This bowler hat from Victor Osborne at Forward by Revolve might look more or less trad from afar, but it’s actually a little bit funkier than most, and with a cream ribbon encircling the brim. Ribbed cotton contrast details also mean that this choice will match with a good deal of plain tees, hoodies, and windbreakers– awesome!– and it offers a pretty easy means of accessorization that’s hardly the fedora route. Vintage vibe. [$88 at forward by revolve]

It’s getting to be “hat” time of year again… sorry, we’re just genuinely excited about wearing lightweight toppers again as the temps inch up in the mercury. If you’re the type who has trouble keeping even his best pieces clean, this Brixton Straw Castor from ’80s Purple will please you– black, glossy straw won’t reveal any smudges. Available in sizes s-m-l with a dapper ribbon trim. [$42 at '80s purple]

Editor’s Note– We’re men.  Our style is portrayed less through flash and “glamour” than it is through simplicity and functionality.  The hat isn’t a tool for us– a cop-out, a cover up, it is a form of expression equivalent to the most front-facing features of our wardrobes.  We wear our hats proud on our heads because they symbolize quite deeply something about who we are– they are our calling card, our best foot forward, our Sunday Best when a fashionable push comes to shove.  To celebrate the Hat and the Modern Man, we introduce StyleCrave’s weekly style feature by our latest addition– Mr. Simon Crompton.

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This sleek fedora shape says good-bye to the traditional flat wools and instead has a woven appeal in rich brown. If you’re not exactly in a cool climate or you need to switch things up for vaca, this Coal Considered option is amazing. Available in medium and large sizes, with a wide gray band to match with cords and blazers. I daresay that you could also rock some stubble with it. [$47 at 80s purple]

Dapper but not at all overbearing, this cap is an easy way to accessorize. Jeans and tees might be a little on the boring side, but plunking this puppy down can really get your outfit on the fast track. Feather detailing at the side is a great detail, especially when paired with that statement band in black. Available in actual sizes, too, from S-XL. [$47 at 80spurple]

Late season joggers will find this idea to be an instant hit.  While it’ll be 78 degrees and sunny in Chicago this Sunday for the Chicago Marathon, the forecast beyond that is not looking so pleasant.  Nike has released their Nike Performance HatPhone for just such weather.  The HatPhone is a pair of headphones weaved into a cold weather skull cap.  Toss it on your head, plug it into your iPod and you’re on your way.  [$55 at Nike]

Scarves are one of the last things we think about buying. When we’re preoccupied with the switch from sandals to sneakers to boots, scarves go on the back burner. This one brings back old construction methods and handcrafted techniques to give each one a unique look and feel. Dry clean only, one size fits all. [$135 at revolve]

It’s October.  I hate to be the bearer of bad news, but in just a matter of weeks the mercury is going to drop– and you’re going to need to stay warm.  Our friends at Nobis.ca reached out to StyleCrave to share their fall line of headwear with Crave readers.  Nobis designs a wide range of hats from skull caps to ball caps to fedoras and more.  Based on the inspiration from Nobis’ Queen’s Street Toronto design team, these fresh, new designs are garnering quite a reception from lifestyle media– StyleCrave included.  Fall fashions can be a reason to look forward to brisk weather, and Nobis’s headwear is no exception.  After the gallery below, learn how you can win one of five free hats from our friends at Nobis.ca…

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