Is the Eastland Classic II true to size?

Most owners say it fits close to size, though some find it runs slightly large. If you are between sizes or plan to wear thick socks, consider sizing down.

Is $104.99 a good price for the Classic II?

DSW lists it at $104.99 as of November 7, 2026, and it is the only new listing we track. With one seller, there is no lower competing price to compare against right now.

What is the upper made of?

The upper is leather, and the outsole is rubber. The insole is OrthoLite foam for cushioning.

Can I wear these loafers all day?

Yes. The cushioned OrthoLite insole and rubber outsole make them suitable for long days on your feet, though the leather may need a short break-in.

What sizes and colors are available?

This listing is for a US size 9 in black. Availability in other sizes and colors depends on the store.

Where is the Eastland Classic II cheapest?

At DSW, for $104.99, as of our latest check.

Eastland Classic II

Best price now

$104.99at DSWObserved at 8:33 AM

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Our take on the Eastland Classic II

The Eastland Classic II is a women's penny loafer in smooth leather with a rubber outsole and an OrthoLite cushioned insole. It is a classic, low-profile slip-on built for all-day wear at work or on weekends. The best new price is $104.99 at DSW as of November 7, 2026, and only one store currently lists it new, so comparison shopping is limited.