Start The New Year Right: 2020 Clothing ESSENTIALS For Men

A whole decade has come and gone, so where does your wardrobe stand? Have you entered the new year a man who looks like he can get sh*t done, or are you still wearing your high school hoodies?

Start The New Year Right 2020 Clothing ESSENTIALS For Men header

If you're still struggling with style, don't worry. There is yet time to revolutionize your closet. That's the topic of today's article I'm going over clothing essentials that every man needs to look into buying this year.

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Click Here To Watch The Video 20 Wardrobe Essentials Every Guy Should Own in 2020

Buckle up, gentlemen let's talk about those clothing essentials

Men's Shoes

When building an outfit from the ground up, it only makes sense to start with shoes. As the literal foundation of your wardrobe, these clothing essentials can make or break an outfit from the get-go. Let's go through a few categories and discuss how you can bring them in.

1. Sneakers

I get it you're just getting started. You've only ever owned sneakers and you think the brogues are a bit much this early on. If you're that kind of guy, then where better to start than upgrading what you already have? Avoid running shoes at all costs (unless you're going to the gym). Instead, opt for a pair of canvas sneakers.

black dress sneakers

Leather sneakers are a good choice for men just getting started with style.

White is classic, but so is blue! Especially if you want the shoes to flow along with your jeans. Not a fan of canvas? There are plenty of leather sneakers out there in a plethora of colors and styles. The toughest part is zeroing in on what resonates with you.

2. Dress Boots

What's not to love about a great pair of dress boots? First off we have the heel. Boot heels are usually higher, making the man wearing them look taller and more confident in turn. A personal favorite of mine? Chelsea boots. They've been around for centuries first as cavalry boots, and then as the staple of rockstars. You can dress them up and dress them down with ease.

black chelsea boots

Dress boots such as the Chelsea offer a measure of rugged elegance to a man's look.

Another staple of men's boots are the Chukkas. These bear a military heritage dating back to World War II, and thus they are more rugged. Nevertheless, you can still rock them with chinos and a sports jacket. It's no surprise why dress boots are considered to be clothing essentials.

3. Casual Dress Shoes

Is it too hot to wear boots? No worries, because there are loads of other casual shoes to suit your tastes. Penny loafers are great for this. They're lightweight, they're timeless, and they slip on and off perfect with no show socks and a summer wardrobe.

oxford brogue shoe infographic

There are different designs for brogues. The more holes there are, the more casual it is. Click here to learn more about Oxfords and brogues.

I'd be remiss if I didn't include the classic brogue. This look is about as timeless as it gets. You can even choose from various styles ranging from quarter-brogues to full brogues depending on your own aesthetic. You can easily pair these with a casual suit, or dress them down.

4. Formal Dress Shoes

Here we have it the classic black Oxford shoe. This is THE shoe you want to have if you wear suits often, if you work in the corporate sphere, or if you attend many formal events. If you want to push the bar a bit, you can opt for a cap toe, but don't venture far beyond that. Remember, the point is to keep it formal.

oxford derby shoe infographic

Know the difference between Oxford shoes and Derby's. Oxfords have a closed lacing system, making them sleeker and thus more formal than the Derby.

Do you know what else I love? Wholecuts. These shoes are made with a single piece of high-quality leather. While it makes them more expensive, it also ensures their quality and they can easily function as formal shoes shoes that make you stand out from the crowd.


When it comes to clothing essentials, accessories comprise the small but critical details in a wardrobe that make it stand out. Without them, you'll be as plain as bread and who wants that?

5. Glasses

Most guys don't consider this, but the right glasses can take your look to new heights. If you research your face shape, you can find some frames that work in conjunction with your head and really make for a cohesive appearance.

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On top of that, glasses convey intellect. Even if you wear contacts, consider slapping on those glasses when you want to show the world you know your sh*t. If you're giving a big presentation, I advise you to consider this. Don't forget to experiment with a wide range of colors and patterns on your frames.

6. Neckties

Is anyone surprised that I decided to incorporate neckties in here? You shouldn't be. Men's ties are a staple of the professional wardrobe. If you don't own one yet, what are you waiting for?

tie clip men

Don't hesitate to explore bolder patterns if you have the classics down already.

Say you already own a few solid-colored classics. Why not embrace some patterns and textures? A knit tie would work exceptionally well in casual settings while still lending an elegant edge. If you love your classic silk ties, then try some small repeating patterns. A red tie with accents of blue can match with ANY navy suit or sports jacket in your closet.

