StoreDeal.ai store
Shop
  • Deals
  • Deal checker
  • Black Friday
  • Buying guides
  • Brands
  • Stores
Travel
  • Flight deals
  • Hotel deals
Company
  • Research
  • Press
  • deal.ai apps
Black Friday 2026
  • Walmart
  • Best Buy
  • Target
  • TVs
  • Laptops
  • Headphones
  • Apple
  • Gaming
  • Vacuums
  • Kitchen
  • Toys
  • Smartwatches
  • Tablets
  • Furniture
  • Mattresses
© Deal.ai Inc.
TermsPrivacy
Deal.ai › Compare

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

Both are Eastland leather loafers, but they are different shoes for different jobs. The Classic Penny Loafer is the dressier, more cushioned pick: hand-sewn one-piece moccasin construction, an OrthoLite insole and a 7/8-inch heel. The Sawgrass is a flatter, lighter driver-style loafer with a chain-link vamp, a foam footbed and a quarter-inch platform. Owners of the Classic praise the soft, near break-in-free leather; the Sawgrass draws people who want a casual slip-on with a bit of shine.

  • Choose the Classic Penny Loafer if you want a polished, cushioned loafer for the office and everyday wear, and you can size down a half size.
  • Choose the Sawgrass if you want a flat, casual driver-style loafer with a chain-link detail and a low platform.

Prices

  • Eastland Women's Classic Penny Loafer: $67.00 at Poshmark (last seen Nov 9)
  • Eastland Sawgrass Women's Loafers: $48.00 at eBay (last seen Nov 7)
  • Difference: the Eastland Sawgrass Women's Loafers is $19.00 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 little break-in
  • OrthoLite insole wicks moisture and stays comfortable all day
  • Polished leather works with office and dressier outfits
  • Round toe and penny strap are a classic, versatile shape
Cons
  • Runs large, so many buyers need a half size down
  • Higher 7/8-inch heel than a true flat
  • Smooth leather shows scuffs more than textured finishes
Eastland
Eastland Sawgrass Women's Loafers

Eastland Sawgrass Women's Loafers

4(6 ratings)
$48.00at eBayChecked Nov 7
See all prices and details
Visit eBay

Store links may earn us a commission.

Pros
  • Flat, low platform is easy to walk in
  • Chain-link vamp adds detail to a casual outfit
  • Memory foam footbed cushions the step
  • Cotton lining and rubber pods suit everyday wear
Cons
  • Memory foam packs down faster than OrthoLite
  • Chain-link detail is casual and less office-appropriate
  • Cotton lining wears sooner than leather

What separates them

Eastland Women's Classic Penny LoaferEastland Sawgrass Women's Loafers
ConstructionHand-sewn moccasin from one piece of leatherStandard moc-toe with tonal stitching
InsolePadded OrthoLite with moisture controlMemory foam footbed
Heel and platform7/8-inch heel, no platform0.25-inch heel and 0.25-inch platform
StylePlain penny loafer, dressierChain-link vamp, casual driver look
OutsoleLightweight rubberRubber with driver-style pods
LiningLeather-lined moccasinCotton lining
SizingRuns large; order a half size smallerStandard US women's sizing
WeightAbout 2 lb per pairLighter flat build

Price history

$67.00$47.99
Nov 7Nov 10
  • Eastland Women's Classic Penny Loafer: lowest $67.00 on Nov 10 at Poshmark.
  • Eastland Sawgrass Women's Loafers: lowest $47.99 on Nov 7 at Walmart; $62.99 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 Sawgrass Women's Loafers

  • eBayNew

    In stockSold by presto_shopping

    $48.00Free shippingChecked Nov 7
    Visit eBay
  • BlueflyNew

    In stock

    $47.99+ $4.99 shippingChecked Nov 7
    Visit Bluefly
  • PoshmarkNew

    In stock

    $48.00+ $6.49 shippingChecked Nov 7
    Visit Poshmark
  • ModeSensNew

    In stock

    $48.00+ $12.00 shippingChecked Nov 7
    Visit ModeSens

Also available at

  • WalmartCheck price at Walmart

Store links may earn us a commission.

