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Classy Men’s Outfits: Elegance for Every Season

Classy outfits for men don’t have to be stuffy. Here’s a guide on achieving sartorial refinement.

I think it’s safe to say that class is something we can all aspire to. The term itself, however, is pretty vague. Of course, the easiest way to define it is by showing class, elegance, or refined sensibilities.

So, how does one translate this to clothing? What exactly do classy men’s outfits entail?

Well, for one thing, I don’t think everyday class should involve stuffiness. A classy gesture may involve holding the door for someone or giving up your seat at a bar for a lady. 

So, in addition to social graces, the charm school pleases, and thank yous, class means an overall high standard of behavior. 

Of course, this includes how you dress. Here’s how to express class and refinement through your wardrobe. And don’t worry — we’ll cover every season and every dress code. 

7 Classy Men’s Outfit 101

I’m a big proponent of always wearing what you love and what makes you happy. Class doesn’t mean compromising your style. 

Do you want to be perceived as having class in the conventional sense? If so, you might want to keep the following considerations in mind when putting an outfit together.

Abide by Dress Code

Class, politeness, and respect are all pillars of the same family. Don’t disrespect an establishment or an event host by ignoring the dress code.

And here’s a life hack. Abiding by dress codes is an easy way to look stylish. Even if you don’t understand fashion or don’t think you have a sense of specific personal style, knowing the rules is a good idea.

Unless your job says otherwise, smart casual is a good way to go when it comes to everyday style. When in doubt, be a little dressier than you think you should be.

Follow Seasonal Conventions

Of course, dressing for the season is equally as practical as it is fashionable. Go ahead and find brighter colors for summer, lighter colors for spring, earth tones for fall, and darks and winter whites for winter.

It shows that you have a sense of order with the way you dress. And what’s classier than having an innate sense of the social calendar?

And if you don’t love brighter colors or pastels for the warm seasons, that’s okay! Just go for lighter men’s neutrals like beige and slate blue, warmer neutrals, and avoid stark blacks.

As Always, Fit Is King

At the end of the day, don’t go for anything overly baggy or overly skinny. There’s really no one timeless fit, but several moderate fits that take turns as being the “classic-fit”. 

It’s a case of constant revisionist history. What was “timeless style” in the ‘60s is not “timeless style” in the ‘80s and isn’t what we consider “timeless” today.

If you stick to slim and regular fits, depending on what best flatters your body type, you’ll always look classy. 

Or, at the very least, make sure you have a good balance of fits. If an oversized overcoat is in vogue right now, then anchor it with slim (not skinny) base clothes.

Use trends as accents, similar to the example I mention above about anchoring trendy fits with more classic fits.

Moreover, only incorporate trends if they’re true to your style. 

For example, the mid-2020s saw the gender-bending pearl necklace for men trend. Perhaps you were born in June, and pearls are your birthstone, and you’ve always wanted to try wearing pearls. 

You’re certainly welcome to take advantage of the window of opportunity like this, but class is all about balance. For balance, go for a subtle pearl bracelet or pearl cufflinks and wear well-structured, traditionally masculine garments in deep tones.

Or, you can just avoid trends completely. That’s the easiest approach.

In fact, the main reason for knowing trends isn’t to follow them blindly. It’s to avoid the polar opposite of what they are. If super skinny fits are in, you don’t have to participate. Just avoid super baggy clothes. If super oversized clothes are in, again, you don’t have to participate. Just avoid super skinny clothes.

Dressing with class has a through-line of avoiding fads but also a balance of never looking irrelevant. Classy isn’t musty.

Stick to Three Colors

For the most part, you want to stick to three colors on your person. Sometimes, if you mix neutrals with subtle contrasts, you can get away with extra pops and accents here and there.

Menswear neutrals include black, brown, tan, beige and ivory, navy, gray, cool shades of blue, olive, maroon, and those in the maroon family. 

Primaries are good accents, as are fall tones and garden tones in the spring.

Quality Over Quantity

It’s better to have two good suits than six bad ones. It’s better to have five good button-up shirts that you rotate throughout the week than several fast-fashion shirts.

I understand that quality clothes can be expensive. Perhaps you invest in one good suit and one or two good shirts, then fill the rest of your wardrobe with cheaper options to last the week.

As you’re able, you can start to replace cheaper pieces with more high-quality pieces.

There’s nothing wrong with looking the same every day as long as you look good. Besides, power dressing, which isn’t the same as classy dressing but has a lot of overlap, is all about having a uniform.

By the way, even the cheapest discount garment can look like a million bucks when tailored.

Accessorize

You absolutely need at least one watch and one or two good pairs of welted leather shoes, full stop.
Ideally, you should have a dress watch and an everyday watch, as well as classy leather sneakers and good leather dress shoes.

Rolex Datejust 16030 taupe dial - The Modest ManRolex Datejust 16030 taupe dial - The Modest Man

Now, here are some classy outfits for guys in every season, starting with some classy summer outfits for men.

