5. Rihanna
Okay, to be honest, Rihanna’s outfits are usually pretty insane, so if anyone could pull off the walk of shame look, it would probably be her. She’s used to taking style risks, but come on — this outfit is a bit much, even for her. On her walk home through New York City, Rihanna has her curls pulled up into a messy bun, jewellery on, and is rocking a long pink nightgown paired with Converse sneakers and a denim jacket. That’s a look. While most women would be totally embarrassed to traverse the city in a look like this, Rihanna is still serving it and totally unapologetic. And that’s exactly why we love her. If this were a shorter dress, we may just have been able to believe it was a sexy slip dress, but in this colour and length? She’s full on strutting through Manhattan in pajamas.
4. Jessica Simpson
Jessica Simpson built her pop career on her good girl reputation, as the squeaky clean alternative to pop princesses like Britney Spears and Christina Aguilera. However, since splitting with former hubby Nick Lachey, Simpson has definitely had a couple high profile relationships in Hollywood — and there has been some intrigue. First of all, John Mayer called the blonde bombshell “sexual napalm.” Then, there was the whole rumour about her hooking up with Maroon 5 frontman Adam Levine. The paparazzi captured her a few times in the morning hours in outfits that were clearly either from the night before, or cobbled together from whatever her partner had on hand for the morning walk of shame. Some celebrities opt to rock a more casual look on the regular, but Jessica Simpson generally prefers clothes that are tight and show off her curves — so this outfit is a little suspicious, to say the least.
3. Harry Styles
It isn’t just female celebrities who are captured doing the walk of shame — this picture of Harry Styles proves sometimes it’s the man that gets kicked out and sent home after a night of fun. This shot was taken way back in 2012, when Harry Styles and pop princess Taylor Swift were having their short-lived relationship. Styles is leaving the hotel where T-Swift was staying, and it just proves that men have it easier when it comes to the morning after. While women often have to head home in tight dresses and super high heels from the night before, Styles kind of just looks like he got dressed this way, in a simple grey tee and pair of black jeans. The only thing that really gives it away is the fact that he’s carrying some kind of overnight bag and extra shirt in his hands. Busted!
2. Kim Kardashian West
Nowadays, Kim Kardashian West and Kanye West are officially a thing. They have two adorable children together, and are spotted everywhere together. However, back when they were just dating, they were just another newly formed Hollywood couple — and Kim Kardashian had to do things like taking the walk of shame. In this picture, she’s clearly borrowed some type of loose tank to pair with last night’s skintight leather leggings, and her normally ultra glam hair and make-up is a bit more subdued. The hair is just loose and tousled, and she seems to be covering up her face with her sunglasses because she’s not rocking a full look. Luckily nowadays, she never has to do this — the walk of shame isn’t really a thing when you’re married and staying in the same hotel room.
1. Jennifer Aniston
Jennifer Aniston is a happily married woman now, living her life with hubby Justin Theroux. However, for about a decade, after her split with former hubby Brad Pitt, Aniston was one of Hollywood’s most iconic single girls. She had a few relationships and rumours circulating, but for the most part, she kept a pretty low profile in the dating scene. However, that doesn’t mean she’s immune to getting caught by the paparazzi when she’s doing the walk of shame. In this shot, Aniston is shown leaving a hotel where John Mayer was staying (to be honest, we blocked out the fact that she dated him for a hot minute because she’s clearly way, way too good for him). Luckily, since she didn’t show up at the hotel the night before in a glamorous gown, this walk of shame outfit isn’t too crazy — she just looks a little more casual than she normally does.
