How to dress like you are spending the summer in Italy

strolling the streets, paddling in the pool, and eating sun dried tomatoes

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Shoes

There is something enticingly naïve about pairing weathered and worn, white Chuck Taylor Converse with a pair of indiscriminate white ankle socks, which peek out from above the laces looped around the leg. As cliché as it may be, the timeless combination conjures callow summers in between high school and carries an adolescent exuberance. Indeed, summer is a time to relax and slip back into the lazy daze of late nights and even later mornings, so channeling your younger years is a necessary pursuit.  

Shorts

The instructions are in the name, keep them short. Not only are we trying to get a complete tan, but the days of ‘lil Jon’ dictating the optimal length of shorts are thankfully left to rest in the past, so please keep it above the knee. This entire look could be straight out of the eighties, so it’s free reign to rummage through your parent’s packed away high school mementoes and dig out some neon and patterned shorts. Honestly, the more garish, the better.   

Shirt

Although the shorts catch the eye, the shirt is the true centerpiece of the ensemble. Leave band tees in 2014, and instead opt for oversized button downs. Their versatility lies in the ability to 1) dress them up, 2) dress them down, 3) layer and 4) show how laissez-faire you are (the less buttons buttoned, the more laissez-faire). If the weather permits, don’t be afraid to neglect the top three or four buttons. Maybe even roll the sleeves up and get a forearm tan. The look instantly becomes more ‘Italian summer’ and less ‘frat boy’. Moreover, there is an overabundance of dress shirts in the world, so finding gems is easy enough. Just the other day, I journeyed down to our friendly neighbourhood thrift store, Rumors Boutique, and secured five basic dress shirts for pennies.

Accessories

Since the entire look is relatively simplistic, it’s important not to go overboard with accessories. A simple leather banded watch and a long pendant necklace are always good calls (a little goes a long way). Maybe even throw some rings and a pair of sunglasses into the mix. I recommend matching jewelry tones with complexion, the idea being that darker skin tones are best complemented by gold, and lighter skin tones by silver.