The wisest sartorial statements are the ones that are perennially in style, go with just about everything, and are made with lasting quality. Some luxury makers are better at rising to this challenge than others, of course. The ones that do are able to create high-end, but everyday companions that can be seasonally tweaked, but no matter which make or model you buy you can rest assured they’ll endure.

To round out the perfect masculine ensemble, a go-to watch, shoe, and bag are always de rigueur. Some of the season’s best straightforward examples came from brands like Cartier and Jaeger-LeCoultre, whose respective Tank and Reverso models are as current as they were at their dawn in the early 20th century, while Patek Philippe’s annual calendar has been the benchmark for all others since its inception in the early ’90s. Small updates in sizing, bracelet styles, or hues give them a refresh without rewriting the look.

Meanwhile, once you’ve got the time sorted, you’ve got to pound the pavement. And what better way than in effortless style? The Hermès Sac à Dépêches Togo or the Berluti’s calf-leather boots will instantly smarten up your suit or your weekend look. And Mark Cross’s sleek and soft leather gloves will carry any wardrobe through the brisker seasons.

Even if your style leans far from traditional, classics will always be a necessity no matter your style. Consider investing in pieces that will carry on year-after-year, and, in the case of your watch…potentially, well into the next generation.

Jaeger-LeCoultre 45.6 mm by 27.4 mm Reverso Tribute Monoface Small Seconds in 18-karat pink gold, $41,300; Dries Van Noten gray wool blazer, $1,365; Hermès white satin shirt, $1,425; Loro Piana black calf-leather shoes, $1,280.

Patek Philippe 38 mm Annual Calendar Ref. 4946R-001 in 18-karat rose gold, $66,863; Ferragamo suede tote bag, $2,950.

Prada buckle leather bag (styled with additional belts), $7,300; Mark Cross vachetta leather belt, $575; Canali calfskin-leather belt, $350.

A. Lange & Söhne 34 mm 1815 in 18-karat white gold, price upon request; Dior wool jacket, $2,600, and cashmere sweater, $1,400; Mark Cross nappa leather gloves, $720.

Cartier 33.7 mm by 25.5 mm Tank Louis Cartier in 18-karat rose gold, $13,500

Berluti black calf-leather boots, $2,600

Chopard 41 mm Alpine Eagle in Lucent Steel, $15,500; IWC 40 mm Ingenieur Automatic in stainless steel, $12,300.

Vacheron Constantin 42.5 mm Patrimony Moon Phase Retrograde Date in 18-karat white gold, $55,000, limited to 270; Louis Vuitton men’s black leather jacket, $5,900.

Photo Assistant: Timothy Mulcare / Fashion Assistant: Ari Stark / Model: Bek Markas