On Wednesday night I had the great pleasure of attending a dinner to celebrate Tommy Hilfiger.  The brand is 25 years old and opening a slew of new stores around the world, including here in Toronto. 

And they're changing things up a bit.  

If you've seen a fashion magazine lately, you've likely been sucked into the fantastic four-page ad from their new campaign. The Meet the Hilfigers angle is cheeky and sexy: Beautiful people, beautiful clothes and gorgeous photography. And there's something about a giant group portrait that really gets me, so this one soaked up my attention for more than a few minutes.

I'd never really considered myself a Tommy customer, but, suddenly, in just one picture, I saw it.  

Tommy's new diffusion line (TOMMY) is classic American, all tweeds and plaids and checks, rich colours and ivy league-touches.  Chunky knitwear, collegiate stripes, and terrific leather goods.  Everything looks moneyed and effortless, at-once casual and gussied-up.

The new line comes at a time when popular style has settled into prep, with a twist.  Elbow patches and button-down-collars, but paired with military or leather.  Kicky skirts with menswear, for the ladies, and snappy colours for the guys. They're checked-in to everything that's happening right now: reclaimed vintage, nerdy stuff, midcentury, and doing what great designers always should: Leaving room in every piece for the consumer to make it his own.

Canadian Fashion Icon (italics required) Jeanne Beker hosted the dinner, alongside Hilfiger's (handsome) CEO, Gary Sheinbaum.  He was a super nice guy and couldn't get over how fun and nice Canadians are.  When he asked me why we're so cool, I told him it's because the world's expectations of us are low, so we always exceed them.  (Ha!)

The event was held in Parkdale at one of the city's newest and hippest spots, Parts & Labour.  Exectuive chef, Matty Matheson assembled a lovely 6-course meal, from a maple-infused soup to a shockingly-tender loin of beef served with lentils and beets. I've been hearing about P&L for a few months, and now it's on the list.  If a restaurant can pull-off a great meal for 45 people, chances are it'll be spectacular for 4.

(Photo above from Wireimage. The rest are mine, except, of course, the TOMMY ads.) 

You must remember Jesse from these photos.  Aside from being totally dreamy, he's also in an aptly-named band, Brighter.  They're four sunny guys who play cheerful pop-rock.  When food gave way to booze, the band played a couple of songs, to everyone's delight.

Oh!  And I'm thrilled to announce my first-ever giveaway.  Tommy has generously gifted a fantastic duffle bag (it's huge, like a slightly-shrunken, ultra-chic hockey bag.  Perfect for weekend trips to the cottage.)  And you can win it!  Keep it for yourself or check a Christmas gift off your list.  (I will update with a photo soon!  In the meantime: trust me.)  See below.  Enter now!  

Follow me.  Follow Tommy.

(And, hey, why not retweet this too, while you're at it.  Thanks!)

UPDATE Joe over at www.joeisthenewblack.com has posted a photo of the TOMMY duffle.  I've got two to give away, one in camo and another in bright orange.  Your odds of winning are way up, people!  My own photos of the bags will come soon.

UPDATE 2 Check out sneak-peek #1 of the bags here!