10 Reasons Why You Always End Up Wearing the Wrong Thing

For better or worse, fashion is a world of rules. And while it’s undoubtedly a channel for creativity, there are certain precedents that reign true so far as style is concerned. With varying guidelines for different seasons and occasions, not to mention adopting ever-changing trends, keeping up with what is “in” and “out” can feel exhausting to say the least. While it’s all too easy to feel the need to buy into all the rules and tips about what to wear and when to wear it, something about constructing an outfit so meticulously can start to feel a little insincere.

This month, we’re all about advocating for fearless fashion, so we’re taking the opportunity to consider what makes our outfits “wrong”—and accept the fact that that’s okay. In fact, it’s more than okay; it’s completely normal, and if you listened to every guideline and piece of advice, we’re willing to bet you’d end up with nothing to wear at all. No matter the occasion, no matter the season, we’re sorry to tell you… but you will always end up wearing the wrong thing. But at the end of the day, there’s a certain beauty in that. It’s the age-old adage at its finest: “You can’t please everyone.”  And that’s especially true where style is concerned.

Because fashion sense is something so personal, the fact that it varies widely from person to person should be something inspiring—not limiting. The next time you find yourself questioning whether or not you can pull off a trend, take a moment to tap into your fearless side and shun any “rules” in exchange for whatever makes you happy.

To break it down, we’ve called out ten reasons why you’ll always end up wearing the wrong thing. And called out a few examples of great outfits and pieces that prove that sometimes wearing the “wrong thing” is oh so right.

1. You'll break a fashion rule


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This white pant and sweater combo proves that the old rule of avoiding the light trousers during the colder is one that should be ignored. By pairing her camel sweater with white trousers and boots, the outfit provided a clean alternative to winter blacks that can begin to feel a bit repetitive.

Reformation Fawcett Jean ($168)

These will be your new favourite jeans.

2. The colours will clash


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If 2018’s street style has proven one thing, it’s that bright colours can (and should) be paired together. Case in point: The pink-and-red phenomena that has taken over the world’s most fashionable cities. We have a feeling this trend won’t be fading anytime soon.

Maggie Marilyn The Believer Cropped Striped Merino Wool Sweater ( $433 ) ($216)

Find a more fun sweater, we dare you.

3. Your outfit won't be "flattering"


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While nipped-in waists and skinny jeans can slenderise your figure, that doesn’t mean that you need to avoid baggier silhouettes altogether. This season’s resurgence of wide-leg pants and oversize jackets proves that though the style may not be as traditionally “flattering”, it’s still a chic option regardless.

Ksubi Daggerz Cropped Denim Jacket ($317)

This jacket will go well with any outfit.

4. You'll wear something "ugly"


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We’ve spoken before about the ways that a subtle hint of “ugly” can transform an outfit, and this season’s favourite accessories are confirming it. From dad sneakers, to mini sunglasses, to the infamous bucket hat, a little “ugly” is proving to be a game-changer to take your outfit to the next level.

BDG Plaid Bucket Hat ( $32 ) ($53)

Meet your new favourite hat.

5. You'll wear something dated


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Thought that the days of logomania were long gone? Think again. This year, there’s been a resurgence of logo-centric styles from Fendi jackets to Gucci tee shirts and beyond.

Fendi Kan I Small Flocked Leather Shoulder Bag ($3693)

Fendi is everywhere lately. 

6. Too much going on


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Anything goes this season, and unique combinations (such as skirts with sneakers) are proving that there’s no such thing as “too much”. We’d even encourage you to add in a metallic bag, for good measure.

P.A.R.O.S.H. Floral and Polka Dotted Pleated Skirt ( $735 ) ($368)

More is more in 2018.

7. Too little going on


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On the other end of the spectrum is minimalist style at it’s finest. This look proves that even something as classic as jeans and white top can be an amazing outfit when adapted with interesting silhouettes and shapes.

Jacquemus Pinhao Ribbed Tank Top ( $340 ) ($238)

A new take on a classic black tank top.

8. The proportions won't be right


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One of the most iconic street style looks of the year, Centenera’s Céline skirt suit proves that unconventional proportions can outshine traditional tailoring when done right.

Off-White Oversized Double-Breasted Blazer ($1762)

Even with a pair of jeans, this blazer will make a for a chic look.

9. It'll be impractical


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No one said that the itty-bitty bags of 2018 were practical. There’s nothing logical about a purse that can barely fit an iPhone, but nevertheless, they sure are adorable which is reason enough for us to get behind the trend.

Simon Miller White Gold Bonsai 15 Mini Leather Bucket Bag ($580)

One of 2018's favourite bags is even cuter in this miniature version.

10. You'll be overdressed 


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We’ve all been there. Some days you just want to throw on a pretty dress and fur coat and live your best life. But if you’ve ever put together the ensemble, only to feel a little over-the-top, you’re not alone. However, we’re arguing that sometimes going a little overboard is just what the doctor ordered. Next time you hesitate, remember to embrace fearless fashion, and wear it if it makes you happy anyway.

Zimmermann Melody Floral-Print Silk-Crepon Maxi Dress ($1100)

There's nothing more dainty than a floral maxi dress.

Now you know the ten reasons why you'll always wear the wrong thing. But more importantly, now you can see why it actually doesn't matter; so go on and embrace your fearless side this season. 

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