10 Most Dripped-Out TV Characters of All Time, Ranked

We watch TV shows for their innovative stories, great plots, and fun characters. But sometimes, those characters transcend the shows they’re in because of their incredible drip. Indeed, we do tend to remember some characters for their brilliant sense of style and fashion, considering them synonymous with the fashion trends of the times.

There are some modern characters who could enter the dripped-out hall of fame as honorary members, like Villanelle from Killing Eve and Issa from Insecure, but others — modern and classic — are just the G.O.A.T.s when it comes to memorable drip. The 10 most dripped-out TV characters of all time aren’t just fashion icons; they can be pretty cool, too.

10

Kendall Roy, ‘Succession’

Played by Jeremy Strong

Succession has that rich people drip all over the place; the Roys are dressed to the nines in high-fashion brands in every single scene. The funny part is, a lot of the fashion in Succession looks pretty plain, like Kendall Roy’s Loro Piana baseball hats, which go for around $500, but the quality of these items is often incomparable to anything affordable to “regular” people. Succession is about a family of billionaires fighting for dominance over their father’s media empire, and it’s a real modern Shakespearean tragedy.

Kendall Roy (Jeremy Strong) is the oldest of Logan Roy’s (Brian Cox) children with his second wife. Kendall is much like his dad but eager to break familial patterns and venture out on his own. Whether he’s sad, happy, trying to win over his father’s affection, or planning a coup, Kendall is dripped out; some of his most fashionable moments include a green cashmere sweater and gold pendant and the $11,000 suit he wore to his brother’s wedding. Dripped out is an understatement — Kendall Roy might as well be wearing bills on his body.

9

Midge Maisel, ‘The Marvelous Mrs. Maisel’

Played by Rachel Brosnahan

The Marvelous Mrs. Maisel is a comedy-drama set in the late 1950s and early 1960s, and the fashion is heavily inspired by — and nails — that period. It follows Midge Maisel, a divorcee who accidentally gets into stand-up comedy and becomes one of the first-ever female stand-up comedians in 1950s New York. The beautiful Rachel Brosnahan portrays her, and she’s known for some iconic fashion off-screen, too. As Mrs. Maisel, Brosnahan shines in the 1950s fashion, wearing gorgeous dresses, full-combo outfits, and stunning accessories.

Midge Maisel comes from an upper-class family and is fashion-obsessed, so all of her outfits and ensembles are carefully thought out. Donna Zakowska, the costume designer for the show, explained the process behind each of Midge’s outfits in a book, and she even won an Emmy for Outstanding Period Costumes. The one thing Zakowska emphasized was the importance of the color pink on Midge’s personality and character, which became less muted and more vibrant as Midge gained confidence after her divorce. Mrs. Maisel is one of the best-dressed characters of all time, no doubt about it.

8

Pray Tell, ‘Pose’

Played by Billy Porter

Pose is one of the best shows of the past decade, and one that’s been somewhat unfairly forgotten and underappreciated. This Ryan Murphy and Brad Falchuk series depicts the lives of LGBTQ+ characters in New York City during the 1980s at the height of the HIV/AIDS epidemic. It focuses on the personal lives of many of its core characters but also on ballroom culture, queer nightlife, and societal and cultural issues of the time, and most of the main characters are Black and Latino. One of them is Pray Tell, a ball emcee played by Billy Porter.

Pray Tell is one of the best-dressed TV characters, always dripped out in the coolest, glitziest, and most amazing outfits ever seen. Porter himself is a fashion icon, so nobody could embody Pray Tell better than him. Pray Tell is also a fashion designer in the show, and his color combinations and intricate sense of accessorizing make every look feel complete and unique. He’s not the only fashion icon on the show, either. The stunning Elektra (Dominique Jackson) always has impeccable looks, too.

