Chris Pine Gives A Fashion Masterclass At The 2023 Kentucky Derby

Derby Day Drip.

Chris Pine Gives A Fashion Masterclass At The 2023 Kentucky Derby

Image: Maggie Huber

The star-studded Kentucky Derby has rolled around once again and it was replete with style statements. Some were good, some were not. Here, we take you through our biggest winners and losers of the men’s fashion game at Churchill Downs.

Chris Pine has long been a source of style inspiration to men around the world, sporting overlooked colours that deserve a place in your wardrobe and even revitalising some of your most embarrassing 90s looks.

This weekend, he maintained this characteristic run of form by sporting a dapper look to the Kentucky Derby which was a veritable masterclass in how to dress for such an occasion. Sadly, others didn’t nail the brief anywhere near as well, missing understanding the assignment, as our Gen Z counterparts might say…

WATCH: Throwback to a less auspicious day out for Chris Pine…

Pine, the 42-year-old Star Trek actor, made a dashing appearance at the 149th edition of the world-famous Derby in Louisville, Kentucky on Saturday. Hosted at the Churchill Downs race course, the event is like catnip for celebs, with each trying to out-dress the next. Unlike many, however, Pine really delivered the goods.

Donning a pastel blue blazer over a white shirt and white pants, the look was completed with a dark navy tie, classic wayfarer shades, and an all-important pocket square. Safe to say, this is a flawlessly executed race day look.

Chris Pine is race day class personified. Image: Getty

Why? Well, it’s simple. First, it’s about tone: a suit is too formal and too corporate, but no jacket isn’t formal enough, so the mismatched blazer and pants look is the perfect compromise. Second, the colour palette screams springtime and early summer. Third, so do the textures: thin, lightweight, and luxurious.

While Pine soared, others plummeted. Let’s turn to Jack Harlow. The 25-year-old rapper was also in attendance and was doing his best to look stylish in a double-breasted grey tweed suit with red accents worn over a black button-up top, accessorised with diamond earrings.

This isn’t a strong Derby Day look. However, this isn’t to say it’s not a strong look per se, it’s just not the right look for the occasion. At an album launch, red-carpet event, or Hollywood party, it could really work. Here, however, when compared to Pine’s, Harlow’s feels too buttoned-up, the colour palette is dark and dreary, plus tweed is far too heavy a material to be wearing this time of year.

Harlow looks like he’s dressed for an entirely different event. Image: Getty

After wearing a similarly mediocre outfit at last week’s MET Gala and having an altogether too memorable time at the Derby last year – drawing some criticism for getting rowdy with Drake while filming the Churchill Downs music video and being carried across muddy paddock by two black men – this is an unfortunate miss that the rapper could’ve done without.

Other famous faces spotted at the event included music legend Smokey Robinson, who recently released a new album (shockingly titled ‘gasms’ – eurgh), and two-time NFL MVP Patrick Mahomes. The football superstar went with a look that fell somewhere between Harlow’s and Pine’s but that sadly sacrificed many of the winning aspects both had to offer…

Hard pass: Patrick Mahomes goes overboard with the colours. Image: Hollywood Life

A green and blue checked blazer went well with a pastel purple shirt but clashed with a polka dot tie and almost fluorescent blue trousers. Tying it all together were tan brogues which – frankly – was not what this outfit needed. Springtime is all about colour, but not too many, and not all at once.

When it came to the race itself, a 15-1 long shot named Mage emerged victorious in the famed event, with fan-favourite Angel of Empire finishing in third place.

Don’t get me wrong, I like Harlow’s look, but it’s just not the right vibe for this event. They say you should “dress for the job you want, not the job you have”, but when it comes to Derby Day the attitude should be reversed: dress for the event you’re actually attending, not the one you wish you were attending.