Don & Megan Do Westport

Just imagine if this dynamic couple were to spend the day in town…

Photograph: Courtesty Everett Collection © AMC

Megan's Day

A city girl at heart, the second (or is it third?) Mrs. Draper snuffs out the threat of catching Betty's suburban ennui by indulging her taste for enviable, edgy fashion

Henry Lehr
The jeans in the window catch the eye of the modern-day Megan Draper. Even if every pair were white, her artistic eye would catch the differences in cut, weight, shade and embellishments. This independently owned store is flush with neutral jeans, tees, blouses and more that can be pulled into fierce outfits. 21 Main St., 203-226-9772;

Steven Alan
Visiting a beach town with NYC influences, Megan would fuse relaxation with luxury at Steven Alan, which leaps the retro-contemporary divide deftly. Proof: Limited-edition Twentieth Anniversary Monroe sunglasses in cognac ($195) and white Oxford sling backs ($285). 100 Post Road E., 203-663-1784;

Lynne Scalo
Megan’s repertoire includes filling her home with artistic pieces with a designer’s eye. She’d gravitate to Lynne Scalo’s boutique, stocked with the statement pieces a home diva needs to set the stage for modern glamour. 23 Jesup Rd., Westport, 203-222-4991;

Megan could converse in her native tongue at Diptyque, a French boutique that shares her romantic side. The perfumes and candles are heavenly. The new skincare line, L’Art du Soin, was inspired by the Mediterranean basin; consider Precious Oil for Body and Bath ($78) with Florentine Iris and  sweet almond, Argan and macadamia nut oils. 47 Main St., 203-222-3553;

Bags in hand and talking a mile a minute, Megan still wouldn’t overlook Vince. A Linen Circle Cardigan ($345) in an overcast gray will speak to her moody side and the urban leaning of the summer leather Drape Neck Jacket ($995) would give her a sunny boost. 115 Main St., 203-429-0617;

Walin & Wolff
Keeping Don on his leash means shoes that command attention. Walin & Wolff carries designers like Stuart Weitzman (Naked in Cava, $395) who meet the demands of such a woman. 30 Post Road E., 203-557-4876;


Don's Day

A complex man, No one really knows Don or even where he is most of the time. If in town now, here’s a few spots he might hit.

Bar Taco
New and buzzy, to flirt with young ladies
20 Wilton Rd., 203-222-8226;

Rive Bistro
French romance to seduce an old flame
299 Riverside Ave., 203-557-8049;

With oarsmen nearby, he can network with the prep-school crowd
521 Riverside Ave., 203-227-3399;

Tavern on Main
Classic, to entertain clients with Roger and Pete
150 Main St., 203-221-7222;

The Whelk
Cool and tasteful, to meet a smart, leggy stranger off the commuter train
575 Riverside Ave., 203-557-0902;

Neighborhood joint to avoid Roger—but there’s Peggy
41 Saugatuck Ave., 203-227-0511

Viva Zapata
Escapist, rebellious, to give into his instinct to run
530 Riverside Ave., 203-227-8226;

Black Duck
When Don’s perfectly pressed persona is out at the dry cleaners and Dick Whitman’s here
605 Riverside Ave, 203-227-7978

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