Editor’s Note: The views shared in this roundup reflect the personal opinions and experiences of each contributor. While some participants mention their companies or practices, this article is editorial in nature and not a paid advertisement. Mentions of brands or businesses are included solely to illustrate each contributor’s fashion philosophy.

“Fashion is the armor to survive the reality of everyday life,” said Bill Cunningham—and for many, it’s also a language of quiet rebellion. While traditional dress codes once served as markers of status and decorum, today’s evolving norms invite a more expressive, personal approach to style. In fact, psychological studies have shown that dressing in alignment with one’s identity can boost confidence and performance. So what happens when people challenge long-held fashion “rules”? In this roundup, experts share the style conventions they’ve intentionally broken—and why doing so might make more sense than following outdated norms.

Embrace Daytime Sparkle and Embellishments

It’s not so much a rule, but I am strongly against the outdated belief that sequins, glitter, and heavy embellishments should only be reserved for evening wear. At Terani Couture, I have always challenged this notion.

In modern times, most functions and events are held in enclosed establishments. Plus, camera technology has advanced to the point that it can capture the beauty of the entire dress without sequins or glitter interfering with the exposure.

Also, I mean, why limit the sparkle to after dark when so many of life’s most beautiful moments happen during the day? If a woman feels amazing in a beaded and sparkling gown at 2 PM, she should absolutely wear it.

After all, women should feel empowered to wear what makes them feel radiant, regardless of the hour.

Sas Terani, Owner, Terani Couture

Mix Upcycled Pieces for Sustainable Style

One fashion rule I intentionally break is the idea that you need to “dress for the occasion.” This often leads to overconsumption—buying new clothes for every event or social gathering. In our brand, we focus on reusing and upcycling, and I apply the same principle to my personal wardrobe. I mix upcycled pieces or items I’ve had for years, even for business meetings or formal events. This approach not only saves money but also reduces waste. In fact, since adopting this mindset, I’ve noticed a 40% decrease in personal clothing purchases, and I feel more confident knowing I’m contributing less to the fast fashion cycle. By breaking the rule of always buying new, I’ve realized that clothes can be versatile and still look professional or stylish. More importantly, it sends a powerful message to both my team and customers about the value of sustainability. Rethinking how we approach fashion can have a bigger impact than we realize—both environmentally and financially.

Soumya Kalluri, Founder, dwij, Dwij

Blend Metals for Personalized Jewelry Design

One fashion rule I’ve always ignored is “don’t mix metals.” At Nature Sparkle, I encouraged our design team to blend white, yellow, and rose gold in a single piece. Many doubted it at first, thinking it would look mismatched. But we launched a small mixed-metal ring line inspired by everyday contrast—like sunrise shades meeting cool silver tones. It felt natural and personal. Customers loved how the combinations reflected their own layered stories.

In just three months, this line contributed to a 38% increase in custom design orders and a 27% rise in repeat customers. What I learned is that rules often limit self-expression. People aren’t looking for perfect matches—they want pieces that feel like them.

For other business leaders, take the so-called rules as suggestions, not limits. Listen to what people connect with emotionally, even if it goes against tradition. Sometimes, what looks different ends up being exactly what people were waiting for.

Yoad Bet Yosef, Owner, Nature Sparkle

Redefine Clinical Attire in Aesthetics

One fashion rule I intentionally break is the expectation that medical professionals, especially in the aesthetic field, must always dress in traditional clinical attire. While I certainly adhere to high standards of cleanliness and professionalism, I choose to wear more stylish, yet still appropriate, clothing that reflects the luxurious and approachable environment we’ve cultivated at Lumi Aesthetics. I believe this approach should be reconsidered because it helps to create a more relaxed atmosphere where clients feel at ease from the moment they walk through our doors.

Aesthetics is all about enhancing natural beauty and making clients feel comfortable in their skin, which is why I think the clinical “white coat” image can sometimes create unnecessary barriers. I want clients to feel as though they’re stepping into a space of elegance and comfort, not just a sterile clinic. My attire reflects that philosophy; it’s part of building a space where beauty meets luxury and professionalism in a way that feels personal and inviting.

Many clients come to us with the desire to not only rejuvenate their skin but also restore their confidence. The process is deeply personal, and feeling like you’re in a space that respects that can make all the difference. By breaking the rule of traditional medical attire, I ensure that the environment at Lumi Aesthetics mirrors the transformative experience we aim to provide through our non-invasive treatments.

In the world of aesthetic services, it’s essential to make every client feel special. It’s not just about the treatments themselves, but the entire experience from the first consultation to the moment they leave with their newfound confidence. I’ve found that by opting for professional yet fashionable attire, clients feel more relaxed and open to the process, knowing they are in good hands, both professionally and personally.

Neda Hovaizi, Clinical Director, Lumi Aesthetics

Pair Sneakers with Suits for Confidence

Here’s one I intentionally break: I wear sneakers with suits. Not fashion sneakers. Not “smart casual” dressy trainers. Actual running shoes—sometimes with obnoxious colors and visible tech foam soles. And I do it in investor meetings, on stage, at formal dinners. Why? Because it flips the whole “dress to impress” idea on its head—and makes you the context, not the outfit.

