The gray flannel suit is already something of a bargain. No other suit breaks apart quite as easily—allowing the jacket and pants to be worn separately in a range of styles and situations. But as a rule, flannel season only runs about three to four months. So you really don't want to dip into your savings to pay for it, especially when you're gearing up for gift-giving. Not only are these styles all under $500, they're crafted from a rich and rugged wool with a touch of stretch, making sweater layering possible and comfortable. Which brings us to how to wear it. Of course, you can go classic (white oxford, dark knit tie and some wing tips), but remember to embrace the season as well. Think patterned sweaters, colorful vests or a pair of striped socks under a cuffed trouser and some boots. Keep in mind, the lighter the color, the easier it is to wear casually.