Curious how men’s classic style has changed over time? From the Greatest Generation to Gen Alpha, we’re breaking down the biggest fashion wins—and the most memorable fails—of every generation.
See what trends stood the test of time, which ones didn’t, and how each era shaped the way we dress today.
A Note on Generational Eras and Style
Please note: while we’ve structured this guide around generational labels, we recognize that the major tastemakers during any given era were not necessarily the people born in that generation, but often those from the generation before it.
So, when we reference the style of the “Greatest Generation Era” (1901–1927), we’re referring to the dominant clothing styles worn during that time, not just by individuals born in those years. People, after all, dress in a range of styles throughout their lifetimes, influenced by the trends, culture, and societal norms of the day.
This breakdown follows the timeline of generational eras to help highlight how classic menswear has evolved with each period.
Explore how the principles of classic menswear adapt with time.
The Greatest Generation (1901–1927)
This era laid the foundation for modern menswear as we know it. The lounge suit became a daily staple, and formal wear traditions flourished. But it wasn’t all sartorial success—some restrictive norms and impractical habits held back the potential of classic style.
Fashion Win: The Lounge Suit
Transformed how men dressed daily by introducing comfort and versatility to formality.
Fashion Fail: Shirts as Underwear
- Shirts worn strictly as underwear.
- Limited outfit creativity and overcomplicated layering unnecessarily.
| Honorable Mentions – Wins | Honorable Mentions – Fails |
|---|---|
| Winchester collars | “Fake” shirt bodies |
| Military coats entering civilian style | Excessively tall shirt collars |
| Formal hat styles (Homburg, top hat, bowler) | Tie-on glasses |
| Emphasis on evening and formal wear | Rigid formalities and few options |
The Silent Generation (1928–1945)
This generation brought a refinement to formalwear and helped solidify the silhouettes we still associate with classic menswear today. However, some adventurous missteps, like Oxford bags, didn’t age well.
Fashion Win: Modern Formalwear Standards & Hat Styles
- Standardization of modern formalwear and popularization of classic hat styles (fedora and flat cap)
- Established a visual standard for suits and headwear that’s still influential today.
Fashion Fail: Oxford Bags
Oxford bags and wide-legged trousers that were impractical and awkwardly proportioned.
| Honorable Mentions – Wins | Honorable Mentions – Fails |
|---|---|
| Drape-cut suits with high-rise pants | Kitsch necktie prints |
| Spectator shoes | Overly rigid, glossy hairstyles |
| Overcoat variations |
The Baby Boomers (1946–1964)
As society relaxed, so did men’s clothing. Baby Boomers embraced casual jackets and broke from rigid dress codes. But with this comfort came oversimplification, and menswear lost much of its flair.
Fashion Win: Casual Jackets (Harringtons, Leather, Field Jackets)
Functional and stylish—easy to dress up or down.
Fashion Fail: Oversimplification of Menswear
Muted palettes, fewer accessories, and less experimentation dulled everyday outfits.
| Honorable Mentions – Wins | Honorable Mentions – Fails |
|---|---|
| Greater flexibility in formalities | Boxy, overly broad silhouettes |
| Turtlenecks as layering staples | Body shirts that sacrificed comfort |
| Emergence of mod style |
Generation X (1965–1980)
With Gen X, we saw a revival of flair—color, texture, and a love for casual classics like polos. At the same time, fast fashion’s roots began to show, driven by synthetics and flashy trends.
Fashion Win: Rise of Casual Shirts and Polos
A staple that balances casual comfort and classic sharpness.
Fashion Fail: Synthetics and Maximalism
Bell bottoms, shiny disco suits, and polyester overload led to fast fashion’s rise.
| Honorable Mentions – Wins | Honorable Mentions – Fails |
|---|---|
| Suede outerwear | Graphic tees |
| Peacock Revolution’s embrace of bold textures and colors | Decline of traditional hats |
| Sport coat and odd-jacket combos | “Dog ear” collars |
Is Buying Fast Fashion Clothing EVER a Good Idea?
Millennials (1981–1996)
Millennials mixed vintage sensibilities with new tech and eco-consciousness. Denim became king, but their love of logos sometimes overshadowed the substance of their style.
Fashion Win: Mainstreaming of Denim
From workwear to everyday staples, denim was reimagined in stylish and rugged ways.
Fashion Fail: Excessive Branding
Logos overtook quality and turned outfits into billboards.
| Honorable Mentions – Wins | Honorable Mentions – Fails |
|---|---|
| Flannel shirts | Cartoonish power suits |
| Denim jackets | Cargo pants and baggy silhouettes |
| Rugged casualwear and vintage style revivals | |
| Emphasis on sustainability | |
| Layering innovation |
Gen Z (1997–2009)
Gen Z made fashion more inclusive and expressive than ever. Classic style became a personal passion, not a social requirement. Still, some trends swung too far into the eccentric.
Fashion Win: Normalizing Fashion & Grooming Interest
Open embrace of style as self-expression for all men.