There’s this outdated belief that professionalism has to come in leather and laces. But when you show up confidently pairing something tailored with something totally anti-tailored, it sends a different kind of message. You’re saying: I’m not here to blend in. I’m here to lead with my own logic. It subtly reclaims power from the room. Especially in industries like tech, where most people dress for status signaling, this can be disarming—in a good way.

Plus, here’s the underrated kicker: you walk differently when your feet are actually comfortable. You literally move through the world with less tension and more rhythm. It changes how you hold your body. It changes how long you’re willing to stay on your feet after a pitch. It even affects how grounded you feel during high-pressure conversations.

So yeah, “suits go with dress shoes” is a rule I’ll gladly keep breaking. The real fit is confidence, utility, and a dash of rebellion.

Derek Pankaew, CEO & Founder, Listening.com

Rock Monochromatic Outfits with Texture

One fashion rule I love breaking is the idea that wearing one color head to toe is “boring” or “too much.” I actually think monochromatic outfits are incredibly chic and empowering. Wearing a single color—especially bold tones like red, olive, or cobalt—can elongate your silhouette, simplify styling, and make a statement without being loud. The key is mixing textures, layers, or subtle shade variations to add depth and dimension. This approach makes getting dressed easier and lets accessories or cuts shine. Fashion is meant to be expressive, not restrictive, and this “rule” limits creativity. So yes—I’ll absolutely wear all black, all beige, or all green and feel confident doing it.

Qianqian He, Founder, BOXKING GAMING

Integrate Activewear into Everyday Fashion

One fashion rule I love breaking is the idea that you can’t mix workout wear with your everyday outfits. You know the old advice: keep gym clothes at the gym. But I totally disagree. Wellness isn’t just something I practice in the kitchen or with my skincare; it’s a lifestyle, and that includes what I wear. I often throw on a great pair of leggings with an oversized blazer and sneakers or pair a sports bra with high-waisted jeans and a denim jacket. It’s about comfort, confidence, and expressing your energy through your clothing. Why should we have to sacrifice ease just to check a box labeled “fashion rules”? That mindset feels outdated to me. Today’s women are running businesses, raising families, and building dreams, and they need wardrobes that move with them. Athleisure isn’t just a trend; it reflects how we live now. I think it’s time we stop putting fashion in these rigid boxes. Personal style should be fluid and functional, especially for women always on the go. So if blending activewear with streetwear works for your life, wear it boldly. That’s what fashion should be about: freedom, not rules.

Daisy Cabral, Visionary Founder and CEO, Teami Blends

Wear White Year-Round for Versatile Style

One fashion rule I intentionally break is the “no white after Labor Day” rule. Growing up, I always heard that white clothing was reserved for summer months, but over time, I’ve come to believe that this is an outdated and unnecessary guideline. I wear white year-round, whether it’s a crisp white shirt in the winter or a cozy white sweater in the fall. I find that white can actually bring a refreshing brightness to colder seasons, and it pairs well with darker tones for contrast. It’s a versatile color that works in any season, and I think it’s time to reconsider such rules that limit creativity and personal expression. Fashion should be about how you feel in what you wear, not adhering to arbitrary restrictions.

Nikita Sherbina, Co-Founder & CEO, AIScreen

Choose Business Casual for Approachable Plumbing

I intentionally break the fashion rule that says plumbers should always wear heavy-duty uniforms or overalls when meeting with clients. I believe it’s important to strike a balance between professionalism and approachability, so I often opt for business casual attire instead. This allows me to create a more relaxed atmosphere for my clients, helping them feel at ease, especially when they’re dealing with the stress of plumbing issues.

The traditional look of a plumber in full gear can sometimes create a barrier between the professional and the client. Plumbing issues can already feel overwhelming, and I’ve found that a more approachable style helps to ease the tension. It shows that I’m here not just to fix the problem, but to provide a service that feels personal and focused on the client’s needs.

When homeowners or business owners are dealing with plumbing issues, they want someone they can trust, who speaks to them in a straightforward and accessible way. The way I present myself matters just as much as the quality of my work. It’s about building a relationship and making clients feel comfortable asking questions and expressing concerns without the intimidation of a strict uniform.

Plumbing is a hands-on, service-driven profession, but that doesn’t mean we can’t offer a more human, relatable experience. By breaking this fashion rule, I hope to show that professionalism doesn’t have to come with a stiff exterior. It’s about making the whole process, from the first phone call to the final fix, feel as stress-free and approachable as possible.

Louis Natale, Owner, Proven Plumbing

Mix Clashing Patterns for Creative Expression

I purposely mix patterns that “clash” because life isn’t about playing it safe. Breaking this rule makes outfits more fun and personal. Fashion should be about creativity, not strict matching — it’s time we rethink those old limits.

Chris Brewer, Managing Director, Best Retreats

Keep Clothes Beyond Trends for Personal Style

I frequently wear the same clothes for years, even after they’re considered out of style. Not only does this practice make more economic sense, but it also helps me ensure that I am buying and wearing clothes that speak to my personal style and keep me comfortable, rather than just looking good.

Manasvini Krishna, Founder, Boss as a Service

Share Your Insights

We’d love to hear how you break the mold when it comes to personal style! Share your thoughts in the comments:

• What’s one fashion rule you love breaking—and why?
• Have you ever felt more confident by going against the norm in how you dress?
• Which of these style rule-breakers inspired you the most?

Let’s keep the conversation going—your style story matters!

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