If you're like us, there's not an item in your wardrobe you wear more than jeans. And when it comes to denim, one brand remains the first and last word—Levi's. If you want the utmost quality and craftsmanship, opt for a pair from the Levi's Vintage Clothing line, which recreates classic styles from the brand's archive. Like this 1950s biker style, that features a comfortable, slightly boxier silhouette.

1955 501 jeans,
$278 by Levi's Vintage Clothing

There's a reason cashmere is king—it's the strongest, warmest and softest form of wool there is. Which is why they make such swanky sweaters. And when it comes to such an all-time preppy classic, you can't go wrong with Ralph Lauren. The proportions are just right, because the brand has made and remade this navy crewneck hundreds of times. This version of the wear-with-anything sweater has been specially treated for easy care, while maintaining its breathability and sumptuous texture.

Cashmere crewneck,
$248 by Ralph Lauren

A leather jacket is a classic piece, but can sometimes feel a bit extreme. It takes some confidence to pull one off. But if the jacket is actually suede, leather's less shiny side, it's somehow easier to wear. And more comfortable and breathable too. A good one is definitely going to cost you, but a suede jacket doesn't need to convinece you to buy it, it just sits back and waits to improve your style—because it always does. And there's no better one, in our opinion, than Todd Snyder's Dylan jacket. Which might be why so many of Hollywood's leading men have worn it here and there.

Suede Dylan jacket,
$998 by Todd Snyder

For special occasions, the office and anytime you don't know what to wear. When choosing the fabric, we like a refined twill or oxford cloth—both of which travel well and have a nice texture without drawing too much attention to itself. Keep it pressed and keep it clean. It's as easy as that.

Twill dress shirt,
$250 by Eton

A soft, luxurious long coat in a warm shade of tan? It's a classic color and a versatile piece of outerwear that isn't going anywhere anytime soon. If you're looking for an investment, this version from French label Sandro, is the perfect fit, length and feel. It looks good dressed up with a suit or thrown over a hoodie and some jeans.

Wool Apollo coat,
$730 by Sandro

A pair of navy trousers that toe the line between dressed up and down are most definitely a wardrobe must-have. Wear them to work or a wedding with a pair of lace-up shoes and a proper blazer. And then again the next day with a pair of white tennis shoes and a denim jacket on a weekend date. French label Officine Generale's dapper twill pants are inspired by workwear trousers worn by Breton sailors, but have a refined finish and a more contemporary silhouette.

New Fisherman twill pants,
$275 by Officine Generale

Maybe there's no such thing as the “perfect” sweatshirt. Because they can be so many things, from super-heavy and oversized to breezy and tie-dyed. But if you want one that will last you, that will always be in style and never let you down, you'll want to invest in a John Elliott sweatshirt. Specifically, his raglan crew in a custom knit French terry material. It's ridiculously soft, a little lighter than your average sweat and cut to be comfortable and forgiving.

Raglan crew,
$178 by John Elliot

A vintage Levi's denim shirt is never a bad look, but they can take some time and money to track down. This one, from Saturdays NYC, is made from comfortable medium-weight denim that's suitable for year-round wear. It's fitted with two chest pockets—an external and internal one—and cut in a comfortable fit that works both tucked and untucked.

Kenmare shirt,
$135 by Saturdays NYC

A few years ago, a blazer would certainly have been on this list. But in 2020, an adaptable chore coat will serve you a whole lot more. Because a good one, like Taylor Stitch's Ojai jacket, can serve as a modern replacement for a navy blazer because it's cut from a handsome double-sateen cotton. But it also works as off-duty outerwear, thanks to the rugged ring-backed buttons, slanted side-entry pocket openings and durable double-needle stitching throughout.

Ojai jacket,
$188 by Taylor Stitch

Tom Ford famously said that a man should always change up all of his underwear and socks every six months. That might be a bit extreme, but there's something to be said for fresh underwear. And when a garment sits against your skin for the better part of a day, shouldn't it be of the most uncompromising quality?

Boxer brief,
$85 (for 3-pack) by CDLP