Check Out Philly Style's Top Covers From the Last 25 Years

As Philadelphia Style celebrates its silver anniversary, we look back at the celebrities, artists, power players, tastemakers, models and musicians that moved the needle in the City of Brotherly Love.

1. SUMMER 2011
Philadelphians know that Taylor Swift’s unofficial first “era” started at the Jersey Shore, playing peppy country tunes on her guitar at bars around Stone Harbor. Philadelphia Style interviewed the aspiring singer-songwriter a few times before she landed a cover in 2011. With a 78-city tour planned that included her first appearance at the Linc for the album Speak Now, we thought her star couldn’t rise any higher. More than a decade later, we know she was just getting started.

2. SUMMER 2002
Miami has always been a top destination for Philadelphians. No place has grown to represent the Magic City more than the former home of Gianni Versace, then known as Casa Casuarina. South American model Cindy Taylor cut a slick silhouette emerging from the property’s swimming pool for the cover. Inside the issue, Elisa Zuritsky and Julie Rottenberg sat down to talk about writing for HBO’s Sex and the City and we took an indepth look at the buzz around a new cosmetic injectable called Botox.

3. SPRING 2009
Cole Hamels appeared on the cover of Philadelphia Style a few months after the Phillies won their first World Series in 2008. To say that the then 25-year-old pitching phenom played a role in the Phils victory would be an understatement. Fresh off his MVP performance in the National League Championship Series against the Los Angeles Dodgers, Hamels completed the 2008 postseason with an undefeated record. Hamels would go on to appear in Philadelphia Style many times in the years following, particularly for his annual fundraiser Diamonds and Denim.

4. SUMMER 2014
Pop artist Peter Max collaborated with Niche Media to create one-of-a-kind covers for every title in the portfolio for the July/ August editions. For Philadelphia Style, he chose the Liberty Bell dotted with flowers inspired by Fairmount Park as the theme. MSNBC Morning Joe co-hosts Joe Scarborough and Mika Brzezinski interviewed Max, who put each cover’s painting up for auction to benefit The Humane Society. Happily, the special edition coincided with the 10th anniversary of Best of Style.

5. LATE SPRING 2015
Daytime talk-show host Tamron Hall was the face of our annual Women of Influence Issue in 2015. At the time, the Temple University alumna was making her mark as the first Black woman to coanchor Today, charming viewers with her quick wit and colorful style. The issue also featured several female Philly powerhouses, from Meryl Levitz to Helen Gym and Risa Vetri Ferman, who all had a chance to meet Hall at a luncheon held in her honor timed with the issue’s release.

6. SUMMER 2015
“DNC, A to Z!” screamed the headline of one of our most memorable editions. The City of Brotherly Love hosted politicos and celebrities alike for the Democratic National Convention and Philadelphia Style was there for all the action, covering the events, parties and people that mattered for five days in late July. Philadelphia artist and muralist Meg Saligman’s Our Flag Unfurled (2011, six weeks after 9/11) graced the cover. Saligman painted the mural on a warehouse near the Benjamin Franklin Bridge and was restoring the piece in time for the DNC.

7. SUMMER 2005
Three hundred and fifty-six. That was the number of winners recognized in the debut issue of Best of Style. The annual awards edition was an undeniable hit with Philly tastemakers who pored over the feature to chart every fashionable move they made. The year’s big dining winners? Continental Midtown for Best New Restaurant, Django for Best BYOB, Denim for Best Lounge and Le Bec-Fin for Best French Restaurant.

8. SPRING 2017
The NFL came to PHL for the 2017 NFL Draft. Brent Celek and Rodney McLeod, who would go on to help win the Eagles’ first Super Bowl in 2018, appeared together in a joint cover and talked with us about football, family and free time. Philadelphia Style also hosted a roundtable at the mayor’s office with Mayor Jim Kenney and leaders from city organizations like the Pennsylvania Convention and Visitors Bureau and PHL Sports for insights into the three-day event.

