Let's just start with checking your calendar. Its 2011. That means that if you are wearing jeans from ten years ago, this is not a badge of honor. I mean, great, you can still fit into those pants and all, but the thing is, styles of denim change for men too, not just for women. While some of we women may chase the constant updates of style a little more closely than other women and men, it is still important to make sure that the waistband of your pants are not hanging down super low or located anywhere near your armpits. Every man should own dressier dark jeans for a night out or to step it up a notch from your favorite Levis.
And speaking of waistbands, if you are wearing a t-shirt with your shorts or pants, please keep your waistband hidden. My biggest pet peeve ever...t-shirts tucked into your pants---double yikes. Don't do it. Please. And don't clip anything to your belt either...you have a back pocket, use it.
T-shirts. We all love them. Just not when they are too short, too tight, or making some statement about being with stupid. Cool graphics, yes! "Funny phrases", no! Add a couple plain black & grey basics to your closet each year--Velvet Men makes great ones.
I think shoes are a big deal. You don't need to run around in Gucci loafers all the time (unless you are able, and then good for you!), but try to skip the cheap shoes. Its the worst. Take care of your shoes and they will last for years-- its a worthwhile investment. No puffy all white sneakers either unless they are the classic Jack Purcells. (love yours, Jono!) And have some fun! I happen to think Converse sneakers are very sexy on men, particularly when paired with khaki pants and an (untucked) button down shirt. Big kisses.
Also on my list of loves for men: leather sneakers, Ray Ban sunglasses, a tweed sport coat worn with jeans, a new white t-shirt underneath any and all shirts, a well fitting outerwear jacket, dry cleaned dress shirts (especially white) paired with jeans, pants without pleats (always), solid cashmere v-neck sweaters, motorcycle boots, a good watch, and an awesome smile. Gets me every time.