Fashion Fail: Over-the-Top Eyewear
Statement glasses often overshadowed otherwise cohesive looks.
| Honorable Mentions – Wins | Honorable Mentions – Fails |
|---|---|
| Classic style worn for passion, not obligation | Denim overkill |
| Glasses and eyewear normalized and stylized | Mixing tailoring with tees |
Generation Alpha (2010–2024)
The youngest style generation is still forming its identity, but we’re already seeing strong signals: global influence, hybrid garments, and digital-first fashion communities.
Fashion Win: Hybrid Clothing Like Shakets & Sweater-Blazers
Blends of function and form that nod to tradition with a modern twist.
Fashion Fail: Overly Skinny Fits for Formalwear
Disproportionate silhouettes that restrict movement and don’t flatter.
| Honorable Mentions – Wins | Honorable Mentions – Fails |
|---|---|
| Standardized dress sneakers | Workplace casualization (hoodies, sandals, sweats) |
| Renewed interest in prep and old-money styles | Loud color blocking |
| Global menswear community through social media | Male rompers |
| Hypebeast overkill |
Sweater Blazers: Timeless or Trend?
Summary: What Each Generation Got Right (and Wrong) in Style
| Generation | Biggest Win | Biggest Fail |
|---|---|---|
| The Greatest Generation (1901–1927) | Invention of the lounge suit | Shirts worn strictly as underwear |
| The Silent Generation (1928–1945) | Standardization of modern formalwear and popularization of classic hats | Oxford bags |
| The Baby Boomers (1946–1964) | Casual jacket styles (Harringtons, leather, field jackets) | Oversimplification of menswear |
| Generation X (1965–1980) | Rise of casual shirt styles, especially polos | Maximalism meets synthetics |
| Millennials (1981–1996) | Mainstreaming of denim | Excessive branding |
| Gen Z (1997–2009) | De-stigmatizing interest in grooming and fashion | Trendy, over-the-top eyewear |
| Generation Alpha (2010–2024) | Hybrid clothing like shakets and sweater-blazers | Overly skinny fits for formalwear |
Outfit Rundown
Today, I am wearing a camel blazer, with a green cable knit sweater, blue and white striped button down shirt with a pocket square that has a lot of different brown, red, and light blue tones that really help warm up the rest of the outfit.
I’ve chosen navy blue trousers, green boots, and Fort Belvedere socks with blue and red stripes to complete the look. For the fragrance, I’m wearing High Heel White by Roberto Ugolini.
And remember, you can find amazing socks like these and other great accessories from the Fort Belvedere Shop here.
Conclusion
Every generation leaves its mark on menswear—some styles stand the test of time, while others quickly fall out of favor. But the constant across time? A desire to look good, feel confident, and express individuality through clothing.
From lounge suits to polos to shakets, each era contributed something worth considering (and maybe something to avoid). Use their wins to guide your wardrobe and their mistakes as reminders of what not to do.
Let us know in the comments if you’d like to see more expansive breakdowns of the wins and fails of any particular generations.
Frequently Asked Questions
What is a “fashion win?”
Positive trends in clothing are always subjective, but for us, a “win” as it pertains to classic style involves a clothing trend or development that advances the basic tenets of classic style itself: a timeless silhouette that naturally enhances the physique and usually does so in an elegant, understated way.
What is a “fashion fail?”
Although similarly subjective, we would generally call a menswear fail anything that distracts from the natural and timeless elegance of classic style by relying on obtrusive, gaudy, or excessive detailing, or that is too boring, muddy, or plain.
Has every generation had style fails?
Yes, it has. Contrary to the assumption that every aspect of the Golden Age of Menswear was elegant and refined, even these largely stylish epochs made some mistakes.
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Another awesome article y’all! I just wanted to mention that in my personal opinion, I think that Gen Alpha should’ve been left out until a few more years. The max age of Gen Alpha currently is 14-15, which is barely midway into the teenage years, meaning there is minimal development in their personal style and/or taste. I’ve found the beginning stages of finding personal taste and style begin in the early teen years and are more developed by late teens and early adult hood. I believe a more accurate gauge for Gen Alpha “trends” would be when they become late teenagers and early young adults.
Also, I believe a lot of the “fails” for Gen Alpha are better attributed to Gen Z. I’ve seen male rompers and “hypebeast overkill” in Gen Z rather than Gen Alpha.
Again, awesome article. I just wanted to share my thoughts on the last two generation’s fashion trends. Thank you for being an informative and essential resource for menswear!
Thanks for the support, Samuel! Just to clarify – the generations featured are the way we’ve categorised the “current” styles of those years, not what those born in that generation are wearing.
Well done and succinct video commentary on the fashion generational run thru. Indeed, remarkable as stated long before, “There is nothing new under the sun!” and the cliche’, “In time, everything repeats!” The one clothing angst in current era, people wearing PJ’s as outer wear in public!! IMO, this is a grand Faux Pas in decorum, style and social dress.