Vines Sandals

New for Summer 2019

Shop my Vines

New for the season

Dress Collection

Shop Dresses

Rising Tide

The Chesapeake Original

Shop Rising Tide

Helly Hansen

Spring 2019

Shop Helly Hansen

It's On!

Get a Crab and Beer Belt

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

Featured Products

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

Get on Board with CBO. Be the first to know! Subscribe to news

Sign up for our newsletter and be the first to hear about deals!

We proudly care the following brands

"About this time the custom arose of referring to the Eastern Shore with capital letters, as if it were a special place; this tribute was never paid the western shore."

― James A. Michener, Chesapeake