15 Times Rihanna Had Us Wondering “What Was She Thinking?”

in Cringeworthy
15 Times Rihanna Had Us Wondering “What Was She Thinking?”

Queen Rihanna can literally do anything she wants to and we’re here to celebrate just that, even though it doesn’t always work.

This curated collection of some of her crazy style choices is all in one place so you can look through them at your own pace, because trust us, they will take some getting use to. We’ve also included a number of quotes from the queen herself so you can not only get an inside look at her style, but also you’ll get to know a bit more about the woman behind the looks. If we’ve learned anything by putting together this master list of Rihanna’s style it’s this: you have to have confidence no matter what you wear. You can never let an outfit swallow you up and spit you out because of a lack of confidence. If you love yourself and have the confidence, you can literally pull off anything you want to just like Rihanna! From extravagant reds to pinks, cargo pants and corsets, literally anything can be rocked with style if you know how to own it like a queen!

Before we get started, we want to point out that while these outfits are out of this world, we are in no way making fun of her choices in style, we actually love her style and literally anyone can do whatever they want when it comes to their own personal expression. But it doesn’t mean that the majority believes this too. In most cases, these are considered fails! Individuals from anywhere in the world should be able to do whatever they want as long as they can feel that love for themselves and don’t hurt anyone!!

15. Pink Heels and Fur

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“It’s all about honesty. This is not failure, it’s lessons. It’s not the end. If you learn from mistakes it’s not failure. If you go and do the exact same f***ing thing then that’s the stupidest thing ever and it probably won’t work the second time.” – Rihanna

This is seriously quite a unique look. It’s a look that will get you curious about the limits of fashion. While we love how bold Rihanna is always trying to be, the breakdown of this outfit is quite a bit. Pairing a white fur coat with a bright blue graphic hoodie, long basketball shorts that are quite baggy, with knee-high pink pointed nylon heels. Where do we even begin! If you’re someone who would really wear this in real life we need to take a couple of pages from your book of confidence!

14. Casual and Heels

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“Being a size zero is a career in itself so we shouldn’t try and be like them, it is not realistic and it is not healthy. You shouldn’t be pressured into trying to be thin by the fashion industry, because they only want models that are like human mannequins. They know that if we see an outfit on a mannequin in a shop window we will love it and want to buy it whatever size we are. That’s why they have size zero models – they want to sell clothes. But you have to remember that it’s not practical or possible for an everyday woman to look like that.” – Rihanna

While we love a casual look, this one sure is pushing the line when it comes to Rihanna’s fashion sense. The joggers that are cropped, with an old sweatshirt, and pointed heels, it’s memorable, that’s for sure. It’s like she decided to throw on a bunch of stuff she had lying around and make an outfit out of it. While we do have to appreciate that she takes these risks and wears outfits that work for her, we can’t always agree that it’s best. The whole casual look with heels has really been something we see often as a trend, especially with the Kardashians, but this is just too much.

13. Corset Cargo

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“Sometimes I’ll wear something and think, I’m going to get so much flack for this tomorrow, but if I want to wear it, I will. If I dress too sexy, then I’m [called bad things]; if I dress sophisticated, then I’m a grandma. At the end of the day, I just wear what I want to wear.” – Rihanna

Another baggy outfit which apparently Rihanna loves to death! But this time she’s paired the unique look with a waist cinching corset. This outfit consists of a bagging billowing and long sleeved plaid top that looks like a flannel, paired with a matching corset. She’s also wearing large navy baggy cargo pants. She’s decided to go with chic sunglasses, an extravagant ponytail, and an elegant necklace that could almost be a choker. While it might not be something that everyone loves, at least Riri is wearing what makes her happy at the end of the day, right?

