By Alexis Bennett
Nov 03, 2018 @ 3:00 pm
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First, let me start off by saying I have been a trend lover my entire life. But 2018 has been a vey special year for fashion. A year that has challenged my devotion. A year in which the most popular items are following the "if it ain't ugly, it ain't cute" rule. And — the reason we're here — a year when Kendall Jenner has consistently tried to convince us all to get on board with those bizarre style moves.

I can't speak for everyone, but I have to admit that she's kind of worked her magic on me. Remember when she was spotted wearing biker shorts waaaay before they were all over the runway? Seeing her wear them over and over again convinced me to finally try them out last month. And before you shake your head and say, "never, no thanks," remember there was once a time when wearing leggings as pants wasn't socially acceptable. So who knows where the biker short movement will be in the next five years?

Another trend that Jenner's making me start to re-think: the ugly sneaker movement. I've been doing my best not to give in, but Jenner's clunky, orthopedic-looking shoes are starting to grow on me.

In honor of the risk-taking style star's birthday, we decided to roundup some of her ugliest —and by ugliest, we mean best — style moments below.

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Jenner was an early adapter during the initial revival of the fanny pack. And now, she's making a chic case for the Prada chest pack, which kind of looks like a sexy bullet-proof vest, if you ask me. A white tee, khakis, and By Far slingbacks ($415; net-a-porter.com) completed her trendy outfit.

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This just gives me all types of Jim Carrey in Ace Ventura: Pet Detective vibes. (Remember how he always wore unbuttoned blouses with white shirts underneath them?) And, somehow, in an understated way it looks cool with that Balenciaga graffiti bag ($2,300; saks.com).

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There's a lot to digest here. The no-pants trend, the skinny sunglasses, and are those garter straps hanging underneath her sweater? And let's get into those brown tights. Perhaps, Jenner was inspired by Kate Middleton's love of stockings.

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OK, this one leans more on the prettier side of the ugly spectrum, but not everyone can pull off wearing a dress with shoulder ruffles that are larger than a basketball. 

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Again, Jenner is here for the evolution of the fanny pack. This time, she courageously took on the belt bag trend and nailed it with a Private Policy outfit.

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The half-and-half trend isn't for everybody, but Jenner made it look tempting in red, white, and blue pants by Calvin Klein ($511; mytheresa.com).

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There goes those damn chunky sneakers ($975; farfetch.com) again. There's no escaping this trend.

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I, personally, adore this Alexandre Vauthier gown, but an all-over feather look, which several stars have been flocking to lately, is tough to pull off in real life.

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You can't nail the park ranger trend without a stiff pair of cargo pants. And let's not overlook those thick-soled sneakers.

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Sock boots, scarf boots ... I'm not sure what to call this one. And yes, Jenner upped the ante with biker shorts.

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Jenner's so into the cargo-pants trend, she even gave this denim Balenciaga pair ($1,790; mytheresa.com) a spin.

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No, those are not tube socks paired with black pumps. It's an exaggeration of the sock boot trend, and, yes, they look sick (in a good way) with a pair of biker shorts.

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The oversized trend has been taking over for a few years now. But recently, Jenner took it to the next level, and I wish we had video footage of her walking in this avant garde outfit.

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Our eyes have gotten used to seeing Jenner wear her favorite Jimmy Fairly skinny sunglasses. Here, she wore them with a House of Holland blazer ($695; farfetch.com), pants ($478; farfetch.com), and Barneys New York mules ($295; barneys.com) — all in one of the trickiest colors: yellow.