Our Story

Located in beautiful downtown Saint Michaels, Maryland, Chesapeake Bay Outfitters has been outfitting its patrons’ “Shore Style” for over thirty years. At Chesapeake Bay Outfitters, we pride ourselves in providing stylish and classic women’s and men’s clothing, footwear, and accessories, with an understated resort vibe.

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Cashmere Galore

Women's Shoes

Featured Products

• 

  Jude Boot

  MSRP:

  Was:

  Now: $134.00

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• 

  Makia

  MSRP:

  Was:

  Now: $110.00

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• 

  Ansley Water Resistant Slipper

  MSRP:

  Was:

  Now: $100.00

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• 

  Tulip Slip On White Sole

  MSRP:

  Was:

  Now: $79.00

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Women's
Tops

Men's
Shoes

Men's
Tops

Women's
Accessories

Men's
Accessories

Men's
Swimwear

Men’s Sperry Billfish – The Icon

Sturdy and rugged, this three-eye boat shoe features enhanced shock – absorbing soles the true workhorse of the fleet.

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What's New

• 

  Men's Schooner Boat Shoe

  MSRP:

  Was:

  Now: $155.00

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• 

  Men's Clovehitch II Boat Shoe

  MSRP:

  Was:

  Now: $140.00

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• 

  Ascot Slipper - Espresso

  MSRP:

  Was:

  Now: $110.00

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• 

  Ascot Slipper - Chestnut

  MSRP:

  Was:

  Now: $110.00

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