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Eastland Women's Classic Penny Loafer vs Eastland Classic II Penny Loafer

Both are Eastland penny loafers in polished leather with OrthoLite insoles, so the choice comes down to fit and finish. The Classic II adds a slightly taller block heel, a moc toe with penny slot, and comes in wide widths, which suits women who need room across the forefoot. The Classic Penny Loafer is the simpler, lighter, hand-sewn one-piece build with a lower 7/8-inch heel and a round toe, and owners say it needs little break-in. Buy the Classic II if you want a wide fit or a bit more heel; buy the Classic Penny Loafer if you want the lighter, more flexible everyday shoe.

  • Choose the Classic Penny Loafer if you want a lighter, lower-heeled loafer with a flexible hand-sewn one-piece leather build and a round toe.
  • Choose the Classic II Penny Loafer if you need a wide width, prefer a 1-inch block heel, or want the classic moc-toe penny-slot look.

Prices

  • Eastland Women's Classic Penny Loafer: $67.00 at Poshmark (last seen Nov 9)
  • Eastland Classic II Penny Loafer: $72.00 at Zappos.com (last seen Nov 9)
  • Difference: the Eastland Women's Classic Penny Loafer is $5.00 cheaper than the Eastland Classic II Penny Loafer at the latest prices (Nov 9)
Eastland
Women's Classic Penny Loafer

Eastland Women's Classic Penny Loafer

Women's Classic Penny Loafer

5(2 ratings)
$67.00at PoshmarkChecked 22 h ago
See all prices and details
Visit Poshmark
Pros
  • One-piece hand-sewn leather needs almost no break-in
  • Light on the foot with a flexible rubber outsole
  • OrthoLite insole wicks moisture for all-day wear
  • Low 7/8-inch heel suits long days on your feet
Cons
  • Only standard width, so wide feet may feel pinched
  • Runs large; many need to size down half a size
  • Round toe is plainer than a moc-toe look
Eastland
Eastland Classic II Penny Loafer

Eastland Classic II Penny Loafer

4(236 ratings)
$72.00at Zappos.comChecked 22 h ago
See all prices and details
Visit Zappos.com
Pros
  • Wide width option fits fuller feet
  • 1-inch block heel gives a little lift without instability
  • Classic moc-toe penny-slot styling
  • Cork and OrthoLite insole molds to the foot over time
Cons
  • Synthetic lining is less breathable than leather
  • Heavier than the Classic Penny Loafer
  • Rated 4 out of 5 from 236 ratings, so some owners report fit issues

What separates them

Eastland Women's Classic Penny LoaferEastland Classic II Penny Loafer
ConstructionHand-sewn from one piece of leather, wraps the foot with minimal break-inMoc-toe silhouette with decorative penny slot; standard stitched build
Heel7/8-inch heel, low and flat1-inch block heel
Width optionsStandard width onlyAvailable in wide
WeightAbout 2 lb per pair, lightweight rubber outsoleHeavier feel from the block heel and rubber/synthetic outsole
InsolePadded OrthoLite with moisture controlCork and OrthoLite combination
LiningLeather-lined upperSynthetic lining
Toe shapeRound toeMoc toe
Sizing noteMost customers order a half size smallerRuns true to size for many, with wide fit available

Price history

$99.99$67.00
Nov 7Nov 10
  • Eastland Women's Classic Penny Loafer: lowest $67.00 on Nov 10 at Poshmark.
  • Eastland Classic II Penny Loafer: lowest $72.00 on Nov 10 at Zappos.com.

Prices at every store

Eastland Women's Classic Penny Loafer

  • PoshmarkNew

    In stock

    $67.00+ $6.49 shippingChecked 22 h ago
    Visit Poshmark
  • EastlandNew

    In stockReturn policy

    $115.00Checked 22 h ago
    Visit Eastland
All 2 stores and price history →

Eastland Classic II Penny Loafer

  • Zappos.comNew

    In stock

    $72.00Free shippingChecked 22 h ago
    Visit Zappos.com
  • 6pm.comNew

    In stock

    $79.97+ $3.95 shippingChecked 22 h ago
    Visit 6pm.com
  • Nordstrom RackNew

    In stock

    $79.97+ $9.95 shippingChecked 22 h ago
    Visit Nordstrom Rack
  • AmazonNew

    Availability unknown

    As an Amazon Associate, Deal.ai earns from qualifying purchases.

    $72.00Free shippingChecked 22 h ago
    Visit Amazon
All 16 stores and price history →

Specs compared

SpecEastland Women's Classic Penny LoaferEastland Classic II Penny Loafer
Upper materialSmooth, polished leatherLeather
InsolePadded OrthoLite® comfort insole with patented …Cork, Ortholite
OutsoleLightweight rubber outsoleRubber, Synthetic
Heel height7/8"1.0
ConstructionHand-sewn from one piece of leather—
FitMost customers prefer ordering this style a hal…—
Product weight2 lb—
Toe styleRound-toe—
Size (US)—11, 8
Fastening—Slip-On
Color—Blue, Natural
Heel Type—Block Heel
Show all 16 specsShow fewer specs
SpecEastland Women's Classic Penny LoaferEastland Classic II Penny Loafer
Age Group—Adult
Lining—Synthetic
Gender—Female
Width—Wide

What reviewers say

Eastland Women's Classic Penny Loafer

Owners of Eastland's hand-sewn loafers generally praise the soft, flexible leather and the easy, almost break-in-free fit. Complaints center on sizing, with many saying the shoe runs about a half size large, and on modest cushioning for long days standing.

What people mention
  • SizingCriticisedMany owners say the loafer runs about a half size large and recommend ordering down.
  • ComfortPraisedBuyers describe the padded insole and soft leather as comfortable for all-day wear.
  • Break-inPraisedThe hand-sewn one-piece upper is reported to feel broken in almost immediately.
  • CushioningMixedSome find the footbed thin for long stretches on hard floors.

Eastland Classic II Penny Loafer

  • 4 / 5236 ratings

Questions and answers

Which is better for wide feet?
The Classic II. It comes in wide widths, while the Classic Penny Loafer is standard width only. If your forefoot is broad, start with the Classic II in wide.
Which needs less break-in?
The Classic Penny Loafer. Its one-piece hand-sewn leather wraps the foot and owners report a nearly break-in-free fit. The Classic II's stiffer moc-toe build takes a few wears.
Which is better for standing all day?
The Classic Penny Loafer is lighter and has the lower heel, which most people find easier for long shifts. The Classic II's cork insole molds to the foot but the block heel adds weight.
Should I size down in either?
Size down a half size in the Classic Penny Loafer; most customers do. The Classic II generally runs true to size, so order your usual size, going wide if you are between widths.
Is the Classic II worth stepping up to?
Yes if you need a wide fit, want a bit more heel, or prefer the moc-toe penny-slot look. Otherwise the Classic Penny Loafer is the lighter, more flexible everyday pick.
Which lasts longer?
Both use leather uppers and rubber outsoles and hold up similarly with care. The Classic II's cork insole can be replaced or re-cupped by a cobbler, which can extend its life.

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