Esquire magazine was the original catalyst to my career in fashion. Had it not been for their “Best Dressed Real Man in America” contest in 2009, I likely would not have found the confidence, or credibility, to pursue style blogging as a career. Honestly, I’d probably be investment banking or just finishing law school.
Esquire has been a great partner and it’s great to be back in the October issue of the magazine!
One of my favorite outdoor heritage brands, Timberland, is releasing some new style-conscious designs this Fall. I used to live in the classic 6″ boots, which I still rock from time to time. My style is more refined now, but so is the Timberland collection. Alex and I teamed up with the brand to creative direct their new styles and Esquire campaign.
The new goods are slightly more style-forward than what Timberland has done in the past (think slim leather bombers and sharp-but-tough boots), while remaining true to the brand’s rugged “outdoor performance” roots.
I’ve been slowly breaking-in their new Men’s Earthkeepers Tenon bomber jacket, a versatile piece that is great for commuting to business meetings in NYC, and even better for a weekend getaway far outside the city.
Here’s how I styled it.
1. Office Commuter
As you may know, I collect leather jackets and they’re one of my favorite things to wear/purchase… This washed bomber is slim-fit and soft to the touch, giving it that “broken-in” feel from day one.
For the “business casual” crowd, or those who leave their suit jackets at the office, a simple “trucker style” leather is a great choice your morning commute through the Fall/Winter. Personally I rock it with the collar up, like most of my outerwear.
The best part is, once you leave the office, simply remove the tie and you have a versatile outfit for wherever the night may take you.
For this collaboration I paired the jacket with the Men’s Earthkeepers Tremont boot in oxblood, a rugged but clean plain-toe lace-up.
- Gold Plated hand-engraved shades by Matsuda
- Men’s Earthkeepers® Tenon Bomber Jacket
- Blue striped cotton shirt by Michael Andrews Bespoke
- Tie Vintage
- Brown alligator belt and silver buckle by Ralph Lauren Purple Label
- Grey flannel suit trousers by Michael Andrews Bespoke
- Men’s Earthkeepers® Tremont Boot