The term sprezzatura is an Italian word that first appeared in 'The Book of the Courtier' by Baldassare Castiglione published in 1528, where it is defined as: a certain nonchalance, so as to conceal all art and make whatever one does or say appear to be without effort and almost without any thought about it.

In today's fashion the term sprezzatura, as a men's style of dressing, has come to mean many different and varying things, due to general overuse and lack of knowledge about this style trend in general. Defined as nonchalant attitude, unstudied apparel, carefree, 'artful dishevelment', clothing rebellion, the key concept of sprezzatura is always: men’s outfits should never look too perfect.

The trick to successfully pull off this artful dishevelment is subtlety in a great sartorial know-how. 

Any fashion quirk is subtle and understated. It takes confidence and the end result should always be an impeccable outfit.

David Gandy Street StyleDouble Button Suit Sprezzatura Style
Italian Gentleman Sprezzatura Fashion

Sprezzatura Beginner Tips

Being a savvy in the art of sprezzatura takes time and practice, but there are a few simple twists and changes. Start by twisting your tie knot or give your iron a bit of rest. Looking a little rumpled and relaxed can be just what you need. Finally, try going sockless every now and then.

Mens Fashion Sprezzatura Outfit

Get the look: Unity shawl collar cardigan | Paul Fredrick bengal stripe dress shirt | Ray-Ban High Street Wayfarers | Tag Heuer Carrera watch | Paul Smith tan leather brogues

Sprezzatura Advanced Tips

Once you mastered a side dimple for your tie, start knotting it so that the tail is longer than the main body. It is a men's classic sprezzatura style of wearing ties. Better yet, loosen up – undo that top button of your shirt and relax your tie as well. The same rule applies to your shirt cuffs when paired with a cardigan or sportscoat.

See also: Fall 2013 Menswear Trends

Spezzatura Style Outfit For Men

Get the look: Giorgio Armani one button jacket | Michael Kors gingham shirt | Solid silk narrow tie | Linda Farrow Luxe 208c sunglasses | Ben Sherman chinos | Sperry Top-Sider Tremont Kiltie shoe

The trick to pull off the sprezzatura style is to pay attention to the other traditional style rules, like colors, textures and patterns, by allowing one rule slide. For example, a single button fastened on the jacket or a part of the collar outside the jacket lapel, even when you're wearing a more casual jacket.

Mens Style Sprezzatura Fashion
Get the look: Paul Fredrick gingham sportscoat | Gingham trim fit shirt | Persol square keyhole sunglasses | TokyoBay pocket watch | Pakerson leather wingtip shoe | Frye James leather bag

Sprezzatura Master Tips

There are rules that you need to be bold enough to bend. This is what separates men who have become a study in sprezzatura from the average guy at a club on a Friday night. Some may seem extreme, like wearing your watch over your shirt sleeve but still under your jacket, having your belt buckled at the side or using one of your socks as a pocket square, simply because it’s such a great color or pattern.

There are those who look at the loud colors, ill-fitting clothes or sunglasses worn at night and say that it's not stylish, it's sloppy. As far as fashion trends go, men's sprezzatura style is a matter of taste and preference.