Stacy London and Clinton Kelly look back at What Not to Wear makeovers that did NOT hold up

Fashion is defined by its changeability so it was inevitable that some of the makeovers on TLC's long-running reality show, What Not to Wear, would not stand the test of time.

Not to mention there were some looks that had us scratching our heads even back when they aired. The show, which aired from 2003 to 2013, featured style gurus Stacy London and Clinton Kelly ambushing an unwitting fashion victim and giving them a head-to-toe makeover, which included a shopping spree after some consultation.

The duo stands by most of their choices, but they admit that they sometimes tried to nab some of contestants' discarded clothing items they'd dubbed unfit for fashion. "I tried to steal this big sweater that we stole from one of the contributors that had a huge tiger on it," London confesses. "And I was like, 'I would've bought this at a vintage store.' But we wound up giving it back to her because it was cool."

Kelly also would like to take this opportunity to slightly revise his opinion on "mom jeans."

"All the s--- we talked about mom jeans," he notes, "how were we to know that mom jeans would've become the most popular thing in the world?"

Kelly and London are returning to Prime Video with Wear Whatever the F--- You Want this spring, but before they get the chance to work their magic on a new crop of folks looking for a fresh look, we asked them to take a walk down memory lane with us and review some of what we consider their worst looks on the original show.

Gina's blue shirt

Is this shirt trying to hypnotize us? There's way too much happening with this blue orb pattern and the slinky off-the-shoulder cut is utterly early 2000s. But London and Kelly still love it.

"That's a Pucci print," says London. "I don't know if it's Pucci, but this doesn't bother me at all."

Kelly adds, "It doesn't bother me at all either."

"I see what you're saying," London allows. "That sphere looks big and it might look weird on a woman's chest, but those kind of graphic prints go in and out all the time. If I was somebody who wanted something off the shoulder with that drape-y sleeve, which I think would be great for Miami now, I don't see anything wrong with it."

The cheetah stole

We don't even know where to start with this — that swath of faux fur is both ugly and impractical.

"I don't know what it's doing there," London says. "It doesn't seem to have that much of a purpose."

Is it meant to be a daytime or evening look? Kelly's not sure, while London notes, "We were trying to do it as evening. It's a cami and a leather pencil skirt, but to be honest with you, we would've had to go a little bit more formal and a little bit more modern vintage for a stole like this to actually work today."

Kelly concurs, adding, "If you styled this in a modern vintage way, it could be a chic and fun statement piece."

Motley Crue bedazzled tee

Though London and Kelly often made participants discard their ratty t-shirts, they weren't opposed to a well-placed and elegant graphic tee. But we're not too sure about this bedazzled Motley Crue t-shirt paired with a sensible blazer. Except we might be alone on that.

"I'm totally down with that," says London, while Kelly adds, "I love it."

"Why would that ever be a problem?" London asks.

The ever-present pointed kitten heel

The pointed toe that was massively popular in the early aughts is making a comeback. Unfortunately.

"That was when we were using rules that are essentially geometry or color forms," explains London. "That witchy pointy shoe with the right trouser or skirt really does accentuate the length of a leg."

It's the rules that London and Kelly cite as the reason for the show becoming the cultural juggernaut that it was. "We were making a lot of the rules," notes London. "We knew that [the show] was supposed to be entertaining and some of the stories were emotional, but we didn't realize that people were going to start shopping by our rules. That we were also giving people a list of things to go do on Saturday and look for a pointy-toe shoe or a bootcut jean or any of those things." 

"I would do personal appearances" adds Kelly, "and the audience would be filled with women and pointy toe shoes, dark-washed, straight leg jeans, embellished blouses, a jacket and a statement necklace. I'd be like, what?"

"It's the formula we created," London says. "We created a formula for people to dress in a way that we didn't realize was really easy to follow so people weren't just tuning in to be like, 'She's a train wreck.' It was, 'Maybe I can learn something from this.' They really did take those rules to heart."

Bootcut jeans

Speaking of things making a comeback, we can't not mention bootcut jeans. London and Kelly probably sold nearly every participant on the show a pair, perpetuating the popularity of that cut at the time.

After years of skinny jeans and wide-leg cuts taking over the market, the bootcut is having a renaissance, thanks partly to Kendrick Lamar wearing a pair during the halftime of Super Bowl LIX. (Or were those flare jeans?)

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"The funniest thing about that is," interjects London. "Kendrick Lamar, everybody was arguing, 'Are they bootcut or are they flare?' I hope, for his sake, they're bootcut because he's way too short to be wearing a flare."

However, London advises that people invest in one of every style of jean as a long-term purchase. "Denim is a great blank slate, and if you've got the right denim shape on, you can pretty much participate in all different kinds of trends without having to go whole hog," she notes. "It's important to have a collection of differently shaped jeans. Because we love to wear denim. [Then, you have a] jean that is going to come in handy every time there's a new denim cut. You should have one that you love on your body type. If some don't work on your body type, that's different. But having a collection of different silhouettes is very important."

De-personalizing

There were plenty of crimes against fashion on What Not to Wear, but sometimes it did feel as if contestants were having their personality muted in favor of wearing something trendy or "flattering." Perhaps the most glaring example of that was Ed, who was very into the 1990s swing craze and dressed in a way that reflected that. On the show, he seemed to trade in bright, whimsical colors for muted, personality-less looks.

But Kelly will not hear any slander against it. "I'm going to have to disagree with you," he says. "That picture of Ed is pretty tame compared to some of the other things Ed wore. He wore zoot suits. We brought him down to a slightly more stylish level."

"I'm finding this exercise to be a little annoying, quite frankly," Kelly continues, "because I kept in touch with Ed for literally 10 years after this episode. He was so happy with the experience and his new look, and he found a real love for clothes. I don't give a s--- if somebody doesn't like it. Ed was really, really happy."

In the end, Kelly and London stand by all of their choices, regardless of how well they've aged — if for no other reason than it was never really about the clothes. "We kept in touch with a lot of different guests," London says. "The stories really were after the clothes. The clothes were just the jumping off point to feel like, 'Things can change and they can change quickly, and if I can change the way I look, I can change my circumstances'. It really did make people feel a lot more powerful in the world."

And that's something that never goes out of style.