How to Dress Casual: A Helpful Guide for Men

Did you know that many men feel like they’re not allowed to talk about fashion? If you’ve been feeling that anxiety as well, you’re not alone. Even if it seems like the other men in your friend group would scoff at the idea of a makeover, they might very well feel the same way.

You’re trying to upgrade your style, but you don’t know how to dress casual in a way that doesn’t make you look frumpy. Now what?

Let’s talk about it. Read on for a few basic fashion tips so you can assemble your casual wardrobe.

Basic Fashion Tips

First of all, let’s talk about the basics of men’s fashion (and fashion in general). Many men don’t have the same exposure to fashion as women do, and they don’t make an effort to choose an actual style. Why not change that?

Learning how to be stylish isn’t about copying what other people are doing. Your first step when you’re trying to pick out a casual wardrobe for yourself is to determine what you want your personal style to look like. You don’t have to follow trends or match anyone else if you don’t want to.

Do you love the “ranch” look? Are you more of a “goth” (or goth-adjacent) person? Do you love the street style aesthetic?

Regardless, you can turn all of these styles (and more) into casualwear.

Browse the web and try to pinpoint things that appeal to you. Look for men with your build to see what that style would look like on you. Don’t be afraid to take notes or even create a little inspiration board that you can refer to when you go shopping.

Remember that one of the most important things about style is confidence. People will think that you look cool, even if your outfit is unusual, as long as you walk with your head held high.

Styling Casual Shirts

Let’s talk about shirts first. You’re likely going to have more shirts than pants or accessories, and you have plenty of options. You can make almost any shirt into a stylish piece for a casual outfit.

We’ve broken this up into sections to make it easier. Here are a few tips for styling various types of casual tops.

Choosing T-Shirts and Sleeveless Shorts

“Casual” is such a broad term that it makes choosing t-shirts and sleeveless shirts pretty vague. This will all depend on your personal comfort level and your ideal style. You can make any T-shirt work as long as it’s in good condition.

If you’re into the loose and flowy street style, you can wear oversized T-shirts. They pair best with either very tight pants or very loose pants (you can look at Korean street style for the loose and flowy inspiration).

Most people, however, choose tighter tops. They don’t have to hug your body, but they should be well-fitting and comfortable.

You don’t have to spend a lot of money on a casual T-shirt, even if some people choose to spend thousands. Hit up your local thrift store to buy some basic shirts in flat colors and you’ll be well on your way to an outfit.

Some people think that band tees are too “childish” for men’s fashion, but you really just have to know how to style them right. A non-ripped band tee and a pair of dark pants is a great start to an outfit.

Even sports jerseys can be appropriate as long as you choose matching accessories.

Don’t be afraid of sleeveless shirts either. Leave the muscle shirts for the gym, but tank tops are comfortable on hot days.

The biggest tip for casual t-shirts is that they must be clean. Showing up with a stain is a fashion faux-pas.

Button-Ups: Make It Casual

Many people think of button-ups as business-casual at best, but you can definitely wear a button-up in a casual outfit.

The most common way to do this is with flannel shirts. They’re stylish and comfortable and you can wear them with most t-shirts or sleeveless shirts.

We recommend wearing them open rather than closed. Wearing them closed often looks too constricting (and a bit more formal). This is true for both flannel shirts and normal button-up shirts.

The biggest and best tip for men when it comes to wearing button-up shirts is to roll up your sleeves. Roll them up to your mid-forearm. This makes your outfit look more casual and many people even find it attractive.

Sweatshirts and Blazers

So what if it’s a chilly day? Layer up with a sweatshirt or blazer.

Sweatshirts are actually stylish right now, and we recommend picking either a plain one or one with a small decal. It’s also popular to wear shirts with college-style text across the chest.

While hoodies are fine for cold weather, crew-neck sweatshirts are more stylish and versatile.

Blazers are often “dressy,” but they don’t have to be. If you wear a blazer with a t-shirt underneath (even a band t-shirt), it makes the blazer look more casual and cool.

Most people opt for plain grey or black blazers, but if you’re feeling bold, don’t be afraid of bright colors or patterns. This is a great way to upgrade an otherwise drab outfit and make it stand out.

Styling Casual Pants

So what about pants?

We know it’s tempting to stick with your oversized torn-up jeans (and there’s definitely room for them in your casual wardrobe), but why not branch out a bit?

If you’re going to wear torn jeans, make them look intentional (even if that means making your pre-existing tears bigger). The “distressed” look is always in.

If you’re not aiming for the oversized look we mentioned before, buy well-fitting jeans. Try a few different cuts to find the most flattering pair for you.

You can also wear non-jean pants, but avoid anything too “business-y” for your casual look.

Tight khakis or plain black pants look great with most outfits and they still look casual. Again, you can also opt for something bold. Thick vertical stripes (we love black and white) can look great if you wear them with confidence, as can bright colors.

Are Shorts Appropriate?

Men, don’t be afraid to show off your legs. When it gets hot outside, why would you wear thick and uncomfortable pants? Shorts are in.

Thick and baggy cargo shorts are okay, but most people don’t know how to style them. They end up looking sloppy.

Aim for shorts that sit on or above the knee, even if only by a centimeter or two. You can wear shorter shorts, but it takes a certain level of confidence to pull them off, so fashion newbies might feel a bit intimidated.

Shorts with a plain short-sleeved top and an open button-up look fantastic.

Accessories and More

It’s time to accessorize. Yes, accessories are still appropriate for a casual look for people of all genders. If you don’t already have an accessory drawer, it’s time to go shopping.

Here are a few tips for styling casual accessories.

Jewelry: Yes or No?

Don’t shy away from jewelry! There is nothing that makes jewelry any more “feminine” than any other type of accessory. Even if you’re wearing diamonds and opals, the jewelry is only as feminine as you make it.

If you’re wearing jewelry, keep it coordinated. For example, if you have gold piercing jewelry, stick to gold tones for your necklace and watch. You can mix metals but when it comes to casual outfits, the cohesion can really pull the entire look together.

Don’t wear anything too flashy for a casual outfit.

Belts and Suspenders

Belts and suspenders aren’t necessary as long as you’re wearing well-fitting pants, but that doesn’t mean that they’re not great accessories.

You might be wondering if we’ve traveled back in time by mentioning suspenders, but they can actually be fantastic for pulling a look together. A pair of suspenders with non-jean pants and a white t-shirt is a legitimate look!

Unless you love the “cowboy” look, we recommend not opting for giant belt buckles. Novelty belt buckles are okay, but keep them reasonable.

Casual Shoes

So what about your footwear?

Plain running sneakers can look out of place unless you’re opting for an athleisure look. They can be stylish, but make sure they’re clean. Opt for a single-color sneaker for a cool and versatile option.

If you want a classic look, why not kick it old-school with Converses? Go to this site to see a wide variety of Converse options. This shoe never goes out of style.

Finally, we love boots for men’s fashion. Doc Martens are classic and they come in a wide variety of styles. They take some breaking-in, but it’s worth it.

That’s How to Dress Casual

Learning how to dress casual isn’t hard. Look through a few online magazines, take note of what appeals to you, and try to mimic it. Remember: don’t be afraid of accessories!

You can create a stylish wardrobe that you’ll wear with confidence.

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