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

Both are Eastland penny loafers in leather with rubber soles, but the Classic Penny Loafer is the better-built of the two. It uses hand-sewn one-piece moccasin construction and an OrthoLite moisture-wicking insole, and owners report little to no break-in. The Classic II is the older, plainer version with a basic cushioned insole and a 3.6 out of 5 rating from 22 ratings, which is middling. Buy the Classic Penny Loafer unless you specifically want the Classic II's look or find it in your size.

  • Choose the Classic Penny Loafer if you want the more comfortable, better-made loafer for all-day wear at work or while traveling.
  • Choose the Classic II if you prefer its simpler stitched look and want a basic leather slip-on.

Prices

  • Eastland Women's Classic Penny Loafer: $67.00 at Poshmark (last seen Nov 9)
  • Eastland Classic II Loafers: $39.99 at eBay (last seen Nov 7)
  • Difference: the Eastland Classic II Loafers is $27.01 cheaper than the Eastland Women's Classic Penny Loafer at the latest prices (Nov 7 and 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 23 h ago
See all prices and details
Visit Poshmark
Pros
  • Hand-sewn one-piece leather upper flexes with the foot
  • OrthoLite insole wicks moisture and stays cool
  • Little to no break-in period
  • Polished leather works with both casual and dress outfits
  • Lightweight rubber sole with reliable traction
Cons
  • Runs large, so you likely need a half size down
  • Polished leather shows scuffs more than matte finishes
  • Only one colorway described
Eastland
Eastland Women's Classic II Loafers

Eastland Classic II Loafers

Eastland Women's Classic II Loafers

3.6(22 ratings)
$39.99at eBayChecked Nov 7
See all prices and details
Visit eBay

Store links may earn us a commission.

Pros
  • Classic penny holder styling
  • Leather upper with rubber outsole
  • Simple slip-on for everyday wear
  • White stitching adds visual detail
Cons
  • Basic cushioned insole, no moisture control
  • Stitched upper takes longer to soften
  • Rated only 3.6 out of 5 by owners
  • No sizing guidance, so fit is a gamble

What separates them

Eastland Women's Classic Penny LoaferEastland Classic II Loafers
ConstructionHand-sewn from one piece of leather, moccasin styleStandard stitched leather upper
InsolePadded OrthoLite with moisture-wicking technologyBasic cushioned insole
Break-inOne-piece construction gives a near break-in-free fitStiffer stitched upper, needs some wear to soften
Sizing guidanceRuns large; most shoppers order a half size downNo sizing guidance given; order your usual size
OutsoleLightweight flexible rubberRubber
Heel7/8 inch stacked lookFlat
Owner feedbackLong-standing classic with a reputation for comfort3.6 out of 5 from 22 ratings
StylingPolished smooth leather, round toeBrown leather with white stitching detail

Price history

$72.00$39.99
Nov 7Nov 10
  • Eastland Women's Classic Penny Loafer: lowest $67.00 on Nov 10 at Poshmark.
  • Eastland Classic II Loafers: lowest $39.99 on Nov 7 at eBay; $72.00 on Nov 10.

Prices at every store

Eastland Women's Classic Penny Loafer

  • PoshmarkNew

    In stock

    $67.00+ $6.49 shippingChecked 23 h ago
    Visit Poshmark
  • EastlandNew

    In stockReturn policy

    $115.00Checked 23 h ago
    Visit Eastland
All 2 stores and price history →

Eastland Classic II Loafers

  • eBayNew

    In stockSold by imagicbox

    $39.99Free shippingChecked Nov 7
    Visit eBay
  • JCPenneyNew

    In stock

    $80.00Free shippingChecked Nov 9
    Visit JCPenney
  • QVCNew

    In stock

    $84.98+ $8.95 shippingChecked Nov 9
    Visit QVC
  • AmazonNew

    Availability unknown

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

    $72.00Free shippingChecked Nov 9
    Visit Amazon

Store links may earn us a commission.

All 21 stores and price history →

Specs compared

SpecEastland Women's Classic Penny LoaferEastland Classic II Loafers
Upper materialSmooth, polished leather—
InsolePadded OrthoLite® comfort insole with patented …—
ConstructionHand-sewn from one piece of leather—
OutsoleLightweight rubber outsole—
Heel height7/8"—
FitMost customers prefer ordering this style a hal…—
Product weight2 lb—
Toe styleRound-toe—

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 Loafers

  • 3.6 / 522 ratings

Questions and answers

Which is more comfortable for standing all day?
The Classic Penny Loafer. Its OrthoLite insole cushions and wicks moisture, and the one-piece hand-sewn upper flexes instead of pressing on the foot. The Classic II has a plain cushioned insole and a stiffer stitched upper.
Which one lasts longer?
The Classic Penny Loafer. One-piece moccasin construction has fewer seams to split, and the leather is described as polished and easy to maintain. The Classic II is a simpler stitched build.
Do they fit the same?
No. Eastland says most shoppers order the Classic Penny Loafer a half size smaller. No sizing guidance is given for the Classic II, so start with your usual size there.
Is the Classic II worth stepping down to?
Only if you prefer its brown leather with white stitching look. On comfort, construction and owner ratings, the Classic Penny Loafer is the stronger shoe.
Can either be worn with dress clothes?
Yes. Both are leather penny loafers that pair with slacks or a skirt. The Classic Penny Loafer's polished leather reads dressier; the Classic II's contrast stitching is more casual.
Are these true penny loafers?
Yes. Both have the saddle with the penny holder across the vamp, a leather upper and a flat rubber sole.

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