Getting dressed is an expression of your self, but when it comes to great pieces, they can have attitude of their own. All of our Italian shoes have personality, but these four are some of our favorites.

The Double Monk Strap

The double monk strap is definitely a stand out Italian shoe. It’s not the most common style, but the men who wear them always look like they know something others don’t—namely that you should really buy a pair of double monk straps. They’re perfect to wear in a relaxed working environment or at a casual soiree. Pair them with a relaxed suit or smart trousers—they’re not quite appropriate with formal wear.

The Wholecut Oxford

So fresh. So clean. The wholecut oxford is the Big Man On Campus of the shoe world. They fit into any situation and will never go out of style. Basically, if you have no idea what shoe to wear, the wholecut oxford is an easy choice to make. From work to cocktail parties to dates, wearing this style tells the world you’re a Classic Man.

The Chelsea Boot

 The bad boy of Italian shoes, the Chelsea boot looks like a risk, but it’s really just reward. Elevate your casual style with this Mod staple and you’ll look cooler than Mick Jagger circa 1967. Whether you pair them with jeans, corduroys, moleskins, chinos, or twill pants, the Chelsea boot is an easy-to-wear staple that belongs in your closet.

The Driving Shoe

 Soft and supple, the driving shoe is easy like Sunday morning… which happens to be the perfect time to wear it. We can’t think of a better shoe for a picnic or a casual brunch and there’s no other style that pairs as well with shorts. Some may call the driving shoe preppy, we just think it’s great.