Top 10 Best Men’s Fashion Styles of All Time: 1920 to 2022

How to look good as a man? Retro Gentleman Look | Casual Look

Best Men's Fashion & Style Choices For You

&

What are some of the most popular men's fashion styles?

Men's Fashion Store & Men's Accessories Brand GENTCREATE.com

How Men's Fashion Changed Throughout History

From time to time, people embrace various fashion styles. From 1940s men’s styles, to the 21st century men’s styles, several transitions took place from the Edwardian men’s fashion, to men’s spring style, to men’s alternative fashion styles, to the fashioned men’s hairstyles.

However, there are certain fashion styles that remain popular timelessly. Notwithstanding, it is particularly important to have a good sense of fashion in the 21st century. Keep calm, because this read helps you with it. In this article, we are basically focusing on men’s styles and men’s fashions. To be more specific, it is primarily regarding the top 10 best men’s styles of all time!

Gentleman Vintage Style Picture

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

Men's fashion has changed dramatically over the years.

In the 1980s, it was all about power suits and white shirts with suspenders. In the 80s, men's fashion was very much influenced by punk rock music and heavy metal.

In the 1960s, men wore slim-fitting suits with narrow ties and skinny lapels. 60s fashion for men was characterized by slim jeans, ties, wide-leg pants, Nehru jackets and bell-bottoms. 

In the 1970s, bell bottoms were popular as well as leisure shirts made from natural fabrics such as cotton or linen. 70s retro style often included sideburns or a mustache with big hair.

The 1950s brought more conservative styles back into style such as fitted jackets and straight trousers for a more polished look that would continue on through to present day. In the 50s, men wore suits to work every day but were also starting to wear more casual clothes on weekends such as khakis or jeans paired with a button down shirt.

Why is Looking Good Important for Men?

Looks might not be everything. But before considering anything else, the very first thing to look at is how attractive a person is. Generally, someone might think that it is mostly females who are after styles and looks. But in actual fact, men’s styles and men’s fashions are equally important as female fashions and styles. If you are going out for some professional work, you need to look like a proper professional.

And if you are going out to chill and have some fun, you need to have that fashionable chilling look. If you are on a casual outing, still, you need to maintain your gentleman aspect. In fact, nothing can make you a proper gentleman firsthand than your attire.

When someone sees you, they should feel like saying “look at this distinguished gentleman!”. This is why men’s fashions and men’s styles are of immense importance. So, by now, you may have understood the impact that proper and attractive clothing can have on you.

To make any man a gentleman, it is the proper men’s styles and men’s fashions that you must choose. Some styles are only for a very small period of time. After their advent, they hit a hype and soon disappear.

Besides, there are some fashions that do not undergo any downfall. Those all-tie fashions are the most predominant ones out of all.

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

No doubt, you would be curious to know all about men’s fashions and men’s styles that are timeless. So, what are all these all-time looks? Here is the list that we prepared for you.

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. Style Look
9. City Look
10. Ivy League Look


We know that you all need to know about all these timeless looks in detail. Continue reading to get to know all about them!

1. Retro Gentleman Look

The first look that we are going to consider among all the men’s styles and men’s fashions is the retro gentleman look. Back in the day, it was this retro gentleman look that was quite common everywhere.

- But even today, we can see that the retro gentleman look is quite popular among gentlemen. This is the men’s style that was popular in the early to mid-20th century. But the specialty is that this did not go out of fashion after it reached its peak. However, now you might be wondering how to dress to get this retro gentleman look!

In particular, you can try a bowling shirt with trousers. Further, you can try a leather jacket with jeans or a retro shirt with a jacket. And why not? Bag base retro flight bag, retro shoulder bag made out of leather, or else a retro leather briefcase would also be perfect additions to elevate your retro gentleman look!

Retro Gentleman Photo - Gentcreate

How to look like a gentleman?

The most essential element is a tie. A tie can be worn with a basic shirt or dress shirt. It is not necessary to wear a suit at all times, you can wear jeans and t-shirts or blazer with some nice trousers if you want to look good. Although it is not necessary, wearing formal clothing makes people feel better about themselves and they are able to act more professional when they are in an interview for example.

