Top 10 Best Men’s Fashion Styles Of All Time: 1920 To 2024

Looking stylish and on-trend as a man isn’t just about impressing others – it’s a form of self-care that boosts your confidence from the inside out.

Throughout history, certain iconic fashion styles for men have emerged and withstood the test of time to become true menswear classics.

This comprehensive guide breaks down the 10 timeless men’s fashion styles that every stylish American gentleman should know, from the roaring 1920s all the way to 2024.

We’ll cover the essential clothing and accessories for nailing each iconic look, whether you’re a rugged outdoorsman, a sharp professional, or just a dude who likes to look cool while kicking it.

How Men’s Fashion Changed Throughout History

Fashion is ever-evolving, with new trends coming and going each decade. Men’s fashion styles have transformed dramatically over the past century, influenced by music, politics, celebrity trendsetters, and more.

A Brief History of Men’s Fashion and Style from 1950s to 1980s

• 1950s: The conservative post-war era ushered in fitted suits, straight trousers, and a polished look for the office.
• 1960s: The rebellious 60s youth kicked off slimmer suits, skinny ties, and patterned shirts.
• 1970s: This groovy decade welcomed bell bottoms, sideburns, bold patterns and colors.
• 1980s: Power suits with suspenders were big, influenced by pop culture’s corporate raiders.

Why is Looking Good Important for Men?

Looking your best isn’t just about surface-level attraction – it’s a crucial form of self-care that impacts your overall confidence and presence.

Think about how great you feel walking into an interview, date or meeting looking fresh and put-together!

Taking pride in your appearance through stylish yet practical menswear conveys self-respect and garners respect from others as well.

Whether you’re crushing it in the boardroom or a party, dressing intentionally in a look that fits your lifestyle allows you to show up as your best self.

Top 10 Timeless Men’s Fashion Trends & Styles to Follow

While fashion fads will come and go, these 10 iconic styles for men have transcended decades and cultures to become true classics in the world of menswear:

1. Retro Gentleman Look
2. Casual Look
3. Athleisure Look
4. Business Casual Look
5. Rugged Gentleman Look
6. Urban Gentleman Look
7. Hipster Look
8. Street Style Look
9. City Look
10. Ivy League Look

1. Retro Gentleman Look

Channeling old-school sophistication and charm, the retro gentleman look hearkens back to the early-mid 20th century’s dapper 1920s mens fashion styles. This iconic aesthetic oozes classic cool with vintage-inspired pieces like:

• Bowling shirts
• Leather jackets
• Retro button-downs, vests or sweaters
• Vintage travel bags like duffles or messenger bags

To nail the 1920s mens fashion gatsby vibe, think tailored silhouettes, quality materials like wool, cotton and leather, and refined details like pocket squares or tie bars.

The key piece? A classic tie, whether worn with a full suit for evening wear or just a shirt and trousers for day.

How to look like a gentleman?

The most crucial element to achieve a true gentleman look is a tie, whether worn with a basic shirt and jeans or as part of a full suit ensemble. Opt for quality materials like cotton, wool, and leather over synthetic blends.

Finishing touches like a pocket square, tie bar, and well-polished dress shoes add the perfect refined touches. Just remember – the real sign of a gentleman is carrying yourself with poise and confidence!

2. Casual Look for Men

Who says casual has to mean sloppy? This versatile fashion style for men lets you express your personality while looking smart, put-together and anything but boring.

Unlike the retro dapper vibe, a great casual look is all about modern, laid-back pieces with an effortlessly cool factor.

Key casual wardrobe essentials every guy should own include:

• Well-fitting jeans or chinos in dark washes
• Crisp casual button-downs or polos
• Unstructured blazers or lightweight jackets
• Canvas or leather casual bags like messengers or weekenders

To pull it off, think casual yet intentional. Shoot for streamlined silhouettes that flatter your body, not too loose or baggy. Layering textures like a shawl sweater over a tee or rolling up your sleeves can instantly elevate your casual style cred.

How To Look Smart In Casual Clothes?

Nailing the smart casual dress code is easier than you think when you follow these tips:

• Choose the right accessories: A simple leather belt, classic timepiece, and stylish shades instantly elevate any casual outfit.
• Lace up stylish yet casual shoes: Suede chukkas, boat shoes or crisp white sneakers > running shoes.
• Layer fabrics and textures: A wool blazer or shawl sweater over a tee adds dimension.
• Tuck in tops or roll up sleeves: This polishes up even the most basic casual pieces.

3. Athleisure Look For Men

Athleisure is the trend that keeps on giving, blending activewear with streetwear for lounge-worthy looks that still leave the house.

This sporty men’s fashion style is ideal for weekend errand-running, casual dates, grabbing drinks with your crew or just looking cool and comfortable on your day off.

