The idea of following rules in fashion seems undoubtedly outdated, especially in 2021. For decades, we’ve allowed arbitrary guidelines to rule our style choices. No white after Labor Day? Never mix gold and silver jewelry? Says who? Not us, that’s for sure. Fashion is meant to be fun—a crazy concept, I know—and showcase self-expression, so the idea of restraints around that sentiment have reached the point of archaic.
Even as workplace dress codes begin to relax and more people are dressing for their own comfort, some of these rules may actually make sense; You may still want to forego wearing a white dress to someone else’s wedding or check with HR before showing up to the office in jeans and sneakers.
So while the idea of rules may be evolving, we’re left with at a slightly overwhelming crossroads of how to pick and choose which guidelines to follow or forget. In an effort to make it a bit less complex and a lot more fun, we’ve connected with a handful of the industry’s most influential insiders, including celebrity stylists, influencers, and more to decode the future of styling cues.
Madison Guest, Celebrity Stylist
Madison Guest is a celebrity stylist to fashionable starlets like Victoria Justice and Dominique Fishback. To Guest, fashion rules are totally out the window. She says, “Truthfully, I think almost all 'fashion rules' are completely dated. No sequins during the day? Blah. No shorts after age 30? Get a life. Growing up in the South, I was always taught 'no white after Labor Day until Easter,' and I lived by that for a while. Until I learned the beauty of winter whites. Now I love nothing more than a head-to-toe white look in the winter!”
And her best advice on breaking the rules? “If my mom and her friends still live by them, it’s time to break them!” she says.
Caroline Vazzana, Author and Founder of Making It in Manhattan
While she may be referred to as the modern-day Carrie Bradshaw, Caroline Vazzana is a style icon in her own right. Known for her bold colorful looks, she shares that, “When it comes to fashion, rules are supposed to be broken. I honestly don’t find myself sticking to any trends or rules in particular! My formula is that if I like it and feel confident, that’s all that matters.”
For Vazzana, anything goes. “It’s all about taking risks. Mixing prints, bold color pairings, sequins with feathers. Life is too short to wear boring clothes, and after a year of being inside, it’s time to break the rules and wear something fun!” she says.
Arielle Siboni, Bloomingdale's RTW Fashion Director
Arielle Siboni, Bloomingdale’s RTW Fashion Director, helps guide the fashion choices of one of the world’s most iconic retailers, so it’s safe to say she knows a thing or two about making smart style moves. “I think in today's world, most fashion rules are outdated. Some that come to mind are: ‘Don't wear more than one print at a time’ and ‘don't wear white after labor day.’ I personally love print-mixing and wearing winter white. Fashion is a reflection of who you are and there shouldn't be any rules surrounding that.”
But, in terms of rules she adheres to, Siboni says that “The only rule I follow, and recommend that others do too, is that you should always leave the house in an outfit that makes you feel great.”
Plus, she says, “Another rule I try to keep in mind when making purchases and getting dressed is 'never say never. Our tastes evolve over time and there are trends I wear now, that I wouldn’t have gravitated towards a few years ago. Clogs, which are having a moment right now, are a good example of this, and I just bought my first pair!”
There's still one important rule she’d never break, though: The dress code. “If something calls for black tie, I wouldn't show up in jeans. However, even 'black tie' has evolved these days and wearing a pair of dressy pants is totally acceptable,” she says.
Cassandra Dittmer, Stylist
Cassandra Dittmer, the LA-based stylist who keeps sustainability and ethics top-of-mind when making style decisions, says, ‘Wearing an item once or not outfit-repeating is totally outdated. It's much more fashionable, sustainable, and realistic to rewear outfits and pieces.”
Her best advice for choosing when to nix or follow rules is that, “The best fashion is truly what makes you feel happy and, at the end of the day, confidence transcends any fashion rules. When you are trying silhouettes or trends that are new to you, it's important to pair them with something you know you love. I don't think any fashion rules are hard rules. Fashion is so personal and the rules are really just guidelines that orient you as needed.” she says.
Brett Heyman, Founder of Edie Parker
Brett Hyman is the founder of the cheeky accessories and home decor brand Edie Parker. Although her brand’s essence includes the perfect touch of whimsy, she still adheres by a couple of more traditional fashion rules to guide her personal style decisions. “I think this ‘rule’ is outdated, but personally I still skip stockings with sandals," she says. "And I would never wear logos head to toe, but again, that’s a personal preference. Other than that, never say never.”
At its core, the rules are out the window, and wearing whatever it is that sparks joy for you is the most important. "At its best, fashion celebrates individuality, so I don’t think rules apply," she adds. "My personal policies are ever-changing with age and the confidence that comes with it.”
Tara Swennen, Celebrity Stylist
As a celebrity stylist who has worked with fashionable leading ladies from Kristen Stewart to Lana Condor, Tara Swennen uses personal style as a foundation for knowing when or when not to follow the rules. She says, “One of the biggest mistakes people make is buying trendy pieces for the sake of the trend. Sometimes a modified trend is the key. This lets you wear something of the moment without it feeling manufactured. In this case, invest in pieces that emulate fast-fashion trends while still being classics.”
“Although there is always a time and a place for modesty and formality, fashion is an extension of one's personality and therefore an art form,” she says. “One should always do what makes them feel their best. That is truly the number one rule. These days, my rule is the bolder the better: gender bend, mix prints, dress someone else's age. Life is short, have fun with it!”
Michelle Li, Style Editor at Tradesy
Michelle Li is known for her forward style and achieving a coveted ‘cool girl’ look while adhering to a reasonable budget. The style editor at Tradesy says that, “dressing ‘on trend’ and not wearing something from ‘last season’ is completely outdated. Trends move at the speed of light now and between the pace of the 24-hour news cycle and social media, you could argue that anything is a trend if you want it to be.”
“I always find great items from past seasons that I call ‘the one that got away.' The Miu Miu dress from the spring/summer 2015 collection, the Blumarine top that’s now vintage because I was too young to wear it the first time,” she says.
Mixing high and low or new and old while staying true to your own taste creates a personal style that’s totally unique and easy to follow. Li says, “I have pieces of clothing that I won’t wear because they don’t align with my personal style. There is no one authority that can make a blanket statement about what you can and can’t wear.”
Leesa Evans, Stylist
As an industry veteran, stylist, and founder of The Health and Wellness of Style, Leesa Evans’ knowledge is sure to be trusted. When asked about style rules she follows, Evans shares, “To me, fashion rules are based solely on personal taste; that said, these are two rules that always work for me: the only true neutrals are mid-camel and mid-gray. Any and all colors look great with these. [The second is] feeling confident in your clothes is more attractive than any trend could ever be.”
Plus, she says that “It's always fine to break the rules when it brings you joy; and it's also important to be respectful and follow the rules when you are invited to someone's special day.”
Rebecca Allen, Founder of Rebecca Allen
Rebeeca Allen, founder of her eponymous footwear brand, says that, “I adhere to only following trends that suit [me]. I always look to buy things that really flatter me. Every once in a while, I'll fall in love with a trend that might look ridiculous on me, but if it makes me happy, I'll go for it!” And this is certainly great advice for making sure you feel comfortable in your own skin while having a little fun with fashion, too.