Owner Pamela Watson stocks all the essentials for the Town and Country set—Calypso, Elizabeth McKay, J. McLaughlin, and a healthy stash of pearls—but you can update the look with chevron-knit scarves or elephant-stamped bangles. Wear an old outfit to the shop’s Little Old Dress Party, held the last Thursday of the month. Watson and her team will determine whether your ensemble is destined for revival—with, say, a fresh brooch—or the donation pile.
62 Maryland Ave.; 410-280-8845.
In the basement of a gingerbread-style house built in 1708, this laid-back shop breathes West Coast attitude into midshipmen territory, selling surfer-chic clothes for guys and gals by Rip Curl, Billabong, Hurley, Element, and a house line. Beachy home accents and jewelry make fun gifts—such as flip-flop coasters that scream “destination wedding.”
10 Francis St.; 410-990-4475.
Owner Michele Deckman attracts a loyal following with fashion shows, personalized attention, and her well-edited selection of flowy cocktail dresses, girly going-out wear, lingerie, and oversize totes. Coveted Hello Skinny jeans and emerging designers Abi Ferrin and Bryan Bradley share space with Alice & Olivia and Black Halo.
30 Market Space; 410-280-9195.
Outdoor enthusiasts swear by this Mid-Atlantic outpost of the environmentally minded brand—launched by a Norwegian sea captain in 1877—for stylish but sturdy sailing fleeces, ski jackets, and down parkas. Clothes range from lifestyle to pro-sports-level quality.
132 Main St.; 410-990-4359.
Clotheshorses saddle up to this cheery shop for cool denim, special-occasion dresses, and everyday frocks by 7 for All Mankind, Citizens of Humanity, Ella Moss, Karta, and Tibi. The store draws contemporary-minded shoppers ages 25 to 65.
175 West St.; 410-626-9726.
For 40 years, this upscale men’s store has reflected, as its slogan puts it, “the Annapolis way of life,” outfitting gentlemen with an East Coast mix of office-ready conservative classics and resort wear for the links or sailboat. You’ll find a sea of khakis, handcrafted needlepoint belts, bow ties, and collared shirts organized by classic brands such as Vineyard Vines, Polo, Tommy Bahama, Southern Tide, and Cutter & Buck.
232 Main St.; 410-263-1175.
Owners Fern Elliott and Beth Ingham sell clutches and nature-inspired jewelry by designers near and far, from Baltimore-based Lotus to Betty Carré and MGold from Elliott’s native Brazil. You can belly up to the Jewelry Bar for a custom stone or freshwater-pearl creation, handcrafted by Elliott’s mom, designer Leda Reis.
145 Main St.; 410-263-3309.
Fun-loving fashionistas head to this den full of trendy clothes by Free People, BB Dakota, Gypsy, Glam, and Collective Concepts. Longtime Hollywood set costumer Catharine Incaprera also offers funky Rocket Dog shoes, Designal handbags, and makeup by Sugar.
181 Main St.; 410-295-7878.
Fashionistas flock to Jessica Jordan Paret’s airy boutique for denim (J Brand, Kensie Denim, Level 99) and flirty dresses (Max & Cleo, BB Dakota, BCBG Max Azria) plus several house labels. The inventory is plentiful, and most items ring up under $100. Weary shopping companions can loaf in the Man Lounge, complete with leather sofas.
179 Main St.; 410-626 6030.
“Pink” is the operative word, the shop’s common denominator for a colorful array of upscale halter dresses, flowery skirts, and shrunken polos with pre-popped collars. Prepsters—and their tween counterparts—get their fix of resort and yacht wear from Lilly Pulitzer, Vineyard Vines, Kate Spade, and Jack Rogers. There’s also a swim collection, from teeny bikinis to cute one-pieces.
16 Market Space; 410-216-9994.
Denim devotees, take note: This new offshoot of the Georgetown shop builds on owners Chris and Lindsay Buscher’s tradition of fashionably girly tops and dresses, but it also has been designated Urban Chic’s denim headquarters, which translates to a super-sized stock of designer jeans.
1915 Towne Centre Blvd.; 410-571-2777.