It's hard to figure out what to wear this time of year. One day you're in shorts thinking summer is here, and the next you're dramatically underdressed and running across the street to find some sunshine. Taking a cue from temperature-varying sports like skiing and hiking, the best solution to this problem is to dress in layers. Throw a light sweater on between your shirt and your blazer; add a scarf over your T-shirt and put a cardigan on over that; or, as one guy I saw did, wear a shirt and tie with a sweater over that, with a cardigan over that with a sweatshirt over that. I'm sure that sounds crazy, and I acknowledge that you would need an accomplished sense of proportion to pull that off, but trust me, he did.

Aside from matters of temperature, wearing layers can also be an opportunity to show more sides of yourself through your clothes. My favorite example of this is a photo of Richard Gere from 1980. Had he been wearing only the denim shirt and tweed blazer, he would have looked like your average prep school throwback. But with the addition of a pink zip-up sweatshirt, he looks sportier, younger, and less predictable. Wouldn't you love to give a first, second, and third impression all in one look?

It's hard to believe that this guy has four tops on and still looks good, but he does. Mott Street, NYC, January 2008.

As classic as they are, I feel like there came a time in the last decade when (at least for some) loafers fell out of style -- too old-guard, too stiff, too conservative -- and there was the perfect replacement waiting in the wings: the driving shoe. As brilliantly popularized by Car Shoe, Hunting World, and of course Tod's, driving shoes are significantly more sporty and laid-back than their more formal and businesslike counterpart. They replaced loafers for every occasion -- for the office, for the weekend, for church. In fact I bought all our male family friends Tod's driving shoes in black patent leather with grosgrain details to wear with their tuxedos -- they were like an updated version of the black velvet evening slipper. But recently I've noticed the more formal loafer making a comeback, albeit in a more inventive new context. Perhaps inspired more by Michael Jackson's ironic embrace of loafers than the more predictable Wall Street types, many New Yorkers pair the formality of loafers with a more personalized look -- they wear them with scruffy jeans, beards, even Rasta caps. Who knew I'd be singing the praises of Michael Jackson two weeks in a row??

Gary Cooper, with his wife, Sandra Shaw, wears his penny loafers in the most classic context. Southampton Beach Club, N.Y., 1945. (Photo: Getty)

It takes a special guy to wear a floral shirt. Although they are largely worn and accepted by a wide variety of genres -- well-dressed Europeans, hipsters, rockers, and even American prepsters -- floral prints are an incredibly personal and specific choice to make. A guy has to know himself pretty well and feel pretty good about his choice in clothes to carry off such a bold print. In my mind there are two kinds of floral shirts. There is the refined, sophisticated version like those made by Liberty or Etro that have a more tasteful effect. And then there is the Hawaiian floral shirt, which seems to say that its wearer cares more about humor than taste -- think Jack Nicholson. In either case, a floral shirt is not a conservative look, but it can fit into almost any style of clothes. And if you're really feeling good about yourself you could mix two prints together like Michael Jackson did in date the 1970s -- it may have been his finest moment.

My friend Bart Quillen wears a floral shirt in a more traditional, unaffected way. The tweed jacket adds a nice preppy contrast. Front Street, Brooklyn, June 2007.

I love peacoats of all kinds -- the authentic naval version and upscale designer versions, long and short, navy and black, old and new. There are in fact so many versions today that it's sometimes hard to tell what actually constitutes a peacoat. My idea of one is a dark-colored coat that is military in feel and made of thick wool fabric. It also has to be above the knee and/or double-breasted. There is something about the formality of the tailoring and the stiffness of the fabric, mixed with the casual way that most men wear them today that make them very attractive to me. It's like when a guy who I'm used to seeing dressed-down puts on a suit, I think "Wow, he looks great dressed up!" The peacoat is an easy way to add a bit of "dressing up" to your everyday or weekend outfit. After all, I know I'm not the only girl who likes to see a guy in uniform.

This guy shows a lot of personal style by wearing the top buttons of his peacoat closed but parting it in the front to put his hands in his pockets. His pose is functional and unaffected but looks cunning nonetheless. East 60th Street, NYC, February 2008.