Best Casual Outfits For Guys

by Andreas | Last Updated: August 31, 2019
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Casual dressing lets you lower your guard a little bit during the weekends. It is the opposite of the formal wear that you have been adorning from Monday to Friday. It also lets you express your personality.

Your clothes are the first impression a person gets when they meet you. You can tell from the mix of colors and designs whether the person takes himself seriously or not. You can even lose a potential date based on your dressing.

When searching for the right casual look, you have to find a balance between style and comfort. For most guys, when they hear casual outfits, the first thing that comes to mind is jeans, t-shirt, and sneakers. But, there is more too casual wear than this.

If you are reading this and have crossed the threshold of been called young, then it is time to ditch the sagging jeans and graphic filled t-shirts.

Let’s get started…

Denim Jeans

man leaning on the wall wearing denim jeans

What you want is to dress up like a man with purpose not like a thug. This means ditching the oversized jeans that you need to keep pulling up every two seconds. No modern lady will want you taking her out looking like that.

Denim jeans have been around for centuries. Find the right pair of jeans that fits you right. If you want a more mature jeans look, avoid those that have large logos of dragons on the back or the ripped ones. These are okay for your teenage son, but when you wear them it passes the message that you still need some time to grow up.

Light or dark blue goes fine with jeans – for the legs go for straight leg styles.
The best part about jeans is you can pair them with a variety of other clothing – from formal shirts, leather jackets, t-shirts, polo shirts, sneakers or even leather boots. Levi’s jeans are a great choice.

You can accessorize your jeans with a cool brown leather belt or go with canvas. If it is cold go with a nice scarf to go with your jeans, sweater look.


It is not a must that you wear your jeans all the time; switch occasionally with some chinos. This looks good with t-shirts, polos or a good sweater. Find different colors for a variety of occasions.

You can purchase one khaki, navy, pink, or beige. To ensure a perfect casual look, know how to match the colors with your top. You can roll up the bottom for a more casual look and rock them with some desert boots or white sneakers.


tshirts in clothing line

Yes, I get it Tom and Jerry was a lovely cartoon. If you want to adorn a more mature look, then you need to donate those cartoons and graphic filled t-shirts to your teenage cousin. To dress like a man, avoid too many writings on the t-shirt.

When purchasing a t-shirt go for cotton. These absorb sweat better and are comfortable. Colors can range from black, white, navy blue or grey. When it comes to wearing, ensure that it is a tight fit and does not appear loosely. You can pair this with jeans and a leather jacket. For t-shirts, you can try out Mango, Asos, or Express.

Polo shirts

red polo t-shirt

Polo shirts go well with your jeans. When it comes to color, you are spoilt for choice as there is a wide variety. When wearing polo shirts, ensure that they closely fit your body. Purchase those made from high-quality fabrics. Polo shirts are inexpensive and you can buy a couple on the go.

Casual shirts

Jeans and chinos go well with casual shirts. Find one that does not remind you of the office. You can tuck them in or wear them loosely.

When wearing casual shirts, it is a good idea to unbutton a few top buttons or roll up the sleeves. Match them with your shoes and trouser.

folded casual shirts

Leather jacket/blazer

Any serious guy who has a fashion sense has got to have a pair of leather jacket. A leather jacket comes in handy when you are clubbing on a cold night out and your lady friend is freezing.

However, when purchasing one ensure that you are buying real leather. It can be costly but will be worth it in the long-term. You can pair your leather jacket with a t-shirt or polo with matching leather boots for that cowboy look.

Leather jacket/blazer

Alternatively, you can put on a business-like blazer with matching bright colors. The blazer like the leather jacket should perfectly fit your body. Underneath, you can match the blazer/leather jacket with a t-shirt.

A casual blazer comes in handy when you having an unofficial business meeting where you want to appear relaxed while not being too casual.

Casual knitwear

picture of knitted sweater

During the cold seasons, you can throw in some casual knitwear to keep you from the cold while giving you a casual look. Wool and cotton tend to be the most common materials. You can combine it with your t-shirt or polo shirts. Throw in a warm scarf or gloves to accentuate the look.

Casual footwear

Shoes tell a lot about a man. Wearing the same sneakers every weekend is a big no. Women notice your shoes the moment you start chatting them up and they will often judge you based on them.

Invest in good pairs of shoes. Occasionally swap your sneakers with some desert boots. These low cut, leather boots can be paired with your chinos for a more refined casual look. The shoes are also comfortable to walk in.

Having a pair of loafers or leather boots does not mean you ditch your sneakers. Invest in white sneakers as you can pair them with a wide range of outfits.


Your arms should not be left bare. Get yourself a casual wristwatch and some leather bracelets. Learn how to match the accessories, so that they bring out the casual look. If you are wearing jeans, invest in a good brown leather belt. You can also wear a baseball cap during summer or a hoodie for winter.

