man wearing an outrageous suit

4 Outrageous Suits That Somehow Worked? See if you could pull these off

[Feature image by Mahita Gajanan]

From the ’90s to now, these are some memorably absurd outfits that somehow pulled off a flawless execution. Maybe it’s the confidence with which they were worn; maybe it’s the killer style and swag that balanced out the insanity. Whatever it is, it’s time to give credit where credit is due and pay homage to these divergent thinkers.

Outrageous Suit: All Denim Baby

outrageous suits Justin Timberlake Denim Suit
Amazon Essentials Mens Regular Fit Long Sleeve Denim Shirt

Amazon Essentials Men’s Regular-Fit Long-Sleeve Denim Shirt

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Who: Justin Timberlake

Where: American Music Awards

When: 2001

What makes this suit ridiculous: Denim will always be a staple. But there’s such thing as too much of a good thing, and to say that’s what’s happening here would be an understatement. Timberlake had a lot working against him with this outfit, but he managed to pull off the Canadian tuxedo in a pretty iconic way. 

If you’re unfamiliar with the legend, ’50s jazz artist Bing Crosby was (almost) denied access to an upscale Canadian hotel because of his all-denim outfit. When Levis heard about this, they made him a special denim tuxedo. Decades later, Timberlake rocks the DGAF look at the AMAs, and 20 years after that, we’re apparently still talking about it.

Why this works: Who are we kidding? Justin and Britney knew exactly what they were doing. Every detail of their outfits was planned, from the Wild West silver jewelry to the denim cowboy hat. Ridiculous, yes… but kind of cool. 

Outrageous Suit: Sequin It Up

outrageous suits camryn howard sequin suit
Hollywood Life
Black Silk Black Self Tie Bow Tie 219998 505 1280 0 2

Black Self-tie Bow Tie

Go from Joe Bloggs to James Bond with this black self-tie bow tie. Crafted from 100% silk, this bow tie will make you feel as sophisticated as it looks.

Who: Camryn Howard

Where: 60th Grammy Awards

When: 2018

What makes this suit ridiculous: This is just extra. He clearly went in with the goal of catching as many second glances as possible, and this jacket is certainly worthy of a double-take. Any man who shows up to a red carpet event in a sequin jacket deserves all the attention he commands.

Why this works: He’s playing this right by keeping the rest of the outfit understated. Howard lets his blazer take center stage, pairing it with simple black and white. He’s a little extra, but he’s not obnoxious. 

Outrageous Suit: Jack of All Suits

outrageous suits harry styles
Just Jared Jr.

Who: Harry Styles

Where: iHeart Radio Music Festival

When: 2017

What makes this suit ridiculous: With that gregarious charm, Harry’s never met a suit he couldn’t pull off. This one, in particular, is giving off mad Mad Hatter vibes, but Wonderland never looked better.

Why this works: This works for no reason other than, it’s Harry Styles. Also, the pattern matching doesn’t hurt. You can’t wear a boring plain white shirt with a suit like that. Styles went with a printed shirt and stylized collar, but he didn’t overdo it with clashing colors and patterns. 

This outfit should serve as a lesson on the beauty of dressing for your personality.

Outrageous Suit: Leather Lovers

outrageous suits david beckham leather wedding suit

Who: David Beckham

Where: His Wedding

When: 1999

What makes this suit ridiculous: The audacity it takes to wear black leather suits as a power couple groom and bride is almost unbelievable. We have no choice but to give them props, no matter how outrageous this look may be.

Why this works: It’s his wedding, he can wear black leather if he wants to. In all seriousness, this look is somewhat refined. It’s unapologetically bold, sleek, and well-cut. Fit for a star athlete and his popstar wife. 

Outrageous Suit: Sparkling Hero

outrageous suits jared leto cape
The Daily Mail / Bustle

Who: Jared Leto

Where: MTV Video Music Awards

When: 2017

What makes this suit ridiculous: A better question would be, “what about this isn’t ridiculous?” This look is your 80-year-old grandmother meeting a decked out holiday tree meeting Robin Thicke. But for some inexplicable reason, it kind of slays.

Why this works: After much contemplation and discussion, the answer is still unclear.

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Emilie Allen
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