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WHAT TO WEAR: Date Night

Finding an outfit for date night is tricky. How dressy is too dressy? How casual is too casual? Theses questions are on everybody’s mind when the time comes to pick out and outfit and stand in front of the closet for hours. The best trick for the perfect date night apparel is a balance between Frank Sinatra fancy and surfer boy-chic. Combining these drastically different styles will give you an edge that is cool, casual and masculine. Discovering this balance can take a few tries, and this Fashionisto hit the nail right on the head with his effortless date night outfit. From a nice dinner at an impressive five star restaurant to ice cream cones in the park, this ensemble was perfect.

Khakis are always the way to go because they can be dressed up or dressed down; they are the perfect pant right between slacks and jeans. What more could a guy ask for? The classic trouser has been around for decades and has yet to go out of style due to its versatility and fit. With such a simple and classic pant, this Fashionisto added a fun flare of style with a part denim and cotton button-up shirt. Resembling something from the ’80s, this navy collared shirt was fun, fresh and a little bit dressy.

This Fashionisto dressed up his khakis with a pair of sophisticated oxfords straight out of Sinatra’s wardrobe. A leather belt around his waist, as well as a simple watch around his wrist complete a classic and modern look perfect for any occasion.

One Simple Change: Wear the khaki’s to a job interview by swapping out the navy and denim shirt for a white button-down and navy blazer. Toss on a necktie, keep the oxfords on and you will land the job in no time.