Dressing for the occasion

Since we are talking casually here, you need to match your outfits to fit the occasion. You cannot dress in the same way all the time. Wearing a pair of dark glasses and a hood for a night out is a big no. So, how should you pair your clothing?

Date night

This will probably be the night where what you wear matters a lot. First impressions play a big role in whether that girl you like so much will progress with the relationship or not.

In this regard, the baggy jeans and shouting t-shirt full of drawings will have to go. There is a temptation to overdress when going out for a date. Understand that you are nervous and so is she.

Couple Date Night

You want to appear sophisticated and mature while at the same time modern and sleek. Chinos or well-fitting jeans will do for the bottom part. Pair this with a simple t-shirt or polo.

To complete the look, wear a colorful blazer that gives a casual businesslike look. This enables the lady to take you seriously. The blazer may also come in handy if she forgot her sweater.

For the shoes, get some desert leather boots or white sneakers. Accessorize your look with good quality, casual watch. You can throw in a leather bracelet but do not go overboard with gold and silver chains – you don’t want to pass the message of a pimp. Finish, your look with a dash of light, citrus-scented cologne.

Evening events

For a night out, you do not want to overdress. You need something comfortable to enable you to get your groove on. Blue or black jeans will do, paired with a plain cotton t-shirt. You can stand out with a good leather jacket. For the shoes go with sneakers.


Summers are characterized by hot temperatures. A good pair of shorts, sandals, and a t-shirt/polo shirt will do. You need to stick to light clothing due to excessive sweating.

Shopping/running errands

You cannot just walk out with your pajamas because it is a weekend. When running errands put on something simple while sleek – you never know who you may bump into at the mall.

Jeans or chinos paired up with a plain t-shirt will work. If it is hot replace the jeans with some shorts. Sneakers are best for running errands – they are comfortable and bring out your casual look the best. If it gets chilly, put on a timeless bomber jacket.

Tips for Casual Wear

Keep it simple:

If you are trying to impress do not go overboard by putting too many accessories. A simple bracelet will do. Do not wear a blazer because it looks good on you but the heat is overwhelming. Also, get rid of all those chains on your neck.
Define your personality: you are the one who is going to be wearing those clothes all day, so consider defining your goals.

Are you dressing to impress? or are you looking for something to break the monotony of formal wear? Your personality should define your dressing style. If you are the quiet type, then avoid clothes that will draw too much attention to yourself. If you want to appear mature, then ditch those t-shirts with crude jokes written on them.

casual wear man

Dress to the occasion:

Since you have this outfit that you love so much does not mean it is suitable for all occasions. If it is summer get loose-fitting clothes while in winter dress to keep yourself warm first. The occasion will define what to wear and how to pair up clothes.

Invest in some timeless pieces:

Their outfits and accessories that do not go out of fashion. You can still rock them no matter the age you are in. These timeless pieces are expensive and long-lasting; meaning you will wear them for many years. These items include a good leather watch, leather belt, premium bomber jackets, blazer, leather jacket, and some high-end sneakers.

Right fitting clothes:

It is okay for a child to walk out in loose-fitting clothes but not you. T-shirts or jeans should fit your frame well. They should not be too baggy or appear sloppy.

Ignore the fashion world:

Unless you plan to become a male model, you should give the fashion industry some blackout. What works for them may not accentuate well with your personality. The regular guy just needs simple, casual clothing that breaks the monotony from official wear.

Personal dressing is a skill:

Many people you see well-dressed were poor dressers in junior high or college. But, with time they learned more about themselves and started buying clothes that actually bring out the best in them. The more you try out matching outfits the better you become with the skill.

blue casual suede shoes

Very few people have the resources for a professional stylist – they don’t come cheap. That does not mean you can afford to be a shoddy dresser. Since you need to get up every day, dress up and go about your business, you can as well try out some outfits. The best part is you can ask your friends how well you have paired certain outfits and improve based on their feedback.

Identify what you like:

In business, you are told to emulate your mentors -same with fashion. When glossing over fashion magazines or watching a movie be curious as to what your favorite star wear. The idea is not to copy what they are wearing but to give you ideas to your casual style goals. Today, identify 3 guys who you like their fashion sense and write one style that you like from each.

All your styling problems can be solved by having the right fit: No matter how expensive a pair of jeans, boots or t-shirt is if it does not fit then it will not work on you. Many people have rocked well cheap clothing and it has come out fine – checkout celebrities, what some are wearing can even be considered bizarre but it fits right to their frame.

Spend time with fashion-conscious friends:

One of the easiest ways to become better at styling is to spend time with friends who are rocking it themselves. These kinds of people will notice when your style is off and offer suggestions.

