The great thing about tweed is that it lends an air of traditional good taste to any look -- so much so that you can afford to mix it up a bit, add some irony, or try something new without risking too much. I've seen guys using tweed as a foil to a ridiculously bright colored shirt, crazy rock star hair, or just as a way to give a bit of dignity to downtown grunge. If it weren't for the reliably classic effect of tweed, I'm pretty sure I would have just passed them by, but I didn't -- I stopped and took a second glance. Even Albert Einstein, with his droopy face and mad scientist hair, has the look of a gentleman in his tweed coat.

There as so much that is both uptown (tweed jacket, colored sweater over the shoulders) and downtown (knit hat, graffiti) about this guy. It's a good mix. Mercer Street, NYC, February 2008.

As you've probably noticed, I have a thing for guys in military clothes, and bomber jackets are no exception. Maybe it's a holdover from a Top Gun obsession in my teenage years, or just that uniform thing I've talked about before. Regardless of whether you look like Tom Cruise--or not!--men look great in all incarnations of the bomber jacket--from the most authentic version worn by the Alaskan Air Force during World War II to edgy downtown reinterpretations created by forward-thinking designers. There are also lots of fabrics nowadays for grounded wingmen to choose from. While I am personally most partial to the teal nylon Army-Navy version with a fur collar, or the straight-out-of-the-war-photo shearling version, I do in fact like most kinds I've seen on the street and online, including Axl Rose's leather version (complete with Guns N' Roses logo) from the nineties.

I like this down puffer / bomber jacket combo - it's a sporty, but warm, look for winter. Noho, NY, January 2008.

Ever since I met my husband 11 years ago, I have been waiting for the day the eye doctor would tell him he needed glasses. I love men in glasses! Now that day is here and, in search of inspiration (not that he'll necessary listen to me), I have been noticing every single four-eyed man who crosses my path. Quite predictably, I'm more interested in the unusual frames, especially vintage-looking ones. So I narrowed down my favorite shots from the street and set out to find their original counterparts online, which proved to be a challenging task. Until I got to Michael Caine. As a great fan of Caine's style, I always knew that he was an eyeglasses enthusiast, but I didn't know the extent until I started to dig deeper into my research. Eventually I found a picture of Michael Caine in every single style of glasses that had caught my eye on the street. What does that mean? Does it mean that Michael Caine has been that profoundly influential on the shape of eyeglasses men wear, even today? Probably not. But what I suspect is that he was -- and is -- unafraid to try anything when it comes to eyeglasses and successfully carries off pretty much anything he tries. Here's looking at you, Mr. Caine.

There is a perfect combination of Groucho Marx and Clark Kent in these glasses. They add a lot of style to both men's looks. left: Bryant Park, N.Y., September 2007. right: Michael Caine, 1965. (Credit: Getty)

Double-breasted coats and jackets don't have to look as country club formal as you might assume. Of course, if you choose to wear a navy blazer with brass buttons, you might have to work extra hard to add a playful dose of irony to its conventional aura--or maybe sometimes it's a relief to leave well enough alone. But in most cases, the traditional connotations can be overridden with new shapes, contrasting references, and a healthy sense of your own style. I often see my friend the designer Phillip Lim looking thoroughly modern in traditionally cut double-breasted blazers in fire engine red or cobalt blue, while Prince Harry boldly reinforces the old-school style of his double-breasted suit jackets by tossing a bowler hat into the mix. Perhaps most imaginative of all, though, is Andy Warhol, who threw a black leather motorcycle jacket over a classically cut black double-breasted blazer. But then again who was better than Andy Warhol at mixing references and identifying icons?

Phillip Lim, (pictured with Anna Wintour), looks entirely contemporary in his boxy blue double-breasted blazer. 3.1 Phillip Lim store opening, NYC, July 2007.