There’s something particularly alluring about timeless fashion. I’m always in awe of the kind of outfits you can look at and not necessarily pinpoint what year, decade, or era they’re from. Made from a combination of classic items—be it straight-leg jeans, button-down shirts, chunky knitwear, or open-toe shoes—these looks rely on the forever-favourite wardrobe heroes we wear again and again, season after season.
When it comes to celebrity style, I love stumbling across an image of someone who has been famous for years (think Jennifer Aniston or Naomi Campbell) and playing a silent, internal guessing game about when the photo was taken. For those celebrities who subscribe to a timeless aesthetic, this game can be more difficult than you’d think. But that’s exactly what makes their style great.
Below, I’ve tracked down seven celebrity photos from the ’90s and early noughties which easily look as if they could contain outfits from 2021 (face masks aside, of course). Between the high-heeled mules worn by Tracee Ellis Ross which bare an uncanny resemblance to new-season Bottega Veneta and the beaded bag carried by Cameron Diaz which is almost identical to Shrimps’ current offering, keep scrolling for some throwback celebrity outfits I’d happily re-create today.
Style Notes: My obsession with Friends is well documented on this website. Though, it can predominantly be blamed on an underlying love for Jennifer Aniston’s style. The woman is an icon of timeless style, so much so that it’d be difficult to even pinpoint when this image was taken. A late-’90s look that still feels relevant today? Aniston’s outfit archive contains oh so many.
Style Notes: I wouldn’t blame you if you thought Gabrielle Union’s white shirt in this look was by uber-cool French designer Jacquemus. Given this look is from 2001, it would be impossible, though it is just as stylish as one of his designs. A crisp button-down and jeans is a combo celebs have been wearing for years, and we don’t anticipate it stopping any time soon.
Style Notes: This 1997 Cameron Diaz look has several hallmarks of a 2021 wardrobe. Chunky grey knit? Check. Black miniskirt with side split? Check. Beaded evening bag that looks like it could have been made by Shrimps? Check!
Style Notes: Omit the orange-tinted glasses and this Naomi Campbell maxi-skirt–and–ankle-boots look could have been seen on any and every influencer over the last year. In fact, & Other Stories is currently selling a replica of those square-toe leather boots.
Style Notes: If you told me this photo was taken yesterday, I would believe you. Not only because Tracee Ellis Ross has barely aged a day since this 2002 image but also because this outfit is so timeless. Pairing a roll-neck knit with a pencil skirt and Bottega Veneta-esque mules is an outfit formula that will evidently stand the test of time.
Style Notes: Young Gwyneth Paltrow wore a lot of outfits I would happily re-create, especially this one composed of a leather blazer and straight-leg jeans. It’s simple, it’s effortless, and, most importantly, it’s classic. Bonus point for Brad Pitt, whose outfit is equally as timeless.
Style Notes: Before she was wearing white sequin trousers to landmark historical events (like the Inauguration), Jennifer Lopez was wearing tonal white outfits of a different kind. This jeans-and-knit outfit is the perfect way to weave light tones into your casual winter wardrobe.
