The Best TV Costumes From 1998 to 2008

11:59 AM 6/29/2018

by Whitney Friedlander

From Carrie Bradshaw's designer shoes to the mom jeans on 'Friends'

The Best TV Costumes From 1998 to 2008 New- Photofest-H 2018

It's debatable whether people should be evaluated by their clothing. After all, how much can you really tell about someone based solely on what they’re wearing?

Well, for characters in television shows, the answer is quite a lot. Costumes create backstories for our favorite fictitious friends and — if we look closely — can carry hidden messages (such as paranoia, as we’ll learn further down from Veronica Mars costume designer Salvador Perez). They also spark fashion trends in the real world among fans who are swept up in the narrative.

The Hollywood Reporter has explored these ideas before, including last year when we delved into the backstories of 10 of the best TV costumes of the past decade. And now we’re doing it again, this time going back a bit further to look at the origin stories for some of the most influential television costumes from the dawn of Peak TV, based on expert input. Below, we offer the best TV costumes from shows that ran during the decade from 1998 to 2008: 

  • Liz Lemon's Glasses on '30 Rock'

    TV Show: 30 Rock

    Years On: 2006 - 2013

    Costume Designer: Tom Broecker

    Actress: Tina Fey

    While actress-writer Tina Fey does wear glasses in real life, they are different than the thick black frames she wore as her alter ego Liz Lemon in NBC comedy 30 Rock. Those were part of costuming her character.

    Costume designer Tom Broecker wanted to push the idea that “smart girls wear glasses” and that Liz would be a “smart, sexy, bookish nerd girl,” in opposition to “vapid blonde” Jenna Maroney, played by Jane Krakowski. The frames were thick both to further enunciate this point and, well, because they’re cute.

    The Liz Lemon frames were actually fake to avoid the camera monitors picking up reflection or other distraction from the glass.

    While Broecker doesn’t remember the exact brand of glasses he used, it's worth noting that Fey’s appearance came during the rise of geek chic in fashion and a few years before designer brands went all in on the eyewear arena.

  • Micro-Mini Power Suits on 'Ally McBeal'

    TV Show: Ally McBeal

    Years On: 1997 - 2002

    Costume Designer: Loree Parral

    Actress: Calista Flockhart

    Series creator David E. Kelley confirms to THR that credit for the feminine spin on a power suit goes to costume supervisor Loree Parral, who worked on the Fox drama’s first season. According to author Josh Levine’s David E. Kelley: The Man Behind Ally McBeal, Parral never saw Ally as someone who was label-obsessed, but she did like nice things (hence the Armani suits, DKNY Lycra tops and Laundry skirts).

    By the time costume designer Rachel Stanley joined the show in season two, Ally (or at least Flockhart) was ready to mix in knee-length options.

    “She wanted a change,” Stanley said then of the female lead.

  • Old-School Cool on 'The Bernie Mac Show'

    TV Show: The Bernie Mac Show

    Years On: 2001 - 2006

    Costume Designer: Michelle Cole

    Actor: Bernie Mac

    The character Bernie Mac’s ode to the Rat Pack on the Fox comedy was simply an extension of the real Mac’s natural aesthetic, says series costume designer Michelle Cole. The late comedian had a flair for button-ups with wide collars and was known to turn up his nose at jeans in favor of pleated pants. She says the character on the Larry Wilmore-created laugher was a “true-on man-man” whether he was going to a comedy show or to visit the school principal.

    “We would have black men calling in looking for his clothes,” recalls Cole, who is now creating a new kind of cool for Freeform’s Grown-ish. “All of his wardrobe was custom; his suits, his shirts [and] sometimes his sweaters we were able to buy at Neiman Marcus or Saks. His shoes always matched. It wasn’t like the men of today where you’ll have a blue suit and a tan pair of shoes. He wasn’t that guy. He might be that guy today because the show was 20 years ago.”

    Cole says that dressing like this meant a lot to Mac, who was born on Chicago’s South Side and held working-class jobs before his comedy career took off. Still, she says “he was always dressed even before he had money.”

  • Buffy's Wedding Gown on 'Buffy the Vampire Slayer'

    TV Show: Buffy the Vampire Slayer

    Episode: “The Prom,” Season 3, Episode 20

    Air Date: May 11, 1999

    Costume Designer: Vera Wang and Cynthia Bergstrom (other episodes and seasons may have had different designers)

    Actress: Sarah Michelle Gellar

    There were so many costumes that stand out in creator Joss Whedon’s show about a teenage vampire fighter who knows how to stick a roundhouse kick (this may or may not be because the WB/UPN show also had its share of costume designers over its seven seasons). But we’re singling out this fairy princess wedding gown, which Gellar’s titular slayer wears in a dream sequence in season three, not just because it represents what would never be (Buffy’s marriage to Angel) but because it signals an even bigger sea change: The gown came courtesy of Vera Wang and marks an early example of the crossover between fashion and primetime programming as Peak TV gained steam.

