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How to Wear Flared Pants Plus Some Inspiration

Depending upon your age or pop culture foundation, flared pants seem like a Y2K relic that’s returned right on schedule.

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Although women’s styles had more of a fanning out shape, men’s pants treaded distinctly into bootcut territory – the western version of this silhouette – and were enhanced with a bit of space around the ankles. Wearing these styles lower on the hips – to the point your undergarments showed – accentuated this facet.

On the other hand, if you came of age during the Y2K years, flared pants soared back in the late ‘90s through the ‘70s revival that also brought with it thick platform heels, wider, chunky belt buckles, and psychedelic prints. Their reign lasted from about 1996 until skinny jeans officially took over somewhere around 2007.

This time around, the admiration builds off both eras – it’s a bit ‘90s and simultaneously ‘70s through an androgynous, floral-printed Harry Styles-esque lens. There’s a hint of Saturday Night Fever through relaxed, somewhat drapey leisure suiting, and at the same time, the form is a direct homage to ‘90s wide-legged skater fashion.

So, whether you’re spotting everyone under 25 in a pair of “puddle pants” or you’re looking to update your own wardrobe, here’s how you can get started:

What are Flared Pants?

No matter the decade, flared pants tend to have a slimmer or skinnier upper half that fans out in a bell shape from the knee – hence the name of “bellbottoms” from the ‘60s and ‘70s.

The form can be found in bootcut jeans – flared out, albeit not as exaggeratedly, to fall over a pair of boots – but varies from wide-legged pants, which tend to have a uniform-width pipe style.

Flared pants emerged sometime in the 1960s, defined casual wear and even suiting for most of the ‘70s, and suddenly disappeared by the 1980s, replaced with slim- to skin-tight high-waisted jeans for both genders.

Man wearing flare pants
MILAN, Italy- September 25 2020: Christian Degennaro on the street in Milan.

The Y2K version hit these maximal notes in another way: Although the form was comparably more subdued, the Ed Hardy years meant distressing, bedazzling, embroidery, and studs all over.

They also mimicked women’s jeans with a mid- to low-rise cut that hit no higher than the hips.

Now, though, we’re more critical of the period. The 2000s were both tacky, and stood upon significant body shaming, even before the spandex-heavy skinny jeans took over. This current iteration goes wider – think a true return to the ‘70s disco era – and aims higher, now hitting and accenting the waist.

This feels more like admiration for the ‘70s and has fueled what some dub the “Coke bottle silhouette” for men – that is, a cinched, defined waist, even if he’s wearing a blazer along with his high-waisted flared trousers.

How to Wear Flared Pants & Our Recommendations

In the present, skinny jeans are receiving a more critical look for their form-fitting, body-accentuating characteristics. You can’t hide anything, and worse, certain materials highlight less-than-desirable attributes.

As the corollary to this, flared pants are being revisited for their lengthening qualities: In the right proportions (read: not too fanned out), they give the illusion of height and can also camouflage footwear that adds a few inches.

On this last note, while you can lace your boots over your skinny jeans, your footwear should tuck into your bootcut jeans or whichever flared silhouette you choose. Look for trouser lengths that hit right at your shoes – rather than bag or pool around – and with boots, look for something that fits right against your skin to avoid a pipe effect.

In the present, flared pants encompass the following styles:

Relaxed Suits

Whether you’re specifically seeking something double breasted or simply a style veering away from the skinny cuts of the last 20 years, flared pants head straight into disco territory.

Call it a bit rakish, call it a leisure suit, but these pants sit just above the waist, flare out distinctively past the knee, and are accompanied by an equally loose jacket – single- or double-breasted or even cropped.

ASOS Flary Pants For Men

ASOS DESIGN Skinny Flare Suit Pants In Brown Vintage Check

Checks in a mix of brown and off-white give us ‘70s cinematic style.

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Casablanca striped tailored flared trousers

Casablanca Men's Striped Tailored Flared Trousers

Thanks to the strong front crease, high waist, and effortless fit, these pants scream mint-colored disco fantasy. Pair with a wide-collared shirt, for obvious reasons, or upgrade your polo game.

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Bootcut Jeans

This quintessential cowboy style got laughed at for several years. Especially in certain contexts, it can appear a bit costume-y, but on the other hand, it captures the lengthening essence of the flared silhouette in a more subdued fashion.

BDG Venice Bootcut Pant

BDG Venice Bootcut Pant

Periwinkle blue veers away from the typical indigo while enhancing a more relaxed bootcut silhouette.

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Old Navy Wow Boot-Cut Non-Stretch Black Jeans for Men

Old Navy Wow Boot-Cut Non-Stretch Black Jeans

Go timeless while taking it slightly back to the ‘90s with this budget-friendly, fully cotton pair playing it straightforward.

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Wes Lang x Amiri Big Skull Flare Pants

Wes Lang x Amiri Big Skull Flare Pants

A slimmer, mid-height bootcut shape forms a canvas for the striking designs of Wes Lang.

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20-plus years ago, no one wanted to use “bellbottoms” to describe flared pants: It felt too ‘60s and too counterculture during an era of reworked preppy fashion, skater influences, and sportswear.

Today, though, the name feels apt, both in what they’re describing and the allusion to going against expectations.

Compared to bootcut jeans, bell bottoms retain that mid to high height and slimmer form yet have a more prominent fan toward the ankle.

Topman Flared Jeans

Topman Flare Jeans

A wider-cut, somewhat baggy leg joins non-stretch denim for a full-on retro look and feel. 

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Kapital Flared Distressed Embellished Jeans

Go for a DIY vibe with this sturdy, embellished Japanese denim pair.

Wide-Legged Track Pants

While track pants have leaned more toward joggers in our era of athleisure, their late ‘90s heyday – all snapped seams and Adidas 3-Stripes details – tended to feature flared ends. Today’s versions return to this Y2K sportswear staple.

Palm Angels Men's Classic Side-Stripe Track Pants

Palm Angels Classic Side-Stripe Track Pants

A classic bell bottom silhouette meets the materials, attributes, and elastic waistband of ‘90s track pants.

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Off-White flared cotton track pants

Off-White Flared Cotton Track Pants

Keep it simple yet strive for quality with this flared, solid-color track pant.

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High-Waisted Flared Pants 

Considering the progression of menswear, this retro-influenced amalgamation was only inevitable. This on-the-nose Harry Styles-helmed trend exists in truly classic forms to wild printed interpretations.

Balenciaga Flared Jeans

Balenciaga Flared Jeans 

If you’re interested in just treading on the edge of extreme, here is where you get started.

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MSFTSrep Acid-Wash Flared Trousers

MSFTSrep Acid-Wash Flared Trousers

A cloud-like acid-wash combination gives these wider-cut high-waisted flares a dreamy quality.

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Cropped Flared Pants

These are high-waters by any other name but essentially reinvigorate the cropped trousers trend we started spotting around 2017.

Ernest W. Baker High-Waisted Flared Trousers

Ernest W. Baker High-Waisted Flared Trousers

This classic high-waisted fit falls to just above the ankles.

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Relaxed-Fit French Terry Jogger

Lululemon Relaxed-Fit French Terry Jogger

Reach fully fashionable and comfortable relaxation.

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Flared Pants for Men

Ivan Yaskey is a Philly-born menswear fashion blogger and copywriter. When not writing about men's style he's also an EDM and synthpop enthusiast.