Women's Clothing in Saint Michaels, MD

“We came by on two different days and both women working here were the sweetest. Forgot flip flops for our trip and I bought the most comfortable pair that was relatively inexpensive. My wife also bought herself a fantastic sweater.”

“I was looking for a last minute Mother’s Day gift while in town for a wedding. Ms. Courtney was very customer friendly and not only helped picked out the gifts, but she helped wrap my gifts since I was out of town. Very nice store. Even better staff.”

“A wonderful, eclectic store that my wife and I always visit when we're in St. Michael's. The book choices always fascinate us and the people who work there are extremely welcoming and knowledgeable. Our favorite store anywhere!”

“We popped into Chesapeake Bay Outfitters during the evening of Midnight Madness. We were warmly greeted by shop keepers Matt & Birgit. They were in good spirits and had ample Christmas Cheer. Every year the S.M.B.A. holds their annual kick-off to holiday shopportunity. Businesses welcome natives & visitors to shop, eat & stay at local establishments. COVID-style Midnight Madness made the event look very different in 2020. Stores stayed open late but not as late as the previous 19 years since it first started in 2001. Big crowds were not authorized to gather this year however, the virtual drawing still made it a festive & exciting event. As we browsed CBO, friendly & helpful sales associate Trish, assisted us in the footwear section. The sheer number of people working the floor makes interaction more likely. I love this! It enriches the shoppers experience! I tried on a pair of Ugg ankle booties, but I had to resist them as well as a pair of Madeline booties. I forced myself to focus on gifts for others...but nothing haunts you like the things you didn’t buy. So true! Although we didn’t make a purchase on the evening of Midnight Madness, we had a blast browsing their inventory & got the lay-of-the-land. We returned two weeks later & made purchases just in time for Christmas! We even helped our good friend select a Tommy Bahama light blue pullover for her husband...which he tremendously loved! We have shopped here many times throughout the years, as-well-as this past spring when the shops were able to reopen for business after the shutdown. That’s when my boyfriend bought me a pair of Ugg Tuolumne sandals from CBO. I hit the deck, the boards & the beach in these cushioned footbed flats. The shiny silver uppers complimented my casual and semi dressy looks. I practically lived in them all summer. Great leather & rubber! Fantastic quality! I absolutely love them! I even encouraged tourists who gave me flattering remarks to go to CBO and check out the other colors. If you’re searching for, relaxed-island-living inspired clothing you have found the right shop! Matt & Birgit continue to embrace the love of the Eastern Shore through their selections. There is a great deal of nautical looks to keep the clientele of returning boaters happy. My compliments to CBO for their new corner location in the revamped Town Center. It’s a totally different vibe compared to their previous location. Change is difficult for some long-time patrons to accept, but give it a chance! This space comes with a past. It possesses the original concrete floors from the former Acme Market. You may recall this portion of the building as the produce, frozen food & canned-goods section. The high ceilings call attention to the exposed beams, playfully dressed up with nautical pendant flags & snowflakes (for the holidays). There is a radiance of bright-white lighting. I love span the windows along the front, you feel so connected to all of the excitement on Talbot Street. I admire the neon-lit Chesapeake Bay Outfitters sign. CBO has decades of history! The current owners discovered the sign when they made the big move from their old location. It was practically buried when Matt uncovered it. He found a happy home for it along the entire length of the back wall by the footwear. It’s the perfect display to lend ambiance to the place & fill the tall empty white stretch of wall. It’s vintage & HUGE, absolutely superb! Chesapeake Bay Outfitters prides themselves on their recognizable name brand collections. I highly recommend CBO’s coastal living inspired clothing. They’re full of colorful preppy resort wear for leisure, travel and the beach. They also offer top-notch, fabulous cashmere cover-ups & ponchos for the chilly months. Going for a boat ride or just enjoying a day trip in St. Michaels? You’ll love lines such as Nic & Zoe, Jude Connally & Lysse. There’s plenty of clothing lines here that are made with UPF50+ sun protection for boating, tennis or golf. They also carry boots, loafers & top s”

“Anytime we visit Saint Michael’s this is a must stop for us… we always find the most interesting and well designed pieces, considering we have a very eclectic home style. We have bought furniture and multiple other smaller items- the ducks are a must!
We always enjoy visiting with staff, especially Alex! From order to delivery it’s always so streamlined and we feel appreciated. We will be back, and they have gained a couple of regulars! Thank you-”