This past weekend was rough in the city. It was cold… down to the single digits cold. With Valentine’s Day behind us we’re in the deepest part of winter. There’s nothing to look forward to but spring. This freezing gloom has me daydreaming of far off destinations—places where the sun is shining and I can dress to impress, not just to survive the piercing cold winds. Places like…

(Click on the titles to see our Polyvore collection of winter escape outfit ideas.) 

Buenos Aires, Argentina

It’s summer in the Southern Hemisphere and I’m willing to wait the 14 hours to get down there if it means I can show up in The Poitier Double Monk Strap in Blue Suede. The snow, salt, and slush would ruin these beauties so they’ve been sitting in the closet, patiently waiting for their debut. I think they’ll get the attention they deserve strutting down the cobblestone streets of the San Telmo barrio. Paired with a wide brimmed hat, skinny khakis, a short sleeved button-down, and a pocket square for a little flair this outfit is sweeter than an alfajor.

Austin, Texas

I don’t even have to leave the United States to defrost. Apparently down in the capital of the Lone Star State winters run like our summers—if that’s true I don’t want to know what their summers are like. One of the most appealing things about a quick jaunt to Austin is how easy it is to pack. A few vintage pearl snap button down shirts, a pair of well-worn jeans from Mott & Bow, and The Newman Chukka Boot in Cafe Suede will have me looking just like a local. Pack the clothes and a toothbrush in the Paul Evans Italian Leather Backpack in Cognac and I’m ready for all the beer, tacos, and live music the city can throw at me.

Fiji Islands

I don’t think a fantasy getaway list is complete without a pristine beach scenario. At this point you could send me to any beach and I’d be happy, but for the sake of content let’s pick Fiji. Turquoise waters? Check. Powder-fine sands? Check. The perfect footwear? The McQueen Driving Shoe in Meile. These comfortable, casual slip-ons will get you to from the airport to the beach without sacrificing style. Throw on a pair of getaway shorts in blue and a lightweight Japanese chambray shirt and you’ve got an outfit that is as relaxed as you soon will be. Also, bring a hat. Sun damage is never in style.