If you have been rocking baggy jeans and t-shirts for a long time, it would be prudent to first ditch the old friends as they will not appreciate the new you. If you do not have such kind of friends, don’t worry.

Wingtip, Dress Shoes,

You can start by following some people with a great fashion sense on Instagram and Facebook. Trust me, they will be more than willing to tell you where they got that cool outfit.

Start with classic before trendy:

When people want to start having a clothing style they make the mistake of going with what is trendy. This may mean glossing over fashion channels and magazines in an effort to identify the right outfit that is “fashionable”.

The problem with this strategy is it keeps in in vicious cycle where you are always in the mall shopping for the most trendy outfit. What is cool today becomes outdated tomorrow. Classic casual styles have withstood the test of time. Trendy clothes have come and gone and left them still standing. You will never hear of rocking jeans, a casual t-shirt paired with leather boots or jacket going out of fashion. This is the best place to start when you are trying to identify a personal style.

Logo t-shirts and wear:

If you want ladies to take you seriously, then avoid ever going for a date or night out with t-shirts/hoodies with logos splashed everywhere. This is kind of wear is appropriate when you are sleeping or gardening -we can excuse college guys who have yet to earn a paycheck – but not you.

The reason companies like dishing them out are that they make them cheap. Solid colors bring out your personality better; invest in white, blue, or black then as you get more comfortable with your personal style try out more bold colors like orange or pink.

Go for quality:

Cheap is expensive. There is no point buying a pair of t-shirts/polos only for them to fade after a few wears. Go to high-end departmental stores and buy some good quality jeans/chinos that will last along. Quality clothes will come with durable accessories. For example, it is unusual to find original Levi’s jeans having problems with the zipper.

You can never go wrong with neutral colors: A closer look at most men’s wardrobes will reveal a fetish for neutral colors. You will find lots of greys, navy blue, some black; the reason for this is you can pair up neutral colors with almost anything. Take a white t-shirt for example.

You can wear it underneath a leather jacket, pair it with jeans or chinos, and if it is summer dress it down with a pair of shorts and sports shoes. This would not be the case for an orange or green t-shirt. However, the modern man still needs a pair or two of bright colored shirts and t-shirts – especially when you are planning on taking her out to the beach.

Step out of your comfort zone:

This may seem like a contradiction after starting how cool neutral colors are, but occasionally try out some white pants for a change. Pair it up with a brown blazer and a black shirt. You will never know how good you rock the outfit until you try it out.

Dressing up:

The main reason men don’t fancy shopping for clothes is the amount of time spent dressing up. If there is a line at the departmental store then it will take you forever to get the right clothes size.

A simple trick to help you get what you want faster is to get the size you think fits you, then an additional pair size up and down. If it is a pair of chinos and you think your ideal size is 36” also pull up 34” and 37”. This will make it easier to find the right fit.

Tucking the t-shirt/polo:

I don’t know where men got this idea of tucking in their t-shirts/polos. The idea for casual wear is to loosen up a bit and let go of formal. Leave your shirts untucked – in fact, go the extra mile and loosen up some top buttons while rolling down your sleeves.

Business casual:

There those moments you may be called for an unofficial business meeting outside office hours and spaces. If it is summer, dressing in a three-piece suit at a golf club or camping trip will come out as off. The tuxedo won’t also do for the night out with investors.

Instead, replace the jeans with some good fitting chinos. Top it up with a light blazer; underneath you can have a plain t-shirt or polo shirt. The jacket you choose should be one button. You can pair your chinos with dressier shoes or trainers. Complete your look with a good casual watch that speaks of class. This will give you a laid back casual style that is still ideal for business meetings.

Don’t forget to complement your outfit with the right cologne.


Ultimately, the best tip for casual outfits for guys is to experiment with different styles. Adorning, just jeans, and t-shirts will become boring and at times may not be suitable for the occasion. Classic casual styles have withstood time and continue being popular even with emerging trending wear. Your clothing style reflects your personality, so start getting rid of those college wear if you want people to take you seriously.

When purchasing clothing wear, do not always go for what is cheap. The fabrics should be high quality, comfortable to wear and durable. Invest, in some timeless pieces like a good casual watch, designer sports shoes, leather/bomber jacket, leather wallet, and belt. These items will last you a lifetime if they are made of high quality. Lastly, do not be afraid to step out of your comfort zone and try out new designs – you may end up looking super cool.

Andreas, the founder of CharmingMale, is an enthusiast of becoming a "charming guy" without becoming someone else. He has been an average skinny dude most of his life, yet after years of hustle, disappointments, he become a better male version of himself. He discovered that, even if you are an average guy, as long as you are willing to put in some effort of improving yourself and developing the skills, you can become a better man that people will respect and admire!