If the employer sees that the candidate has taken time out of their day to get dressed up then it shows that you take your job seriously enough to look your best for it!

2. Casual Look for Men

Among the top 10 best men’s styles of all time, the next style we are going to look into is the casual look. This is one of those styles that allow you to completely express yourself in a smart way.

The casual look is far from a formal and business professional look. Anyway, you want to make sure your attire helps you to express who you are and what you want to achieve.

Nevertheless, you should basically consider what type of occasion it is. The term casual look can widely vary depending on the occasion. The business casual look is a separate segment.

- But apart from that, you have options like considering whether to choose a smart casual style, cocktail attire style, and so on. If you have received a wedding invitation specifying smart casual wear, you can skip the jeans and opt for a pair of quality chinos instead. Although a tie is not necessarily needed, you can have one just in case, plus a pocket square to spruce up your blazer or jacket.

When it comes to a casual beach party, wearing a pair of shorts with a tucked-in shirt to a smart casual beach party, on the other hand, is entirely fine. All the same, denim jeans, chinos, shirts, and blazers are okay to be worn as casual outfits. However, it is better to avoid briefcases if you are to dress casually for a normal outing.

Style bags such as vintage leather messenger bags, vintage shoulder bags made out of leather or canvas, vintage coach crossbody bags, or vintage backpacks would be perfect men’s styles to escalate that casual look.

Classy Stylish Gentleman Vintage Fashion Mens Style Gentcreate

How To Look Smart In Casual Clothes?

1. Choose the right accessories: The right accessories can change your look completely. It is not only about the color of your clothes but also about how you use it! For example, if you wear a brown leather belt with jeans and white shirt, you will look like an office worker who just came home from work (not smart at all!). However, if you wear that brown leather belt with a black t-shirt and dark jeans, your outfit will be much more stylish!

2. Choose the right shoes: Shoes are important because they can make or break an outfit. You should always choose casual shoes that go well with whatever pants/shorts/jeans etc…you are wearing for example boat shoes would be great with shorts but not so good with formal pants etc… So before buying any pair of shoes think about what kind of clothes you usually wear them with to avoid any embarrassing situations! Also remember that there is no need to buy expensive casual shoes as cheaper options often look just as good!

3. Accessories: Accessories are really important in every outfit! You can wear a simple pair of jeans and a white t-shirt but if you add a nice belt, watch and some sunglasses you will look much more stylish! The same applies to your shoes; even if they are not very expensive you can make them look great with the right accessories (like socks, watches etc…)

3. Athleisure Look For Men

Next, we are going to consider athleisure style men’s clothing as one of the top 10 best men’s styles of all time. Athleisure is a casualwear category that combines elements of athleticwear.

In that category, we can include workout clothing that is mainly on comfort, movement, and moisturewicking, with streetwear, especially casual clothes popularized by fashion trends, social media, and pop culture. Of course, athleisure is most comfortable on weekends.

Whether you're going out for lunch, drinks with the guys, a sporting event, or a casual date, athleisure may be a trendy option.

Bomber jackets, casual slacks, crew-neck sweaters, polo shirts, and sports-inspired bags are all must haves for pulling off this trend in style. Of course, an athleisure look is a great one that you can try. It is obviously special in terms of men’s fashions and men’s styles.

Man in Athleisure Casual Outfit Fashion Style Gentcreate

What is Athleisure Style?

Athleisure is a style that combines fashion and comfort. If you are looking for the best way to dress in Athleisure Style Look as a man, here are some tips to help you

1) Wear sweatpants or joggers with sneakers or casual shoes. These pieces will be the basis of your outfit; they will give it an athletic look. You can wear them with different t-shirts depending on your mood (you can choose from long-sleeve t-shirts, short sleeve t-shirts, graphic tees…). If you want to be more formal, add a blazer over a shirt and tie it up with sneakers. This way you’ll have an elegant look while being comfortable too!

