The Fashion That Makes Me Feel Fearless

It can feel quite scary to dress outside of the fashion box. Many of us find comfort in maintaining the style status quo, embracing trends like “normcore” and “quiet luxury” that, in many regards, represent the fashion industry’s tendency to celebrate assimilation rather than individuality. But it’s often those who wear fashion fearlessly that turn the tides on trends; the people with such a unique sense of personal style that there’s no questioning their taste, power, or influence. But it isn’t intimidating; quite the opposite: The right sartorial mindset can create a kind of contagious self-assurance.

So we called upon some of our favorite fashion lovers — designers, red carpet hosts, reality TV stars — to tell us what pieces in their closets they wear to break free from the banality of blandness and to personify bold beauty and intrepid irreverence. Ahead, the stylish, surprising, and even inspiring items our experts reach for when they want to feel fearless. Because when you wear something that stands out, it can give you the confidence to be standout.

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Brandon Blackwood

To be fearless, one must “begin to trust yourself, decisions, and actions more,” says designer Brandon Blackwood. “Only then can a truly authentic representation of yourself shine through.” The pride Blackwood has not only for himself, but for his ready-to-wear and accessories lines which has helped his eponymously named brand become a cultural and commercial success. From his famous clients (Beyoncé, Lizzo, and Sheryl Lee Ralph, to name a few) to his “cousins,” as he calls his rabid customer base, Blackwood is able to create a sense of familiarity amongst his tribe that is rare in today’s fast-paced market.

The Item: “My nameplate necklace, which was made by Helen the Jeweler. It says my last name “Blackwood” and is something I hold dear to my heart.”

The Moment: “I remember I was doing a huge talk for the Wall Street Journal. It was probably my biggest speaking engagement, and I was a ball of nerves. I remember fidgeting with my necklace before reading. Seeing my family’s last name and thinking about all the support I have gotten from them really calmed my nerves. It felt like I was wearing armor.”

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Jennifer Fisher

As a female founder in her fifties and the face of her eponymous jewelry brand’s latest campaign, Jennifer Fisher knows what it’s like to have your aesthetic under a microscope. She believes that dressing without fear means that, “Your fashion choices should be something that you personally gravitate to without questioning a) what people are going to think and b) how it’s going to look.”

Her Fearless Fashion Philosophy: “I always trust my gut and go with my instinct on how I feel like dressing and wear what makes me feel my best.”

The item: “There’s nothing like a statement bracelet that makes you feel like your own personal superhero.” The statement piece that makes her feel as brave as Wonder Woman? “My favorite fearless piece of the moment is the new diamond Cuban link bracelet from our JF lab diamond collection.”

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Jessel Taank

“There’s something quite liberating about creating your own rules and not falling victim to trends,” says Jessel Taank, breakout star of the most recent season of The Real Housewives of New York and a new entrepreneur. Last month, she launched OUSHQ, one of the first e-commerce platforms dedicated to Indian and Middle Eastern designers.

The Item: Feeling an overwhelming sense of pressure on the night of her launch dinner, Taank wore a hand-woven, high-collar holographic halter dress by Delhi-based designer Abhishek Sharma that helped her shed her nerves and feel fearless in that moment.

The Impact: “I wanted to wear that dress to the launch dinner, knowing that it would be a conversation piece but also that I could justify why I started OUSHQ! There is a library of untapped talent that I’m helping to bring to the forefront, and this dress was a perfect exhibit of and personification of this — I felt confident and 100 percent fearless at that moment.”

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Jordan Roth

Jordan Roth doesn’t actually think dressing confidently is about fearlessness. The Broadway baron and fashion connoisseur instead believes it’s about “moving forward through the fear. Not letting fear close us off to ourselves — which doesn’t have to require never being afraid,” Roth says. “The deeper courage is to do it anyway, despite the fear, rather than waiting for fear to disappear.”

The Item: What does Roth wear to move past the fear? “My Rick Owens platform boots. I have them in a bunch of colors. The classic black was first; then I made a special order for white and red ones (pictured here at the recent Valentino Couture show in Paris). I wore a green pair to the Met Gala a few years ago.”

