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Deal.ai › Buying guides

Best women's Eastland shoes

Researched by Deal.ai's shopping agent across stores on November 7, 2026. Prices below are today's.

Top pick: Eastland Women's Classic Penny Loafer — the one-piece hand-sewn leather upper with a padded OrthoLite insole is the most comfortable, longest-wearing shape Eastland makes, and it's the pair that works with jeans and a skirt alike.

Who the others suit:

  • Classic II Loafers / Classic II Penny — the same classic look in a lighter, more casual version; good if you want the penny-loafer silhouette without the dressier finish.
  • Sawgrass and Patricia Moc loafers — soft, flexible driving-moc feel for everyday errands; the Patricia in gold metallic is the fun, statement pair.
  • Syracuse slip-on — buckle detail and a rubber/polyurethane sole, so it grips better on wet pavement.
  • Seastar Boat Shoe — hand-sewn moccasin with rawhide lacing; the pick for docks, decks and summer weekends. The Summer Boat Shoe is the canvas, warm-weather version.
  • Evie Penny Loafer — a small heel and textured rubber sole when you want a bit of lift.
  • Marcella 1955 Edition — a chunkier, heritage-styled slip-on for a more rugged look.

I didn't find Eastland boots in this search — say the word and I'll look specifically for those.

The picks

  1. Eastland
    Women's Classic Penny Loafer
    #1

    Women's Classic Penny Loafer

    • Upper material: Smooth, polished leather
    • Insole: Padded OrthoLite® comfort insole with patented moisture control
    • Construction: Hand-sewn from one piece of leather
    • Outsole: Lightweight rubber outsole
    • Heel height: 7/8"
    • Fit: Most customers prefer ordering this style a half size smaller
    $115.00at EastlandObserved at 8:33 AMPrices and history →
  2. Eastland
    Eastland Women's Classic II Loafers
    #2

    Eastland Women's Classic II Loafers

    $39.99

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at eBay
Observed at 8:34 AM
Compare 9 stores →
  • Eastland
    Eastland Classic II Penny Loafer
    #3

    Eastland Classic II Penny Loafer

    • Size (US): 11, 8
    • Fastening: Slip-On
    • Color: Blue, Natural
    • Heel Type: Block Heel
    • Outsole: Rubber, Synthetic
    • Age Group: Adult
    $114.99at Rack Room ShoesObserved at 9:00 AMCompare 3 stores →
  • Eastland
    Eastland Sawgrass Women's Loafers
    #4

    Eastland Sawgrass Women's Loafers

    • Brand: Eastland
    • Color: Black
    • Shoe width: Medium
    • Casual & dress shoe style: Loafers
    • Material: Leather
    • Shoe heel style: Thin
    $47.99at WalmartObserved at 8:37 AMCompare 8 stores →
  • Eastland
    Eastland Patricia Moc Loafer
    #5

    Eastland Patricia Moc Loafer

    • Fastening: Slip-On
    • Manufacturer Color: Gold Metallic
    • Color: Gold
    • Outsole: Rubber
    • Age Group: Adult
    • Gender: Female
    $65.00at PoshmarkObserved at 8:37 AMCompare 11 stores →
  • Eastland
    Eastland Women's Syracuse Slip-On Loafer
    #6

    Eastland Women's Syracuse Slip-On Loafer

    $69.99at EastlandObserved at 8:34 AMCompare 4 stores →
  • Eastland
    Women's Seastar Boat Shoe
    #7

    Women's Seastar Boat Shoe

    • Upper material: leather
    • Lacing system: 360-degree rawhide lacing system
    • Construction: Handsewn moccasin construction
    • Insole: leather lined insole
    • Outsole: Textured rubber outsole
    • Heel height: 1/2"
    $100.00at EastlandObserved at 8:34 AMPrices and history →
  • Eastland
    Women's Summer Boat Shoe
    #8

    Women's Summer Boat Shoe

    • Upper material: Durable Canvas
    • Lining: Fabric-lined
    • Insole: comfort insole
    • Outsole: Rubber outsole
    • Heel Height: 1"
    $90.00at EastlandObserved at 8:34 AMPrices and history →
  • Eastland
    Women's Evie Penny Loafer
    #9

    Women's Evie Penny Loafer

    • Upper material: Leather upper with fabric lining
    • Insole: Fully-lined, cushioned insole
    • Outsole: Textured rubber outsole
    • Heel height: 1 1/3”
    • Closure: Slip-on design
    $135.00at EastlandObserved at 8:34 AMPrices and history →
  • Eastland
    Eastland Womens Marcella Loafer 1955 Edition
    #10

    Eastland Womens Marcella Loafer 1955 Edition

    • Weight (oz): 16.0
    • Platform Height ("): 0.25
    • Fastening: Slip-On
    • Manufacturer Color: Brown
    • Color: Brown
    • Outsole: Rubber
    $59.99at Tractor Supply CoObserved at 8:33 AMCompare 4 stores →