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



Cutaway Oxfords



Croc Voleur Derbys



1461 Smith Derbys

Dr. Martens x Engineered Garments


Patent Patty Loafers




Toga Virilis


Web Horsebit Loafers



Classic Longwing Brogues

Thom Browne