When it comes to your wardrobe, less can truly be more – if you're smart about how you put it all together. We've curated a closet's worth of the essentials, which can be mixed, matched, and worn pretty much year-round. "Good clothes are available everywhere now," says Nick Wooster, the veteran fashion retailer and consultant. "But balance lower-end purchases with higher ones – if you're wearing a shirt you picked up for 25 dollars, pair it with a bench-made dress shoe or your nicest pair of tailored trousers. As men, we have the luxury of being able to wear pretty much only five colors: navy, gray, khaki, black, and olive. Invest well in those colors and you'll get so much more out of your wardrobe."
The Rugged Bag
Have a bag for every situation: a grown-up's backpack (like this one from State), a rugged leather tote, and a sleek briefcase. Find the right ones and they'll last a lifetime – unlike that duffel bag you've been lugging to the gym. [Club Monaco Nate Leather Tote, $349; clubmonaco.com]
Credit: Photograph by Greg Broom