9. FALL 2008
Niche Media’s acquisition of Philadelphia Style ushered in a new era for the nearly 10-year-old independently owned publication. Besides the oversized format and revamped departments, Philadelphia was now on the map alongside Niche’s other city titles in the Hamptons, Miami, Los Angeles and Chicago. With Jon Bon Jovi on the cover, the star-powered edition featured Philly-centric musings from Daryl Hall, Tory Burch, Jonathan Adler and Harry Kalas and kicked off with a see-and-be-seen launch party at City Hall.

10. WINTER 2002
At the height of his popularity on the Buffy the Vampire Slayer spinoff Angel, Malvern Prep alum David Boreanaz was joined by wife Jaime Bergman to talk about their life as newlyweds and his popular TV show. Philadelphia Style also began digging into more substantial dining content, snagging interviews with Bobby Flay timed with his first show on The Food Network and Jose Garces, who was still sharpening his culinary skills at Alma de Cuba.

11 DECEMBER 2006
Philadelphia Style’s tradition of putting top models of the moment on the cover continued with Leticia Herrera, shot on location at Miami’s Casa Tua, and the magazine’s hugely popular round-up of the best party pictures now had a formal front-of-book department dubbed "Social Studies." We interviewed Milo Ventimiglia while he was starring on the superhero drama Heroes and caught up with Nicole Miller about her namesake brand in one of many interviews with the fashion designer.

12. JUNE 2021
We couldn’t think of anyone more fitting to be the face of Philadelphia Style’s first-ever Power Issue than Oscar-nominated director and West Philly native Lee Daniels. In 2021, his Hulu movie The United States vs. Billie Holiday was one of the year’s most talked-about films. There was also a feature on the top technology thought leaders in the city and an interview with Joan and Ellen Shepp timed with the 50th anniversary of the namesake Center City boutique.

13. FALL 1999
It was 1999, we were on the eve of a new millennium and Philadelphia was hurdling toward a renaissance that would forever change the face of this city—and Philadelphia Style was created during the throes of this revitalization. Together with Neil Stein, Stephen Starr and the rest of the local luminaries who had huge dreams for this city and weren’t afraid to go after them that year, the launch of our premier issue proved that Philadelphia Style wasn’t an oxymoron—and that we had just as much happening on the fashion and lifestyle front as any other world-class city.

14. JUNE 2018
The first issue of Modern Luxury Weddings Philadelphia came to life in 2018, kicking off a biannual publication featuring the most stylish real weddings, luxe details and inspiring love stories each season. The first issue featured the newly engaged Kylie Kelce (McDevitt) as “Bride About Town,” followed by the nuptials of Marta Krupa and Marco Andretti (grandson of esteemed race car driver Mario Andretti). For the past six years, Modern Luxury Weddings Philadelphia has continued to fill its pages with notable newlyweds.

15. JUNE 2022
Patients travel from all over the country and beyond to seek medical care in the City of Brotherly Love. In a post-COVID-19 world, health took on a whole new meaning. It was with this idea in mind that Philadelphia Style launched the first edition of Modern Luxury Medicine + Doctors Philadelphia in 2022. Leading doctors from Abramson Cancer Center, Sidney Kimmel Cancer Center and the Department of Health were featured in the issue along with Rothman Orthopaedic Institute’s Dr. Alexander Vaccaro, who appeared on the cover.

16. LATE SPRING 2017
We caught up with Patti LaBelle, otherwise known as Philly's Godmother of Soul, for our annual Women of Influence issue. As always, the proud Philadelphia resident was juggling multiple projects. She appeared on the cover timed with the release of her first album in 10 years, Bel Hommage, describing the jazz record as “something you’d never expect from Patti.” LaBelle was also reveling in her status as a culinary influencer, readying for her third season of the Cooking Channel's Patti LaBelle's Place and fourth cookbook release.

17. MAY 2019
Three times was the charm for John Legend’s third appearance on the cover of Philadelphia Style. Legend led an all-star ensemble of bold-faced Philly names to celebrate our 20th anniversary including Patti LaBelle, Governor Ed Rendell, Ellen Yin and Mayor Michael Nutter. There was also a sweeping timeline charting two decades of the moments that mattered in the City of Brotherly Love’s dining, fashion, real estate and arts and culture scenes.

