No matter how much I say a style is versatile, I know there are guys out there who are just plain stumped when it comes to pairing their Italian leather shoes. Despite its sleek simplicity, the Chelsea boot is no exception to this. You can easily create several looks with this boot when you pick a high quality pair in a color and shape that pairs seamlessly into your wardrobe.

There’s a reason Paul Evans’ Chelsea boot is coined “the Dean.” This handcrafted Italian leather shoe may be luxe, but it looks effortlessly cool paired with a simple white tee shirt and a pair of dark slim jeans. It’s a look James Dean himself would rock. You can easily transition the look to a grade dressier by switching out denim for trousers—either chinos or dress pants would do the trick. When you’re wearing a casual outfit with your Chelseas, make sure that your trouser cuffs cover the top of the boots to keep that long, lean silhouette.

Get the classic Mod look by wearing your Chelsea boots with a well-tailored suit. This is the style that made The Beatles the international sensations they were; it will certainly look good on you. The Dean Chelsea boot kind of looks like a dress shoe, what with it being made of luxurious Italian leather and all, and they’re a great choice when you want to shake your look up.