Royal December

Princess Diana by Patrick Demarchelier for US Harper’s Bazaar, December 1995

One thing I noticed while doing these throwback cover entries is that almost every cover star I’ve talked about remains relevant to this day. Even if Britney and Christina never release another new album, they’re still icons and we still talk about them one way or another. Celebrity in the 90s/early 2000s remains top-tier, and Diana remains the most famous face of the 90s, IMO. It’s pure coincidence that she gave an exclusive cover story to Bazaar, which, thirty years later, would get an exclusive cover story from her future daughter-in-law, who herself is also globally famous and has faced her share of media scrutiny. (Side note: the Dec. 2025 issue of Bazaar was the only cover this month that was fine. All the others looked rough as hell. The same can be said for the comments about Meghan’s cover, but that’s another rant for another day.) 

By George

Cindy Crawford on the debut issue of George magazine, October/November 1995. 

There was something both fun yet absurd about George magazine. I understood why the magazine wanted to marry politics with celebrity/pop culture stuff of the time, but given what became of politics since its debut issue 30 years ago, maybe they should’ve left politics as usual aka boring, but functional and for the people. I have one back issue (the February/March 1996 issue, to be exact, and I’ll try to find a scan/post on this soon) that talked about how each of the 1996 would-be presidential candidates would benefit from some plastic surgery. Only in this country did (and still do) we need our politics to go the sensationalist, tabloid-esque route to get people’s attention, even if the issue at hand does not benefit the average American. Like, OK, Bob Dole would look better with “$6K veneer caps”. And what was his stance on universal health care again? 

However, I cannot tell a lie: George had some fire covers, their debut issue included. Cindy Crawford as George Washington in a midriff-baring outfit is just genius. Her wig game was even on-point! 

September’s Star Face

Yasmin LeBon on the cover of the premier issue of US Elle magazine, September 1985

Though Elle magazine had been in existence since 1945, the publication was only sold in France before expanding to other countries in the 1980s, with the States getting its own edition in September of 1985. Their minimal use of cover blurbs and promoting models of color on their covers were big reasons why I once favored Elle more than Vogue, especially in the 90s when Vogue gave the same two or three white models a cover four times a year. And while many 80s fashion mag covers look dated nowadays, the simplicity of this cover (simplicity in 80s fashion?), with that pop of yellow in a backdrop of black and Yasmin giving FACE, makes it quite the timeless image.

A Christina Summer

Christina Aguilera on Rolling Stone magazine, Double Issue, July 2000

This cover is oh-so 2000. The first Best New Artist Grammy winner of the new millennium on the cover, wearing low-rise bottoms and a playful smile with a CD player in tow, and headlines on Napster (IYKYK) and Slipknot. And if you’re wondering, yes, a Boy Scout can be gay. 

Seeing that Christina has been reviving her Genie In A Bottle days lately, from bringing back her wardrobe from that era to revamping her debut album on its 25th anniversary last year, I wonder if she’ll do something for the 25th anniversary of her first Rolling Stone cover this month.

Also, I want her shirt! 

Strike A Pose For June

Madonna, photographed by Herb Ritts for Interview magazine, June 1990

Once upon a time, magazine covers featured celebrities with some actual talent and substance, and everyone and their grandparents knew who they were. Some celebs got bold in their portraits, and no one took more brazen pics than Madonna herself. This could very well be my favorite mag cover of hers. It just POPS. You don’t get more in-your-face than grabbing your crotch. That a female celeb did *that* made it more ballsy; I bet the incels and prudes in 1990 sent hate mail to Interview then. I can’t imagine what the reaction would be if, say, Taylor Swift or Sabrina Carpenter struck the same pose on a mag cover these days. Although it would be pretty cool if either of them did that.

The editorial and her interview is also worth a look! 

When Vogue Was Vogue

Nicole Kidman by Irving Penn on US Vogue, May 2004

Y’all. I was there when this cover dropped, and the jaws of many fashion hounds dropped when we saw this cover. It was simple, all the way down to the singular cover blurb, yet elegant AF. This is not your Zoomer’s Vogue, but what Vogue used to be when they were the fashion bible. An actual fashion icon in Nicole (who had gotten another cover just eight months before this cover), giving fashion. No absurd photoshop, no hints of anything tabloid-y, and no need to look for the Playboy rabbit head on the cover because this was a true fashion magazine cover, dahling. And that’s on period.

Hollywood Dreams

Vanity Fair, April 1995 issue, with *takes a deep breath in* Jennifer Jason Leigh, Uma Thurman, Nicole Kidman, Patricia Arquette, Linda Fiorentino, Gwyneth Paltrow, Sarah Jessica Parker, Julianne Moore, Angela Bassett, and Sandra Bullock

Thirty years ago this month, Vanity Fair did that and gave ten of the top actresses of the time the cover. All at once! Their multi-star covers and star-studded portfolio would become a spring tradition for the publication, albeit a tradition that’s gone awry recently. Never forget the first, however, where it was just straight-up star power that sold the issue–no weird setups or questionable photoshop. (Placing queen Angela in the back of the fold-out cover will forever remain a choice to me, though.)

Wink For March

 

drew i-d 3-95

Drew Barrymore on i-D Magazine, March 1995. 

The Wink–the signature mark found on every (?) cover of the gone but not forgotten i-D Magazine, a UK-based fashion/lifestyle publication. Seeing models like Christy, Naomi, and Gisele on their covers back in the late 90s got my attention, and it would be there that I would notice a common theme among i-D’s covers. Thanks to that mag, now when I wink for fun, I like to think I’m winking for my own i-D cover. 

Also, mid/late 90s Drew remains iconic! Here, she was in her Wild Child Era, fresh off posing nude for Playboy, and was a month away from flashing David Letterman.