As we all become more aware of the inequities of fast fashion, the idea of investing in higher quality, timeless design becomes even more appealing. By supporting the labels that put more time, effort, and thought into their products, we not only benefit our own wardrobes with better-looking pieces, we also do our bit to combat fashion’s ongoing problem with waste.

In 2023 we buy and throw away more clothing than ever, making fashion one of the most polluting industries in the world. This goes for our footwear, too. So, it's important to buy shoes that won’t go out of style within the season and are made using premium materials. Timeless footwear is the answer.

However, it can be difficult to know where to begin. Investing in products is a big decision, which is why we’ve hit the net to round up some surefire investment footwear. From Gucci's iconic Horsebit Loafers to derby shoes from Dr. Martens, we back these timeless footwear selections to stay in style for this year and well beyond, as well as not breaking on you when you put them through their paces.

Browse the timeless footwear that you'll be loving for a lifetime below.

The Row Jules Leather Derby Shoes

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Jules Leather Derby Shoes


The Row

Buy at Harvey Nichols

Heading to lunch or a job meeting? Some occasions require you to rock a pair of derbies. With a background of timeless attire, The Row brings a beige pair to ease your outfit choices up.

Off-White™ Sponge Penny Loafers

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Leather Penny Loafers



Buy at Mr Porter

Those on the fence about formal footwear can see themselves in with this playful twist on the style. Off-White™ subverts the classic penny loafer with a military-green sole at the top. Opt for this groundbreaking piece rather than the classic OGs if you want to switch things up.

Gucci Horsebit Leather Loafers

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Horsebit Leather Loafers



Buy at Mr Porter

Since its release in 1953, the Gucci loafer has been the undisputed king of loafers. To this day, the brand's signature piece still runs high as they sell out like hotcakes. You better get your hands on a pair ASAP.

Bottega Veneta Glossed Derby Shoes

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Glossed Leather Derby Shoes


Bottega Veneta

Buy at Mr Porter

Hiking gear is still taking the fashion world by storm and Bottega Veneta knows it. Keeping a classic hiking boot silhouette, the smooth leather paired with turquoise lace will elevate any casual fit.

MM6 Maison Margiela Ankle Boots

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Back Zip Leather Ankle Boots


MM6 Maison Margiela

Buy at Matches

Even if Tabis are an all-time favorite, some are still skeptical about purchasing the unconventional shoes. However, if you are a fan of its shape and cylindrical heel, these might be the ideal alternative for you, thanks to the absence of the split toe.

New Standard Ease Leather Mules

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Ease Leather Mules


New Standard

Buy at Matches

Mules are that grab-and-go pair of shoes we could never get rid of. New Standard cracks the code with these black semi-chunky leather mules. Rock these staples during date night, at the office, or even when grocery shopping.

Marsèll Gommello Derby Shoes

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Navy Gomme Gommello Derbys



Buy at ssense

When it comes to footwear, Marsèll always likes to add some fun to its composition. This pair of navy derby shoes can be crowned as the comfiest of them all, thanks to its rubber sole and smooth leather top.

Dr. Martens 1461 Oxfords

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Black 1461 Oxfords


Dr. Martens

Buy at ssense

These have been a go-to choice for decades, and trust me, 10 years from now, these will still be your go-to choice.

Axel Arigato Blyde Chelsea

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Blyde Chelsea


Axel Arigato

Buy at Axel Arigato

To top the list off, Chelsea boots are another timeless goodie. Axel Arigato looks to super-soft leather uppers to ensure the Blyde Boots are easy to pull on and kick off if you're in a rush.

Want to keep browsing? Download the Highsnobiety app for all the hottest products and brands from the the Highsnobiety Shop. Highsnobiety has affiliate marketing partnerships, which means we may receive a commission from your purchase.

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