Breaking Fashion Rules

When I think of breaking fashion rules, Iris Apfel is the first person that comes to mind. She just turned 101; follow her on Instagram for fashion inspiration and her fun style of dressing up. “More is more & less is a bore.”

image from Instagram

With her iconic oversized glasses, penchant for color, layers of heavy, bold jewelry, and daring style, you know Iris Apfel even if you’ve never read Harper’s Bazaar, Vogue, or Vanity Fair.” From Fashion icon Iris Apfel’s surprising connection to Salem

In my weekly newsletter and weekly post, I write about “what to wear” and trends that are popular at the moment. In addition, I write about trends I’ve read about, sometimes in more than one publication. I don’t expect my readers to wear everything included in those posts. Instead, you can use the information I provide to add items to your closet, create new outfits, or talk about it with friends and family.

Reading fashion magazines and seeing pictures of celebrities wearing certain trends might influence how you dress but don’t feel obligated to wear certain pieces because they are trending.

From Fashinnovation, “Fashion trends have always been defined by the elite in society. First, they were defined by the royal families, who would set trends to be followed. Now, celebrities and influencers are the ones who set fashion trends. But ultimately, you are the one to decide what you think is fashionable or not and make your mark on the history of fashion.”

The first rule to break is, “Fashion rules are meant to be followed and taken seriously.” Read 50 Fashion Rules to Break Right Now in Stylecaster.

After researching, I’ve come up with my top fashion rules to break.

“Don’t wear white after Labor Day”

This weekend, the fashion rule that comes to mind is “Don’t wear white after Labor Day.” How did this rule come to be? The History Behind the ‘No White After Labor Day’ Rule. I hope you will be comfortable breaking this rule after reading the history of how it began.

Since Labor Day typically represents the end of summer, a ‘rule’ was established that you shouldn’t wear white after Labor Day if you didn’t have the money to take fall and winter vacations. It was also used as a way to identify those who needed to work and those who didn’t. Those who didn’t have to work could wear white because it wouldn’t get dirty, while those working would wear dark clothing to hide the dirt they’d pick up working or walking through the city.”

From Stylecaster, “As countless designers have proved during the past few seasons, white isn’t only appropriate when the weather gets cold, but also amazingly fresh and modern-feeling.” A pair of white jeans or pants is an accessible white item to keep in rotation during the fall and winter.

For women:

The Perfect Vintage Wide-Leg Crop Jean in Tile White $128.00 at Madewell
High Rise Pleated Wide-Leg Trouser with Washwell $39 at Gap

For men:

From The Free Weekly, The why, the when and the how of white pants, “I think of white pants as divided into four categories from most casual to near-professional: 1.] white super-casual sweatpants, 2.] white jeans, 3.] white lightweight cotton chinos or linen pants, and 4.] off-white (“winter white”) lightweight wool dress trousers. Each has its own useful place.”

Slim-fit flex jean in white $44.50 at J.Crew Factory
ABC Slim-Fit Pant 34″ Utilitech $128 at Lululemon

To break this rule, wear as many white items as you want to after this weekend, including white shoes.

Mixed prints are too busy

From Stylecaster, “Actually, mixed prints can look extremely fresh, and elevate your look from ordinary to street-style ready in no time.”

For women:

Read 7 Ways to Mix Prints Like a Pro in InStyle. “There’s just something so fun and eye-catching about seeing, for example, bright stripes seamlessly styled with plaid pieces.”

Animal prints like snakeskin and leopard have proven to be versatile, and oftentimes, they go undetected. Treat them as solid neutrals and style them with something floral for an unexpected twist.

Devon blazer in plaid Italian stretch wool $328 at J.Crew
Calf hair belt in leopard $29.50 J.Crew
Classic-fit soft gauze shirt in tossed floral $59.99 at J.Crew

For men:

Read A Guide to Pattern Mixing in Articles of Style.

Unconstructed Italian Linen Blazer $300 Bonobos
Stretch Oxford Shirt $89 at Bonobos
Men’s Classic-Fit Ultraflex Patterned Sport Coat $89.99 at Macy’s

Don’t combine certain colors:

Brown and black don’t mix

From Stylecaster, “This has long been a fashion rule that’s made to be broken, as black and brown actually go together quite well.”

For women:

From an Indigo Day, How To Wear Black And Brown Together. “For years, I think we all felt that black and brown can never go together. It was a huge fashion faux-pas to mix the two. You’re either wearing brown or you’re wearing black. Never both. But really both are neutrals and can truly be worn together when done right.” 

Photo by Hannah Lozano
Photo via @alinagavrilov_
SCULPTED SUIT BLAZER $98 Banana Republic Factory
The Way-High Drape Pant $118 at Everlane

For men:

From Top.Trends.Guide., How To Wear Black Pants with Brown Shoes. “Brown shoes can exude personality and modern style while looking professional and stylish. The challenge is pairing brown shoes with black. While not a traditional look, there are many ways you can wear black pants and brown shoes.”

Michael Kors Men’s Solid Classic-Fit Stretch Dress Pants $34.99 Macy’s
Men’s Macarthur Wingtip Oxford Shoes $99 Macy’s

Navy and black don’t go together

From Stylecaster, “This fashion rule still has its fair share of subscribers, but let us make it clear: Navy and black look super-chic together.”

For women:

From Edits, Style rule breakers: how to wear navy and black together. “Whether in a single garment or combined in a head-to-toe look, black and navy blue look ultra-sophisticated together. It’s dark without being gothic, and sleek without being too stuffy.”

