Modern Man’s Guide to Holiday Event Dressing

Now that we’re in the swing of the holiday season, you’re bound to be invited to a holiday party of some sort: the office party, friendly get-togethers, New Year’s Eve outings.

How’s a guy supposed to dress for such occasions?

We asked Jeff Farbstein, our head buyer at Harry Rosen who presides over the world of menswear. Not only does he attend basically every type of holiday party every year, but he’s got dressing for them down to a science. His best advice, he told us, is to “treat holiday events differently. It’s not dressing for work, a wedding or the average night out. It’s the holidays. It’s winter. It’s festive. You really should think about what you can do differently but still express your style and have the right appearance when you show up.”

To help you get in the holiday mindset, we’ve curated some appropriately festive looks for the season. Let’s take a look.

~ Cara K.

Suit vs Tux

Often we’re transitioning from work to a holiday event and doing a complete change can pose some challenges. Instead use some pieces to transition into the evening. Here we’ve replaced the shirt and tie with a super-soft turtleneck. It makes for a sophisticated look under this charcoal-coloured double breasted suit. BOSS demonstrates how the best versions will broaden your shoulders and narrow your waist for a classically handsome appearance.

One of the merits of a black-tie affair is that it offers a simple set of instructions — all you need worry about is whether your tux shirt is clean and pressed and the pants still fit. But it is the holidays so it may be time to consider a modern update on the classic tux. This grey one from BOSS is less serious than all black and even less preppy than navy blue.

Harry Rosen

Armani Collezioni Turtleneck w/ BOSS Double Breasted Suit

Harry Rosen

Dolce & Gabbana Tux Shirt BOSS Tux

Tom Ford & Armani

When it comes to the holidays and style, one constant each year is the velvet jacket. Trust Tom Ford to offer one of the most decadent adaptations of this menswear classic. “Night is the one and only place that I think that men can really dress in an extravagant way and still look classic and chic,” the designer explains. Here he has sculpted a masculine silhouette complete with strong padded shoulders and generously sized lapels in a rich Bordeaux shade.

Next level tuxedos add flair to the formalities of black tie. This Armani Collezioni design is updated in a deep aubergine colour that promises to act as a stylish beacon in a sea of black. The look pays respect to traditional dress codes albeit in slimmed down proportions.

Harry Rosen

Tom Ford Velvet Jacket & Dress Pants w/ Stripe

Harry Rosen

Tom Ford Dress Shirt Armani Collezioni Tux

Pattern vs Bold

Aside from the obvious visual bravado, velvet has some practicality as well. In cooler weather, it’s as simple as being warm. And the weight of the fabric itself lends structure. It feels good to wear and has a certain heft by nature. Fact is, it’s hard to find a wimpy velvet jacket. And this version from Tom Ford is one of the strongest out there. Not only does it feature the pinnacle of menswear’s signature details – broad shoulders, generous peak lapel, expert tailoring – but it’s fashioned in a tonal floral pattern adding an additional festive punch.

Let’s not underestimate the sartorial power of a timeless suit when attending social events this holiday season. Consider opting for a midnight blue suit with a slight sheen to transcend office environments. The impressive luster of Z Zegna’s wool ups your fashion ante and offers an after-hours elegance. Of course, proper tailoring is key. This sleek Drop 8 model to accentuate your best features.

Harry Rosen

Armani Collezioni Dress Pants & Turtleneck w/ Tom Ford Floral Velvet Tux Jacket

Harry Rosen

Eton Check Dress Shirt Zenga Midnight Suit

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