12. Dread Head

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“When I was fourteen and first started going out, I always wanted to be the opposite of everyone else. So I would go to the club in a polo T-shirt and pants and sneakers and a hat on backward, just so I would not be dressed like other girls.” – Rihanna

Rihanna went the extra mile with this look, but it honestly is quite casual and normal if you can look past the hair (which we love to death). But there are many ways to take on this style for yourself, just remember to not appropriate please! Take a thrifted sweatshirt that’s a bit baggy and cut a looser neckline so it can drape over your shoulders. Then get a pair of baggy jeans and cut them up a bit at the knees. Pairing that with a pair of classic white sneakers and you’ll be set! This outfit looks cool and is stylish as hell!

11. Extravagant

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“Even for him [Chris Brown], like, he knows now that he’s never going to do that again. And now, young girls also, they learn from it, and I really hope young men can learn from it. Even more than the girls, the men really need to learn from it. Because everyone’s focusing on the women, but the problem isn’t the women.” – Rihanna

This Met Gala dress is something of dreams! This abstract, romantic, and bold dress will make your head turn in a snap. It’s amazing how beautiful yet odd this dress really is. While we might not suggest wearing this to work or casually every day, there are some other ways you can easily incorporate some of the bold elements in this dress into your wardrobe. Right now the color of the year is red, so embrace that red or like in this dress, the maroons! Be bold just like the queen!

10. All Green

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“I respect what other people have to say. The bottom line is that everyone thinks differently. It’s very hard for me to accept, but I get it. People end up wasting their time on the blogs or whatever, ranting away, and that’s all right. I don’t hate them for it. Because tomorrow I’m still going to be the same person. I’m still going to do what I want to do.” – Rihanna

Wearing all bright green can be pretty hard, especially when it’s made out of a material like silk. Not only are you standing out because of the bright color, but you’re also standing out because of the bold pattern and texture of the overall outfit. It’s a pretty shocking look compared to her other outfits which might even be surprising. Because generally even though some of her outfits are insane and amazing, this one seems the most normal while not even being normal!

9. Casual Fenty

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“I think that Madonna was a great inspiration for me, especially on my earlier work. If I had to examine her evolution through time, I think she reinvented her clothing style and music with success every single time. And at the same time remained a real force in entertainment in the whole world.” – Rihanna

This outfit is probably one of the most insane on this list, simply because it’s not an outfit that you would ever picture Rihanna wearing. Basically just a jacket and slides. Granted the clothing and shoes are her fashion brand collaboration with Puma, but still. Maybe she was going for a bedhead look because even her hair could fit in with that kind of look in this particular instance. While we might not ever wear this kind of outfit, we’re so happy to have a celeb like Riri who really doesn’t care what other people think, now that’s unique!

8. The Trench Coat

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“You just want something else that someone else has, but that doesn’t mean what you have isn’t beautiful, because people always want what you have, and you always want what they have – no one is ever 100 per cent like, ‘Yes, I’m the bomb dot com – from head to toe!’” – Rihanna

This outfit is one that doesn’t get as much attention as it should. The focus is all about the coat, a unique and beautiful abstract piece that was created just for Riri. Rihanna decided to pair this look with a patterned bucket hat, a denim triangle bra, denim shorts, and a tied denim shirt around her waist. Of course she decided to wear striking white heels with this look too. If you want to wear a look like this you have to come to terms with your confidence. Literally anyone can pull off this outfit if you work hard enough on your confidence.

7. Camo and Jeans

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“It’s amazing how lonely you can feel and like nobody understands…The moment you are vulnerable, someone always reaches out….They go through the same things. I want them to feel comfortable knowing that I have flaws as wells. I want them to know those flaws. I’m afraid of the pedestal…I want to be a peer to my fans” – Rihanna

Just look at all the elements in this look! From the army green bomber jacket, the green baseball cap, the patterned head wrapped scarf, the shoulder bag, the crop top, necklaces, wide legged baggy jeans, and a matching denim jacket. Of course we couldn’t forget about the platform green shoes! We don’t know if we’d wear this look, but we sure do appreciate Riri coming out of her comfort zone and expressing her style this particular way, it sure is amazing! Do you think you would wear something like this in the future?

