1. The Gray Flannel Suit
Old School:
Once the ultimate symbol of conformity during the buttoned-up 1950s, this woolen warrior will now help you break from the dark-blue-suited pack. (Thanks, Mad Men!) Remember: Stripes and pattern trends come and go, but the gray flannel never fades. Splurge for a decent one now and we guarantee in three decades when your adult kid comes over to borrow money, he’ll try to steal your suit, too.

New School:
Calvin Klein suit $595, and tie, $40; Armani Exchange button-up, $55; Tommy Hilfiger 
V neck, $148; Ciré by Grandoe gloves, $85; Perry Ellis belt, $35; Moscot eyeglasses, $279; Maruti oxfords, $41.

pureDKNY blazer, $700; Eubiq NY shirt, $185; Blue Notch jeans, $199; Urban Outfitters shoes, $68; Nixon headphones, $120; John Varvatos scarf, $145; Nice Collective wallet, $140.

TIP - One Suit, Many Uses: Gray’s a neutral, so it’s easy to coordinate. Pair the pants with a navy blazer for a classic preppy look or dress it down by wearing the jacket with your jeans.

2. Levi's 501 Jeans
Old School:
Levi’s made History’s first blue jeans in1873. (The originals are on display in the Smithsonian.) These riveted roughneck miner pants are as steeped in American iconography as Coke and Mickey Mouse. The uniform of cool from Steve McQueen to Jack White, a relic of the past they are not: They’ve remained the template for nearly every jean since (except those bedazzled horrors). Sure, Levi’s makes some serious dad jeans (see: Comfort Fit 560s), but the cut of the classic 501 slices through trends and magically transforms any schlub into a button-fly stud.

TIP - Break ’Em In Fast: 
Chuck new jeans in the wash, then dry them for 10 minutes. Wear them while they’re still damp, so they form to your fit. After five times, they’ll feel like your old faves.

3. The Plaid Shirt
Whether you're a child of L.L. Bean or the Latin Kings, the All-American plaid flannel should already be in your sartorial arsenal. It improves the more you wear it, it’s a chick tractor beam, and it’s super affordable.

4. The Leather Jacket
The bulky, buckle crazy perfecto bike jacket (think Misfits fans/Brando in The Wild One) is classic, but its sleek, streamlined cousin, The Racer, is infinitely more stylish and has ruled the roost since Fonda and Hopper hit the road.