1. Unlike lesser tees, John Varvatos's fitted green Short Sleeve T-Shirt is refined enough to wear to even the swankiest clubs ($125; johnvarvatos.com). 686 makes more than just technical snowboarding outerwear, but you don't need to know who Travis Rice is to rock the company's 70/30 acrylic-and-wool Primitive Knit Sweater ($60; 686.com) or ARD Cadet Tweed Jacket ($80), an understated mashup between a military coat and a pinstripe blazer. That's the stylist's vintage belt and Gap's low-rise, straight-fit Corduroys ($50; gap.com) down low.

2. This white cotton Long Sleeve Dress Shirt ($145) from John Varvatos has a clean look and a close fit. With contrast stitching at the shoulders and a slim-fitting shape, the Rugby Crewneck Sweater ($45) is the smartest we've yet seen from Gap. Too much military inspiration is too much, which is why we like Gap's restrained all-cotton Military Dobby Jacket ($88). And these Boot-Cut Modern Indigo-Wash Jeans ($79; bananarepublic.com) by Banana Republic are as dressy as chinos but much more comfortable.

3. Thanks to its precise tailoring and slim fit, John Varvatos's Plaid Cotton Long Sleeve Shirt ($165) simply looks (and fits) better than your typical work shirt. Smart details like snaps along the collar and cuffs lend a contemporary look to Victorinox's Snap Front Mock Knit ($175; swissarmy.com), with its soft cotton liner and linen exterior, and the company's washed cotton-twill Military Jacket ($425) is the perfect travel companion: good-looking enough for dinner but, thanks to four secure pockets, utilitarian enough for all-day excursions. Equally unfussy and practical are Gap's cotton Chino Pants ($50).

4. With a bold but not too bright rugby stripe, J.Crew's Vintage Thermal Cedar-Stripe Henley ($45; jcrew.com) is modeled after old-school work shirts. Nautica's 100 percent cotton V-Neck Sweater ($70; nautica.com) is the perfect shade of green, while—detecting a theme here?—their cotton-twill Breeze Blazer is yet another modern take on the classic army-navy-surplus jacket ($148). Shown here with the model's own belt and John Varvatos's all-cotton, straight-leg Dark Authentic Fit Jeans ($165).