonderland | via Andy Heart / The Frankie Shop

 This boxy 80s-inspired rendition of the blazer may not be everyone’s cup of tea (especially if you don’t miss shoulder pads), but it offers a fun opportunity to play with shapes and raid your closest male’s wardrobe. The loose fit and ubiquity of pockets render this piece 100% wearable. 

Combat Boots
Combat boots in 2021 fashion trends with wearability
via Getty images | via The Fashion Tag

 Flat, durable, and functional, these boots are truly one of the longest-lasting trends in footwear. They’ve been a mainstay of the counterculture and punk movement since the 80s and are still deemed super-cool by tastemaker fashion houses like Prada and Dior. Now leveled up, you can sport them in matte or shiny patent leather with feminine touches like platforms, heels (you glutton for punishment) and shades of beige or white.

Chunky White Sneakers
Chunky white sneakers in 2021 fashion trends with wearability
via GirlsInsights | via Getty Images

At last: permission for ultimate podiatrist-approved comfort without sacrificing trendiness. The white sneaker, rendered especially “chunkier” with bulky tread, is fit to wear with skirts, dresses and trousers, either semi-formal or casual. Arch support included.

 Kitten Heels
Kitten heels in 2021 fashion trends with wearability
via thestylestalker.com

 Low kitten heels, especially mules in bright colors and satin finishes, make for a cutesy yet comfy footwear choice. This is a great place to play with color while conveniently not wrecking your ankles (I see you, cobblestones).

High Straight-Leg Boots
High straight-leg boots in 2021 fashion trends with wearability
via Paul Gonzales

If you’ve ever struggled to find tall boots that don’t strangle your calves, rejoice in discovering that straight-leg boots are very much “in” right now. Clean lines extend upward from the heel to the knee in classic black, snakeskin and white, which has turned out to be the best-selling color for leather boots right now.

For a complete list of early 2021 fashion trends, see our full analysis here featured on The Find.


Cover photo by Can Şerefoğlu via Unsplash.

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