    Bergstrom, who was the show’s costume designer then, says the impetus for the dress came from Gellar’s own relationship with Wang (the star wore another dress from the designer’s label for her actual wedding to Freddie Prinze Jr. in 2002). 

  • '90s Trends on 'Friends'

    TV Show: Friends

    Years On: 1994 - 2004

    Costume Designer: Debra McGuire

    Actors: Jennifer Anniston, Courteney Cox, Lisa Kudrow, Matthew Perry, David Schwimmer and Matt Le Blanc

    Yes, the shag haircut worn by Jennifer Anniston’s Rachel Green will forever be associated with the early days of Friends. (Thanks, Chris McMillan!) But the number of clothing trends that rolled through creators David Crane and Marta Kauffman’s immensely popular NBC sitcom? That credit goes to costume designer Debra McGuire. Due to the show’s longevity, she had the unique challenge of shepherding six characters from awkward 20-somethings to actual grown-ups.

    Each of the six characters had his or her own tableau — specifically a color palette that looked like it would make sense in the show’s setting of New York even though it was filmed in LA, says McGuire, whose credits also include Fox’s New Girl and ABC’s Fresh Off the Boat.

    Cox’s Monica was “black, white, burgundy and she was kind of in this cooler New York palette” while Anniston’s Rachel “came in with the blues and greens of that world.” Kudrow’s Phoebe took a page from McGuire’s own “old hippie” aesthetic to embrace the bohemian lifestyle. All those lovely rings and other accessories? They were either relics of McGuire’s former career as a jewelry designer or ones she commissioned from recent art school grads or her personal connections.

    McGuire says she gave Perry’s Chandler a “vintage throwback” look, with stripped shirts “inspired by 1940s men,” while Schwimmer’s Ross was a tweedy professor. Le Blanc’s Joey came from “over the bridge” and looked it in those early years with a beat-up leather jacket (which, sadly, McGuire had to make by distressing a perfectly good Armani coat).

    Another factor that made the costumes so relatable is McGuire's avoidance of freebies from fashion houses, saying now that if she didn’t make it or find it herself, she wouldn’t use it. An obvious exception, however, being that Anniston’s Rachel worked at Ralph Lauren, it made sense story-wise for her to wear that label.

    Not surprisingly, McGuire says she routinely gets emails from millennial and Gen-Z fans (or their well-meaning boyfriends) who are just discovering the show and want to know where they can find some of these costumes. She tells them to go to a dressmaker.

  • Simon Adebisi's Hat on 'Oz'

    TV Show: Oz

    Years On: 1997 - 2003

    Costume Designer: Tina Nigro

    Actor: Adewale Akinnuoye-Agbaje

    What makes a homicidal maniac stand out in a crowded prison of homicidal maniacs? Give him a teeny hat and dare anyone to take it from him. Series costume designer Tina Nigro and actor Akinnuoye-Agbaje, who played the Nigerian inmate on creator Tom Fontana’s genre-breaking HBO series, came up with the idea together.

    “We started playing around and we talked about how some Nigerian men wear the traditional hat to the side,” she tells THR. “He picked up a knit cap and we started cutting and rolling it so he could wear it like that.”

    As to how Simon would be allowed to break prison protocol with his uniform, Nigro says it was all about power.

    “The more power the more you could get away with,” says the costume designer, who is now working on a very different project: Netflix’s Unbreakable Kimmy Schmidt. “I loved dressing him because he was so into it and owned a costume even [when his character was on kitchen duty].”

  • Carrie's Tutu on 'Sex and the City'

    TV Show: Sex and the City

    Years On: 1998 - 2004

    Costume Designer: Patricia Field

    Actress: Sarah Jessica Parker

    Flower pins or gold necklaces? Manolo Blahnik or Jimmy Choo? The number of fashion trends and labels that gained prominence via creator Darren Star’s ode to female friendships is endless. So let’s highlight one of the first and most obvious examples: The frilly tutu that Sarah Jessica Parker’s heroine, Carrie Bradshaw, wears in the HBO show’s opening credits.

    According to Jennifer Keishin Armstrong’s new book, Sex and the City and Us, there was one simple reason Patricia Field wanted Carrie wearing this when a bus splashes her on Manhattan’s Fifth Avenue: “She’ll stand out.”

    And to think, Armstrong reports, that Star actually fought to have our gal in a “blue, businesslike sheath dress.”

  • Tony Soprano's Track Suits and Leather Jacket on 'The Sopranos'

    TV Show: The Sopranos

    Years On: 1999 - 2007

    Costume Designer: Juliet Polcsa

    Actor: James Gandolfini

    One of Tony Soprano’s greatest tricks was hiding the evils and cons brewing beneath his regular Joe beat-up black leather jacket and track suit.

    “The thing about Tony Soprano was that even though he was a mob guy, there was kind of an everyman vibe about him,” costume designer Juliet Polcsa says of series creator David Chase’s memorable character. She says he got a “suburban New Jersey guy jacket” because “its purpose was not to make a statement” and is surprised that it’s so memorable because “to me, it was a treasured basic.”