Key athleisure wardrobe pieces every guy needs include:

• Joggers or sporty shorts
• Bomber or warm-up jackets
• Lightweight crew neck sweaters
• Box-fresh sneakers
• Sporty backpacks or duffles

To channel true athleisure style, the key is nailing the proportions and layers. Fitted joggers or shorts show off your assets, while roomier tops like bombers create an authoritative yet casual vibe.

Throw on a blazer or quarter-zip over a tee to merge this off-duty aesthetic with more polished pieces.

What is Athleisure Style?

At its core, athleisure combines high-fashion with ultimate function and comfort for an edgy, street-smart aesthetic. To ace this iconic look:

• Start with joggers or track pants paired with sneakers as your base
• Wear athletic-inspired shorts made from thin, breathable fabrics
• Top it off with hoodies, track jackets or bombers in technical fabrics
• Add masculine accents like sporty rubber watches or flat-brim caps
• Carry your gear in a slick backpack or sporty duffel

4. Business Casual Look For Men

In today’s modern office and post-COVID world, the business casual dress code is increasingly the new norm.

This polished yet relaxed fashion style for men fuses the professionalism of traditional businesswear with a modern, casual spirit.

It’s the ideal aesthetic for creative agencies, upscale startups, and industry networking events.

Building a business casual capsule wardrobe is easier than you think with these key pieces:

• Crisp flat-front slacks or chinos
• Polos, crisp button-down shirts or fine gauge sweaters
• Unstructured blazers or sport coats
• Leather Oxfords, derby shoes or lifestyle sneakers
• Leather folios, briefcases or messenger bags

When executing the business casual look, aim for a tailored yet easygoing vibe by skipping the blazer and tie.

Elevate chinos and a knit polo with a fitted sport coat and dress shoes, or go tie-optional with slacks, a buttondown and stylish sneakers. Just avoid pieces that are too casual like shorts, graphic tees or flip flops.

5. Rugged Gentleman Style & Look

Does your idea of a great weekend involve chopping wood and roasting s’mores over a campfire? Then the rugged gentleman look is for you.

This ultra-masculine aesthetic combines hardy, outdoorsy pieces with refined details for an “I look like I just emerged from the woods – but make it fashion” kind of vibe.

Key rugged gentleman style hallmarks every guy needs include:

• Denim, chino or flannel-lined pants
• Flannel or chambray button-up shirts
• Field jackets, puffer vests or shearling coats
• Rugged leather boots or weatherproof hikers
• Canvas bags, leather duffles or waxed backpacks

To pull off this iconic look, it’s all about nailing the right blend of hardy and refined pieces.

Tuck a thermal henley into your favorite pair of worn-in jeans, then throw on a waxed field jacket and lace up some sturdy boots. The outdoorsy color palette of deep greens, browns and navy grounds the ensemble.

But pay attention to the small details that elevate your look from sloppy to stylishly rugged – a leather briefcase adds a polished touch, while a classic wool watchcap prevents any outdoorsman clichés. Just don’t go overboard on the lumberjack accessories.

6. The Urban Gentleman Look For All Men

If you prefer a more modern, metropolitan vibe, then the urban gentleman look is for you.

This sharp men’s fashion style seamlessly blends classic menswear pieces with present-day trend-driven details, resulting in a tremendously versatile aesthetic at home in the city streets or swanky cocktail lounge.

Nail this iconic style with a mix of these wardrobe staples:

• Slim-cut trousers or dark denim
• Crisp button-up shirts or turtlenecks
• Tailored topcoats or leather moto jackets
• Streamlined leather dress shoes or Chelsea boots
• Sleek leather folios or messenger bags

To achieve the perfect urban gentleman look, focus on a streamlined, sophisticated silhouette by sticking to trimmer cuts and minimalist color palettes like shades of gray, black, white and camel.

Then add eye-catching pops with statement pieces like a fedora, printed silk scarf or standout watch.

Don’t be afraid to blend modern athleisure influences by wearing joggers and a hoodie under your topcoat. It’s all about dressing for your environment while maintaining an air of refinement.

7. Hipster Look For Men

Are you the kind of guy who thirsts for the latest underground music, loves checking out obscure art exhibits, and lowkey prides himself on knowing about things before they were cool? Then the hipster aesthetic is likely calling your name.

While the hipster movement may be rooted in the early 2000s, the fashion styles for men that define this quintessentially modern look first emerged in the 1950s counterculture. To channel that signature hipster vibe, stock up on these essentials:

• Slim or skinny jeans (the more worn-in, the better)
• Plaid or printed button-down shirts
• Slim blazers or denim jackets
• Desert boots, chelsea boots or retro sneakers
• Canvas totes or vintage-inspired messengers and duffles

Once you have the base pieces down, the true mark of a hipster is in the styling details. Roll up those skinny jeans to show off your selvedge denim and ankle sock game.

Throw on an oversized scarf or beanie for that “I just stumbled out of a thrift shop” insouciance.

