
With the weather turning chilly in the evenings, it’s time to start thinking about layers. Eating outside is still very much an option, but as the sun starts setting a little earlier, having some extra warmth goes a long way.
I also like this time of year because it gives us an excuse to add some texture. Boiled wool, tattersall checks, suede…those heavier fabrics and patterns give a look some depth without making it feel overdone. It’s an easy way to dress for the season while still keeping things comfortable and casual.
Here’s how I like to do it:

From Top Left:
1. Eton Boiled Wool Shirt-Jacket: Sort of jazzy… A nice, dressy sport coat alternative.
2. Peter Millar Tempest Sunglasses: These have a nice, Italian feel. These are private-labeled from an Italian manufacturer and worth the money.
3. Beretta Fine Italian Tattersall Shirt: There’s always room for tattersall. Don’t sleep on the checks.
4. Peter Millar Alpine Wool 5-pockets: I’m big on 5-pockets these days, and a wool option is a smart way to dress them up.
5. Rolex GMT Master II “Sprite”: Such a cool look. The subtle green gives this watch a little character.
6. Martin Dingman Henry O-Ring Alligator Belt: I mean…O-ring and alligator? Martin really outdid himself on this one.
7. Grant Stone Traveler Espresso Suede Penny Loafers: I just got these (post coming), and I couldn’t be happier. Don’t sleep on Grant Stone. They are a little heavier than their Italian cousins, but that’s why they have a place. They wear very well.
8. Fleetwood Mac Greatest Hits: You’ll both know the words to almost every song. And isn’t that the point?