The Rationale: The sky-high platforms serve a practical purpose as well. “They give me the perfect power lift (literally and metaphorically) with a good 5” more height,” says Roth. “Literally, I can just put them on in my closet as I’m getting dressed, and the moment my foot clicks in, my body responds, my walk responds. Power, freedom.”

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Kelly Cutrone

Kelly Cutrone’s enduring and unapologetic confidence has inspired countless fashion and public relations hopefuls throughout the years. As an author, reality TV star, and creator of the PR firm People’s Revolution, the multi-hyphenate is now adding Alexis Bittar model to her resume, “I recently entered the BittarVerse, where I played an exaggerated version of myself.” Cutrone says. The BittarVerse videos are love letters to New York and the wonderfully extreme characters, like Amanda Lepore, Mel Ottenberg, and, of course, Cutrone, who inhabit the great city, wearing fabulous baubles and bangles from the brand.

Her Fearless Fashion Philosophy: “One needs to be comfortable in their skin and with their attire. It’s about self-expression at the end of the day.” 

The Item: Her Bittar bangles. Asked to describe a moment when she felt fearless wearing them, Cutrone mischievously recalls, “I left my townhouse on Madison Avenue with my new bangles, I confidently slayed the streets of New York, knowing I looked great and secretly smiling because truth be told, they are more than a Bangle. They’re a self-defense tool. Pepper Spray is so OVER.”

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Laverne Cox

E! host Laverne Cox may seem like she’s forever confident on the red carpet in extravagant fashions, but early in her life, she didn’t always feel that way. “For years, I fought surrendering to the high femme person who was fighting to get out. When I finally surrendered the freedom waiting on the other side was so liberating. Fear kept me from my freedom.”

The Item: Cox often turns to her massive archive of vintage to feel fearless and current go-to is a Manfred Thierry Mugler jacket inspired by the Lost city of Atlantis. The piece is meant to evoke a mythical sea creature to come to life with its fin-like silhouette and patchwork of suede and patent leather scales. 

The Impact: “My journey to myself for many years felt impossible, like a wild, implausible fantasy. This jacket reminds me that our wildest, most implausible fantasies can be made a reality.”

The Moment: “I have yet to wear this outside my apartment; when I wear this at home, it reminds me of when I played dress up at home as a kid and dreamed that this garment could transport me into the most glamorous, fabulous spaces of the world. Tending to this child who still lives inside me and who dreamed the impossible, caring for her, and giving her space and time to play is truly what makes me feel fearless.”

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Rachel Zoe

“To me, being fearless is all about feeling confident,” says Rachel Zoe. What does the style icon, business mogul, and Baby2Baby board member gravitate toward for that extra boost of confidence? “When I wear sequins, especially gold, I feel most like myself.”

The Item: Zoe recently stumbled upon this shimmering Marc Jacobs floor-length gown at Allbright Fashion Library in L.A. when she was on a last-minute hunt “for a major moment.” The meaning behind her purchase goes beyond just the shiny facade, sharing that “Marc is such a dear friend and I feel so special in his creations, always, because I know what he puts into designing each piece; there is always a story behind it…this was his homage to Norman Norell and was one of his personal favorites.”

The Moment: Having made a legendary career out of red-carpet dressing, Zoe certainly knows the importance of feeling good in what you’re wearing at a star-studded event. “I’m so proud to be on the board of Baby2Baby, and I wore this gown to the annual 2023 gala last November — amongst an amazing group of other incredible, fearless women — and it felt perfectly glamorous and effortless!”

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Reneìe Loiz

Los Angeles-based makeup artist and groomer Reneìe Loiz has a flock of celebrity clientele that includes Quinta Brunson, Cynthia Erivo, Kirby Howell-Baptiste, Sherry Cola, and Adele, who all look to her to make them feel fearless on the red carpet. While Loiz has plenty of ammunition in her beauty artillery at her disposal, she turns to hair accessories to give her confidence.

