The Ins and Outs of Chesapeake Bay Outfitters

By Sandra Zunino

A fixture in St. Michaels for more than 30 years, Chesapeake Bay Outfitters has a long history of retail success.

Purchased by Ilene Morgan and her husband Frank eight years ago, the store was once a five and dime and later converted to a clothing store by the previous owners.

The store’s name occasionally lends to confusion as customers find sportswear, resort wear and footwear for the entire family opposed to active outdoor wear, but Ilene says locals have grown so familiar with the name, she is reluctant to change it.

While most of the existing brands carried by the former owners are still available, Ilene greatly expanded the inventory in all categories of menswear, women’s and children’s clothing as well as shoes. In fact, Chesapeake Bay Outfitters has become known for its large selection of footwear. “We carry the best casual footwear selection in the area outside of a mall,” says Ilene, “At least that’s what we’re told by our customers.”

Chesapeake Bay Outfitters fashions cater to the Eastern Shore casual lifestyle including name brands such as Fresh Produce, Tommy Bahama, Columbia Sportswear, Woolrich, Royal Robbins and Life Is Good. Its Bunnies By The Bay line of infant wear is a big hit among customers.

When it comes to shoes, Chesapeake Bay Outfitters customers find boat shoes and water-friendly styles by Sperry Topsider, Sebago, Teva and Keen. Other quality footwear brands include Born, Clarks, Jack Rogers, Mephisto, Merrell, Naot, Privo, Sofft, SoftSpots and UGG as well as FitFlops as seen on Oprah.

Both Ilene and store Buyer and Chief Merchandiser Ruthie McGuire select the store’s merchandise lines. Ilene says for success in retail, it is important to appreciate the product you sell and she absolutely likes the clothing she carries, but also realizes she needs to think about her target market. “When you buy, you are really buying what your customers want,” she says.

As an owner, Ilene is usually onsite during some part of every day, but says she is confident in her staff. “I have a good staff,” she says. “They pretty much run the store operationally.”

Providing good customer service is paramount at Chesapeake Bay Outfitters. When hiring for retail especially, Ilene says it’s crucial to find employees who are upbeat and outgoing. “A good sales person has to like people,” she says, “and must be socially engaged with the customer.”

The store’s hours are 10:00 a.m. to 5:30 p.m. daily and Saturdays from 10:00 a.m. to 6:00 p.m. While business typically booms in St. Michaels after Memorial Day and falls off after Labor Day, this year Chesapeake Bay Outfitters will maintain its summer schedule through winter. “St. Michaels is becoming a year-round destination,” says Ilene. “We had people in the store every day last year that we were open, so this is the first year we are staying open seven days a week.”

To help support the local community as well as market its merchandise, Chesapeake Bay Outfitters participates in fundraisers by providing fashion shows. “We always give out discount coupons for the store at the shows,” says Ilene.

The next show will take place on Friday, October 16 from 5:30 p.m. to 8:00 p.m. for the Soroptimist International of Talbot County Girls Night Out. Admission is $45 per person and benefits the Children’s Advocacy Center. Contact Terri Hiner at 410-822-7178 for more information.

For more information about Chesapeake Bay Outfitters, call 410-745-3107 or visit and click on shops.