2) You can also wear shorts in this style but only if they have an athletic design (such as track pants). They will make your legs look more muscular and toned while giving off a sporty vibe at the same time! In addition to having shorts made of thicker fabrics such as cotton or jersey, another thing that makes them ideal for athleisure is their cut: straight leg ones are perfect so they won’t get caught on your sneakers when doing sports activities! Another good option would be baggy ones which emphasize comfort.

3) For tops we recommend wearing loose shirts made of thin materials such as cotton or linen that fit well into this trend without giving off too much informality! Do not forget that if something has been made with the idea of being casual, it should be casual.

4) If you want to add a touch of elegance and class to your athleisure look, you can choose pieces such as trousers or pants made out of thin fabrics such as cotton or linen. They will give you a more sophisticated look while at the same time remaining comfortable! It is also possible to wear them in combination with sneakers if they have been designed for this purpose (for example: joggers).

5) Accessories: wallets, watches and sunglasses are essential in order to complete this style and make it look more masculine at the same time! If we talk about sunglasses, it is important that they have an athletic design so that they don’t take away from otherwise athleisure look.

4. Business Casual Look For Men

Although this is also part of the casual category, this is a lot more distinct from others of that. Business casual attire is a dress code that combines standard business clothes with a more relaxed style that is nonetheless professional and acceptable for an office setting.

As a business casual, you may, for example, wear slacks or khakis with a polo or shirt instead of a jacket or tie. As for footwear, you can go for closed-toed shoes like lifestyle sneakers.

Further, you can go for an optional belt that suits your attire. In colder months, wearing a sports coat or a cardigan is also a great choice. When considering bags, options like vintage coach briefcase, a brown leather vintage briefcase, and vintage leather briefcase would suit better if your business casual look is closer to a professional setting. If not, you can opt for men’s vintage, and canvas backpacks even.

With more distant work and virtual meetings becoming increasingly common, you may only have to care about your appearance from the top-down, sometimes. However, when you are going to be dressed in business casuals for official work, it is best to consider whether your attire complies with your company’s dress codes.

Classy Gentleman Vintage Fashion Casual Mens Style Gentcreate

5. Rugged Gentleman Style & Look

Now, it is about the rugged gentleman look. The rugged gentleman look is also one of the top 10 best men’s styles of all time.

This is a style of outfit that can give you a more masculine feeling and look. What are the types of clothing that you can try to get yourself a rugged gentleman look?

- You can opt for rugged shirts, rugged leather jackets, rugged blazers, rugged vests, and scarves, denim pants, and rugged boots to rock the rugged gentleman look. Indeed, wearing rugged knitwear is also a great option for you to adapt to.

Classy Gentleman Vintage Fashion Mens Style Gentcreate

6. The Urban Gentleman Look For All Men

Indeed, when considering men’s styles and men’s fashions, the urban gentleman look, or the modern fashion trends, can never be ignored! In the present era, men seem to be deviating from the complete official or casual look to a simple mix of both official and casual.

Thus, several amazing urban gentleman trendsetters emerged in the fashion industry over the past years.

- However, if you prefer to fit for an urban gentleman look, trying out a bomber jacket would surely be an interesting choice! Apart from that, bright-colored pants would also suit you the best, if you love to style in that urban gentleman look.

The convenience they offer to match it with a blazer, a bowtie, a shirt, or a sweater simply makes it an asset to any urban gentleman. By chance, if you are a leather lover, you have nothing to worry about, because leather jackets, leather pants, as well as leather sachets, can also give you that urban gentleman look.

Apart from that, leather style bags, such as messenger bags, shoulder bags, and vintage coach crossbody bags, would also enhance the awesome urban gentleman look that you have created with your attire!

Vintage Fashion Mens Style Gentcreate

7. Hipster Look For Men

Excited to dress like a hipster? If so, your style is surely going to please anyone’s eye while giving out your free sense of mind. Still, we suggest that it is better to have a proper idea about what hipster look fashion trends rule the men’s fashion world. Simply, wearing denim, ripped jeans, patterned shirts, beanies, and hats is capable of giving you that hipster look.