7. Headwear

The Flat Cap and Newsboy are not going out of style anytime soon. While Thomas Shelby and The Peaky Blinders certainly may have a hand in their renewed popularity, they've also been around for hundreds of years. With humble beginnings as a working man's hat, it's perfect if you're looking to transition away from baseball caps and snapbacks. Trust me, it'll work in the same contexts.

peaky blinders flat cap

If you need style inspiration for rocking the Newsboy, look no further than the Peaky Blinders. Click here to learn how to find your style icon.

If you're in South Florida, Texas, or the Philippines, then a woolen Newsboy may not appeal to you. Your best bet might actually be a classic Panama hat. Not only will it air out, but it'll protect your lovely head from the sun.


You don't want to run around in your underwear, right? You certainly don't want to default to the dreaded cargo shorts either. Here are a few trouser types which I consider to be clothing essentials for men.

8. Dark Denim

What's great about a well-fitted pair of jeans is that they can really slim up your profile. You don't necessarily need a navy pair, though that is the most common. Whatever you do, just make sure the colors are dark and bold. That way, they'll blend with a simple t-shirt or a sports jacket.

jeans mens summer style mistakes

Jeans that fit well should be a foundation piece of any man's closet.

9. Performance Pants

These have surprisingly become more popular in recent years, and I'm happy to bring them in as clothing essentials.

Performance trousers are as versatile as they are comfortable.

They are my go-to pants for the summer and are great for those of you in hotter climates looking to upgrade. You can wear them with a sports jacket of course, but you can also dress them down a bit.

10. Flannel Trousers

No, not wool flannel but cotton flannel. This style is far more lightweight and it's even less expensive than full-on wool. The napped surface adds a bit of texture, which can liven up the outfit.

Use flannel to add a bit of texture to your outfit without raising any eyebrows.

When it comes to flannel, gray is going to be infinitely adaptable, but don't be afraid to try out some browns and tans as well.

What To Wear On Top

From T-shirts to suits, I'm bringing you clothing essentials to make sure you bring your a-game.

11. T-Shirts

The key with plain t-shirts is fit. Unfortunately, no amount of tailoring can help you if you don't have the body to look good in one of these. However, if you're slim with a bit of muscle, then go for it! Personally I would opt for a v-neck. Why? Because they draw attention to the upper part of the chest.

plain t shirt white

Integrating solid t-shirts can be a subtle tactic to improve your style. Click here to learn about other seamless style secrets.

White is classic of course, but there's always gray, navy, black, etc.

12. The Henley

Henley's work on a similar level to T-shirts. However, they do accentuate a bit of effort being put into the outfit. The buttons also bring in a bit of a dressier aesthetic.

The Henley may be casual, but it also shows you put thought into your look.

I recommend long-sleeved henleys for all men. Whether you're slim or a little bigger around the waist, long sleeves work to bring out your forearms and thus introduce some masculinity to the ensemble.

13. Classic Polos

Polos date back to the late 1800s, when British colonial officers took a liking to the Indian sport of the same name. They're great by themselves, but they can also be paired with a sports jacket for a classy and unique look.

young mens style polo

A polo paired with a sports jacket epitomizes the country club look.

That being said, please avoid cheap polos. It might sound obvious as to why they break and fade easily. Look for manufacturers that make them in bold, vibrant colors and that ensure quality in their products. It's worth paying a little more for longevity.

14. White Dress Shirt

As a core feature in the interchangeable wardrobe, the white dress shirt can go with virtually any outfit imaginable. You can pair them with jeans, with slacks, with any sports jacket and any suit. Even if you mastered the classic dress shirt, there's a lot you can do to improve.

Experiment with a shirt bearing a contrasting collar to bring a bit of accenting in. Another thing to try changing up is the weave Oxford shirts, for instance, are formal but add a bit of rugged texture. Instead of a pointed collar, try a spread!

white dress shirt

Need to learn how to wear the classics? Click here to learn a few tricks for rocking a dress shirt.

Tired of those boring old barrel cuffs? Your next purchase might include French Cuffs that overextend and fold back on each other, requiring cuff links to keep them in place. Most guys think their place is the Galla and nothing more, but they're wrong. You can easily integrate French Cuffs with casual looks, adding flair in the process.

15. Striped Dress Shirts

The stripe is timeless and hard to beat. It's also extremely easy to mix and match with various outfits. They come in a wide range of colors, but for starters, try a blue/white combo. This can include blue on white or vice versa. Have at it, gentlemen.

dress shirt rack

You will never have to worry about variety when it comes to striped shirts.

