Jacquie -
I have a date. (no smart-ass comments please!) What should I wear that doesn’t look like I’m trying too hard?
Get back to me soon or I’ll end up wearing my Spiderman t shirt.
Jason*, I’m going to take my inspiration from the well-dressed dudes on Gossip Girl.
(Jason* swears he has never seen an episode of Gossip Girl, so I’m gonna make it easy for him.)
A great date night outfit is a must-have for any single guy and it’s really simple to put one together. You need 4 basic pieces plus a nice (read: clean) pair of boxer briefs and splash of something sexy-smelling.



While a ratty Spiderman tee could be a hip choice, I suggest something less-pit stained and more of a conversation piece. A politically-inspired tee will give her something to comment on when that first awkward lull occurs.
A casual blazer adds instant cool to almost any outfit. It’s a wardrobe staple for guys. I like the simple, affordable styles from Gap.
Nothing beats a classic pair of Levi’s. I’m a fan of the shrink-to-fit, takes a little bit of effort but you’re almost guaranteed a perfect pair of jeans.
While I’m a huge sneaker fan, a nice pair of dress shoes can make your style sleek with little to no effort. I like the Kenneth Cole ‘Crazy Cool’ oxford, it’s part sneaker, part dress shoe and you’ll get a lot of wear out of them without being uncomfortable. Check out Like.com for more shoe styles like this one.
Good luck Jason*!
*Named has been changed to avoid utter humiliation.
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