10 Timeless Footwear Options to Invest In
In an era where trends move faster than ever, the allure of footwear that actually lasts in terms of both quality and style feels more relevant than ever. Pieces crafted with care aren’t just built to endure, they also carry a kind of timeless appeal that transcends seasonal shifts.
While 2025 offers no shortage of flashy sneaker drops and micro-trends, the truth is that the shoes you’ll reach for again and again are the best ones. Footwear that can stand up to daily wear while still feeling sharp years down the line is worth the investment.
To help cut through the noise, we’ve rounded up some perennial heavy hitters in the world of well-designed shoes. Consider this your shortcut to shoes that don’t just look good for a season, but keep earning their place in your rotation well into the future.
Browse the timeless footwear that you'll be loving for a lifetime below.
Brunello Cucinelli Derby Shoes
Heading to a business lunch or job meeting? Some occasions require you to rock a pair of dapper derbies. With its history of fine Italian attire, Brunello Cucinelli's rich burgundy pair can be trusted to carry you through the many important, formal get togethers to come.
Paraboot Michael
On the fence about footwear as formal as the above? Something more playful, less severe, but never mismatched, like one of Paraboot's classic Michael shoes, could be for you.
Sebago Classic Loafers
Since its founding in 1946, the Maine-born loafer and boat shoe brand Sebago has been a quiet king of both categories. To this day, the brand's signature easy-on models sell like hotcakes and for good reason.
Fracap Commando Boot
The M128 Commando Sole Scarponcino Boot is a standout model from the Italian heritage brand Fracap, renowned for its commitment to artisanship. Handmade in Italy, these suede hiking boots exemplify quality, durability, and creativity in one.
Jacquemus Derbies
Despite a reputation for more, say, leisurely aesthetics, Jacquemus can do serious, too, as evidenced by its no-nonsense lace-up shoes. And here you thought it was all sun hats, linens, and beach bags.
Our Legacy Mule Loafers
Mules are that grab-and-go pair of shoes we could never get rid of, and Our Legacy really cracked the code with these black buckled leather camion clogs. Rock these during date night, office hours, or even when grocery shopping.
Officine Creative Boots
A black lace up boot is the sort of shoe you won't necessarily think of first thing when it comes to versatility, but you may be surprised to find will come in handy for many an occasion or weather condition.
Dr. Martens 1461 Oxfords
A go-to choice for longer than you've been alive, Docs'll probably remain go-tos long past your lifetime, too.
Hereu Loafers
Last but not least, something a little more extravagant. Hereu's Mary Jane-esque loafers are special, to say the least, but no less timeless because of it. A long-treasured statement shoe, this purchase will call out to you for what one can assume will be some of the better days of your life.
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