Why Society Doesn’t Want You to Dress Up

Decades ago, dressing with intention was simply part of the fabric of daily life. Today, choosing to don a well-cut jacket or polished shoes can feel like a subtle defiance of an unspoken social code. What has shifted? Let’s find out.

Table of Contents

Fashion Needs Conformity

The fast fashion industry thrives on change. By promoting trends designed to fall out of favor quickly, what Oscar Wilde called “a form of ugliness so intolerable that we have to alter it every six months“, brands encourage frequent purchases.

Man in a clothing store examining a gray t-shirt, representing the low-quality, trend-driven nature of fast fashion.

Trends encourage replacement.

Classic style focuses on timeless, versatile pieces meant to last, which runs counter to fast fashion’s profit model.

Casual is cheaper to make.

T-shirts and jeans cost less in fabric and labor than a tailored jacket, yet can be marked up heavily.

Storefront display with mannequins dressed in casual basics.

Profit favors dressing down.

Companies make more money selling casual basics than high-quality tailored garments.

Dressing up often means ignoring trends, which can make you stand out. And not everyone welcomes that.

“The person who follows the crowd will usually go no further than the crowd. The person who walks alone is likely to find himself in places no one has ever seen before.”

Albert Einstein

Presumed Pretensions

Popular media often paints the well-dressed as snobbish or elitist.

Films like Titanic and Charlie Chaplin’s “Tramp” character pit humble heroes against wealthy, overdressed antagonists.
Professions like finance and law, often linked with suits, are sometimes associated with ruthless behavior, rightly or wrongly.

In real life, negative encounters with dressed-up individuals or with overly critical voices in the classic style community can reinforce this stereotype.

Negative stereotypes often portray well-dressed men as looking down on others’ style choices.

Yet history shows dressing up has been a habit across all classes, even during hard times like the Great Depression. The difference lies in attitude, not attire.

What makes a man look truly professional?

See the Key Style Rules

Lingering Resentment

Some people associate formal dress with obligation.

Childhood memories of itchy suits for weddings or school events.
Workplace dress codes that felt restrictive or uncomfortable.

Perception & Prejudice

How Past Experiences Shape Views on Dressing Up

This history can lead to resentment toward those who choose to dress up, as if they endorse mandatory formality.

You can avoid misunderstandings by:

Avoiding judgmental remarks about others’ clothing.
Making it clear you dress well for yourself, not because you believe everyone else should.

Hiding Behind Clothes

In a casual society, dressing up is often linked to special occasions such as weddings, galas, or big meetings, which can make it seem performative. Some assume formality hides insecurity or inexperience. In tech circles, for example, casual “uniforms” like Steve Jobs’ black turtleneck are seen as the mark of “true” innovators.

Peter Thiel’s remark reflects Silicon Valley’s bias toward casual dress as a marker of innovation.

The best way to counter this is to prove through competence, confidence, and kindness that your clothes enhance who you are, rather than define you.

Which style tricks are you missing?

Steal the Style Tricks

I Can’t, So You Can’t

Sometimes criticism comes from a place of self-doubt. People who feel they cannot dress well, whether due to budget, fit challenges, or lack of knowledge, may project those insecurities.

The solution is empathy:

Share your own learning curve and mistakes.
Offer encouragement without pressure.
Invite others to try dressing up for themselves.

Be Unique

Ivan's outfit for Society Don't Want You to Dress Up

And while we know that dressing up when others don’t requires a lot of confidence, we teach you exactly how to do it here. You might find yourself inspired to wear something like the outfit I have on today.

So, with my outfit today, I wore this navy suit; it has a Glen check pattern to it. I absolutely love it; it’s very classic. I also went with a contrast-collar, cuffed shirt, and it’s a light blue striped shirt. I really like it; I kind of went with that banker style today.

I paired the look with this Fort Belvedere tie. I really love the color, and it has some medallions to it in a reddish color, also bringing out a few different colors but in a very muted sense. I decided to pair it with a pocket square from Fort Belvedere as well; it has a yellow trim, going hand in hand with the colors that are also in the tie.

For my shoes, I decided to wear these dark brown Oxford cap-toe brogues. I really love them; I feel like they go really nicely with this whole outfit.

Fort Belvedere

Buff & Red Printed Madder Silk Tie

Shop the Madder Silk Tie

Burgundy Red Silk Wool Pocket Square with Printed geometric medallions in olive green, light blue, cream and orange with beige contrast edge by Fort Belvedere

Fort Belvedere

Burgundy Medallion Silk Wool Pocket Square

Add Rich Texture to Your Chest Pocket

What really changes when you dress up?

See All 101 Changes

Breaking the Stigma

Once you understand these forces—industry trends, stereotypes, and personal resentments—you can see why dressing up can feel like swimming against the current. The key is to dress well with intention, not to impress or exclude, but because it reflects your taste, values, and self-respect.

Carry yourself with warmth and approachability, and you will find most people respond positively, even if you are the most dressed-up person in the room.

Feel there’s a point we missed in this video about why society doesn’t want you to dress up? Let us know in the comments

FAQ

Can I dress up for fun/whenever I want?

Yes, dress in the way that makes you happiest and feels like an authentic version of yourself! Just keep in mind that there’s a time and a place for everything. Within classic style, there’s different “levels” of dress code and dressing well doesn’t necessarily mean always having to wear a three piece suit for every single occasion. Learn what you like and don’t like and be willing to make mistakes. You’ll find your signature style soon enough!

Why don’t people wear suits anymore?

While it’s true that suit wearing used to be far more commonplace, and was the unofficial “uniform” for men throughout the 1900s-1960s, cultural norms have made the suit far less popular than it used to be. This is largely because of the counterculture movements in the 60s & 70s, as well as the stereotypes that tailoring is uncomfortable and stuffy nowadays, though just because it isn’t as commonplace doesn’t mean it’s “weird” or “wrong” to do it. Millions of people still do it every day. It just takes a little more courage since it’s not as commonplace as it once was.

I want to dress well but am worried what others will think. What do I do?

Getting into classic style is a journey, and it won’t happen all at once. It doesn’t make sense to go all in and spend a ton of money on a bespoke wardrobe right out the gate. Your taste will likely change as you get comfortable wearing tailoring and you probably won’t feel comfortable or confident enough yet to make such a drastic change so suddenly. Get the essentials and start to experiment with what you gravitate towards slowly. People are less judgemental or likely to notice slow changes over time. Make it a goal and build up to that ideal image you have in your head. Soon enough, you’ll be dressing the way you want and everyone you know will be used to it.

How do I start dressing better when it’s hard to know where to start?

Given classic style knowledge isn’t readily taught in most social circles, you have to figure out where you’re currently at and what you’re trying to build up to. Often, one of the easier approaches is mastering fit with the clothing you do have. You can start to either incorporate classic elements like accessories into your wardrobe gradually, or can tailor what you do have so it looks better on you. Then it’s figuring out what holes you have in your current wardrobe and what you can do to add to them

Why do people treat me weird when dressing up?

While it’s inevitable that you’ll occasionally get people who treat you negatively for dressing in a way that’s against the grain, if it’s happening excessively, you might want to look at the context. There could be less than desirable signals in your body language or disposition when talking to others or dressing several levels in formality above what’s considered “normal” for the occasion. Generally, people respond well to a positive & accepting attitude & confidence goes a long way. Practice dressing well and be approachable, and issues with others should decrease.