Style Evolution: Desmond Tan

In light of Desmond Tan's 31st birthday, we take a look at how his style has changed over the years.

Style Evolution: Desmond Tan
Style Evolution: Desmond Tan
28 Aug 2016

Style Evolution: Desmond Tan

If his past styles are any indication, Desmond Tan, who turns 31 today (Aug 19), is entering a brighter era of fashion. Believe it or not, the dapper Duke didn't always have an affinity for Hugo Boss and Old Hollywood hairstyles. Like any of us who made it through the early 2000s, Desmond dabbled with orange hair, side-swept bangs, and even sequins. 

Keep reading to see how his style has evolved over the years. 

Star Search (2007)
Star Search (2007)
29 Aug 2016

Star Search (2007)

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

Star Search (2007)
Star Search (2007)
29 Aug 2016

Star Search (2007)

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 will definitely be better than his twenties. 

2008
2008
29 Aug 2016

2008

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

Fly Me To Beijing (2008)
Fly Me To Beijing (2008)
29 Aug 2016

Fly Me To Beijing (2008)

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

2009
2009
29 Aug 2016

2009

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

Little Note screening (2009)
Little Note screening (2009)
29 Aug 2016

Little Note screening (2009)

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

2010
2010
29 Aug 2016

2010

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

Star Awards 2010 Show 1
Star Awards 2010 Show 1
29 Aug 2016

Star Awards 2010 Show 1

Chen Hanwei who? Desmond was rocking frilly lace shirts way before they became a trend.

Beijing TV Festival 2013
Beijing TV Festival 2013
29 Aug 2016

Beijing TV Festival 2013

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

Celebrate TV50 (2013)
Celebrate TV50 (2013)
29 Aug 2016

Celebrate TV50 (2013)

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

The Dream Makers Roadshow (2013)
The Dream Makers Roadshow (2013)
29 Aug 2016

The Dream Makers Roadshow (2013)

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 

It’s A Wonderful Life Roadshow (2013)
It’s A Wonderful Life Roadshow (2013)
29 Aug 2016

It’s A Wonderful Life Roadshow (2013)

Just NO to this Donald Trump cosplay. 

It’s a Wonderful Life (2013)
It’s a Wonderful Life (2013)
29 Aug 2016

It’s a Wonderful Life (2013)

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

Star Awards 2013 Show 2
Star Awards 2013 Show 2
29 Aug 2016

Star Awards 2013 Show 2

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

Chinese New Year Music Video shoot (2014)
Chinese New Year Music Video shoot (2014)
29 Aug 2016

Chinese New Year Music Video shoot (2014)

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

2014
2014
29 Aug 2016

2014

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

Star Awards 2014 Show 1
Star Awards 2014 Show 1
29 Aug 2016

Star Awards 2014 Show 1

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

The Journey: Tumultuous Times press conference (2014)
The Journey: Tumultuous Times press conference (2014)
29 Aug 2016

The Journey: Tumultuous Times press conference (2014)

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

2014 TODAY photo shoot
2014 TODAY photo shoot
29 Aug 2016

2014 TODAY photo shoot

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

Mata Mata 3 (2015)
Mata Mata 3 (2015)
29 Aug 2016

Mata Mata 3 (2015)

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

Mata Mata 3 Press Conference
Mata Mata 3 Press Conference
29 Aug 2016

Mata Mata 3 Press Conference

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

Star Awards Show 2 (2015)
Star Awards Show 2 (2015)
29 Aug 2016

Star Awards Show 2 (2015)

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

Star Awards Show 2 After-party (2015)
Star Awards Show 2 After-party (2015)
29 Aug 2016

Star Awards Show 2 After-party (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. 

Star Awards 2015 (Show 1)
Star Awards 2015 (Show 1)
29 Aug 2016

Star Awards 2015 (Show 1)

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

Star Awards Part 2 (2016)
Star Awards Part 2 (2016)
29 Aug 2016

Star Awards Part 2 (2016)

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

Photo: stylexstyle

The Truth Seekers (2016)
The Truth Seekers (2016)
29 Aug 2016

The Truth Seekers (2016)

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

The Truth Seekers press conference (2016)
The Truth Seekers press conference (2016)
29 Aug 2016

The Truth Seekers press conference (2016)

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’. 

Star Awards 2017 Live Show 1
Star Awards 2017 Live Show 1
17 Aug 2017

Star Awards 2017 Live Show 1

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.

Photo: Channel 8

Voyage (2017)
Voyage (2017)
17 Aug 2017

Voyage (2017)

Only Desmond and his abstastic bod can do this costume justice. 

Photo: Instagram/@thedesmondtan

Bonus: Teen Desmond
Bonus: Teen Desmond
17 Aug 2017

Bonus: Teen Desmond

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

Photo: Instagram/@thedesmondtan

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Style Evolution: Fiona Xie
Style Evolution: Rebecca Lim
Style Evolution: Jeanette Aw
Style Evolution: Rui En

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