30 Casual But Classy Outfit Ideas for Men to Look Sharp

Summertime is for partying and hanging out. You want to be comfortable and casual, but still have a sense of class, as if you are spending the summer in Connecticut on your yacht. You may not have a summer house in Connecticut or a yacht, but your clothes can create the sense that you do!
 

Check out these tips and ideas for casual but classy outfits for guys to look sharp and fresh.

Since the beginning of fashion history, Nantucket Reds, made famous by Murray’s Toggery Shop on Nantucket, have been the go-to pants for children, teens, and adult men for the classy, casual look. No matter what you pair with these, and whether you choose shorts or pants, this style makes you look classy while being comfortable and relaxed.

Tips for pairing: boat shoes (my preference would be Sperry’s), a tucked-in polo (almost every color seems to match the Nantucket red hue except for other red/pink shades), and a brown belt. Heck, even a t-shirt that says “Shark Week” paired with Nantucket Reds makes for a classy men outfit.

A Vineyard Vines quarter-zip pullover is a great staple to have. You can have anything underneath the pullover, but no one has to know what it is! Vineyard Vines also has some great summer colors and patterns to make you not only comfy but dressed to impress.

All four of these guys look put together and clean cut. This is the magic of the quarter-zip pullover. If they were wearing graphic tees, it would not have the same effect as they have with the pullovers. The amazing thing about these is you can wear them with any pants, as jeans and khakis are shown in the picture.

Have you ever noticed men’s clothes are 100x more comfortable than women’s? That’s because guys’ clothing is made with better materials because they don’t need ruffles or accents on their clothes like women do.

This simple look, of a tucked-in button down and navy blue pants actually is probably more comfortable than women’s pajamas. The shirt is from Express is a lightweight cotton which is great for the summertime. The white of his sneakers also brightens up the look and makes it more casual.

How can someone in a casual, cotton hoodie look so classy? This blogger pulls off a 9 Euro hoodie (that’s $10.50 USD for those who don’t have an exchange converter on hand) with plain light-wash skinny jeans and white sneakers. It’s all about being comfortable and looking fresh!

The gray Puma sweatshirt makes this outfit look comfy. However, the look is put together, clean, and polished to make it look classy.

Clean whites of clothes and shoes is what makes an outfit like this, something made for working out, look classy. The shorts, although they appear to be classy pants, are actually just gym shorts. However, the outfit looks put together and there is white in every part of the outfit, tying it all together.

Out of these three classy, casual outfit options for guys, which do you think won the vote on Instagram? Which one is best for a party and most fashion-forward? 

Let’s take a look at a few more outfit options for guys before I reveal the answer. 

The color block tee is perfect for guys who want simple and neutral. The white sneakers also go with the white of the tee, making your eyes go up and down while appreciating every aspect of this outfit. 

This casual outfit is for all guys. It is paired well with work boots and a leather jacket that can keep you warm on the fall days. However, remove the jacket and switch the boots out for boat shoes and you have a perfect hang-out summer look. 


Ok back to the game. Ready for the answer? Drum roll please....


The answer is 2! The second/middle outfit option won the vote! Why? The khaki pants make this outfit classy and lightens up the look as a whole, rather than the first option which is monochromatic and the second option which is all dark.

Ok the winner of the last one versus two more outfits for guys. Which one do you think will win?

But first, let me introduce you to this:

Some men prefer tighter clothes (just as women can enjoy baggy clothes, men should be able to enjoy skinny jeans). This tight gray polo goes well with the dark wash skinny jeans. The entire outfit accentuates all the right muscles!

Back to the second round of the game!


The answer is number 3! The second outfit could not uphold its title against this patriotic, summertime look. I think it was the Oxford shoes and matching belt that won this round!

Since denim was invented in 1873, it has been a staple in both women and men’s fashion. At first, only pants came in denim. However, denim has taken over the fashion industry and is offered as almost every clothing item (except socks. I have never seen denim socks). What makes denim great is that it is comfortable, versatile, and durable. Check out these ideas for men’s outfits including denim.

