We begin Chris' style journey at Star Search, when he had yet to discover his adventurous streak, as evidenced by his clean-cut styling. And who knew cropped boxy vests were once a thing for guys?

This photo is proof that not even a face as symmetrical is immune as Chris’ looks good with a middle part. 

Er, did Chris rush down from his part-time job at Olio Dome?

Chris was a dead ringer for Meteor Garden's Dao Ming Si in this retro Channel 8 music video. 

Whoa, whoa, whoa — Chris’ wire-rimmed spectacles and short hair brought out his elegant cheekbones more starkly than ever. 

We never thought we’d say this but Chris looks pretty good in a bob cut.

32-year-old Chris’ boyish looks shone brightly beneath his boyband-esque bangs and oversized military jacket.

Photo: Sina 

Aside from the hair, which was seemingly cut by a lawnmower, this look isn’t actually that bad — we’ve always preferred Chris with eyewear, even if the frames are a little too faddish. 

Knowing Chris’ daring side, this outfit is almost hilariously pedestrian — he looks like he’s about to sell us real estate. 

Sure, Chris looks pretty dapper in his three-piece suit but we can’t help but stare at that safety pin on his tie.

Apart from the iconic bikini run through Tiong Bahru Market, Chris’ hot bod was also one of the big talking points of the Beach.Ball.Babes.

While this hairstyle might be one of Chris’ most iconic looks, it’s far from his best — we’ve seen poodles less fluffy than that “afro”!

Photo: qq.com

Dear Chris, regardless of how casual the setting, there's no excuse for turning up at a press conference looking sloppy and like you just rolled out of bed.

When it comes to men of a certain age, there are older gentlemen… and there are uncles. Take a guess at what we classify this look as.

While we’re willing to close one eye at the fluffy hair, excessive jewellery, and 70s-style lapels, we simply cannot forgive that cummerbund-belt thing. Seriously, why is that even there?

Chris’ slightly dishevelled wedding attire has a weird sort of charm (it’s not often that guests get a peek at the groom’s bare chest at his wedding). 

Were we the only ones who breathed a sigh of relief when Chris gave up being experimental and went for a timeless look for his big day?

Chris channelled Clark Kent in those sexy glasses at a Dolce and Gabbana event and looked super HOT. 

This juvenile outfit would look way cuter on their kiddo Zed than it does on his otherwise dapper dad.

Yes, those are the same checked harem pants. Guess it's as comfy as it looks. 

Chris went full K-pop star in his flashy red suit jacket and oversized sunnies at the Breakout press conference. And sure, the outfit’s a little ostentatious, but doesn’t he look so confident wearing it? 

Even though this photo was taken almost a decade ago, we can totally see Justin Bieber rocking the same thing today. (That’s not a compliment, Chris.) 

We can’t even be mad at this outfit. Say what you might, but Chris looks straight up BADASS — like a pimp crossed with a vampire. 

Chris lounged around in what appears to be separate halves of two different pairs of pyjamas at the Secrets for Sale press conference. 

Was this outfit inspired by a Magic Eye Book or what? 

Talk about a good-looking couple: Chris’ double-breasted jacket gave him a vaguely nautical aesthetic that we can only hope will be repeated at future award shows.  

Like fellow veteran Chen Hanwei, Chris has become less conventional with age. While his funky style certainly has its detractors, we can’t help looking forward to seeing what he will wear every time he’s due to make an appearance. 

Was Chris so busy that he didn’t have time to trim his hair?

Chris decided to dress like a cross between a disco ball and Chinese lantern for CNY. How festive.

Photo: Catwalk

Like fine wine, Chris gets sexier with age.

At the Crescendo press conference, Chris showed that he doesn’t need to do much to look good — his handsome salt-and-pepper streaks speak for themselves. 

Even when he was all suited up in a tux, the Best Actor nominee still oozed swagger with his rock star shades.

Photo: TPG

What better way to make a fashion statement than with a pair of PJs and eye-catching sneakers?

Photo: Singapore Fashion Week

Textured and printed blazers were a thing at the 2018 Star Awards, and Chris' shiny DSquared2 piece was the last word in sophisticated cool.

Business on top, party on the bottom. Chris turned up for the wrap party of HBO Asia's Workers, in which he plays a construction worker, in a striped shirt, black blazer, and, um, cargo bermudas. Did he take that from the wardrobe of his character?

Photo: TPG

We thought the "black band" on Chris' shirt was part of the design until we spotted his belt beneath the rip. Well, if there's any local artiste who can rock homeless chic, it's Chris.

Chris looked especially suave with his combed back hairdo, black frames and navy double breasted suit — exactly what we’d envisioned a silver fox to be.

Looking at this family OOTD made us feel all warm and fuzzy on the inside. Fann and Chris’ matching T-shirts by Thom Browne are probably the most stylish and non-cheesy couple outfits.

Speaking of non-cheesy, this has got to be the sleekest father-son twinning look. 

Someone commented that Chris looked like Johnny Depp in this pic and now we cannot unsee it.

Chris cleaned up nicely for a Bvlgari event. It's amazing what a tux and hair gel can do.

Despite his unkempt locks and scraggly beard, Chris still cut quite a dash when he embraced his inner hobo during the Circuit Breaker.