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.

What To Read Next

*If you submitted your e-mail address and placed an order, we may use your e-mail address to inform you regularly about similar products without prior explicit consent. You can object to the use of your e-mail address for this purpose at any time without incurring any costs other than the transmission costs according to the basic tariffs. Each newsletter contains an unsubscribe link. Alternatively, you can object to receiving the newsletter at any time by sending an e-mail to info@highsnobiety.com

Web Accessibility Statement

Titelmedia (Highsnobiety), is committed to facilitating and improving the accessibility and usability of its Website, www.highsnobiety.com. Titelmedia strives to ensure that its Website services and content are accessible to persons with disabilities including users of screen reader technology. To accomplish this, Titelmedia has engaged UsableNet Inc, a leading web accessibility consultant to help test, remediate and maintain our Website in-line with the Web Content Accessibility Guidelines (WCAG), which also bring the Website into conformance with the Americans with Disabilities Act of 1990.


Please be aware that our efforts to maintain accessibility and usability are ongoing. While we strive to make the Website as accessible as possible some issues can be encountered by different assistive technology as the range of assistive technology is wide and varied.

Contact Us

If, at any time, you have specific questions or concerns about the accessibility of any particular webpage on this Website, please contact us at accessibility@highsnobiety.com, +49 (0)30 235 908 500. If you do encounter an accessibility issue, please be sure to specify the web page and nature of the issue in your email and/or phone call, and we will make all reasonable efforts to make that page or the information contained therein accessible for you.