To make jeans classy, pair them with a button down and oxford shoes, as shown in this picture. Denim is comfortable and the epitome of casual, but if you’re trying to be freshest at the next summer party, you want to dress them up a bit.

A denim jacket is best with simple accompanying clothes. Avoid mixing denims, so these black pants are a great pairing for guys.

A denim shirt gives a fresh look. Again, like the denim jacket, you don’t want to pair it with more denim, so wearing khaki pants with this denim shirt was a great idea!

Ripped denim shorts can look classy? Yes! How this gentleman pulls off a classy look with his jorts is wearing dark boat shoes and a white tee. He also maintains clean, tan legs (if you have legs that look like Chewbacca, you might want to work on that before trying to pull off this look).

Another denim shirt, but this shirt plays with the idea of dark and faded wash denim. The shirt is paired with light khaki shorts and white high top sneakers.

Tips for pairing: white long pants and brown Oxford shoes would also keep this outfit classy! 

One of the greatest tips I could give you for making your outfit classy yet casual would be to make sure you are matching. It only takes one article to not match that will throw off a whole outfit and change the whole look. I’ve already identified some matching outfits (when shoes and belts match, when shoes and tees match). Check out these for more ideas.

The way the hat matches the polo and the polo matches the shoes makes this outfit perfect all over. Men who love to match will love this outfit.

If you have a purpose for this leather murse (man purse), then this matching outfit is for you! The murse matches the jacket perfectly creating a balance in this outfit.

If you’re looking for an outfit that reminds people of Florida vacations, this is the outfit! The shirt has palm leaves and the pink shorts, described as “Flamingo Pink” matches the shirt perfectly. This outfit looks so comfortable for guys! This look is ready for a summertime party!

A blazer will make a casual outfit made up of a t-shirt, jeans, and sneakers into an outfit with class and style for men. Blazers are also very versatile, as they can be also used for different outfits in different ways. Definitely, something to have in the closet!

…Yes, blazers even make a t-shirt with an astronaut wearing a blazer look classy. This is your chance to wear your fun graphic tees and still look sharp. 

If I said guys could pull off a powder blue blazer, you’d look at me like I just came from the set of Dumb and Dumber. If you already went out and got a full powder blue tuxedo, ditch everything but the blazer and you can use that to class-up jeans, a button up, and sneakers.

Even without the water in the background, the outfit looks like it would appear on a boat. Regardless of your ability to pose in front of a waterscape or go boating with your friends this summer, this look is casual and classy and will have the water vibe no matter where you are!

A collared shirt under a sporty sweatshirt like this offers the class into this casual look. Without looking like you just came from the gym, you instead look like it was intentional. 

Don’t be afraid of patterns! This lightweight white shirt with tan traditional patterns looks great for a laidback outfit.

Tips for pairing: khakis and flip-flops (possibly one of the few outfits I would say men wearing flip-flops would be okay!).

Is there anything classier than suspenders? Classy and vintage suspenders can transform jeans into a classy blast from the past. Men who wear suspenders tend to have old souls and wisdom beyond their years.

Ripped jeans can look classy for guys if the shirt is properly fitting and the shoes are bright and clean. Out of these two outfits pictured, I definitely prefer the first one, as the jeans and shoes look more for guys than the darker, tighter jeans and the slipper-looking shoes.

If you are a sports fan and like to wear jerseys (football, soccer, baseball, etc.), you can get away with the sporty classy look. Pair a loose jersey with skinny jeans for a good balance.

You may have seen this trend in men’s fashion, but layering jackets, like this gentleman has done with a tan leather jacket and a denim jacket underneath, actually helps to give style to a comfy outfit. The jackets provide layering colors and textures.

Making your outfit classy yet casual for men is not as hard as it may seem. There are a few tips to take into account when choosing your outfit and shaping your fashion style that, as long as you follow them, you will be the sharpest and freshest guy at any party!

Here is a recap of all the tips offered to create a classy yet casual look:
 

Stay classy, guys!