Top it off with some man-jewelry pieces like a vintage pocket watch, thick-rimmed glasses or a beard sculpted to lumberjack perfection and you’ll be well on your way to achieving the ultimate hipster look.

8. Street Style Men’s Fashion Look

For those who live by the code “Dress cool or don’t even bother,” mastering the street style look is a must.

Born from urban culture, this relaxed men’s fashion style pays homage to subcultural sartorial influences from skaters to hip-hop with an emphasis on looking effortlessly fresh.

The basics of pulling off a street style aesthetic include:

• Graphic tees, hoodies or baseball jackets
• Ripped, distressed or wide-leg denim
• Sporty track jackets or puffer vests
• Retro high-top sneakers or skate shoes
• Cross-body bags or mini backpacks

The key to getting street style right is making intentional choices that blur the line between loungewear and an actual outfit.

Try french-tucking an oversized graphic tee into purposely baggy jeans, then finish it off with a baseball cap and fresh white kicks.

Or layer a vibrant track jacket over a hoodie for a look that screams “stylish while sedentary.”

Essentially, street style gives you license to embrace your inner hype beast while still appearing pulled together.

Just make sure your accessories hit the cultural mark – carry a cross-body bag not intended for your grandpa.

9. City Fashion Look For Men

If you spend your days hustling in a major metro hub, the city look is a smart and sophisticated style that will keep you looking fresh through any urban adventure.

This timeless men’s fashion style for guys prioritizes clean, pared-down pieces built to withstand the rigors of the concrete jungle.

Staple wardrobe pieces for mastering the city aesthetic include:

• Dark denim, trousers or crisp chinos
• Slim button-up shirts or lightweight turtlenecks
• Tailored top coats or blazers
• Leather dress shoes, chelsea boots or sleek sneakers
• Classic leather portfolios or messenger bags

Inspired by slick leading men from Cary Grant to Daniel Craig, the city look emphasizes architectural suiting and outerwear silhouettes in an understated color palette like black, gray and camel.

But the overall vibe is more laid-back and practical than a formal businessman for effortless mobility.

Make the look your own by injecting subtle pops of personality. A boldly printed pocket square, leather driving gloves or luxe watch always looks perfectly at home in the urban environment.

Just avoid appearing too schlubby – remember, you’re representing world-class style at all times.

10. Ivy League Fashion Style For Men

Emerging in the 1950s, the Ivy League look is a true American menswear icon rooted in East Coast collegiate heritage.

This quintessential fashion style for men channels an air of geeky sophistication and refined traditionalism that never goes out of style.

To capture the timeless Ivy League aesthetic, you’ll need a few heritage-inspired staples in your arsenal:

• Oxford button-down shirts
• Classic khaki chinos
• Shawl or cable-knit sweaters
• Blazers or wool topcoats
• Boat shoes or buck loafers

Clean, tailored lines and autumnal hues like burgundy, mustard and forest green set the tone, grounded by heritage patterns like houndstooth, argyle and tattersall.

But don’t take things too literally – mixing classic pieces with modern fits prevents you from looking stuck in the past.

A slim-cut navy blazer with a crewneck sweater, tailored chinos and leather loafers keeps the aesthetic current and cool.

Adding pops of personality via printed socks or vintage-inspired accessories allows your Ivy style to shine through.

After all, part of the appeal of the Ivy look is exuding an effortless, cultivated elegance…without trying too hard.

FAQ’s

Why Is 1980’s Retro Fashion Men So Popular?

Men’s fashion from the 1980s is still popular today because it symbolizes pop, vintage, and electric style, and is still relevant today.

How To Look Good in 80s retro men’s fashion?

Rock bold colors, loud patterns, and layered clothing. Think neon, acid wash, and graphic tees under denim jackets.

What fashion was popular in the 1920s for men?

The 1920s saw a shift towards slimmer, more fitted suits for men, with fedoras and dress shoes completing the sharp look. Leisurewear also gained ground, with cardigans and sweaters becoming popular.

What is the trend in men in 2024?

For men’s fashion in 2024, think comfort and confidence with a splash of boldness. Oversized fits, classic denim, and pops of color are all on trend.

What was the biggest fashion trend in the 1920s?

The biggest fashion trend of the 1920s was the “flapper” look for women, featuring loose, knee-length dresses and short, bobbed hairstyles. This style reflected a newfound freedom and energy for women in the era.

Who is the best dressed man of all time?

There’s no single “best dressed” man throughout history, as style ideals change across eras. However, figures like Beau Brummell (early 19th century) and Cary Grant (mid-20th century) are often cited for their lasting influence on menswear.

Conclusion

In conclusion, men’s fashion has undergone exciting transformations throughout the decades, from the sharp suits of the roaring twenties to the comfy athleisure trends of today (Top 10 Best Men’s Fashion Styles Of All Time: 1920 To 2024).

Don’t be afraid to explore these different styles and find what makes you feel confident and put-together. Remember, fashion is a fun way to express yourself, so have fun with it!