6. The Red Dress

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“I’m turned on by guys who are cultured. That’ll keep me intrigued. They don’t have to have a single degree, but they should speak other languages or know things about other parts of the world or history or certain artists or musicians. I like to be taught. I like to sit on that side of the table.” – Rihanna

Of course we had to include the famous red dress, a dress that has caused quite a panic in the fashion community. This dress was worn to a movie premiere and she really stood out. Standing on the bright blue carpet her huge red dress was even more visible. But we love it so much because not only was she confident in this outfit, but she looked happy. Even during her weight gain which we stand behind her one hundred percent, she is rocking what she’s got seemingly more than when she was at industry size. A round of applause please for Queen Riri!

5. Edgy

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“Over the holidays, and even during filming, I realized that I actually like my body, even if it’s not perfect according to the book. I just feel sexy. For the first time, I don’t want to get rid of the curves. I just want to tone it up. My body is comfortable, and it’s not unhealthy, so I’m going to rock with it.” – Rihanna

One of our totally favorite looks out of everything Riri has ever worn. From the detailed hair to the lace mixed with leather, even the sheerness of the dress. Everything about this look is Rihanna! We love how this look can easily be incorporated into any casual outfit for an everyday look as well. Just by taking the element of the lace and leather you can easily make sure that these elements stand out in a daily look for yourself. Just experiment and stay inspired by this look because we need to see more of this!

4. Pink Dreams

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“I don’t have time to be lonely. And I get fearful of relationships because I feel guilty about wanting someone to be completely faithful and loyal, when I can’t even give them 10 percent of the attention that they need. It’s just the reality of my time, my life, my schedule.” – Rihanna

This extravagant baby pink dress is so unique. We’ve never seen anything like this before and we honestly feel like she was pushing her own confidence when wearing this dress. We do love the color and the full shape, but it’s something that might have you asking some questions. She wore this dress to the premiere of EuropaCorp, a grand event for a grand dress. One of the most grand in the world. A great way to pull off a look inspired by this dress is by embracing the color pink, baby pink! Add some pink into your life and you’ll be just like Queen Riri.

3. The Sash

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“Now everybody watchin’ what I do. Come walk in my shoes, And see the way I’m livin’ if you really want to. I got my mind on my money and I not goin’ away, ay. So keep on gettin’ your paper keep on climbin’. Look in the mirror and keep on shinin’. Til’ the game ends, til’ the clock stops. We gonna post up on the top spot.” – Rihanna

This bold white outfit not only has a unique knitted dress, but also a large sash and heels with socks. Not to mention the future inspired glasses she’s sporting. Overall this look does have a ton of different elements to it that you might not have imagine would work, but they do! They really do come together in a way that is impressive and stunning. If you want to pull off a look inspired by this look, try incorporating socks and heels, it’s totally in style right now!

2. Lacy Forever

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“When I am putting looks together, I dare myself to make something work. I always look for the most interesting silhouette or something that’s a little off, but I have to figure it out. I have to make it me. I think that’s the thrill in fashion.” – Rihanna

What can we say, this pink all lace look is seriously one of a kind. You couldn’t find anything like this anywhere even if you tried. This custom made jumpsuit is something that we wish we could pull off. Not only is this amazing look full of little tiny details, but she also has a diamond choker on, as well as a long chain with a matching paper fan hanging from it. She’s decided to wear her hair slicked back and keeping all other accessories to a minimum. This outfit is one we would love to be able to rock, wouldn’t you?

1. Orange Crop

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“I used to feel unsafe right in the moment of an accomplishment – I felt the ground fall from under my feet because this could be the end. And even now, while everyone is celebrating, I’m on to the next thing. I don’t want to get lost in this big cushion of success.” – Rihanna

Closing out with a beautiful orange crop top and full ruffled skirt. While some people have said this is a total Halloween inspired look, we beg to differ. This look is just a bold and beautiful as all her other outfits. Whether she’s going for a themed look or not, we love it. This look is unique yet still relatively simple. It’s a look that will get people talking and it sure takes a ton of confidence to pull off. We’d love to know if you’d wear this look and if you’d have the confidence to pull off a look like this to a huge red carpet event. Let us know, because we sure wish we could wear this outfit for an evening.

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