Gift giving season is officially here and if you’re stuck for ideas, we’ve got you. From last-minute gifts to what to get the sneaker obsessed in your life, The Highsnobiety Gift Guide has gathered the best products from across the internet, so no one will be disappointed when the wrapping comes off.

The phrase “beauty is in the eye of the beholder,” has never rung more true than when it comes to sneakers. That’s why we’re of the belief that when it comes to gifting sneakers — especially expensive sneakers — you’re better off buying them for yourself.

Besides the fact that purchasing sneakers is an intimate and fun experience, some kicks can end up running the bill into the hundreds (or even thousands) really quickly. Unless your parents are multi-billionaires (and even then), it can be a little weird to ask for such expensive sneakers as gits. But if you have the money and the itch to add a grail-worthy pair of shoes to your rotation, we’ve rounded up some of the best expensive sneakers to shop ahead of the upcoming Holiday season below.

We’ve focused mainly on expensive sneakers for men, though many of the options below are available in unisex sizing and can easily be worn by anyone. That’s the beauty of sneaker culture: if the shoe fits, everything else falls into place. Our selection is made up of sneakers that can be bought on the resale market, as well as a number of options from expensive sneaker brands, such as Maison Margiela, visvim, or Rick Owens.

Before you read on, note that some of these sneakers are worth more than a small car or a down payment on a house. We’re not actually recommending that you spend your life savings on any of these sneakers, but we know that sneakerheads are always on the search for grails. If you feel comfortable parting with the cash, or even just want to scroll through a list of super-expensive sneakers that may or may not be worth their price tags, enjoy.

The Best Expensive Sneakers to Treat Yourself to This Holiday Season

Tom Sachs x NikeCraft Mars Yard 2.0

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Mars Yard Shoe 2.0 Tom Sachs Space Camp



Buy at StockX

Tom Sachs ongoing partnership with Nike has resulted in multiple grail-level sneakers. We’ve chosen the 2.0 because we think it’s his best design to date that has been made publically available (the 2.5 was tested earlier this year but not been released just yet). As far as expensive sneakers go, this pair is definitely worth the money, as Sachs and his team put in a lot of effort to make sure the shoe holds up, meaning you can wear this pair without worrying about it getting too beat up.

Maison Margiela Replica “Paint Drop”

Replica Paint Drop Sneakers


Maison Margiela

Buy at Highsnobiety

Maison Margiela’s Replica sneaker is a grail for many that started collecting sneakers in the past 10-15 years. The sneaker is an absolute classic, inspired by the German Army Trainer, and oozes luxury. It’s no-frills and marries some of the best materials with interesting (yet understated) colorways.

Off-White™ Nike Air Jordan 1 “Chicago”

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Air Jordan 1 Retro High 'Chicago'


Nike x Off-White™

Buy at StockX

We couldn’t leave Virgil Abloh and his first Jordan Brand collaboration off this list now, could we? Everything, from the hype, to the resale price, to the iconic colorway makes this a grail. The price has only risen since its release in 2017.

JJJJound x New Balance 990v4

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New Balance x JJJJound

Buy at StockX

JJJJound has collaborated with New Balance on a number of sneakers — most recently another 990 and before that a 992 — but this gray 990v4 is perhaps the creative’s best. If you’re looking for underrated (but still expensive) grail-level sneakers, you’ve come to the right place.

Raf Simons Cylon-21

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Cylon 21


Raf Simons

Buy at Highsnobiety

Raf Simons’ new (RUNNER) line hasn’t hit the mainstream just yet, though we’re still convinced that it will eventually. The maestro’s adidas Ozweego collaboration also took a few years before it blew up. This pair is much more luxury-leaning than the Three Stripes collab, however, and may be a good long-term investment.

visvim FBT Lhamo Folk

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Fbt Lhamo-Folk Shoes



Buy at Slam Jam

No one does quality craftsmanship better than visvim, which is reflected in the exorbitant price tags. The FBT Lhamo Folk is an absolute classic, brought to the mainstream by Kanye West and John Mayer. While other sneakers are grails for their hype or clout status, visvims are grails because they make amazing products.

adidas YEEZY Boost 750 OG

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YEEZY Boost 750 OG


adidas Originals

Buy at StockX

If there was one adidas YEEZY to own, it would be the original YEEZY Boost 750 from 2015. The sneaker is Kanye’s first with adidas and therefore literally a piece of history. Only a handful were released, so you’d be one of very few to have a pair in your rotation.

AFEW x ASICS GEL-Lyte 3 “Koi”

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Gel-Lyte 3 "Koi" (Regular Box)


ASICS x Afew

Buy at StockX

Back in the late ’00s and early 2010s, retro runners from the likes of ASICS and New Balance were selling like hot cakes. One of the best releases from that era was the AFEW x ASICS GEL-Lyte 3 “Koi.” If you’re one of the many sneakerheads that live and die by low-top retro runners, this may be the grail for you.

Rick Owens High Top Geobasket

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High Top Geobasket Sneakers


Rick Owens

Buy at Farfetch

All of Rick Owens’ sneakers are grail-worthy, but his High Top Geobasket has proven to be a favorite amongst his fans. Jump into the world of Rick Owens with these all-black sneakers.

Lanvin Curb

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Zig Zag Curb Sneakers

from $890


(Available at 2 Merchants)
(Available at 2 Merchants)

The Curb is Lanvin’s best sneaker in a long while, because it taps into the current ’00s skate trend and offers something that is both familiar and fresh. As it’s luxury, the price tag is maybe not the most digestible, but this is a roundup of expensive sneakers, isn’t it?

Dior B27

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B27 Low-Top Sneaker



Buy at 24S.com

Dior’s B27, similar to the Curb above, is the perfect marriage of skate and luxury. Dior is currently one of the most aspirational luxury sneaker brands on the market, and the B27 is one of the brand’s most wearable.

adidas Stan Smith “Colette”

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Stan Smith


adidas x Colette

Buy at StockX

Similar to the OG adidas YEEZY Boost 750, this Colette Stan Smith is a piece of history. The iconic Parisian concept store may not exist anymore, but its essence lives on forever in these shoes.

Miharayasuhiro Peterson

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Peterson Low Sneakers



Buy at Slam Jam

If you’re looking for something a little different — but still with a grail-level price tag — Maison Miharayasuhiro’s creations are one of a kind. The designer takes classic designs and gives them a melted effect, which will definitely be a conversation starter wherever you wear them.

The Row Dean Slip-On

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Dean Slip-On Sneakers


The Row

Buy at ssense

How much can a slip-on cost? Nearly $800 according to The Row.

Want to keep browsing? Head to the Highsnobiety Shop for more products that we love.

To stay updated on everything happening in the sneaker world, check out the best sneakers to add to your rotation this week, follow @highsnobietysneakers on Instagram, and sign up to our newsletter for early access to the best drops sent straight to your inbox.

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