16. Casual Button Downs

The obvious material to start with here is flannel, which exploded into fashion during the 90s. While great for the cold, they require a proper fit to nail the look.

dress shirt

Button downs are exceptional tools for showing that you give a damn without going overboard.

Another option is denim yes, you can find denim shirts in a plethora of densities. More extreme examples come with a snapping button and a more rugged weave. It's not my style, but if you love the western aesthetic, then go for it.

17. The Hoodie

This one's a bit overworn by guys, but I still think it can be pulled off in the most casual of settings. Don't fall into the trap of wearing it every day it happens for too many men out there.

18. V-Neck Sweater

This is an undisputed classic and its versatility is unrivaled. You can easily throw this over ANY shirt be it a t-shirt or a dress shirt. In addition, it looks fantastic beneath a sports jacket for an added air of sophistication. Wear this combo in conjunction with glasses for a scholarly look.

navy cashmere sweater

Perfect by itself or over a dress shirt. The v-neck sweater just can't be beaten.

Essential Jackets

You knew this was coming what is a list of clothing essentials without the right jackets? No mans closet is complete without at least a few of these

19. Jean Jackets

These are actually lightweight and great for the summer don't let the denim look put you off. Consider this if you want something sleek and casual all in one.

jean jacket

Never underestimate the power of a simple jean jacket.

20. Fatigue Jackets

With a military heritage, this is perfect for those of you looking to cultivate a rebel's wardrobe. One thing to note are the double pockets over the chest which work to build up a man's chest. This is great if you're skinny or if you are looking to draw eyes away from your belly.

21. Leather

The sheer power and sex appeal exuded in a quality leather jacket can never be overstated. This is something you want to spend time investigating we're talking about what style fits you best, what color, what size, etc. It's even worth dishing out a few extra bucks to make sure you have nothing less than quality.

leather jacket Marlon Brando

With men like Marlon Brando making it their staple, it's no secret why leather jackets are hailed as universally badass.

Believe me, it's worth it. As far as clothing essentials go, you don't want to miss out on this.

22. Essential Sports Jackets

A Sports Jacket is made in the style of a suit jacket but is standalone. It can be paired with any number of combinations depending on your color choices. A blue wool jacket is a great place to start for maximum utility. However, you can always move into bolder territory with patterns and colors of all types.

sports jacket

The right sports jacket is useful with any combination of trousers and dress shirts.

With sports jackets, there's really no end in sight. As long as you know your fit, you can be as radical or safe as you want to be.

23. The Suit

Come on, were you surprised? A suit is absolutely necessary for EVERY man's closet. It doesn't matter if you're a CEO or a uniformed man. You need this for the major events in your life I'm talking about weddings, graduations, and that inevitable job interview.

custom suit fit

Let's put you on the right track click here to learn about the essential rules of buying a new suit.

Though we can't drive home the nuances of purchasing a suit in this article, I have plenty of content dedicated to the topic. You're in good hands, gentlemen.

Summary Clothing Essentials

  1. Sneakers
  2. Dress Boots
  3. Casual Dress Shoes
  4. Formal Dress Shoes
  5. Glasses
  6. Neckties
  7. Headwear
  8. Dark Denim
  9. Performance Pants
  10. Flannel Trousers
  11. T-shirts
  12. Henleys
  13. Classic Polos
  14. White Dress Shirts
  15. Striped Dress Shirts
  16. Casual Button Downs
  17. The Hoodie
  18. V-Neck Sweaters
  19. Jean Jackets
  20. Fatigue Jackets
  21. Leather
  22. Essential Sports Jackets
  23. The Suit

If you want to hit the new decade with a bang or you're just beginning your style journey, then you need to reinvent your wardrobe. Already a veteran of good looks? Then expand, expand, and expand. Good luck out there, gents.

This article was brought to you by the best online retailer for glasses. By cutting out the middle man, GlassesUSA offers prescription glasses at up to 70% off retail prices. They offer eyeglasses and sunglasses that range from in-house brands to designer brands like Ray-Ban and Armani.

You can't beat their prices. Starting at just $30 for frames and lenses, you have your choice of over 6,000 styles at an affordable price. Not convinced? They even offer free basic prescription lenses with every frame. Click here to check out

The post Start The New Year Right: 2020 Clothing ESSENTIALS For Men appeared first on Real Men Real Style.

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