The first, ultra stylish piece of headgear we'll be checking out takes simple style and does it just right. Banana Republic's 'Solid Fedora' is the perfect choice for those of you on the hunt for a seriously smooth, top of the line all-around performer. This all black, dry clean only, small brimmed, classically 'pinched' fedora is a clean and stylish without being boring. Boasting a roughly one-inch thick band that wraps around the bill-meets-bowler part of the hat. Made of a ninety-six percent polyester, four percent spandex blend, this hat will give just enough, so you won't trade any comfort for fashion. Coming in at a full price of $49.50, Banana Republic's take is a safe choice for the businessman, or for nightwear that will add a perfect topper to your evening without running the conversation.

Taking the fedora to the other end of the spectrum, let's look to Sombrio for a fabulous casual option. Working within the same black color palette, Sombrio's 'Jump Street Fedora Hat' takes things from wall street to the beach or cabana bar with this fun loving, lightweight cap. Boasting a woven texture in this cotton/polyester blend, it definitely gives a nod to the classic beachside straw hat. Perfect for post-skateboarding relaxation, Sombrio takes the one-inch all black wraparound belt-like accent from Banana Republic's hat, and lightens things up with an extra dark navy blue band with tie-like extra thin diagonal stripe. With a full retail price coming in at $44.95, and sale price as low as $38.21, you really cannot go wrong with this leisure-minded, low-key hat mixed with high style.

Taking a feather from each of these previous hats, Calvin Klein's 'Plaid Band Fedora' offers the perfect mix between the dressier Banana Republic option, and more casual, funkier Sombrio. This all-cotton grey cap boasts an all-over tonal herringbone texture, complete with tonal top-stitching along the rim, and fabulous striped roughly two-inch tie-like band. By taking this band similar to Sombrio's, making it thicker, tiered, and a slightly lighter grey hue, mixed with a blue geometric design, Calvin Klein definitely adds a little punch to this classically shaped hat. Plus, for those of you who love extra touches done right, the flat front brim mixed with curved backside, and the side logo perpendicular to the horizontal tie-band will definitely tickle your fancy. A truly classy choice, this $39.50 fedora is the perfect pick for a day-to-night transition hat that adds a hint of personal style without overpowering.

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