All 9 stores and price history →

Specs compared

SpecEastland Women's Classic Penny LoaferEastland Sawgrass Women's Loafers
Upper materialSmooth, polished leatherLeather
InsolePadded OrthoLite® comfort insole with patented …Foam
OutsoleLightweight rubber outsoleRubber
Heel height7/8"0.25 in
Toe styleRound-toeClosed Toe
ConstructionHand-sewn from one piece of leather—
FitMost customers prefer ordering this style a hal…—
Product weight2 lb—
Brand—Eastland
Color—Black
Shoe width—Medium
Casual & dress shoe style—Loafers
Show all 39 specsShow fewer specs
SpecEastland Women's Classic Penny LoaferEastland Sawgrass Women's Loafers
Material—Leather
Shoe heel style—Thin
Shoe closure—Slip-On
Clothing occasion—Casual
Age group—Adult
Shoe category—Women's Shoes
Heel height style—Flat Heel
Shoe size system—US Women's
Gender—Female
Gore-Tex

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 Sawgrass Women's Loafers

Owner feedback on the Sawgrass is limited, but the pattern matches Eastland's other slip-on loafers: buyers like the soft leather and easy on-off, and some find the fit runs narrow or needs breaking in.

What people mention
  • FitMixedSome owners say the medium width runs snug, especially across the instep, while others find it true to size.
  • ComfortMixedThe memory foam footbed is liked for short wear, but the thin sole draws complaints for long days.
  • LeatherPraisedBuyers describe the upper as soft and quick to break in.
  • Chain detailMixedThe gunmetal chain is a selling point, though a few say it snags hosiery and socks.

Questions and answers

Which is better for wearing to an office?
The Classic Penny Loafer. Its polished leather, leather lining and 7/8-inch heel read dressier, and the OrthoLite insole holds up over a long day. The Sawgrass chain-link detail is casual.
Which is more comfortable for long days on your feet?
The Classic Penny Loafer. The OrthoLite insole manages moisture and the hand-sewn upper flexes with the foot. The Sawgrass memory foam feels soft at first but compresses over time.
Do the Classic Penny Loafer and the Sawgrass fit the same?
No. Eastland says most customers order the Classic Penny Loafer a half size smaller. The Sawgrass follows standard US women's sizing, so start with your usual size there.
Which lasts longer?
The Classic Penny Loafer. Its one-piece hand-sewn leather upper and leather lining outlast the Sawgrass cotton lining and foam footbed, which break down sooner with daily wear.
Is the Sawgrass worth stepping up to over the Classic?
Only if you want a flat, casual driver-style shoe with a chain-link detail. For a cushioned, dressier loafer, the Classic Penny Loafer is the stronger pick.

Ask our shopping agent

It checks today's price at every store, compares the alternatives and answers in about a minute.

Enter to send, Shift+Enter for a new line

More comparisons

  • Women's Classic Penny Loafer vs Eastland Women's Classic II Loafers
  • Women's Classic Penny Loafer vs Eastland Classic II Penny Loafer
  • Eastland Sawgrass Women's Loafers vs Eastland Women's Seneca Falls Boot
  • Eastland Sawgrass Women's Loafers vs Eastland Women's Classic II Loafers
  • Eastland Sawgrass Women's Loafers vs Eastland Classic II Penny Loafer
  • Women's Solstice Boat Shoe Oxford vs Eastland Sawgrass Women's Loafers

Buying guides that pick them

  • Best women's Eastland shoes
—
No
Size (US)—11, 12, 6.5, 5.5, 9.5, 10.5, 8.5, 8, 9, 7.5, 5,…
Platform Height (")—0.25
Fastening—Slip-On
Lining—Cotton
Clothing Size—7.5
Actual Color—Black
size—7.5
Gender Size—Women's 8.5, Women's 10, Women's 6, Women's 6.5…
Women'S Size—Size 8, Size 10, Size 6, Size 6.5, Size 7
Age Group Size—Adult size
Department—Women's
Suitable For Size—Women's Size
Slip Resistant—Yes
Safety Features—Slip resistant
Running Shoes—No
Weightlifting Shoes—No
Fashion Sneaker—No