7

Blair Waldorf, ‘Gossip Girl’

Played by Leighton Meester

If the Blair Waldorf weren’t on this list, a scandal would ensue, that’s for sure. Gossip Girl is one of the biggest shows of the 2000s, and it was defined, mostly, by the fashion and outfits of its protagonists. Though Serena van der Woodsen gave her a run for her money, we really have to give it to Blair; her outfits and fashion were the most iconic part of the show. In many ways, she was the reason many people watched Gossip Girl in the first place, finding inspiration for outfits, fashion choices, and confidence in putting together looks like hers.

Gossip Girl is basically about a bunch of upper-class high schoolers navigating the plights of their educations and personal lives. Many of them behaved like straight-up 40-year-olds, but that’s the appeal of the 2000s, and generally, movies and shows set in high school. Blair, played by Leighton Meester, is the antagonist at first, but she quickly becomes a socialite you want to root for despite her villainous streak. The more Blair was featured, the more the show gained in popularity. One of the things viewers noted about her looks is how well she could pull off bodycon dresses, making them classy; her standout outfits were always gowns, and some of the most amazing ones made the episodes much more fun.

6

Carrie Bradshaw, ‘Sex and the City’

Played by Sarah Jessica Parker

Another character that simply must be on the list is Carrie Bradshaw, because a fashion and lifestyle columnist must be one of the biggest fashion icons of her time. Sex and the City follows Carrie, played by Sarah Jessica Parker, and her three friends — Samantha (Kim Cattrall), Charlotte (Kristin Davis), and Miranda (Cynthia Nixon) — as they date, fall in love, and make waves in their business ventures during the 1990s in NYC. The show was based on Candace Bushnell’s lifestyle column, whose writing alter ego was Carrie Bradshaw. Her stories were turned into a series that became one of the most iconic shows of all time, including being an influential part of the fashion landscape.

Carrie Bradshaw is one of the OG fashion influencers, being one before influencers were ever a thing. Not a cellphone in sight, only prying eyes were able to spot Carrie in interesting fashion moments, and she always managed to dazzle in her unusual outfit combos and fun accessories. Besides her, Samantha is also well-dressed, showing off a bolder and sexier look to go with her personality. In fact, each woman in the friend group would have some banger outfits, though they aren’t as influential as Carrie is.

5

Don Draper, ‘Mad Men’

Played by Jon Hamm

Some of the most fashionable TV shows take place in NYC, or more precisely, Manhattan. This highbrow area is still a place of gathering for the upper-middle class and the wealthy, where we can see some of the coolest fashion on the streets. Mad Men takes place in Manhattan and depicts the employees of an advertising company throughout the 1960s. “Mad” stands for Madison Avenue, where the advertising industry bloomed during the 20th century; the show itself is often considered influential among period shows that depict the mentality, lifestyle, and especially the fashion of the time well.

The protagonist (and often antihero) is Don Draper, played superbly by Jon Hamm. He’s one of the creative directors of the Sterling Cooper advertising agency, and his charm and good looks are often his strong suit. Whether it’s men or women, Draper has a way of winning them over, as his business ethic and creativity are unmatched. Draper’s fashion choices accompany his larger-than-life persona, and even when he’s grilling steaks in the yard, he is dripped out in lavish cottons, linens, and silk. Moreover, as we follow Don’s (failing) personal life, his fashion sense and hairstyle remain unchanged, showing that he marches to the beat of his own drum and remains consistent with himself.

4

Olivia Pope, ‘Scandal’

Played by Kerry Washington

The crisis manager of the US President in Scandal, Olivia Pope, is a beautiful and powerful woman. Played by Kerry Washington, Olivia has the bravado of someone larger than life but hides a big, loving heart beneath the hardened surface. Scandal is most known for Olivia Pope’s affair with President Fitzgerald Grant III (Tony Goldwyn) and the way they genuinely love each other throughout. Still, something else stands out, and that is Olivia Pope’s incredible tailored fits. Even through heartbreak, Olivia is dripped out in the most stunning power suits and fabrics.

