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Fashion trends are not a one-size-fits-all category. While fashion experts lend their personal opinions on what's hot or not for the season, there are always styles that look cool in theory but are daunting to imagine wearing ourselves. The hesitation of trying the latest trends can stem from a fear of a "fashion fail" or simply looking out of place; however, taking fashion risks can lead to more positive benefits in one's life than negatives.


A risk taker is someone willing to take a leap and willing to fail. A risk taker is a rule breaker, change maker, and disruptor. An early adopter and one who isn't afraid to try new things before everyone else. The status quo is not good enough, so they lean into individuality and creativity. Confidence is what a risk-taker leans into the most, allowing one to break away from the mundane, keeping things fresh and exciting.

To gain insight on how to experiment with your style, I’ve compiled nine fashion trends risk-takers aren’t afraid to wear this fall/winter. From edgy, high-glamour looks to playful day-to-night outfits, these are the fail-proof styles I recommend adding to your wardrobe to step out of your comfort zone this season.

1.The Island of Capris

Capris are making a strong case for fall this year, and they don’t seem to be letting up any time soon. With a vintage flair with a modern undertone, there are plenty of ways to style this fashion throwback. Perfect for both a tropical getaway or business casual look, pair these with a feminine crop top and chain belt with heels, or wear them to the office with an oversized blazer layered over a button-up for a professional take. The opportunities are endless if you dare.

2.Bubble Skirts

After years of repressed fashion and closet essentials, it's only right that the latest silhouettes are becoming more extravagant and more interesting to look at. The bubble skirt is just that, a bubble silhouette. Instead of a flat hem like most other skirts and dresses, the bubble skirt's hem is tucked under, with a more voluminous look, whipped texture, and potential for major movement.

Style a fluffy white mini skirt with a leather jacket and tall boots or pointed heels for a fashion-forward fall moment.

3.For the Love of Fold-over Boots

The emergence of fold-over boots has re-ignited a spark in my love of fall footwear. The epitome of street chic, the exaggerated boot shaft can elevate an everyday boot collection with a new addition one could never get tired of wearing. Style with an oversized fall look with a classic bomber, black tee, and motocross pants for a forward approach to streetwear fashion.

4.All Flats

As a millennial, I’ve spent a fair share of my younger years in flats, which is why I’ll be happily watching this footwear trend from the sidelines. Nostalgic at best, the recurrence of the ballet flat can be fashionably subjective depending on who you ask. While personally refraining, I’m enjoying how wearers of all ages are creatively pairing this classic staple with a more fashion-forward approach with designer brand renditions such as Maison Margiela, Miu Miu, and Prada, just to name a few.

5.Black Tie

Once again, women are crashing the men’s section to adhere to this gender-bending addition to ready-to-wear fashion. For women, neckties are a fun yet ultra-chic accessory that elevates everyday casual, work, or even cocktail attire. Notable celebrities who never let a good tie go unworn include Tracee Ellis Ross, Zendaya, Janet Jackson, and Zoe Saldaña, just to name a few.

6.Moto Sunglasses

One of the most popular eyewear trends we’ve seen this year involves wide, chunky frames that balance both over-the-top fashion and functionality. Moto sunglasses are the perfect addition when paired with a maximal or minimal look because, either way, they are the statement. The oversized design adds an effortless high fashion element that exudes power and confidence.

7.Layering Hems

The midi skirt over pants combination can be either intriguing or intimidating. Mastering the art of layers, forward fashionistas around the globe have taken part in this unisex trend that proves that these days, fashion has no gender. A flowing draped effect paired with flowing trousers or structured denim can be styled to perfection with the proper proportions. Keep the layers casual this fall with a pointed-toe pump for a softer, quieter, luxe approach.

8.Hooded Dresses

Straight from the runways, hooded dresses are back on the fashion scene. The breakout trend of the season with recent interpretations from Versace, Saint Laurent, and Alaïa, in which we can also trace their hooded dress back to the 1980’s. Whether with sheer fabrics, draped backs, asymmetrical silhouettes, and bold cutouts, the latest dress trend has been declared a fashion favorite by celebrities and influencers alike. Adding a dose of luxury and mysteriousness to an overall look, hooded dresses have been worn throughout generations, from cultural to religious use.

9.Waist Belts

With lower waistlines creeping back into popular culture, so has the oversized waist belt. There's absolutely nothing subtle about the Y2K era belt trend, nor should it be. Wear a cropped or full-length top or knit sweater along with a denim maxi skirt, or keep it clean with a plain maxi dress if you want to try a softer take on the chunky accessory.

Finish off the look with neutral calf-high boots for an unforgettable vintage look.

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Featured image by Edward Berthelot/Getty Images

 

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