http://men.style.com/theupgrader/style/features/winter_survival/slideshow/121908WINTER?loop=0&slideshowId=slideshow51575&iphoto=4&nphoto=14&play=false&cnt=1

Tom,

Right, don’t wear a pair of worn in shoes to a conservative office. Those shoes should be in good conditioned and shined regularly, so you’re doing well.

Worn in shoes in general are a) more casual than not worn in shoes and b) one of those things in style that is more about attitude than anything.

Well worn shoes create a “too cool to care” look (don’t mean that in a bad way). If you’re wearing Brioni with a sharp crease in your trousers, you’re better off wearing well kept shoes.

If you’re wearing an unstructured jacket and jeans (or even a casual suit, say from J. Crew), you can go for the worn in shoes.

The idea is that you want to present a cohesive “image” - a formal suit but casual, beat up shoes (even though they may be casual, beat up dress shoes) doesn’t fit together that well.

Also, the “feeling” i get from worn in shoes is different. Wear them while walking around Soho or at the park; don’t wear them at galas, museum openings, or to Per Se.

Finally, a word about predistressed anything (but especially shoes): I don’t like them. At all. Worn in shoes, to me, is more about attitude. When you buy a brand new pair of worn in dress shoes, it’s like they designer is trying to manufacture that attitude, and it doesn’t work for me.

Buy high quality things and wear them in yourself. Beat up the pretty things, as they say.

But you wouldn’t wear a distressed pair of shoes at a conservative office right? — in fact, a lot of us shine our shoes on a semi-regular basis — and I’m wondering … Just how casual does the setting have to be for a distressed pair of shoes to be appropriate? Would you wear a pair to a nice dinner party? Would you ever wear a pair with a suit — not at a conservative office, but maybe at say a little less formal wedding?