Mens Classy Outfit Ideas: Classy Summer Outfits for Men

Summer can be difficult when it comes to dressing elegantly. The hottest days make you want to wear a pair of swimming shorts, a tank top, and flip-flops all day. 

However, I have two secrets when it comes to classy summer outfits for men.

First, linen and silk blends are your friends. Second, the dress is short.

Light Summer Palette 1Light Summer Palette 1

For smart casual and even business casual situations, a fine linen suit and linen suit separates are paramount. They’ll provide comfort and a sense of resort chic class. I like to call it the off-duty Bond aesthetic.

For casual situations, you obviously can’t go wrong with classic flat-front shorts. However, in the post-Thom Browne age, dress shorts can really elevate a relaxed combo. 

I’m not a fan of dress shorts with an actual suit jacket, personally. But if you pair them with a well-fitted t-shirt or a polo, they’ll bring a unique look as well as class.

Source: @mrrlittle

Other classy casual pieces to consider in the summer include sunglasses (aviators or wayfarers are tried-and-trues). Additional accessories such as leather boat shoes and a light-colored straw summer hat are other good options.

A Panama hat or a boat hat are excellent choices.

Classy Spring Outfits Men

One thing spring and fall have in common is layers. Layers and “garden tones” are key to putting together classy spring outfits for men.

Pastels are a great way to anchor spring outfits, but I understand they aren’t for everyone. One strategic way to incorporate them is to stick to versions that are closer to neutrals. Remember, pastels are just light versions of colors. 

So, a light slate blue is perfectly spring-like.

A light spring suit, again in linen or a light blend that may include bamboo or silk, is paramount. Go for the aforementioned slate blue color, cool beige, or even an extra light gray. 

Or, go for maroon since it’s a color that naturally occurs among flowers. It’s a dark garden tone, if you will.

Suit separates can really elevate your casual outfits. For example, a knit polo with khakis or light-wash jeans finished with loafers is perfectly sophisticated. Replace the pants with linen suit pants, though, and you’ll double the elegance factor.

Since early spring is rainy and often cool, and late spring is warm and often hot, layers are important. I highly recommend incorporating pieces from the English countryside style to achieve a “gentleman’s” aesthetic.

Some pieces that will take you from fall to spring include a Norfolk jacket, lighter cable knits, and white jeans.

Classy Men’s Fall Outfits

While early spring allows for hints of British countryside style, creating classy men’s fall outfits fully relies on it. Tweed vests, layers, hunting jackets, and flat caps have gentleman written all over them.

Mens Spring Sweaters and Shirts OutfitMens Spring Sweaters and Shirts Outfit

In fact, dressing practically in the fall often results in an overall classy look. I consider fall to be the easiest season for men to dress. 

Think about it. On a crisp day, you’ll likely opt for a button-down over a t-shirt. Going from day to evening often results in major temperature drops, so you may go for a pullover. Cashmere is a good option because it’s light but warm. 

Do you know what else is practical? Tweed trousers or chinos.

You can top it off with a blazer or a Norfolk jacket. For shoes, you can go for suede loafers, service boots, or sneakers.

Suit PairingsSuit Pairings

Leather jackets, Harringtons, and bombers are great ways to add a cool factor to a button-down and chino combination. You can also go for a more Americana approach, utilizing well-fitted jeans and slim workwear.

There’s nothing classier than heritage wear. 

Classy Winter Outfits Men

Classy winter outfits for men are all about stark, cool colors. You want dark neutrals, like midnight blue, navy, black, and the darkest charcoal.

To achieve classy casual men’s outfits during the winter, go for structure, soft texture, and deep tones. A cashmere turtleneck paired with gray jeans is a perfect example.

Replace the gray jeans with gray wool dress pants, perhaps with a glen check pattern, and you’ve upgraded to smart casual. Add a suit jacket and ensure you’re wearing black dress shoes, and you’re now ready for a business meeting.

The dark palette and structured nature of winter outfits are conducive to men’s classy outfit ideas from a traditional sense. Everything just feels a little more formal.

That being the case, make sure you have a good classic winter coat. A thick peacoat, overcoat, or winter trench coat are all top-notch choices. Even if all you’re wearing is a t-shirt and jeans, throwing on a timeless coat will class up your look.

Open DoubleBreasted Overcoat With a SuitOpen DoubleBreasted Overcoat With a Suit

Make sure you have full-grain leather gloves in a neutral color and a good cashmere scarf. If you want a seasonal accent, feel free to get your scarf in winter white or winter light blue. A red and green tartan also works closer to the holidays.

Conclusion: Anyone Can Achieve Class

I know that sometimes going for a “classy look” can feel really conventional. But you can always feel like yourself in neutrals, essentials, and structured outerwear. 

The truth is, classic menswear, and classy men’s outfits, can be boring, but that’s a good thing. It makes it easier for most people to think you look good. Again, use accessories, outerwear, and accent colors to add personality. 

How do you make traditionally classy combinations your own? And, what does dressing classily mean to you? Let’s start a conversation in the comments!

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