How to Dress for Fall

Yesterday was one of those strange days where on one block I'd pass a guy in a t-shirt and shorts and on the next would be a guy in a fur-lined jacket. Fall is, in my opinion, the best time of year to get dressed because it provides the opportunity to layer your favorite pieces so you can easily regulate your temperature. Layering takes the guesswork out of getting dressed when you're not sure what the day's weather will throw at you. Layered dressing also has the advantage of being more interesting than other styles because it leaves room for creativity in combinations of colors, accessories, textures, patterns, etc -- as long as you know how to mix them correctly. You're also not yet covering up your look with heavy duty outerwear, so you can easily show off your steez both inside and out.The first rule for layered dressing is to make sure that the pieces you incorporate are slim. You're better off using more thin layers than fewer thick ones in order to avoid a bulky look. And again, the more layers you use, the more opportunity for interesting juxtaposition.To begin, I suggest selecting a piece and building your look around it. Here are two combos I like:Now that summer is over, you can put those trusty polo shirts in the back of your closet and branch out. Consider the henley. GQ did a piece on it last month, urging guys to ditch their collars and try something new. While the magazine's model rocks his henleys on the snug side, I suggest you rock yours by wearing something fitted but without any pulling across the arms or chest. Think Dexter, not distressing.Try pairing a henley under a dressy sportcoat à la Brad Pitt above. I like this one John Varvatos Star USA microstripe henley ($125),with this velvet sportcoat ($225) from J. Crew.Then you layer the above two pieces over this crewneck t-shirt also from J. Crew in heathered coal ($36).The sheen of the velvet combine with the flat finish of the henley and the heather detail on the shirt, in a way that's just enough "look" without being over the top. Note: another great henley option is this one I found at Hollander and Lexer in Brooklyn recently..This next look I built around a Brunello Cucinelli vest that has inspired me before. I found it again at a great price on Bluefly, and this time I'll talk about it in light brown ($565.25), a major color for Fall.Put it on beneath this grey windowpane Michael Andrews Bespoke sportcoat, with a cotton pocket square (silk would be too dressy for this look), add a white or light blue shirt underneath, and it's game on. I like the idea of this striped cotton pocket square from Paul Smith ($40). The colors are a little unexpected, but it anchors the light grey-tan vest combo.The secret to easy layering is to make sure your closet is stocked with items that coordinate readily with one another. This will not only multiply your options, but it will also provide insurance against the "didn't he wear that yesterday?" factor.