The Dark Academia Shoe Edit: Loafers, Oxfords & Mary Janes

Autumn 2025 is bringing all the moody, intellectual dark academia vibes. 

Dark academia is a romantic, vintage-inspired style rooted in classic literature, old-school fashion, and a love of learning. Fall is the perfect time to lean into its muted tones, prep-school looks, and moody library vibes. Are we in 2025 or 1985? Who can say!

Of course, no dark academia outfit is complete without the right footwear. You won’t find trendy brown sneakers here. This aesthetic calls for something classic, refined, and a little mysterious.

We fell deep into the dark academia rabbit hole on social media and uncovered the best shoes to complete the look. Think timeless loafers, leather oxfords, romantic Mary Janes, and ankle boots that could pass as part of a literature professor’s uniform.

These shoes pair effortlessly with tweed blazers, pleated skirts, high socks, or wide-leg trousers. Whether you’re sipping coffee in an old bookstore or walking to class under gray skies, these shoes will complete your fantasy. Plus, they start at just $27!

We can’t get over the perfect burgundy color of these Mary Jane ballet flats. They’re also available in black, chestnut, and leopard. Runs up to size 11.

You’d better smash the “add to cart” button if you want to get a great deal on these Oxford dress shoes. They run up to size 11.

All three colors of these classic loafers are perfect for the dark academia vibe. Plus, they’re deeply discounted right now. Runs from size 5 to 12.

These must-have Mary Janes just stepped out of your dark academia dreams and into your fall wardrobe. 

Bring the vintage-inspired trend into 2025 with these square-toe boots. They’re on sale!

These Oxford boots give off a scholarly vibe. Choose from three colors. Runs up to size 11.

These faux-leather chunky heel loafers feature a cushioned foot bed for all-day comfort, which is especially key if you spend your days wandering around a university library (or even just your local branch). 

The E! Insider Shop editors and writers search the internet to find the best products out there. We interview expert sources, comb through customer reviews, and use our own personal experiences to make shopping easier for our readers.

As an editorial team, we independently create content and determine coverage based on research, reporting and what we think our readers would like to read about. The goal of our content is to provide a service and inform readers who are on the hunt for the latest products to help make their life better. Items are sold by retailer, not E!. Pricing and availability are accurate as of publish time.