1. The Classic Dark-Washed Jeans
There's nothing like a pair of great-fitting straight leg jeans, and dark wash never goes out of style. Truly indispensable, they can be dressed up or down, and get better with wear. Seriously, if you have a pair of jeans with any sort of kooky stitching or pocket designs, discard immediately.
Above, from left: Levi's 501 Original Jeans in Rinsed, $37 (were $46), at Levi's; A.P.C. New Standard Jeans, $155, at A.P.C.; Oak Indigo Straight Jean, $146, at Oak.
2. The Desert Boots
Though the Clarks classics have laces, pull-on versions are an easy update, and let's face it, the less work the better. Whether in universal black or broken-in beige, suede or canvas, there's a version of these to suit every guy's style.
Above, from left: Clarks Desert Boot, $95, at Clarks; Vanishing Elephant Ferris Leather Desert Boot, $264, at Blackbird; Acne Dune Boot, $489 CDN, at Gravitypope.
3. The Cashmere Pullover
Some dudes do V-necks, some don't. We'll admit, dabbling in neck "intricacies" can get you into trouble. But not with a classic cashmere crew. Whether in merino or a soft cashmere blend, it's a hard call The merino wool crewneck gets an upgrade in cashmere--a definite investment, but it'll add polish to any outfit.
Above, from left: A.P.C. Pullover, $200, at A.P.C.; Brooks Brothers Black Fleece Cashmere Stripe Crewneck Sweater, $450, at Brooks Brothers.
Above, from left: Victor Glemaud Grunge Crew Sweater, $325, at Odin; J.Crew Cashmere Crewneck Sweater, $188, at J.Crew.
4. The Polished Top Coat
Top coat equals entry into grown-up land. Whether going to the opera or on a dinner date, guys really can't be wearing whatever variation of the North Face jacket they still have from their undergrad days...over a suit.
Above, from left: Topman Self Duffle Coat, $280, at Topman; J.Crew Sutherland Herringbone Topcoat, $368, at J.Crew.
Above, from left: Band of Outsiders Polo Coat, $2,070, at Opening Ceremony; Freeman's Sporting Club Pea Coat, $1630, at Refinery29 Shops.
5. The Good Go-to Belt
Every outfit needs a finishing piece, and a leather belt in a neutral color is a functional accent that can be worn daily (and not necessarily to keep up your pants).
Above, from left: UO Solid Leather Belt, $19, at Urban Outfitters; Topman Tan Leather Plaited Belt, $40, at Topman; Tanner Standard Belt with Black Hardware, $87, at Blackbird.
6. Versatile Sport Coat
Part-time blazer, sometimes overcoat, always useful. Tweed is a homespun, English novelist-style variation of black, navy, or charcoal. And you don't have to be a nerd to wear it.
Above, from left: Marc by Marc Jacobs Wool Flannel Blazer, $394, at Ssense; Billy ReidHenry Patch Pocket in Brown Plaid, $625, at Billy Reid.
Above, from left: Nom de Guerre Woolen Blazer, $725, at Inventory; Shades of Greige Two Button Blazer, $198, at Ssense.
7. Plaid Shirt With the Perfect Fit
Perfectly-cut plaid shirts (like Steven Alan's) often come in letter-sizes--how many of us are actually "medium-sized," anyway? Don't fear the tailor.
Above, from left: Gitman Brothers Tartan Button Up, $175, at Acrimony; Woolrich Cotton Plain Upland Button Down, $185, at Bird.
Above, from left: Steven Alan Reverse Seam Shirt, $168, at Steven Alan; J.Crew Secret Wash Button-Down Shirt, $59.50, at J.Crew.
8. A Classic Watch
You probably wish your grand-dad passed down his love-worn Patek Philippe, but most of you guys out there won't be so lucky. For reality's sake, every guy should score himself a refined-yet-rugged military-style watch, ideal for every day and just as stylish for night.
Above, from left: G-SAR Dive Watch, $700, at County Comm; Simon Carter WT 1600 Watch, $175, at Blackbird; M&Co 5 O'Clock Watch, $95, at the MoMA Store.
9. Tailored Khakis
Definitely not your dad's pleated pants (unless he's Johnny Depp), great-fitting khakis are a bare-bones essential, be they cuffed on the beach or tucked into some worn-in motorcycle boots.
Above, from left: United Bamboo Twill Pants, $72 (were $238), at Acrimony; Chimala West Point Chino Officer's Pants, $325, at Bird; Ralph Lauren G.I. Flat Front Fine Chino, $98, atRalph Lauren.