- However, if you are looking for tops to suit the hipster look, button-down shirts in athletic cuts, and slim-cut jackets and blazers would be great choices. Besides, if you need pants that suit this look, tapered jeans and slim-cut trousers are surely the best outfits. However, to get that best hipster look, the costumes that you choose should not be too tight, nor baggy.

 Apart from that, coupling your costume with a vintage 80s leather crossbody bag, or a leather duffel hipster bag, a matching pair of sunglasses and a belt will also magnify the hipster look that you have already created!

Urban Hipster Look Vintage Fashion Style Gentcreate

8. Street Style Men's Fashion Look

If you are an individual who loves the street style look, trust us, you have ample choices! From a pair of jeans to shorts, to shirts, to t-shirts, there is a huge variety that would suit your style and purpose.

-  However, instead of a full suit paired with a leather briefcase, or formal wear paired with a duffel bag you can choose a pair of jeans and a t-shirt or a shirt, that go along with today’s men’s fashions.

Besides, a matching wristwatch, stylish phone case, as well as a style bag such as a shoulder bag or messenger bag, would surely give you that perfect ‘style look’ in a way like no other!

Street Style Look Vintage Fashion Gentcreate

9. City Fashion Look For Men

If you are looking for men’s fashion trends to look sharp with the city look, of course, you have many and more choices! Even the most favorite go-to option of any man, jeans and a t-shirt would give this city look, but you have to pay special attention to choose the right pair!

So, when it comes to jeans, always get that clean, decent pair of jeans that fit you. It is better to avoid very baggy jeans, or jeans with large prints on the back if you are aiming for that city look.

 Then, you can choose a long-sleeved shirt, or a t-shirt, that matches your pair of jeans to magnify the awesome looks that you got. And yes, don’t forget! Adding up a sweater or a blazer for your costume, when necessary, would never harm your city look, as long as it suits your style.

Besides, if you need a bag to carry your belongings, you can simply opt for a leather shoulder bag, or a briefcase, based on your purpose, so that it would preserve your city look!

The City Look Vintage Fashion Style Gentcreate

10. Ivy League Fashion Style For Men

Emerging in the 1950s, the Ivy League look still rules the men’s fashion world! Thus, this happens to be a major focus of many, who are interested in men’s styles.

However, if you prefer this ivy league look, there are certain essentials that you need to add to your wardrobe. One such is the classic polo shirt. Whether you wear it alone or pair it with a sweater or a blazer, it would guarantee you the ivy league looks that you always dreamt of.

Apart from that, crew neck sweaters also happen to be a favorite of many, who prefer the ivy league look. The plain colored sweaters are trendier these days, and thus, you can opt for one as such.

Above all, choosing a pair of boat shoes, a 50s style bag, and a pair of sunglasses, when necessary, will also elevate the ivy league look that you have given yourself with your costumes!

The Ivy League Look College Fashion Style Vintage Fashion Gentcreate

Why Is 1980's Retro Fashion Men So Popular?

1980s retro fashion men is very popular most because of fashion role models in the 80s were mostly dressing up in that particular 1980s retro vibe fashion look.

It will make you look trendy and fashionable without having to spend too much money on clothing. When everyone else is looking boring or outdated, you can be different from them by following this amazing fashion trend!

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

The 80s retro style is a great way to show off your individuality. It's all about having fun and expressing yourself.

As with any fashion, there are certain things you can do to stand out from the crowd and make sure you look as cool as possible.

The first thing you need to do is find an outfit that suits your body shape the best, this will make sure you look good in whatever clothes you wear. You should also have a few staple items in your wardrobe so that when someone asks "where did they get those clothes?" it's easy for them to say "I bought them at Gentcreate."

The Bottom Line

After all, it is the way you dress that gives the first impression. So, decide on the look that you prefer the most, match, match, and match, and choose what suits you the best!

