Growing up, whenever a new school year rolled around, the only thing that made me not want to hide in the Indian Burial Ground near my house was the prospect of getting new clothes, particularly that all-important first day outfit. At this point in my life, I don’t really have an excuse to get a new Fall wardrobe every year but the idea persists. For Back to School 2010, I’m making my selections from a male perspective. So here you have what I would choose for back to school if I were a guy…As you may have heard before, you are way TOO COOL to be still wearing a backpack. A messenger bag, on the other hand, is the perfect fit for one’s manly carrying needs. I’ve been lusting over this Moore & Giles beauty ($485) in Nubuck Bison for some time. It would house my laptop perfectly (I measured – I’m good like that). I love the texture on both the bag and the shoulder strap. This bag crush is not going away anytime soon..Next up on my hit list is a pair of jeans from Billy Reid's collection for Levi's. The designer's prize for winning GQ's Best New Designer Award was to collaborate with Levi's and create a collection of tailored workwear denim. The results go on sale September 10, at 12:01 AM Eastern Time..You can never have too many well-fitting shirts, so here again I'm hitting up Billy Reid and his "dressy-casual whiskey-soaked style." The John T. shirt ($195) in blue & green strikes me as a nice way to incorporate some darker Fall colors without looking drab. Very cool how they've matched up the seams in back to create diagonals in the pattern (see below) -- a little extra Southern flavor on that flavor. I like it with these brown pants, but I'd also like to see it with charcoal grey, either on bottom or as a sweater or jacket...It's a little out there, but I could so rock this Barney's printed wool bow tie ($75). The patterned shirt actually tones down the loudness of this piece's message..If you're boot-obsessed like me, then you too hold the belief that no Fall shopping trip would be complete without a new pair of boots. Right now, I'm definitely vibing with the Diemme Roccia Vet boot (€280), which come from a collaboration between Diemme and Japanese retailer Beauty & Youth United Arrows. With the contrast stitching and colored laces and soles, they strike the perfect balance between stylish and masculine. They come in a couple different colorways -- my pick for myself would be the brown with blue laces above. You can get them here..My final picks are this cotton trench coat ($160) and lightweight denim scarf ( $24), both from Topman. Budget-friendly and machine-washable: doesn't get much better than that....school's back in session!