How to Dress Better than Every Other Guy in Your 20s

Are you tired of fitting in instead of standing out? Check out my expert tips for dressing better than every other guy in your 20s.

As a menswear consultant, I’ve noticed most men don’t really start caring about how they dress until they are well into their 20s. 

Sometimes, they care but are self-conscious or uncertain about how to move forward in their style journey. Does that sound like you? Either way, I’m glad you’re here. 

For me, I’ve always cared. But I didn’t have any guidance and had to figure things out on my own. 

Acquiring your own style profile takes time. 

It’s a journey that requires patience and willingness to learn. However, the journey is fun and will reward you with great dividends. 

Today, I’ll share with you some pointers on how to dress well as a younger guy. 

The Couch Potato Movement

More and more men are putting extra effort into their appearance these days. And I love to see that! 

But the majority still appear to be stuck. Mass marketing seems to play a huge role in what I like to call “The Couch Potato Movement.”

A LOT of men spend their entire day in sweatpants or gym shorts, sweaters or old t-shirts. In other words, clothes fit for lounging around at home, binging your favorite shows from your favorite spot on your favorite sofa.

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There’s nothing inherently wrong with this type of clothing. But it has its place. Athletic clothing, sweats, and loungewear should be reserved for working out or spending time in the confines of your own home.

As a custom clothier, I often ask men about why they like dressing ultra-casually. Typically,  there are two overarching motivators for this kind of attire. First, it’s comfortable. Second, it’s easy.

Those two statements are absolutely true. But did you know that you can be comfortable AND well dressed? And it doesn’t need to take a lot of effort, either.

I think it’s safe to say that most men actually really like the idea of looking “dapper” or “fresh.” They want that “drip,” am I right?

The problem lies most often in their confidence. Lack of confidence is a big motivator for stagnancy. It takes a certain amount of confidence to try wearing something new. 

But taking that step is the gateway into your personal style journey. And a lot of confidence comes from dressing well and discovering your own style.

Why Should You Dress Better?

Confidence

Continuing with this theme, I think self-confidence is an excellent reason to dress better. I have always been self-conscious of how skinny I am, especially my wrists. 

But as I stopped wearing clothes meant to cover up my body, and started wearing clothes that looked interesting to me, I really opened up and gained a lot of confidence in myself. 

My own style journey has been a lot of fun and has helped me feel a lot better about who I am and how I look. I believe it can do the same for you.

Personality

Each one of us is unique. That’s the beauty of human life. Our individual personalities, interests, and abilities are important aspects in human interaction.

I think that style is a great way to outwardly express a bit of our inner character. It’s a first impression of all the fleeting interactions we encounter. It tells others a little bit about yourself without requiring a single spoken word.

As we learn and grow, our personalities can shift. As part of your style journey, your clothing can reflect this. In other words, it’s a great way to express your personality.

Recognition

By recognition, I don’t necessarily mean you should be seeking attention in the clothing you wear. But I do mean that people take notice.

This can open up opportunities for you that you may have never thought possible. Seriously. I’ve had some wonderful conversations with unique people that began as a question or comment about something I was wearing. 

I’ve also been offered jobs simply because I put in the effort to dress well and give off a great first impression. At the very least, it adds to your confidence. And that’s never a bad thing. Just remember, there’s a difference between confident and cocky.

My Top Tips for Dressing Better Than Other Guys

Let’s cut into the meat of today’s topic. Style is individual. But there are many very useful tips and guidelines that will help you to dress better than the guys around you. It’s time to discover your own style identity.

Proportions

There probably isn’t a better place to start than with learning and understanding proportions. Those old clothes in your closet that you swore you’d get rid of could be reworked just by applying some principles of proportion.

Proportions could be a whole topic in and of itself. There’s a lot that we could get into.

But for the basics; apply the rule of thirds to your outfits.

The rule of thirds is a technique used, especially in art and photography, to guide your eyes through an image and to a subject.

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Let’s take a look at how this translates into styling your outfits.

In the image below, look at the outfit as a whole. At first, it may appear like a well-put-together outfit. The clothes are of good quality and the colors work well together. 

But as we look closer, notice how the sweater divides the model’s outfit in half. 

This division actually makes the model’s legs appear short and his torso quite long. And though it’s not a bad outfit, per sé, it’s definitely not an interesting one.

Now let’s take a look at an outfit where the rule of thirds was considered. We divide the outfit (the area from the neck to the floor) into three sections.

In this example, the t-shirt and over-shirt make up the top third of the outfit. The pants and shoes make up the bottom two-thirds. 

This elongates the legs and creates an outfit that is more interesting to look at.

Next time you’re styling an outfit, consider the rule of thirds. It’s a great tool.

Consider Your Build

We’re all built differently. And that’s the way it should be. Consider the way you’re built when styling your outfits.

As an example, I see quite a few heavier-set guys wearing clothes that fit way too close to the body because they think that a slim fit makes them look slimmer. Unfortunately, this isn’t the case.

In fact, it has the opposite effect. Even on a slender guy, slim clothing can make you look bigger. 

My basic rule of thumb is the slimmer you are, the slimmer the clothing you can wear. The bigger you are, the looser the fit of your clothing should typically be.

But there are so many different cuts of clothing. Which means it’s not as simple as slim fit and loose fit.

Experiment With Fit

Let’s expound on that. Don’t just wear slim fit because you’re a slim guy. At least where I live, guys in their 20s still tend to lean toward slim and skinny fits in their wardrobe. 

Be willing to try something different. A slim straight or even a loose straight-cut pair of pants can make a huge difference in your appearance. 

