SSENSE smart shoes 001 Gucci Maison Margiela Rick Owens

Putting a smile on grandmas face this holiday season might mean straying from your regular rotation in place of something with a bit more class. And, with fashion houses such as Balenciaga showing runways without a sneaker in sight for their SS19 shows, there’s never been a better time to shoehorn a quality pair of derbies, oxfords, loafers, or Chelsea boots onto your shopping list.

Where to shop for said shoes? The SSENSE winter sale has already hit markdowns of up to 60 percent off, and is home to some of the most fashion-forward smart shoes around. Discounting thousands of pieces online right now, the sale’s footwear offering spans brands such as Marni, OAMC, and Maison Margiela.

Having naturally already whiled away hours browsing through its sale pages, we’ve brought you some of the sartorial highlights alongside full-price offerings for the season to come. Our selection includes a pair of navy derbys by Dr. Martens x Engineered Garments — sure to stride into your everyday rotations during the winter months you’re preserving boxfresh kicks in — alongside super steezy Gucci loafers with signature green and red webbing, and some characteristically gothic Rick Owens ankle boots which are now half off.

Browse through all our picks below, and click through in time to shop for all your family get-togethers over the holidays.

Chunky Derbys



Buy at ssense

Cutaway Oxfords



Buy at ssense

Croc Voleur Derbys



Buy at ssense

1461 Smith Derbys


Dr. Martens x Engineered Garments

Buy at ssense

Patent Patty Loafers



Buy at ssense



Toga Virilis

Buy at ssense

Web Horsebit Loafers



Buy at ssense

Classic Longwing Brogues


Thom Browne

Buy at ssense

Ankle Boots


Maison Margiela

Buy at ssense

Creeper Chelsea Boots


Rick Owens

Buy at ssense

Now, check out our recent Op-Ed on why every sneakerhead needs a pair of formal shoes.

To stay up to date with more Shopping content from Highsnobiety, follow @Highsnobietyshopping on Instagram and @Highsnobdrops on Twitter.

Our designated shopping section features products that we love and want to share with you. Highsnobiety has affiliate marketing partnerships, which means we may receive a commission from your purchase.

Words by Aaron Toumazou
E-Commerce Editor