show some sock:

pant length:

feeling a bit inspired, i raised my suit pant length up a bit and started to roll up my jeans and chinos. lately i've been really liking the fact that pants are getting a little higher.

here's the problem: the debate is not about whether or not this looks good, because i think that shorter pants look good. since i'm the one putting on the pants, my opinion matters most and i opine that it looks sharp and modern. the debate in my mind is over the classic nature of what i'm wearing. meaning that i'm not sure if shorter pants will look that great in a year or two, and i'm more inclined to invest in things that last.

either way, my pants are shortening up, and here's how to do it. the trick is in the fit, and what's going on underneath. the slimmer and more tapered the opening, the more natural looking shorter pants will be. if you want to go real short, sport a thick cuff or a rolled-up pant. without a cuff on dress pants, you don't want to go overly high, the picture just below is about the right height.

above is an example of an extra high pant. it looks good because of the extra tapering and rolled cuff.

next, what's underneath the pant. go sock-less with some nice suede bucks or bluchers - or - go nuts with your socks and find something that really stands out against your nice leather-bottomed shoes. with socks, dress socks with lighter fabrics, expressive colors, and sharper patterns look best - remember that one of the big reasons for shorter pants is to show some sock (see here for more on socks). for your shoes, think dressier and simple. you need a solid shoe to balance out short pants, every picture in this post is a great example of a shoe that works perfectly.

as a note, this next picture is what most converted my wife to shorter pants. the strong cobalt blue socks, slim taper, and beefy cuff make this look work. also note that the socks are the only bright blue part of his outfit, you don't have to match your socks to anything, and too many bright pieces make it look like you're trying too hard.