Is the Eastland Classic II true to size?

Eastland loafers generally run true to size, but leather uppers can feel snug at first. If you are between sizes or have a wide foot, try the larger size.

Does the Classic II need breaking in?

Yes. The leather upper softens over the first week or two of wear. The Ortholite insole is cushioned from the start.

Can I wear the Classic II to work?

It suits casual offices and everyday wear. The rubber sole and soft leather make it less formal than a dress loafer.

What is the Classic II made of?

A leather upper, an Ortholite insole and a rubber outsole. It is a slip-on with no laces.

When is the best time to buy the Classic II?

The best new price found is $104.99 at DSW as of November 7, 2026. Check the price history before buying to see whether it has dropped lower.

Where is the Eastland Classic II Jet Black cheapest?

At Amazon, for $74.47, 19% under what the other stores charge, as of our latest check.

Where can I buy the Eastland Classic II Jet Black?

6 stores we checked sell it, including JCPenney, Kohl's, Belk, Famous Footwear, Amazon.

Eastland Classic II Jet Black

Best price now

$74.47at AmazonObserved at 8:19 AM

19% under what the other stores charge

Compared across 5 stores. Prices are checked against each store and labelled with when.

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Our take on the Eastland Classic II Jet Black

The Eastland Classic II is a women's slip-on penny loafer in black leather with a cushioned Ortholite insole and a rubber outsole. It is a casual, everyday shoe built for comfort rather than dress wear. The best new price is $104.99 at DSW as of November 7, 2026, the only new price found.