    And the track suits? Polcsa still has wives blaming her for these atrocities showing up in their husbands’ wardrobe. Polcsa says these “Bensonhurst tuxedos” grew out of the reality of what actual made guys wore.

    “As the Feds started to come down on the mob, there was an effort to be less flashy,” says Polcsa, who is now the costume designer for a different kind of crime saga: NBC’s Law & Order: SVU. “It was comfortable. You could put it together. And there you go: You have an outfit.” There was also a bit of brand loyalty there: Where as Gandolfini’s Tony preferred Fila, Tony Sirico’s ride-or-die Paulie Walnuts and Michael Imperioli’s younger Christopher Moltisanti wore silk Genelli joggers.

    Aside from the occasional printed shirt — which Polcsa says Gandolfini liked because it was “kind of the sad clown” idea — Tony Soprano’s wardrobe was fairly basic. “This is exactly what we set out to do when we did Sopranos,” says Polcsa. “We were not doing Goodfellas; we were not doing The Godfather” or other mob movies that have characters with more flash.

  • Karen Walker's Spunky Couture on 'Will & Grace'

    TV Show: Will & Grace

    Years On: 1998 – 2008; 2017 - present

    Costume Designer: Lori Eskowitz-Carter

    Actress: Megan Mullally

    An eccentric character needs costumes to match and Eskowitz-Carter created some memorable ones for actress Megan Mullally’s Emmy-winning role on NBC’s Will & Grace. The costume designer, who's been part of creators David Kohan and Max Mutchnick’s show since its first iteration in the '90s and early aughts, says the trick to dressing socialite Karen Walker is remembering this adage: If you’ve got it, flaunt it.

    “I used to put her in what I thought society women were wearing,” Eskowitz-Carter says of the comedy’s initial run. Even though the early years' budgetary restrictions meant some of it came from Macy’s, she did go for “bold, strong colors, lots of textures and [also] scarves and accessories to go with everything. She had a new handbag with every outfit.”

    Now Karen’s fashion choices have evolved and she’s more daring. “I still pay tribute to the signature pieces like the leopard and the blazers, but now she has a little more of an edge and she pushes the envelope more,” Eskowitz-Carter says. This is partly because Mullally’s body itself has changed and Eskowitz-Carter says she now has an easier time putting her in decollage-highlighting tops and V-neck sweaters.

    “[Megan’s] 58 years old and her figure is unbelievable, so why not flaunt it if you have it?” Eskowitz-Carter laughs. “She has such great boobs that she doesn’t even need to wear a bra.”

    Pretty sure Karen Walker would be OK with that over-share.

  • Hard-edged Justice Seeker with Gooey Center on 'Veronica Mars'

    TV Show: Veronica Mars

    Years On: 2004 - 2007

    Costume Designer: Salvador Perez

    Actress: Kristen Bell

    “Check you out, Veronica Mars. You're like a rocker chick now.”

    Veronica’s dearly departed bestie Lilly (Amanda Seyfried) delivers this sage observation from beyond the grave early on in creator Rob Thomas’ addictive teen drama. Why? Because star Kristen Bell’s ace PI isn’t just mourning her friend’s loss; she’s expressing how upset she is that those who are still alive have cast her out of their preppy, wealthy squad. The innocent pinks and purples Veronica wore during Lilly’s time on Earth have been packed up and used for flashback scenes, while the Veronica we see in present day comes with a don’t-mess-with-me protective coating. 

    “In the pilot, we learn that Veronica used to be one of the popular kids and through a series of events, she’s now an outcast, and she went to school with an armor put on her,” says Perez, who is now more famously associated with Mindy Kaling and her shows Hulu’s The Mindy Project and NBC’s Champions. He says a lot of trips to Wet Seal were required to give Veronica this aura of “don’t you dare come at me” through “militaristic clothes and leather jackets” even if — yeah, actually — she wouldn’t mind some comfort now and again.

    Given that it coincided with the rise of the blogosphere, Veronica Mars was also one of the first series to capitalize on fan reactions in real time. This is especially true for the costumes, as budding fashionistas and wannabe Mars Investigations recruits would sleuth out hidden clues in wardrobe choices. For instance, what did it mean when Veronica stopped wearing her famous thin black leather choker?

    “It meant that Kristen came to the set one day and [just] didn’t want to wear it,” Perez shrugs.

    Sometimes the most obvious answers are the ones we miss.

  • Xena's Leather Bustier in 'Xena: Warrior Princess'

    TV Show: Xena: Warrior Princess

    Years On: 1995 - 2001

    Costume Designer: Barbara Darragh

    Actress: Lucy Lawless

    Sexy and practical for fighting enemy combatants, Xena’s warrior costume was fit for a princess who knew how to take care of herself, thank you very much. In an interview for the ScreenTalk series, costume designer Darragh says her “intent was to find something really interesting and cool and fresh and different.”

    Darragh, whose résumé also includes reteaming with Xena’s Sam Raimi on Starz’s Ash vs. Evil Dead, researched Art Nouveau paintings as inspiration for the costume’s metal work, which gives Xena a protective armor and, of course, lets her look badass.