Retro Backpacks & Vintage Duffel Bags Shop - Gentcreate

Vintage Waterproof Leather Backpack in Khaki Color- Gentcreate
Vintage Waterproof Leather Backpack in Army Green Color - Gentcreate
Vintage Waterproof Leather Backpack in Dark Brown Color- Gentcreate
Vintage Waterproof Leather Backpack in Black Color - Gentcreate
Waterproof Leather Backpack in Gray - Gentcreate
Waterproof Leather Backpack interior view - Gentcreate
Waterproof Leather Backpack - Gentcreate
Waterproof Leather Backpack - Gentcreate
Waterproof Leather Backpack in Brown Color - Gentcreate
Waterproof Leather Backpack in Brown Color- Gentcreate
Waterproof Leather Backpack in Brown COlor- Gentcreate
Waterproof Leather Backpack in Brown Color- Gentcreate
Vintage Waterproof Leather Backpack in Khaki Color- Gentcreate
Vintage Waterproof Leather Backpack in Army Green Color - Gentcreate
Vintage Waterproof Leather Backpack in Dark Brown Color- Gentcreate
Vintage Waterproof Leather Backpack in Black Color - Gentcreate
Waterproof Leather Backpack in Gray - Gentcreate
Waterproof Leather Backpack interior view - Gentcreate
Waterproof Leather Backpack - Gentcreate
Waterproof Leather Backpack - Gentcreate
Waterproof Leather Backpack in Brown Color - Gentcreate
Waterproof Leather Backpack in Brown Color- Gentcreate
Waterproof Leather Backpack in Brown COlor- Gentcreate
Waterproof Leather Backpack in Brown Color- Gentcreate

Waterproof Canvas Backpack

Brown Waterproof Retro Backpack - Gentcreate
Retro Waterproof Military Green Backpack
Waterproof Backpack Gentcreate Black Color
Gray Waterproof Retro Backpack - Gentcreate
Waterproof Retro Backpack Brown Color From Side - Gentcreate
Waterproof Retro Backpack Brown Color - Gentcreate
Waterproof Retro Backpack From Behind- Gentcreate
Waterproof Retro Backpack On The Floor - Gentcreate
Waterproof Retro Backpack Canvas Materials - Gentcreate
Waterproof Retro Backpack Canvas Materials Interior- Gentcreate
Brown Waterproof Retro Backpack - Gentcreate
Retro Waterproof Military Green Backpack
Waterproof Backpack Gentcreate Black Color
Gray Waterproof Retro Backpack - Gentcreate
Waterproof Retro Backpack Brown Color From Side - Gentcreate
Waterproof Retro Backpack Brown Color - Gentcreate
Waterproof Retro Backpack From Behind- Gentcreate
Waterproof Retro Backpack On The Floor - Gentcreate
Waterproof Retro Backpack Canvas Materials - Gentcreate
Waterproof Retro Backpack Canvas Materials Interior- Gentcreate

Waterproof Retro Backpack

Vintage Canvas Backpack
Vintage Canvas Backpack
Vintage Backpack In Gray Color - Gentcreate
Vintage Canvas Backpack
Vintage Canvas Backpack
Vintage Canvas Backpack
Vintage Canvas Backpack
Vintage Canvas Backpack
Vintage Canvas Backpack
Vintage Canvas Backpack
Vintage Canvas Backpack
Vintage Canvas Backpack
Vintage Canvas Backpack
Canvas Backpack - Gentcreate
Vintage Canvas Backpack
Vintage Canvas Backpack
Vintage Backpack In Gray Color - Gentcreate
Vintage Canvas Backpack
Vintage Canvas Backpack
Vintage Backpack In Gray Color - Gentcreate
Vintage Canvas Backpack
Vintage Canvas Backpack
Vintage Canvas Backpack
Vintage Canvas Backpack
Vintage Canvas Backpack
Vintage Canvas Backpack
Vintage Canvas Backpack
Vintage Canvas Backpack
Vintage Canvas Backpack
Vintage Canvas Backpack
Canvas Backpack - Gentcreate
Vintage Canvas Backpack
Vintage Canvas Backpack
Vintage Backpack In Gray Color - Gentcreate

Vintage Canvas Backpack "OG"

Written with love by the Gentcreate Team.

Get exclusive deals from GENTCREATE:

Enter giveaways, get discounts, free stuff, free shipping and a lot more news straight into your e-mail inbox: