I lived in Italy for a while, and navy was huge — to this day I can’t see the color without thinking of all the ways people in Italy wear it. My favorite way just might be this oversized sweater. It’s from the Maison Martin Margiela x H&M Collection, which I was lucky enough to score on the sale rack — I think I paid $20 for this gem.

It’s a thicker knit, which is great for the colder months, but the key here is that the cut of the sweater is actually quite slim. If you go super chunky knit on a boxy sweater, well, chances are good you’re going to look more like a snowman than a sexy man, so just pay attention to things.

The sunglasses were sent to me by Arnette, and I’m obsessed with them. Bigger sunglasses look good on my face — think those Wayfarer styles from Ray Ban and pretty much anything from the 80s. These are a smaller version of that, and I like them because they’re a little more understated and subtle. They’re still done in a tortoiseshell look, which is always classic, but the shape is thoroughly modern. These are the Dropout in Fuzzy Havana/Gloss Black, which you can pick up here.

I paired it with a pair of Levis 510s. They’re a super slim cut, and again, the balance with the sweater helps keep things look polished and put together. I can wear this look in client meetings and still look put together and presentable — baggier jeans and the look could veer too casual, likewise with the footwear.

The shoes are one of my favorite eBay finds. I paid $45 for this pair of stunning Oxblood Bally shoes.  They have great detailing on the cap toe, and the color is totally different from anything in my wardrobe. They photographed a bit brighter because of the lighting, but they’re this really rich, deep oxblood color — totally on trend for the season, but also a great staple to ground out your looks. Sometimes it’s a great chance to get away from black footwear, especially in dressier options.

Photos courtesy Kristin Booker for Giafrese