Peak Lapel Double Breasted Novelty Button Blazer $168 Express
MINI T-SHIRT DRESS $41.97 Banana Republic Factory

For men:

From Thread, Can I pull off: Black and blue together?If you’ve heard the phrase “black and blue never do” you’re probably of the mind that navy and black together is one of those timeless, inarguable fashion faux pas. And yet that particular combination is actually one of our stylists’ favourites.”

Men’s ZERØGRAND Wingtip Oxford $185.00 Cole Haan
Wool-Blend Water Resistant Bomber Jacket $198 Express

Red and pink clash

From Stylecaster, “Somewhere along the way, these two shades got a bad reputation, but when paired purposefully, they can actually look quite modern and eye-catching.

For women:

ASOS LUXE color block suit jacket in red & pink – part of a set $64.00 ASOS
REISS Valentina Color Clash Dress $172 Bloomingdales

For men:

From Fashionbeans, A MAN’S GUIDE TO WEARING PINK. “The main worry for guys is that they could look effeminate in pink,” says Mr Porter contributing style director Dan May. “But no colour is off limits. It’s just the way you style it and the confidence with which you pull it off.”

Slim Fit Stretch Oxford Shirt $115.00 Polo Ralph Lauren

Denim on denim is a fashion faux pas

From Stylecaster, “Also known as a Canadian tuxedo, the easiest trick to rocking double denim without looking like you got lost on the way to the cattle ranch: Pair pieces of varying washes together, such as a light denim shirt with dark denim jeans, or a dark denim jacket with a light-wash pair of denim shorts.”

For women:

Women’s Ex-Boyfriend Cotton Denim Trucker Jacket $68.60 Macy’s

For men:

Light Wash Temp Control Hyper Stretch Denim Jacket $54 Express

Take off one accessory before leaving the house

From Stylecaster, “Why? As fabulous women like Iris Apfel have proven time and time again, piling on the bling can be fabulous and totally idiosyncratic.


Breaking the gender norms

Gender norms are a hot topic in modern society. Gender norms are based on the different expectations that individuals, groups and societies have of individuals. These expectations are based on individuals’ sex and societies’ values and beliefs about gender. These expectations and beliefs define what appropriate gender norms are and decide which kinds of behavior are appropriate for females or males (Blackstone, 2003).” From Diggit Magazine.

Actual menswear is just for men

From Stylecaster, “This is especially true at common outposts like Forever 21, H&M, J. Crew, and Zara, whose men’s stuff—think slim-cut button-downs, sweatshirts, sweaters, and utility jackets—often aren’t as trendy as their for-women counterparts, and offer a slightly slouchier fit.

From PureWow, The Surprising Menswear Trend Taking Over Women’s Closets This Summer. “One I’ve noticed gaining traction: the button-down shirt and boxer short set. And to be honest, I’m obsessed. Think: Tom Cruise in Risky Business, but with a bit more, uh, coverage.

The Deep End Shirt $125 and the shorts $95

And womenswear is just for women

From Diggit Magazine, Modern men are breaking traditional gender norms. “Dresses and skirts are traditionally worn by women. Nowadays, however, it is becoming more popular for men to wear dresses on runways and even red carpets. These men are redefining gender norms, and while some people love it, others find it strange and unusual.”  

In the world of Hollywood, men are starting to redefine gender norms by wearing dresses and skirts on red carpets or on stage. Prince, Kurt Cobain, David Bowie, Jared Leto, Keiynan Lonsdale, and Vin Diesel are all examples of famous men who have worn dresses or skirts. Billy Porter, in particular, has really made a statement with his fashion.” 

Skirts for men might finally be here to stay. From Highsnobiety, “The conversation around androgynous dress has developed significantly from back when Kurt Cobain was performing in a dress but, if we’re being honest, the skirt hasn’t quite made it into the category of “unisex” for much of society. Well, not yet.


From CNN, From Brad Pitt to Lil Nas X, more men are turning to skirts.

When Brad Pitt arrived at the premiere for new movie “Bullet Train” last month, his laidback linen outfit made headlines everywhere — or part of it did, at least. The actor, who is known for hypermasculine roles in films such as “Fight Club” and “Once Upon a Time in Hollywood,” completed his blush pink-and-brown ensemble with an eye-catching twist: a skirt.”

In many parts of the world, however, men’s skirt-like garments are part of everyday wardrobes. The sarong, a typically bright patterned wrapped skirt, is worn by men in cultures across Asia, the Middle East, Africa and the Pacific islands. Variations of the sarong such as the “sulu,” a wraparound style used in both casual and as formal settings in Fiji, and the “lungi,” which is worn in south and southeast Asia, remain popular styles for men of all ages.”

“In recent years, evolving conversations around gender and identity have instigated a collective reckoning about what it means to dress like a man. Gen Z and younger millennial stars, such as Harry Styles and Lil Nas X, regularly bring elements of femininity into their wardrobes — and retailers are taking notice. Online stores like ASOS, Mr Porter, Cettire and SSENSE are among those now stocking men’s skirts, many of which would be indistinguishable from womenswear designs were it not for the male models.

A guest at label Dries Van Noten’s to the Spring-Summer 2023 show wearing a beige pleated skirt. Credit: Edward Berthelot/Getty Images

From ET, Men in Skirts. “The biggest fashion trend of the year! Male skirts are having a moment. Check out how these celebs styled the look on the red carpet.

In Conclusion:

Some people like breaking rules, while others love following rules. I’m a rule follower in most places except when putting together an outfit. Dress for yourself and your comfort. If you love an outfit, don’t worry about whether it’s trendy or breaks a fashion rule.

It’s not about what or who you wear but how you feel when wearing something,” confirms Iris. “Style is about self-expression and, above all, attitude.” Iris Apfel H& M magazine

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