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.

Learn More

Shop Women

Shop Men

Cashmere Galore

Women's Shoes

Featured Products

• 

  Lena Small Tote Crossbody

  MSRP:

  Was: $328.00

  Now: $246.00

  Add to Cart

• 

  Melissa Satchel

  MSRP:

  Was: $388.00

  Now: $290.00

  Add to Cart

• 

  Makia

  MSRP:

  Was:

  Now: $110.00

  Choose Options

• 

  Crab and Life Ring Dog Leash - A Chesapeake Bay Original

  MSRP:

  Was:

  Now: $29.50

  Add to Cart

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.

Shop Now

What's New

• 

  Rising Tide Trucker - Columbia/ White

  MSRP:

  Was:

  Now: $24.00

  Choose Options

• 

  Rising Tide Trucker - Navy/White

  MSRP:

  Was:

  Now: $24.00

  Choose Options

• 

  Rising Tide Trucker - Red/ Grey

  MSRP:

  Was:

  Now: $24.00

  Choose Options

• 

  The Skiff Boat Shoe

  MSRP:

  Was:

  Now: $59.95

  Choose Options