Down low—dark wash denim and suede chelseas are smart. It’s A 50/50 split of smart and casual, which almost always works, and is one of my favorite ways to style an outfit. WHEN TO WEAR IT ...

Our top pick for the best overall black jeans for men is the Mott & Bow Jay Jeans. This pair is crafted from Italian denim that's lightweight ... play a part in your outfit choices.

and spoke with 23 stylish guys who have gone through the denim ringer — designers, retailers, podcasters, fashion writers, stylists, electricians, and denim nerds — to hear about their favorites.