"Sex and the City" featured the adventures of four Manhattan friends – sexy Samantha, sweetly romantic Charlotte, practical Miranda and complicated Carrie – as they quested for love, but often settled for designer shoes. It was often said about this flip modern fairy tale that the fashions were the series' fifth character. To dress the part, round up three friends, pick your favorite character, and tote along a cocktail shaker and martini glasses to toast the single life with a Cosmo or two.
Carrie: Bohemian Writer, Witty Stylist
Carrie Bradshaw, a columnist who writes about sex and relationships, was the series' heroine, and her fashions were a bohemian mix of vintage and thrift-store eclecticism punctuated by ultra-glam designer shoes and handbags. In fact, the show made Manolo Blahnik and Jimmy Choo into household names. To nail Carrie's free-spirited mix, wear a pale-pink tank top with a bouffant skirt – let's face it, a tutu – and your prettiest strappy stilettos. Toss on a long raccoon coat, if you have one. Alternatively, wear skinny jeans and clever T-shirt, accented with a giant fabric flower, her signature. Carry a couple of shopping bags with shoe boxes. Fans will get the joke if you write "I'm sorry, I can't, don't hate me" on a yellow post-it note and stick it somewhere on your person – Carrie's parting gift from a boyfriend with the worst breakup etiquette ever. Carrie doesn't wear much makeup, so go for a natural look with a smoky eye, pink lips and a bit of glow on the cheeks.
Miranda: Legal Eagle, Working Mom
To dress as red-haired lawyer Miranda Hobbes, choose a power suit or career-worthy dress and classic accessories. Carry a briefcase. Miranda didn't mind dressing up for a night on the town, although it was often a simple office-to-evening transformation. But she was just as comfortable in running gear – add a Yankees baseball cap – and transformed into a busy career mom after the birth of her son, when fashion took a backseat to family problems. While Miranda championed a low-maintenance look, you can complement her auburn hair and porcelain skin with neutral eye shadow and maybe a bold lipstick.
Charlotte: Romantic Park Avenue Princess
Gallery worker Charlotte York was the foursome's innocent romantic – from the first season, she admitted she was in search of Mr. Right and happily ever after. For her more demure, upscale look, choose country-club separates – pearls are not optional – or a floral dress. For an evening dress, go elegant in a little black dress that mostly covers up. Think ladylike for Charlotte: The only cleavage will be peep-toe pumps. If you happen to have a Cavalier King Charles spaniel, take her along on a leash and call her Elizabeth Taylor for the night. Play it safe to create Charlotte's look, suggests makeup expert Sean Conklin. Use natural colors on the eyes, and accent her lips with rose or peach sheer lipstick.
Samantha: Sexy Type A Businesswoman
Self-confident executive Samantha Jones was the character who put "sex" in "Sex and the City." Her style was bold, bright and frequently revealing. Choose a stunning red body-con sheath, an attention-getting jewel-tone power suit or evening wear that pulls out all the stops, glamour wise. Add plenty of statement jewelry. Heels are sky high, of course. Carry a Fendi bag – fake is fine, since that's what Samantha's was when she stalked hers, thinking it was stolen, around the Playboy Mansion. What would Samantha do when it comes to makeup? She'd wear bold red, of course. Keep the eyes simple so they don't compete.