![50 Weirdest Celebrity Couple Fashion Moments](https://townsquare.media/site/252/files/2019/04/grimes-elon-musk-relationship.jpg?w=980&q=75)
50 Weirdest Celebrity Couple Fashion Moments
It's hard enough to serve up your relationship to the public on a golden platter—but it's even harder to serve looks with your significant other without the possibility of being absolutely roasted for a double dose of fashion faux pas.
From early 2000s low rise jeans to questionable 2010s gowns, we've seen a lot of messy red carpet and street style looks from some of the most random Hollywood couples imaginable. (#TBT Hilary Duff and Joel Madden!) And yet, we just can't look away.
Below, check out some of the most cringe-worthy fashion fails from our favorite celebrity couples.
Worst Celebrity Couple Fashion Looks
More From WBZN Old Town Maine
![Road Trip Idea: The 2024 ‘Thriller Throwdown’ Is Back In Maine](http://townsquare.media/site/495/files/2024/06/attachment-reginald-groff-thriller-2-.jpg?w=980&q=75)
![Here’s How You Can Win a Trip to Tampa, Florida to Experience Justin Timberlake’s ‘Forget Tomorrow’ Tour](http://townsquare.media/site/241/files/2024/04/attachment-featured_1600x1067.jpg?w=980&q=75)
![You Can Win Pete Davidson & John Mulaney Tickets This Week](http://townsquare.media/site/495/files/2023/10/attachment-john-pete-snl.jpg?w=980&q=75)
![Every Sketch Featuring Pete Davidson from the SNL Season Premiere](http://townsquare.media/site/495/files/2023/10/attachment-Untitled-design-2023-10-16T124751.037.jpg?w=980&q=75)
![John Mulaney, Pete Davidson Coming To Bangor In October](http://townsquare.media/site/495/files/2023/09/attachment-john-pete-snl.jpg?w=980&q=75)
![WATCH: Ben Affleck Mistaken for Matt Damon in Funny New Dunkin’ Commercial](http://townsquare.media/site/695/files/2023/04/attachment-Untitled-design-4.jpg?w=980&q=75)
![The Scene That Didn’t Make It Into This Boston-Based Movie From Ben Affleck and Matt Damon](http://townsquare.media/site/699/files/2022/12/attachment-Untitled-design-2022-12-08T130105.634.jpg?w=980&q=75)
![Adam Sandler Has Strong Response to Claims Chris Rock Went ‘Too Far’ With Will Smith Jokes](http://townsquare.media/site/699/files/2023/03/attachment-GettyImages-950453982.jpg?w=980&q=75)
![Will Smith and Martin Lawrence to Return for ‘Bad Boys 4’](http://townsquare.media/site/442/files/2020/01/bad-boys-3-3.jpg?w=980&q=75)