With Summer officially over and colder weather just around the corner, it’s time to upgrade your wardrobe. From head to toe we’ve got you covered with quality crazy dress socks and the hottest Fall and Winter trends to match.

Now that it’s fall it’s time to put away your flip flops and trade up for something a little more functional and stylish. Giving up the comfort of a summer shoe doesn’t have to be a traumatic experience. Make an easy transition by picking up a pair of Original Driving Shoes from Hunter. From the same people best known for sturdy and dependable Wellington’s comes this classic and comfortable slip on. Easygoing but still trendy, this shoe is the perfect utility player that every guy should have in his closet.

Paired with the relatively conservative vibe of the Original Driving Shoes, any of the crazy dress socks from our Wildchild III pack from our latest Fall/Winter collection will keep things interesting.

If you’re looking for something a little more intricate to put on your feet this fall, look no further than any of the intricately designed Derbys from Gram. Sturdy look with a featherweight feel due to the shoe’s rubber modal sole, these shoes are a classic design, with a street smart sensibility mixed in.

Looking to compliment the design of your shoes without overpowering them? Look no further than our Prepster II pack. The unique space-dyed heather yarn on these crazy dress socks will help you keep thing interesting without pulling too much focus.

Keep your eyes on our blog all month for more Fall and Winter trends to keep your closet happy.