Menswear

How To Dress Your Boyfriend: From a Picnic to an After-Party

Now that TIFF has come and gone, teach your man how to look effortlessly put-together without all the stress. Whether heading to a garden party or gala event.

HTDYB-CalligraphyHed
Adam Butcher from Elmer Olsen // Photo by Alex Evans

Adam Butcher from Elmer Olsen // Photo by Alex Evans

 

After a brief, festival-induced (hello: TIFF!), hiatus How To Dress Your Boyfriend has returned to FLARE.com for its regular Monday dishing on men’s style. Since festival season is now behind us it seemed fitting to advise on how to pull together a (seemingly) effortless look that works for all sorts of events. Take a hint from our entertainment editor Briony Smith and get prepared now, because next TIFF you might just be sharing a picnic blanket with Adrien Brody. For the rest of us, who just want to look good—and who may not be sharing grass at a picnic with celebs—read on!

Finding the comfortable median between too dressy and too casual  can be tough. This is why, when pairing mens separates, it is necessary to think of the least formal item and the most formal item. By ensuring that neither are too far at either end of the spectrum, an outfit can be carried through from a garden party to dinner with friends. Adding minor dressings like a pocket square or tie to an otherwise lax ensemble will provide a more polished look.

That being said, this guide has been divided into three categories: the picnic, the dinner and the after-party. Make minor edits to any of the suggested pulls, swapping in formal accessories or a dressier jacket for the more pedestrian pieces. I call this the quick switch. Not a full wardrobe change, one merely edits out the casual items replacing them with more luxe apparel, but keeping your staple pieces anchoring the look. Note to the wise: leave a man-bag in the car that contains a change of clothes.

The Picnic: 

HTDYBGardenParty

Clockwise from bottom left: Tods suede driving shoes, $340, matchesfashion.com; J Brand kane slim fit chino, $275, farfetch.com; Hackett blue collar-tab striped cotton shirt, $180, mrporter.com; Ted Baker no ordinary joe sportcoat, $395, thebay.com; Banana Republic textured leather belt, $74, bananarepublic.ca

The Dinner:

HTDYBDinner

Clockwise from bottom right: Tods suede driving shoes, $340, matchesfashion.com; Banana Republic textured leather belt, $74, bananarepublic.ca; Ted Baker no ordinary joe sportcoat, $395, thebay.com; Nordstrom trim fit non-iron dress shirt, $53, nordstrom.com; J Brand kane slim fit chino, $275, farfetch.com; Brunello Cucinelli reversible plaid and houndstooth pocket square, $165, barneys.com; Paul Smith matchstick cufflinks, $170, farfetch.com; Burberry Prorsum animal-patterned woven-silk tie, $260, mrporter.com.

The After-Party:

HTDYBAfter2

Clockwise from bottom left: Tods suede driving shoes, $340, matchesfashion.com; MOVADO men’s 3600048 watch, $650, thebay.com; J Brand kane slim fit chino, $275, farfetch.com; Alexander McQueen stained window & skulls t-shirt, $229, harrods.com; Dirk Bikkembergs belt, $105, yoox.com.