By Alexis Bennett
Updated May 20, 2015 @ 6:30 pm

After 22 years on the air, the time has come to say goodbye to the Late Show with David Letterman. We've seen a whole host of celebrities help send off the comedian (who holds the title of longest running late-night talk show host), including George Clooney's final selfie and Julia Roberts on her first horrific visit to the set. But before we officially bid farewell, we're taking a trip down memory lane and reminiscing about our favorite fashion moments through the years. From Jennifer Lawrence's quilted accessory to Madonna's vampy '90s ensemble, see which stars stole the spotlight with their unforgettable outfits.

A bold Prabal Gurung outfit lit up the set and gave us serious color-blocking envy back in 2011.

We were delighted to see Roberts take a break from her usual all-black uniform with a white pant suit.


Barrymore bared her midriff with a cheeky banana-motif cropped tee while giving Letterman a show on top of his desk.

A Preen dress and Alexis Bittar pin made us even more obsessed with the First Lady's style.

5. Cher

After entering the stage from the ceiling on a swing, we got to see a closer look at Cher's fabulous jeweled moto jacket.


Swift was a complete darling in a yellow Dolce & Gabbana number five years ago.

7. Beyonce

Queen Bey charmed in a body-hugging Elie Saab number in 2009.

After the two sisters took on Miami, they joined Letterman in matching chic black-and-white duds. Kourtney sat pretty in a floral frock, while Kim nixed her usual look for a menswear-inspired ensemble.

9. Madonna


In 1994, Madonna dropped jaws in more ways than one. We're still obsessing over her dark '90s style.

Bullock dished on her movie The Proposal and stunned in this ruffled number.

Lawrence looked gorgeous in J. Mendel, but she still couldn't control her nerves. Ever the thoughtful host, Letterman added an accessory—a pink blanket—to help stop her cold sweats.