men's fashion, The Ultimate Guide to Men’s Fashion (Updated 2021), Outdressing

The Ultimate Guide to Men’s Fashion (Updated 2021)

Men have been learning to find their style for a very long time. They look up to figures such as James Bond, Tony Stark, Timothee Chamalet, Harry Styles, and a lot of other men who have vastly different styles.

But the common man, the men who do not have their own stylist, who aren’t celebrities and fictional characters, well… they have little to no idea where to start.

men's fashion, The Ultimate Guide to Men’s Fashion (Updated 2021), Outdressing

It can be overwhelming trying to found your own style, especially seeing how well-put-together some of these men are. Does style mean wearing a suit all the time? Does it mean flamboyancy and the occasional earring? Is that what it takes to be fashionable?

You’ll find as you read on that the answer is a clear no. You can be stylish with just a simple white tee and some jeans, perfecting the “I just threw this on” look.

Really, nothing that looks stylish ever is just “thrown on”; style is a skill, something you learn as you build from the basics.

So the basics are exactly where we should start.

Men’s Fashion #1: The Classics

men's fashion, The Ultimate Guide to Men’s Fashion (Updated 2021), Outdressing
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Classics are called classics for a reason. These are timeless pieces that will never go out of style, and you can’t go wrong without them. You’ll see these looks worn from 20 years ago and until now. 

Its timelessness is what makes it very easy to master. It does not involve many colors and provides some ease in mixing and matching. It’s best that, if you are just beginning to find your own style, you start by looking at what already works on almost everyone.

This probably will not be the style you’ll end up adapting unless, of course, you like its convenience and simplicity. It still is best to build a great foundation where you can easily understand what elements work with each other and what doesn’t.

After mastering this, then you can adorn yourself in more decorative styles.

Men’s Fashion #2: The White Tee

men's fashion, The Ultimate Guide to Men’s Fashion (Updated 2021), Outdressing
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The white t-shirt is considered a classic because it refuses to go out of style. And how can it? Something so simple isn’t anything to be mad about. It’s very easy to style and works on several occasions, from a casual trip to the grocery store to a more formal dinner with a suit jacket thrown on top.

In looking for a white t-shirt, or anything really, the most important thing is the fit. A good fit makes the difference between a random white t-shirt and a stylish one. Slim fits are always great as they usually accentuate the chest and make it look bigger, but always keep in mind what your body shape looks like and how tighter fits might emphasize parts unflattering parts of you!

Another thing to consider is the quality of the material. Cotton is known to be of high quality. It also is a very comfortable tee, so you can look stylish without having to sacrifice comfort.

Of course, wearing this hanging too low on your hips might make you look too loose (unless, of course, that’s the style you’d like to go for), so try reaching for those that stop just above the hips. If not that, try tucking in a part of the shirt into your jeans! 

Later on, you’ll be moving on to dress shirts, exploring more colors and fits. There are different kinds, but the more formal option would be the Oxford shirt.

It’s a button-down shirt that, with the perfect fit, would make you look ready for any kind of occasion. Top it off with a great jacket and you’ll have a more formal look.

Men’s Fashion #3: Denim

men's fashion, The Ultimate Guide to Men’s Fashion (Updated 2021), Outdressing
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Denim jeans are a great pair for your white t-shirt. Not only are they part of the classics, but they are also a piece that is most styled with. This is because it’s quite easy to do so, especially if you have a great fitting pair.

What makes jeans great, though? Although this is quite redundant, it really is the fit that makes jeans work. Too loose, and you look a tad too carefree; too tight and you look like you’re trying to bring jeggings back! (And no, you can’t bring jeggings back.)

So what kind of fit would be best for denim jeans? Jeans that would be loose near the thighs and getting slimmer near the ankles would be the most flattering to most people. These are called slim-tapered jeans.

They look really great for casual wear and more formal settings! Since your fit is similar to how dress pants look, they are sure to look great on you.

What about color? I recommend darker colored jeans that would naturally fade over time. Grow into your jeans and get that faded look that brands usually try to imitate. This will help you create a better relationship with your own clothes and style.

What you can also do is fold the bottom of your jeans, especially if you find that it is too long for your legs. However, this will make you look a bit shorter, so watch out for that. Tailoring your jeans is always the best thing to do. 

Men’s Fashion #4: Shoes

Believe it not, the right pair of shoes can make or break a look. This is why it’s really important to not only look at what type of shoe you wear, but what color coordination you are looking for. For now, we are only building the basic colors, so it won’t be too hard to choose the color.

Firstly, the type of shoe matters. Going for a more casual look? Go for white sneakers! You can wear this even with a more formal look (e.g. dress pants and a suit jacket).

This will make you stylish and set you apart from a sea of black dress shoes. If you’re wearing more basic colors, you can have more flamboyant sneakers.

You can also use more formal shoes, like dress shoes which would match the formality of the occasion. This is more tricky in terms of matching shoe to belt, which is usually what men would usually look at to guide themselves.

A great way to check if your shoe and your belt match is to match the shade, not only the color! So if you’re going for a brown belt, you can go crazy and wear red shoes with the right shade. Auburn could match it.

You can also match blue shoes with black belts. Don’t be afraid to mix and match!


There are a lot of ways you can explore the world of fashion. It might overwhelm you at first, but this is why guides such as these exist. You don’t have to go too wild at first. Build on these basics and use the examples stated here to expand your style and create different looks.

These basics are for people who are afraid to get styling wrong yet want to still look good while experimenting. Just remember that not every look will hit the nail on the head the first time you do it. Keep trying and keep developing!

Look to people who you admire, style-wise, and take elements from their styles that you can incorporate into your daily life.

Lastly, just have fun with it! Who cares if you have one bad look one day; you’ll still be on the way to creating a wardrobe that is perfect for you.

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