the strategist 100

The Strategist’s Menswear 100

Our ideal complete wardrobe, from button-downs to boots.

Photo-Illustration: The Strategist; Photos: Retailers, Alexander Spatari/Getty Images
Photo-Illustration: The Strategist; Photos: Retailers, Alexander Spatari/Getty Images

There are a million ways to wear menswear — not all of them dependent on gender or aggressively getting a fit off — but the hundreds of stylish people we’ve interviewed over the years agree on the value of clothing that fits well, feels good, and stands the test of time (and most trends). It’s hard to find a T-shirt or a pair of boxers that does all three, but imagine if everything in your closet could meet, if not exceed, those exacting standards.

That’s the goal of the Strategist Menswear 100. It’s our ideal complete wardrobe, with all the pieces you’ll need to go to the office (or hop on a conference call), work out at the gym, attend a wedding, run an errand, or just hang out at home. Each item you see below is pulled from our extensive archive of highly recommended products, leveraging the knowledge of professional stylists, athletes, fashion designers, artists, cool dads, well-dressed celebrities, and our own writers and editors. In the rare instances (just two) where we didn’t have an existing recommendation on file, we turned to the Strategist brain trust to fill in the gaps.

Building a new wardrobe is pricey, so we did our best to include budget-friendly picks, like an under-$50 polo for hot weather and super-colorful socks, as well as extra-special pieces worth investing in, like a pair of boots that’ll easily last a decade. And because people come in all different shapes and sizes, we also looked to highlight clothing made for a wide range of bodies. So whether you’re searching to refresh your white sneakers as we enter a new season or looking to reinvent yourself completely, start here.