If you’re a bigger guy, there are still slimmer cuts that could work for you. You just need to be careful. In the end, wear what gives you confidence. Just keep your build in mind as we discussed above.

Here’s a picture of me about 8 years ago.

Look at those sticks, eh? That’s what I liked then. But as I’ve matured, I’ve realized there are many more cuts that are much more interesting—and comfortable to wear.

Here is a more recent picture of me. The difference is major. My build has not changed much. But look at how natural and effortless my pants appear now. 

They are slim straight jeans. Not even a loose cut. So you can see how giving even a little bit of room for your fabric to drape rather than stretch makes a world of difference in appearance.

Have fun trying different cuts. You might be surprised what you fall in love with.

Simplify

Are you a guy that loves bold prints and bright colors? Me too! But most of the time, choosing one such item as a statement piece will go a lot further in communicating great style than decking out in full print.

Stick to a simple color palette for starters. Neutrals are the best place to begin. You can always build from there.

Keep a Supply of Basics

Your basics are the foundation of your best outfits. They make it easy to build an outfit and are an essential part of your wardrobe. Here are the basic items I think every man should own:

#1 A charcoal and/or navy suit

Both are extremely versatile and work well on all skin tones. I believe every man needs at least one quality suit in their closet.

#2 A charcoal and a navy pant

They go with everything and can be dressed up or down.

#3 A white and/or beige t-shirt that fits well

It’s great as an underlayer or as a main layer if the weather is warmer. See my article 7 Secrets to Looking Awesome In a T-Shirt.

#4 A good pair of jeans

Consider fit first. If you have a bit more money to spend, consider selvedge denim.

#5 A neutral-colored pair of sneakers

For this, I personally steer away from stark white and pure black. In place of white, consider an off-white or cream shoe. In place of black, try charcoal or navy.

#6 A high-quality pair of leather dress shoes

Shoes receive high levels of stress due to the amount of walking we do each day. It’s imperative that you save up and buy a pair of dress shoes that will last. 

As for style, my favorites are wholecut Oxfords, monk straps, and tassel loafers.

#7 A high-quality pair of leather boots

You need a good boot that will get you through the winter months. A good boot should keep you warm, provide comfort, and hold up against the elements. All the brands I mentioned above also make excellent boots.

#8 A high-quality coat

A proper coat can be very expensive. But the two items that I think are the most worth investing in for everyday use are shoes and coats. A good coat should be made of 100% wool. It will last forever and will keep you warm.

Lose the Logos

As you build your collection, it’s tempting to buy and wear pieces embellished with high-fashion branding. In my experience, this is a phase that lots of men go through at some point in their own style journey.

I went through the same phase. I believe the idea is that it shows people you have money, even if you don’t. These days I tend to disagree. It lacks the level of sophistication that I’d expect from an individual of wealth.

You can spend a lot less money to look a lot more expensive. 

If you love wearing logos, stick to one item in your outfit that showcases your favorite brand or sports team. I think this is best accomplished with accessories. A hat, a bracelet, a bag, etc.

Have Your Clothing Tailored

The clothes you’ve moved to the back of your closet might just need a fit refresh. Take them to your nearest tailor to have them adjusted to fit your preference. 

The tailor can help guide you if you are unsure what to do with them.

Buy Quality Materials

Buying clothing made from quality materials is one of the surefire ways to help you stand out in a crowd. Where possible, I try to avoid synthetic and stick to organic materials. 

Higher-quality items are definitely more expensive than their synthetic counterparts, but they don’t have to be painfully expensive. Look for sales and foreign manufacturers that offer great pricing on quality items.

Thrifting is another great way to find good quality for less. 

Accessorize

Accessorizing the right way can be a bit difficult. But accessories really can be the glue that holds an outfit together.

Don’t overdo it. Stick to two or three accessories at first. Examples could include a watch, a hat, a bag, a necklace, or a pair of sunglasses.

I personally love a neckerchief or bandana. And I almost always wear a watch.

Your outfit will dictate what accessories to wear.

Utilize Good Hygiene and Grooming

Don’t skip out on your personal hygiene and grooming. A great haircut or a unique scent can go a long way.

Get your hair cut by a barber. Men’s and women’s hair is different. A barber is trained to work with men’s hair. In my experience, a salon will almost never cut it (pun intended)! 

However, depending on the hairstyle you’re going for, a salon might be the right choice — particularly for those of you with long hair. Many barbers specialize in fades and short hairstyles and aren’t as skilled at dealing with long, flowing locks. 

Your scent is meant to be intimate. People will have to be close to you to notice how good you smell.

Note: Some men will have different scents for different occasions or seasons. That’s also acceptable. But it takes finesse and should be reserved until after you’ve found your first signature scent. 

Seek Inspiration 

There’s always more to learn and more to see. Seek out inspiration. Try understanding why certain clothing excites you. Is it the fit? The fabric? The colors? All of the above? 

Take note and watch your style journey explode in a forward direction.

Create a Style Journal

My final tip is to create a folder on your phone for pictures of your outfits. Every time you put together a new outfit, get a quick pic and save it to the folder.

You’ll begin to understand what works best for you, as well as what doesn’t. It’s a great way to watch your style identity reveal itself over time. 

Conclusion: Wear What You Love

In the end, wear what you love. If what you love really is sweats and t-shirts, ask yourself how you can elevate that look. 

Play with fit and proportions. Try incorporating different colors. And be sure to accompany the look with striking accessories.

The best-dressed men always dress for themselves. No one else.

That’s it! Now you’re on your way to dressing better than every other guy in your 20s.

For more, check us out on Instagram where we serve up simple, straightforward tips for self-improvement.