Oh, Desmond. How adorable — and sartorially ridiculous — you were as a newb in the entertainment scene. 

Between the feathered hair, the red suit, and the sequined tie, we’re not sure what Desmond (or his stylist) was thinking — but if his recent outfits are anything to go by, his thirties is way better than his twenties. 

Ah, 2008, when it was acceptable to copy Zac Efron’s hairstyle in The High School Musical. 

There are a lot of things we could say about these outfits, but we’ll keep it to this: Desmond’s personal style has come a LONG way.

Photo: Destanation/Facebook

Basically every real estate fresh grad's profile picture on LinkedIn in 2007. 

Desmond’s wardrobe is proof that with hard work, you can go from raincoat to Gucci in just seven years. 

The hairstyle says, “I’m pretty,” but the leather jacket and smouldering gaze say, “I’m a badass.” Boyfriend goals, 2010 edition. 

Desmond was rocking frilly lace shirts way before they became a trend for guys.

Who knew that the former BFFs had the same taste in clothes too.

Ugh - this “just woke up” hairdo ruined an otherwise polished New Year’s getup. 

As much as we dislike T-shirts under suit jackets, we’ve got to admit that Desmond wears the “hipster intellectual” look well. 

Photo: Destanation/Facebook 

Just NO to this Donald Trump cosplay. 

It’s okay, Desmond, most of us went through a K-Pop idol wannabe phase too.

We were all ready to give Des two thumbs up, then we saw the bedazzled shoes…

This, um, creative, getup looks like it came straight off the set of Doctor Who. 

Because an acoustic guitar can compensate for even the most boring outfits. 

Argh our eyes! Though it’s a bit on the flashy side, Desmond looks red hot in the scarlet suit.

As you can imagine, we were a little surprised to see the clean-shaven Desmond sporting a rugged new look, but thankfully, it was only for a role. 

The neck scarf is a tad overkill but Desmond manages to pull off the denim tuxedo.

Boy, are we glad that this ISN’T Desmond’s style in real life. 

You know that life is not fair when Desmond looks flawless with a chin-length bob, while we look like Severus Snape. 

Comb-overs are always a bad idea, regardless of how much hair you have. 

Desmond was all about the Prohibition-era hair in 2015. 

Did we give Desmond too hard of a time for this outfit? While his 2015 was filled with creative — and questionable — fashion choices, he’s spent the better part of 2016 in conservative suits. 

Desmond looked like a classic Hollywood film star in his navy pinstriped suit from Hugo Boss.

Because who needs clothes when you have those abs, eh. 

Desmond channelled Sherlock Holmes in The Truth Seekers press conference. It’s too bad Singapore’s weather is too hot for trench coats, ‘cos Desmond looks SMOKIN’. 

Err, guess Desmond must have thought so too and decided to "upgrade" his detective look (we prefer this stylo version) for the Star Awards live show.

Only Desmond and his ab-tastic bod can do this costume justice. 

Desmond is the epitome of suave oppa in this button down shirt (preferably loosely buttoned) and slouchy pleated pants getup. Extra points for the sleek ride.

This flashy, cleavage-baring look will go down as one of the most memorable outfits of Star Awards 2018.

There's nothing like an old IC photo to show how far you've come in the past 16 years. 

No tux for his "big day". Instead, Desmond opted for this quirky yet dapper Christian Dior bee suit that shows his playful side. We like!

You gotta hand it to Desmond — when it comes to vacay chic, no one does it like this dude in his wide-legged fisherman’s pants, straw hat and oversized tote.

Seven years after he took he played a shirtless rickshaw puller in A Song to Remember, Desmond bared it all once again as a serial killer who also happens to be very ripped (and has a thing for rubber chickens).

We like the outfit, can't say the same for the platinum locks which make Desmond look more like a yakuza gangster than a K-pop idol.

Now, this is much better. Desmond looked both literally and figuratively cool walking down the streets of Japan decked out in a traditional kimono from head to toe. Of course, it’s definitely a kimoYES for us!

If there’s anybody who can make a harness look cool (in case you're wondering, it's from Louis Vuitton) and covetable as a fashion accessory, it’s got to be Desmond.

While we applaud Desmond for his daring style choices, this Prada turtleneck is too cartoony for our tastes.

Another kimono-inspired piece. We like how the oversized kimono blazer makes him look avant garde without being too OTT. 

Superman curl aside, Desmond looks incredibly handsome in this Dior suit.  

Looks like Desmond has become the king of non-traditional suits. This Fendi number, which looks like a 3D drawing, is whimsical and chic at the same time.

Decked out in an orange tracksuit, Desmond looked like a kungfu star on set. Don’t you think there’s some Bruce Lee resemblance here too?

We’re not crazy about the pink-purple checks, which look like something we’d see on our grandpa's boxers, but at least the suit is well-fitted.

Was this look inspired by traffic lights?

Desmond sure knows how to make a fashion statement. His Dolce & Gabbana suit, which is both bold and eye-catching, has us transfixed.

A netizen commented that Desmond's Alexander McQueen suit looked like it "got splashed by loansharks". We can't say we disagree.

Now this outfit from Thom Browne is slightly better. Wish the pants were less oversized though.

As cool as this Prada leather get-up might be, we can’t help but get hitman/serial killer vibes.