Kerry Washington gained further fame from Scandal, but her character, Olivia, claimed some titles in the real world despite being a fictional character. Many magazines and blogs wrote “how-to” guides about Olivia’s outfits, helping women feel empowered and classy in similar fits. Washington even worked with The Limited to create a Scandal-inspired fashion line, full of tailored pieces and comfortable and luxe fabrics. The best way to describe Olivia’s style would be “old money” with a dash of “power suit.” She massively influenced tailored fashion during the 2010s.

3

Will Smith, ‘The Fresh Prince of Bel-Air’

Played by Will Smith

In The Fresh Prince of Bel-Air, Will Smith plays a fictionalized version of himself as someone who grew up in West Philadelphia but got sent to live with his aunt and uncle in the wealthy LA neighborhood of Bel Air. When Will appears, his behavior (and especially his fashion) clash with the rest of the family, showing the differences in their upbringing. Despite frequent clashes, one thing is certain — Will is dripped out to the max, giving the phrase “fresh prince” a brand-new meaning. The street flair he picked up in Philly is worn even today, with retro ’90s fashion in particular coming back big.

Will meets his cousins, Carlton (Alfonso Ribeiro), Hilary (Karyn Parsons), and Ashley (Tatyana Ali), and he and Carlton are especially different. Carlton is stuck up and pompous at times, and his fashion reflects his personality, as he mostly wears bow ties and sweater vests. Will, on the other hand, streetwise and rough around the edges, has a free-flowing personal style, embodying the beauty of a tracksuit fit and colorful shirts. Whether it’s a full Air Jordan tracksuit or a combo of two wildly different patterns, Will’s style remains relevant to this day.

2

Alexis Carrington Colby, ‘Dynasty’

Played by Joan Collins

One of the OGs of incredible TV drip is none other than Alexis Carrington Colby, played by the inimitable Joan Collins in Dynasty. Yes, the fashion during the 1980s was, for lack of a better word, insane — padded shoulders, glitzy synthetics, massive hair, and colorful makeup — but it was a world people enjoyed. At times, too, there was a character like Alexis, who made a grand entrance in an outfit so iconic that you remember what she wore and how when she delivered her greatest lines. There is an Instagram page dedicated to Alexis’ fashion, called What Alexis Wore, and it chronicles most of her Dynasty looks over the years.

Alexis Colby makes an entrance in the Season 1 finale and introduces herself in the Season 2 premiere; she enters a courtroom in a tailored jacket and pencil skirt, white with black stripes on the side. With a massive white hat and statement sunglasses, Alexis’ face is covered, and then her entrance shocks everyone when she takes off the glasses. Whether it’s this outfit or a satin robe with feathered sleeves while she’s at the hospital, it’s impossible to look at Alexis and not think she’s the coolest villain you’ve ever seen.

1

Fran Fine, ‘The Nanny’

Played by Fran Drescher

A lot of people think of Fran Fine from The Nanny when they think of stylish TV characters, and they’re not wrong — she has the best drip ever, as it perfectly embodies her personality, humor, and character. Her style reflects someone bold, brave, confident, and often willing to be the center of attention. Many of Fran’s outfits in the show were fresh off the runway or statement pieces of the time, like the Moschino polka dot with a watermelon collar jacket or the Todd Oldham Spring/Summer 1995 red mini dress.

The Nanny follows Fran Fine, played by Fran Drescher, who is a bubbly and street-smart woman who starts working as a nanny for a wealthy and influential Broadway producer, Max Sheffield (Charles Shaughnessy). Fran often gets into all sorts of trouble, but the main story becomes her closeness with Max and his family, which ends in the two becoming a pair (sorry for the spoiler; it’s an old show). Though Fran is kind of a street kid, her fashion often reflects the kind of lifestyle she wants or is meant to live. Fran doesn’t really “fake it” — she’s true to herself for the most part — but she does attract a life of her dreams, partly through her fashion statements, too.

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