Rylan was always the first to make a joke about his appearance before anyone else could.
He admitted his enormous white veneers were his "biggest mistake" though he said they earned him a lot of money.
"I got my veneers finished the day before I started hosting Big Brother's Bit On The Side, my first presenting job," he told Notebook in 2017.
"My mouth was swollen from the anaesthetic, they were brilliant-white, brand new. That was the first night everyone saw them, and all people did was take the p**s out of my teeth.
"So no one realised I was a s*** presenter, and by the time they stopped talking about my teeth a few months later, I'd got better at the job."
He also told the Daily Star the teeth were "the best and worst decision of my life."
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Rylan's jet black, slicked back hair was also a trademark of his appearance.
But again, it totally disguised his natural redhead look which he has revealed in throwback pictures from his childhood.
The 33-year-old has spent thousands of pounds transforming himself, including £25,000 on his teeth alone.
We first met him on The X Factor back in 2010, where he had long, flowing blonde locks and a plumped up pout.
"I've always been open with the things I do, whether it's dying my hair or having aesthetic procedures," he told The Mirror.
"I'm not saying surgery is great and Botox is fantastic and fillers are amazing, but if you are genuinely unhappy with something and you’re in a position to change it, then I don’t think people need to be vilified for that.
"When I was on The X Factor I had my lips overfilled – but that is a learning curve."
It's not just his look that Rylan has transformed - he even took on a different name, abandoning the moniker his mum gave him, which was Ross Richard Clark.
He picked the name Rylan when he went into a branch of WHSmith and chose it from the R section of a baby name book.
It's been an incredibly tough year for Rylan, who pulled out from several professional appearances before it emerged he was divorcing his husband of six years, Dan Neal.
He took four months off from his BBC Radio 2 show and dropped out of hosting duties for shows including Eurovision.
A source told The Sun that when Rylan returned to the radio, insisting he was "feeling better", he burst into tears while playing a song and consequently had been offered a year off to focus on himself.
Rylan admitted to making "a number of mistakes" during his marriage which caused its breakdown, and said he "deeply regretted" his actions.
But he hinted at his intention to make a fresh start, joking on stage about joining dating app Tinder as he moved on from his ex.
So perhaps this fresh start is the reason Rylan has been undergoing a "makeunder" of late, replacing his veneers for a more subtle look, and dyeing his hair blonde again.
He joked to Lorraine Kelly on Tuesday that it was part of a "mid-life crisis".
"I’m obviously going through a mid-life, trying to dye my hair blonde, new teeth," he chuckled.
Sporting a lighter brown hair colour too, Rylan explained he was lifting the black dye out in a bid to go back to his fair roots.
"I was hosting hairdressing awards last night, so imagine walking up to the hairdressing awards and going, 'Hi everyone, I'm still lifting the black out, don't judge me!'" he joked.
On the day he had his veneers changed, Rylan tweeted: "After 8 years. It hurts, so much, but sometimes you just have to let go.
"I’ve taken the decision to say goodbye… to my teeth. New smile imminent."
His fans joked that the old ones belonged in a museum, while others remarked they could now take their sunglasses off when speaking to him.
Lorraine said she wasn't sure she could tell the difference with his new teeth, and he replied: "They're a lot smaller."
Rylan also said his four-month break earlier this year was much needed, and that he was now feeling a lot better.
"I wasn't good, I'm not going to lie. Everyone knows that, I'm normally on telly every five minutes, I apologise you have to see my mug all the time," he told Lorraine.
"But no, I had four months off and it was needed actually.
"It's been ten years I've been doing this job, which is crazy, so yeah, maybe the time of was exactly what I needed."
But whatever Rylan changes about his appearance, he believes he will never be satisfied, which might be down to him being branded "fat and ginger" by bullies in his youth.
"I definitely feel more confident, but I don’t think I’ll ever be content," he told The Mirror.
"That’s just who I am. I’ve realised that maybe I’ll never be content and that’s alright."
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