Megan Breaks, 27
Management associate, Tiffany & Co.

Where’s the romper from? “The label is Habitual, and it’s from Century 21 in New York—I just moved here. The bag is Steve Madden. My mom was going to give it to me for my birthday, but she wanted me to have it now.”

When’s your birthday? “November. I have the greatest mom!”

What are you coveting over at Tiffany? “Oh, everything. Anything diamonds!”

Photograph by Rachel Cothran.

We were walking around on a day trip to Annapolis (having dug up a Washingtonian guide to the quaint town) when we spotted Jessica Jordan on Maryland Avenue, wearing one of this summer’s most wearable trends: the maxi dress. Turns out she’s in retail; we dropped by her store to ogle the selection of well-priced dresses and bags—and one very cool fuchsia fainting couch with Lucite legs.

Jessica Jordan, 28
Manager, Paradigm

Where is your dress from? “It’s from Paradigm! The label is Oxford Circus, and it’s not too expensive—I’m pretty sure it was $89. We do a lot of searching around to find gorgeous things that are affordable. We carry some well-known lines like BCBG, Velvet, Sweetees, and Halé Bob, but we also do well with lines that are less known, like Tea and Nougat London. We carry some clothes for the guys, too, like Ben Sherman and Fillmore.”

What do you like about the maxi style? “It feels dressy, but it’s really not. They are so easy to wear!”

What are people wearing in Annapolis? “It’s pretty casual here—my friends and I call it Annapolis casual. For men, that means chinos and a polo shirt, usually in a bright color. Women wear a lot of sundresses, and they wear them day to evening. At the store, we’re carrying a lot of brights. I love purple and turquoise.”

Where are other good places to shop? “Something like 20 stores have opened relatively recently here, and there are some cool stores over on West Street, which I guess you could say is up-and-coming. Horse is a new boutique, and I also like Saucy shoes. They carry high-end lines like Hollywould. And there’s A La Mode, where you can find a bra to wear with anything. I’m wearing one with this dress! Annapolis has become a great place to shop.”

Photographs by Rachel Cothran.

Mikael Strommer, 23

What he’s wearing: Cheap Monday pants he had shortened into long shorts, shirt and sunglasses from Topshop, consignment-store tie, Esprit belt, Urban Outfitters bag, Converse shoes purchased in Beijing for $10, beaded bracelet from an antique market in Beijing.

What country has the best shopping? “Beijing is the best place for shopping in the world—hands down. You can find anything and everything you want, at any price.”

What style differences have you noticed in your travels? “New York was very diverse in terms of dress, and I think it’s more fun that way.Here it seems more homogeneous. People are more friendly here, though! And I like that the buildings aren’t so tall. In Sweden, fashion is very different. In Europe it’s different in general than here. We wear things that are tight. I like clothes that are tight—I would never wear anything from the Gap.”

Photograph by Rachel Cothran.

Sophie Bruch, four, wants to be “a princess” when she grows up.

Sophie’s mom likes to buy clothes for her online; this dress is from Hanna Andersson. Sophie especially likes the embroidered flowers. Her sandals, from Stride Rite, are a play on the ’60s novelty song “Itsy Bitsy Teeny Weeny Yellow Polka Dot Bikini.”

When asked about the favorite item in her wardrobe, Sophie told me quite simply that she doesn’t have a closet. (Her dad says she has a dresser.) However, she does have a brand-new Tinkerbell toy from Target that she’s certain no other Washington fashionista owns. When she’s not wearing “dresses that twirl,” she’s running around town in Disney princess dresses.

Take that, Carrie Bradshaw. This little lady is clearly the heroine of her own fashion fairy tale.

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Photographs by Rachel Cothran.

Names: Anthony Polimero, 60, and Torre Mattison, 34

What are you wearing?
Polimero: “Everything is Palzileri—the jeans, shirt, and vest. The belt is Cortigiani. I don’t remember about the shoes.”
Mattison: “Jacket from Bello, Ted Baker tie and pants, Gianni Barbato shoes, Nagual Designs beaded cuff, ring from Ruka.”

Thoughts on style in Philly?
Polimero: “Oh, I won’t get into that. If people shop here, they will be fine.”
Mattison: “It’s a too conservative, I think—there’s no vision. No one wants to step out and be noticed. And it’s a little too casual. A lot of guys don’t know how to buy suits that fit them. Italian suits have nice high armholes that fit the shoulder and just mold to your body, but a lot of guys think that’s tight. In terms of women’s dress, the older women dress better here. In the next couple years and as more people move here from New York [he points to some condo construction across the street], things are going to change.”

Where are the top places for both men and women to shop in Philly?
Mattison: “For women, Joan Shepp. It’s one of the best stores in Philly. Echo is a bit artier. The owner used to be Eve’s stylist. Of course Bello for men, and a Gianni Barbato store is opening soon here.”

Photographs by Rachel Cothran.

Lisa Zusman, 24, publicist at Linda Roth Associates

“One of our clients is an airport-restaurant management company, hence our quirky locale at Reagan National Airport. But we also do PR for companies all over the area, including hotels, restaurants, and some nonprofits. Best perk fashionwise? I don’t have to wear a suit every day.”

What are you wearing?
“I just cleaned out my childhood home outside Boston and found a dark denim jacket covered with pins. Was that cool even for 1994? One of the pins was from the National Zoo, so at least I had some taste in fun places to go, if not fashion. The one I’m wearing in this picture is from the Gap, and it was one of the first things I knew I had to pack when I studied abroad because it’s so versatile.
“The purse is by Melie Bianco, and if you have little enough in it, you can fold over the top and carry it like a clutch. You can find the brand at Discovery Galleries in Bethesda, but I got mine for less (money-saving tip alert!) via Amazon.com.
“The scarf is from Target. I like folding it in a triangle with the point down the front so looks a bit banditlike.

Photographs by Rachel Cothran.

Jessica Cope, 21
Student, Medical University of South Carolina.

I chatted with her and her mother, Mary, who were taking a shopping break outside of Le Pain Quotidien in Georgetown on Saturday.

What she’s wearing: A skirt from the Cage in Virginia Beach, her mother’s tank top (double the wardrobe!), and a breezy, citron-green sweater. Her bag is Cole Haan. Her earrings are from a street market in Charleston and were less than ten bucks.

How do you like to dress? “I like flowy clothes,” says Cope, who’d just left Intermix with a filmy patterned dress that fits the bill perfectly. “I would never wear really preppy stuff, like Lily Pulitzer.”

Because Cope hails from Charleston, she told us where to shop and eat the next time we’re there, including Intermix-like Biton, the boutique Luna, and restaurants like Cypress and S.N.O.B., which is a cute acronym for the location of the popular (but not at all snobby) eatery Slightly North of Broad.