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Timeless Casual Classics: Exploring Iconic Styles That Never Go Out of Fashion

The world of casual fashion has changed a lot over the decades. It practically changes by the year, especially if you track specific fads and trends, and men’s casual fashion is not immune to those changes. However, there are certain styles and outfits that have transcended the ebb and flow of trends and entered the halls of forever stylish casual looks.

We’re going to explore some of those styles and the pieces that comprise them to help you discover the classics of men’s fashion. Casual outfits need not be complicated, and these classics are sure to help you navigate your casual wardrobe with confidence.

Men’s Casual Fashion FAQ

What are some essential casual wardrobe items?

We’re going to look at some of the most iconic wardrobe items for men’s fashion. Casual outfits typically use one or two stunner pieces with simpler items to accent, and the best options for those in men’s fashion are chinos, shorts, and t-shirts. Some of those might seem bland or cliche, but we’ll explain how to pull them off with confidence and style.

Can I wear shorts in casual settings?

Absolutely! Casual settings are the optimal settings for shorts. You just need to wear the right shorts for the occasion and for your body type, which we will explain in depth.

Can I wear denim-on-denim casually?

If done right, denim-on-denim is one of the quintessential classy, casual outfits for guys. The key, however, is the “doing it right” part. But again, we’ll explain what you need to know.

What’s the secret to pulling off a casual “all-black” outfit?

The key to pulling off “all-black” outfits (or any monochrome outfits, for that matter) in casual settings is knowing which pieces look best with each other. After all, you can be monochrome without looking like a block of uniform color. In fact, diversifying shades of one color and matching different patterns/styles can make monochrome outfits perfect for cool, casual wear.

Iconic Casual Shorts and Bottoms

Men’s pants are too often reduced to a singular spectrum of jeans and shorts in popular media, but real casual fashion experts know there is a broad array of styles and options for men’s pants, and all of them are valid in the right situation. Let’s break men’s casual shorts and pants down so you know how to fully utilize the pieces in your fashion arsenal.


We can’t talk about men’s casual pants without talking about the behemoth of men’s fashion: the jeans. Jeans dominate the cultural depiction of men’s fashion. Casual outfits everywhere are defined by their use of jeans to create a casual denim look that can’t be beaten. Allegedly.

While we disagree with the ubiquitous supremacy of jeans, we can’t deny their value in a casual wardrobe and their iconicness as fashion staples. Jeans are great for comfortable, casual looks ranging from work functions to bar hops. If your jeans are well-fitted and you keep a pair or two of different washes, you can do a lot with them.

Denim-on-denim is also one of those classy, casual outfits for guys that are hard to top. Good-looking jeans with a good-looking denim jacket and a simple (but fitted) t-shirt make a good-looking guy.


Chinos are becoming the jeans of the modern world. With their casual comfort and classy style, chinos are a step nicer than jeans while being even more comfortable. Plus, since they’re not made with denim, chinos come in a variety of colors that can go with any outfit.

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Honestly, a good set of four or five pairs of well-fitted chinos in different colors is all you need for a basic but well-rounded casual wardrobe. They go with almost any top or shoe and work excellently in almost all settings, especially casual ones. Chinos are especially great if you’re a fan of athleisure looks since they can be made to stretch and breathe like a jogger while looking as clean as a khaki.

We recommend our Feel Good Chinos for any occasion. They’re built for athleisure, made with durable materials that look better every wash, and hold their color wear after wear. We’ve got every color you’ll need for a well-rounded set of outfits and sizes meant to fit your body type.


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Khakis ebb and flow in the casual fashion world, but they are keystones of men’s smart casual outfits. Better known for business casual looks, khakis can still do good work in your casual fashion wardrobe, especially if you’re in need of some casual trousers that could still look good in a meeting.

The main rule for khakis is the same rule as all bottoms: they need to fit well. The last thing you want is skinny khakis that rip or wingsuit khakis that look baggy.


In men’s fashion, casual shorts are a mainstay, especially in the summer months. The most important thing is that you need good shorts (AKA, not basketball shorts) that fall above the knee and fit your thighs and butt well. Shorts that are too long and/or too baggy aren’t flattering, but well-fitted ones will make you feel great.

We recommend our Feel Good Shorts for your casual fashion needs. They look and feel good while being made of materials built to last. Get yourself a few pairs for next summer.

Timeless Tops

Enough about pants. What about tops? Let’s look at the best casual fashion tops for men.


If you think T-shirts have no place in any respectable man’s wardrobe, you’ve been led astray. While T-shirts can get a bad rep for not fitting well and/or having poor designs and colors, well-fitted and well-made T-shirts are a staple of casual fashion. Men’s shirts are impossibly varied, but nothing can beat the classic, neutral-tone T-shirt for a casual outfit.

We recommend our Feel Good Tee for any T-shirts you’re looking to buy. They’re made of the highest quality materials and made to fit any body type splendidly. Say goodbye to baggy shirts with poor colors, and get yourself some Feel Good Tees.


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The three-button look of Henleys is an iconic staple in the men’s casual wear world. They can be mid- or long-sleeved and made of several different fabrics, meaning they can look as nice or as casual as you want them to look.

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We recommend our Low Key Henleys. Like all our other products, they’re well-made and meant to last through dozens of different outfits. They’ve got the colors and fits you need to add Henleys to your casual fashion repertoire.

Button-Ups and Dress Shirts

Last but not least, we’ve got short-sleeved button-ups and long-sleeved dress shirts. You might think these are too nice for casual fashion. While the assumption makes sense, it is incorrect.

Button-ups are a perfect option for casual outfits, especially if you want to layer. A basic white tee with a patterned, unbuttoned button-up over it is a mainstay of casual fashion. Men’s outfits can often be too one-dimensional, which means these are a great option.

On the other hand, dress shirts are great for casual office wear. Men often go too casual or too professional with office wear, but dress shirts and jeans are great, middle-of-the-road options.