From 1998 through 2006, we tuned in to Will & Grace like clockwork on Thursday nights. The series offered witty one-liners, top-notch physical comedy, and onscreen friendships unlike any we had seen on TV before. Of course, we’d be lying if we said we weren’t also tuning in to see what Grace Adler was wearing. And when it came to her wardrobe, she never failed to surprise us. The interior designer, played by Debra Messing, was as relatable as characters come. She constantly struggled to find love, she was totally neurotic, and she often fell victim to the latest fashion trends.
Of course, it’s worth noting that at the time, many of Grace’s ensembles were considered to be totally stylish. But every now and then, she threw us for a loop with one of her unconventional looks. Her biggest fashion critic was her assistant, Karen Walker (played by Megan Mullally), who never approved of Grace’s outfits. And she didn’t feel the need to suppress her thoughts on the matter. Instead, she ripped apart Grace’s patterned tops:
Her ruffled tops:
And even her dresses:
Really, the list goes on. But Karen’s assertions about Grace’s looks weren’t always warranted. After all, Grace was just testing out the best trends that the late ‘90s and early aughts had to offer, and we respect her for that.
With the Will & Grace revival set to premiere tonight at 9 p.m. ET on NBC, we’re anticipating many more over-the-top looks to be headed our way. So in honor of the major TV milestone, we’ve rounded up 24 of Grace’s most unforgettable looks to date. Scroll down for a fairly dated—but never dull—walk down memory lane.