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

• 

  Crab and Life Ring Dog Leash - A Chesapeake Bay Original

  MSRP:

  Was:

  Now: $29.50

  Add to Cart

• 

  Chesapeake Bay Outfitters Fringe Bag

  MSRP:

  Was:

  Now: $149.00

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• 

  Maryland Crab Pride Tee

  MSRP:

  Was:

  Now: $26.00

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• 

  Rising Tide STM Polo

  MSRP:

  Was:

  Now: $65.00

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Women's
Tops

Men's
Shoes

Men's
Tops

Women's
Accessories

Mens's
Accessories

Mens'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

• 

  CBO Exclusive Beer & Crab Performance Short

  MSRP:

  Was:

  Now: $80.00

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• 

  CBO Exclusive Performance Maryland Flag Shorts - Grey Mist

  MSRP:

  Was:

  Now: $85.00

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• 

  CBO Exclusive Island Canvas Beer & Crab Shorts - Hurricane

  MSRP:

  Was:

  Now: $85.00

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• 

  CBO Exclusive Island Canvas Navy Crab Shorts

  MSRP:

  Was:

  Now: $85.00

  Choose Options