18. FALL 2015
The world’s attention turned to Philadelphia when Pope Francis attended the World Meeting of Families in September 2015. The occasion was nothing short of history-making: It was Pope Francis’ first-ever trip to the U.S. and only the fourth time in America’s 239-year history that a pope had visited the country. It was also the first time a pope had visited Philadelphia in more than three decades. Mayor Michael Nutter and veteran news anchor Pat Ciarrocchi were among the many names that offered perspective on the monumental event.

19. FALL 2012
“Carson Calling!” read the headline in our September cover story with Allentown native Carson Kressley. We interviewed the tastemaker, TV personality and champion equestrian about his upcoming projects and love for the Devon Horse Show and Country Fair. The sartorial fun continued with a Grace Kelly-inspired fashion shoot and an interview with the founders of Warby Parker.

20. FEBRUARY 2020
Society and party pics have always been a critical component of Philadelphia Style’s content, but with the launch of the annual Modern Luxury Datebook, we took coverage to the next level. The new magazine became the essential guide to the city’s biggest, best and most important galas, balls, fundraisers and fashion shows of the year. Features included spotlights on the city’s most fervent philanthropists like Steve Korman, Stephen Fry and Madeline Bell, the very best fetes—like Philly Fights Cancer, where Hugh Jackman entertained the crowd— an all-inclusive annual social calendar, and pages that celebrated the best dressed partygoers of the year.

21. SUMMER 2017
A pastel-hued gatefold cover with an image of the Center City skyline was chosen for our annual Best of Style Issue. One noticeable addition? e magazine’s new title, Modern Luxury Philadelphia Style. In May 2017, Niche Media was happily acquired by Modern Luxury, joining 84 titles across 24 U.S. cities. Under new ownership, Philadelphia Style increased to 10 issues per year plus ancillary publications in design, weddings and social events. Bold-faced names like John Fry, Yannick Nézet-Séguin, Brandon Brooks and Alex Holley helped us celebrate the milestone occasion by sharing their Philly essentials in the “Best of Style” feature.

22. LATE SPRING 2020
Modern Luxury presented a special edition titled “The Hope Issue” in the wake of the COVID-19 pandemic. Running across more than 20 cities in the portfolio, the issue celebrated the front-line workers who were putting their lives on the line for the greater good and the companies on a local, national and even international level that were finding ways to support communities. Contemporary artist Mr. Brainwash partnered with Modern Luxury to create an original work of art for the cover.

23. SUMMER 2000
As the first huge city-wide event of the new millennium, Philly was chosen as the host city for the Republican National Convention. With an issue theme of “GOP VIP,” Philadelphia Style tapped model Niki Taylor to appear on the cover. Taylor and the elephant were photographed separately and then photoshopped into the final image, cementing its place as one of Philadelphia Style’s most memorable covers. Elsewhere in the issue, Philly’s own Eve and Jill Scott were both featured timed with their debut albums.

24. SUMMER 2009
The cover line read: “Bradley Cooper: Is the Jenkintown native becoming one of Hollywood’s Hottest Leading Men?” We knew the answer early on, catching up with Cooper shortly after The Hangover was released. The proud Philly native, who went to Germantown Academy and competed in the Dad Vail Regatta, talked about life on and off the screen.

25. JUNE 2023
Jalen Hurts. James Harden. Aaron Nola. Our annual Power Issue was an ode to Philly sports with a ranking of the "Top 25 Most Powerful Athletes." We turned to veteran sportscaster John Clark, anchor at NBC Sports Philadelphia and NBC10, to offer some candid perspectives about each player. (Of Jason Kelce, Clark said, “He could honestly run for mayor and represents Philly perfectly. A true Eagle.”) Sixers center Joel Embiid appeared on the cover, fresh off that season’s playoff run and recently crowned the NBA's Most Valuable Player.

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