The Item(s): As someone who finds liberation in switching up her hairstyles, Loiz loves to accentuate her gorgeous locks with berets, beads, and, especially, bows. “I like that they’re statement pieces I can wear to show off my hair. I’ve always had some sort of accessory in my hair since I was a child. A lot of them were hand-me-downs from my older cousins or things I would find at a thrift store.” When asked to describe the power she gets from wearing bows and berets, Loiz shares that “with hair accessories, it may not have always looked good or may not have always turned out the way I liked, but it’s all about owning it and being brave to wear it out in public.”

The Impact: Growing up, Loiz went through a personal journey of acceptance and empowerment, learning to own her natural curls, and wanted to share her experiences with her followers. “Wearing bows in curly hair is kind of tricky because it can get lost in the curls if it’s not the right size and color. So I did a deep dive search to find the right bow to wear for a recent curly hair tutorial ,” Loiz says. “I was nervous that the style wouldn’t work, but I just walked through the steps with confidence, and that video ended up going viral!”

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Sarah Rafferty

From playing a matriarch to a rambunctious household of nine boys and two girls on My Life with the Walter Boys and everyone’s favorite legal secretary, Donna, on Suits, actress Sarah Rafferty knows a thing or two about how clothes create a fearless character. Starring in two of the biggest shows on Netflix, many associate Rafferty’s style with that of the courageous characters she portrays. To tap into that feeling off-screen, Rafferty reaches for something sentimental.

The Item(s): “I have felt at times most fearless, grounded, and joyful when wearing a piece that belonged to one of our family‘s matriarchs…Elsa Peretti jewelry, Pucci prints, or St. John’s knits,” she tells InStyle.

The Legacy: Over the last two decades, Rafferty has collected special pieces from her own travels and events and more than a few from Donna’s closet as heirlooms her daughters can someday feel fearless in. “Do my friends think this is a hoarding problem? Yes. A consciously sustainable practice? Maybe? But most of all, it’s a hope that one day my daughters and granddaughters will giggle with delight just like I did when offered pieces from my grandmother’s steamer trunk.”

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Shibon Kennedy

A vintage Versace men’s pinstriped blazer is what stylist to stars Shibon Kennedy wears to feel fearless. Bought from NYC vintage shop Lara Koleji, the blazer has given Kennedy plenty of confidence each time she’s worn it, and with celebrity clients like Rihanna, Billie Eilish, Rosalía, SZA, Serena Williams, and countless other endeavors, it’s clear to see why it never hurts Kennedy to have that extra boost.

The Moment: Kennedy is also a director, acting as co-auteur of the short documentary We Are the W, about the WNBA, which released in 2022. “I was heading to a pre-pro[motion] dinner with the team and some of the talent. I remember feeling so excited, so in awe, that I was going to be making a film for such an incredible institution. I remember feeling so proud as I started to think about the fact that I had gotten to that point through passion, vision, and talent coming together in my treatment. WOW. I did that! I remember walking into that meeting wearing that blazer so clearly to this day…. I felt so strong, like I could do anything and yet I was in such awe of what was happening. It was a powerfully surreal and totally amazing moment.”

Here Fearless Fashion Philosophy: “I say this a lot, and often when talking about stylistic choices: ‘The only rule in fashion is there are no rules.’ To me, that whole sentiment at its core is about a sense of fearlessness.”

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Tina Leung

Even though Tina Leung was a fashion influencer long before the term was even coined (Leung established her personal style blog called tinaloves.com in 2011), she’s not immune to butterflies. “I still get anxious and a little nervous with the street style photographers,” Leung confesses. This may come as a surprise since the fashionista and reality T.V. star’s confidence has been personified into a superhero alter ego in the digital comic House of Slay. The comic champions AAPI fashion personalities, like Laura Kim, Phillip Lim, Prabal Gurung, Ezra William, and Leung, as superheroes dealing with racism and hatred issues in society. Thankfully for the style and reality T.V. star, designer clothes serve as a protective armor against any bad vibes she comes across.

The Approach: While she usually has to wear a full head-to-toe look from whatever brand she is supporting, Leung finds comfort when she’s able to style herself the way she sees fit. Take, for instance, the Marni outfit pictured her: “I cobbled this look together myself, so I feel fearless because I am 1,000 percent myself here,” she says.

The Rationale: “Sometimes you don’t feel fearless yourself, so you need a little help, and clothes definitely help!”