5 Essentials That'll Transform Your Fall Wardrobe

Florence SullivanPaying more for the things you use constantly may sting at first. But once they’re aged to perfection, you’ll see where that initial investment went. Case in point: these five essentials.Santoni Carlo LoaferFlorence SullivanLoafers ($1,090) and tassels ($190) by Santoni.Italian shoemaker Santoni knows how to combine excellent craftsmanship with exuberant expression. This deep-blue Carlo loafer is an excellent example. Made from supple suede and supremely flexible, it’s already impressive on its own. And when you learn you can toss on a colorful tassel by slipping it through the penny-loafer strap and securing it with a hidden snap? Well, all the better.SHOP NOW​Akoni Vera EyeglassesFlorence SullivanEyeglasses ($890) by Akoni.Your glasses are the first thing people see, and you wear them every day, so there’s no better place to invest in luxury-level quality. Japanese brand Akoni delivers it in spades—top-notch acetate, lightweight titanium, unmatched construction—and its new Vera frames also happen to look cool as hell. With sharp angles and an oversize bridge, they make a statement that doesn’t overshadow the star of the show (you).SHOP NOW​Herno Hero PufferFlorence SullivanJackets ($995 each) by Herno.There’s nothing worse than feeling like another boring guy in a sea of black, gray, and navy on a cold day. The good news is you don’t have to—provided, of course, that you invest in a puffer jacket with charisma to spare. Herno’s Hero jacket is just that, and you can get it in a slew of hues (like the yellow and red you see here).SHOP HERNO​Juan Maiz Casas Overnight BagFlorence SullivanBag ($2,793) by Juan Maiz Casas.Rarely does a piece of luggage rise to the dual tasks of holding everything you need for an overnight and looking like the sort of thing you’d be happy to take into the office. This one manages that magic trick, thanks in no small part to the sumptuous leather—Argentinean, vegetable tanned, and embossed with a pattern that hides scrapes and scuffs—and a sleek silhouette that’ll look equally at home on a private jet and a crowded subway car.SHOP NOW​Berluti Rombo BootsFlorence SullivanBoots ($5,000) by Berluti.Sometimes you need a pair of proper stompers. We’re talking about boots with gusto. Berluti, the Italian specialist responsible for some of the fanciest footwear on the planet, just made them. Taking their cues from moto boots and burnished so they look well loved from day one, they’re exactly what you need in order to add some edge to your cold-weather look.SHOP NOW​Photos: Florence Sullivan Prop styling: Sage LeopoldEsquire Visual Director: James Morris