Young Men’s Style Guide – 21 Essentials To Buy Before You’re 21

Fashion


Young men’s style is tough to get right.

You’re ready to stop dressing like your kid brother… but you’re not ready to dress like your dad.

You want to fit in with your peers… but you also want to get into a good school, get hired – and get ahead.

You want to be yourself. But you don’t want to embarrass yourself.

And you’re not exactly rolling in money for a new wardrobe.

What to do? Read on… here are the essentials you need.

1. The Necktie

What’s This?

Heads up – a ‘necktie’ means the long kind of tie (not a bow tie).

Why Wear It?

You can’t look truly smart without a necktie. Business and formal dress codes require them.

How To Wear It

Choose three or four, and include at least two conservative ones in dark colors with modest or no patterning.

man in dress shirt and tieman in dress shirt and tie

Learn a few different tie knots- click here to see how to tie a tie 18 different ways.

When To Wear It

Wear a tie for job interviews, work, graduation, and smart occasions. If you want to wear one casually, try a knit tie.

It’s safest to wear a patterned tie with a plain shirt and vice versa – otherwise you might clash.

2. A Suit

What’s This?

Essentially, a suit is a matching jacket and pants (sometimes with a matching vest too – a three-piece suit).

Why Wear It?

Don’t think a suit is irrelevant to young men’s style. You’ll need one at some point – don’t wait till you have to buy it in a hurry.

How To Wear It?

A simple single-breasted model in charcoal gray or navy blue is best. Get it adjusted to fit you – some department stores will do this for you or you can go to a tailor. Click here for more on how to buy a suit.

When To Wear It

For formal business occasions like job interviews, and formal social occasions like weddings.

3. Plain White Dress Shirt

shirt sleeve perfect fitshirt sleeve perfect fit

What’s This?

A dress shirt is a shirt meant for formal wear. They tend to be more conservatively styled and colored, with stiffer collars (so they look good with a tie).

Why Wear It?

Two words: job interviews. A white dress shirt is the most formal – it shows you know your stuff and have made an effort.

infographic mens shirt colorsinfographic mens shirt colors
The classic white dress shirt. Definitely a better predictor of interview success than a crystal ball.

How To Wear It

Go for a shirt with a spread or point collar (not a button-down collar – that’s too informal). For the full ‘serious business’ look, wear it with a suit, a white pocket square, a plain or lightly patterned dark tie, and black oxford shoes.

When To Wear It

For interviews and the most formal business settings.

4. Colored Dress Shirts

guy wearing colored dress shirtguy wearing colored dress shirt

What’s This?

Colored dress shirts range from the plainest, lightest, most office-appropriate blue to wild patterned party shirts.

Why Wear It?

Dress shirts are an essential part of all smart dress codes – but they’re also versatile enough to pair with jeans.

How To Wear It

Stick to plain blues and whites or very low-key patterns like herringbone at work. A fun print shirt will get attention at parties.

When To Wear It

For work and social occasions.

5. An OCBD

What’s This?

An ‘OCBD’ or ‘Oxford’ is short for ‘Oxford Cloth Button Down’ – the classic casual shirt. ‘Oxford cloth’ is a type of cotton that’s woven with white threads in one direction and often a color in the other. ‘Button down’ refers to a collar that’s buttoned down to your shirt so it won’t flap around without a tie.

Why Wear It?

It goes with just about everything and is a men’s style icon.

How To Wear It

A blue or white OCBD is the most versatile option, but don’t be afraid of pink – it’s a preppy classic. These shirts are designed for going tieless, but you can pull off a knit tie.

When To Wear It

An OCBD can be everyday wear, especially when you’re on your best behavior (dates, church, meeting your girlfriend’s parents) but NOT office or interview wear.

6. Black Balmoral Oxfords

plan black oxford shoesplan black oxford shoes

What’s This?

Nothing to do with shirts! A Balmoral Oxford is an Oxford shoe (the smartest style of dress shoe) with a toe cap (an additional piece of leather stitched over the toe) and no other seams.

Why Wear It?

It’s the classic business shoe. You’ll need these for almost any outfit that falls above business casual on the formality scale.

How To Wear It

Learn how to shine your shoes!

When To Wear It

Wearing a suit or slacks and a blazer? Wear dress shoes – no exceptions.

7. Stylish Men’s Work Boots

combat work bootscombat work boots

What’s This?

Men’s leather boots can be divided into work boots and dress boots (which can be worn with a suit). Casual boots usually have more room in the toe box, are made of thicker and less shiny leather, and the soles usually have lugs (rubber bumps for traction).

Why Wear It?

Boots are masculine, practical, and make you look taller (no flash of sock to break up the line of your legs). Dress boots might be a little ‘old’ for you – work boots are a more casual alternative.

How To Wear It

Work boots look great with jeans and a casual shirt.

When To Wear It

Casual wear – you can go for a walk in them.

8. Belt Or Suspenders (Braces)

What’s This?

Suspenders (braces in the UK) are an alternative to a belt – elastic or leather straps that clip to your pants and hang over your shoulders.

man wearing belt and suspendersman wearing belt and suspenders
Warning! You can wear either belt OR suspenders. Wearing them together is a bad idea.

Historically they were meant to be hidden under your jacket – now some men like to show them.

Why Wear It?

Belts and suspenders are not just functional, they’re accessories – a belt especially can make or break your outfit (it’s right in the middle there).

Pants with belt loops look naked without a belt.

Suspenders don’t draw attention to your waist or break up the line of your body, so you look taller and slimmer.

How To Wear It

You want a smart leather belt, a casual leather belt you can wear with jeans, and a braided elastic belt for summer (cooler than leather). Formal belts are made from shiny black or brown leather with a simple buckle and are plain and undecorated. Casual belts are made from more rugged matte leather or other fabrics, with a wide range of colors and decorations.

When To Wear It

Wear a belt any time you wear pants with belt loops. If there are no belt loops you have the option of suspenders. You can get a tailor to remove (or add) belt loops.

9. Smart Denim Jeans

man wearing jeans and sports jacketman wearing jeans and sports jacket

What’s This?

Smart jeans are a dark color, well-fitted, and don’t have any rips or wear and tear (real or fake).

Why Wear It?

Moving up from boys’ style to young men’s style means upgrading your jeans.

How To Wear It

Choose the best jeans for your body type. Slim fit will suit most young guys. If you want, you can dress smart jeans up with a collared shirt, jacket, and dress shoes or nice sneakers.

When To Wear It

Any casual occasion – not to work or job interviews.

10. Leather Dress Gloves

What’s This?

“Dress” gloves are gloves you can wear with a suit, generally made from dark-colored leather.

Why Wear It?

Leather is both the smartest glove fabric and the most rugged and sexy – remember James Bond in Spectre?

leather glovesleather gloves
Leather gloves… you won’t get the same effect with woolly mittens.

How To Wear It

Get a pair of black, close-fitting dress gloves, and ideally a more casual pair in a different color – brown is typical, but to set yourself apart get navy or burgundy.

When To Wear It

Any time it’s cold, with smart or casual outfits.

11. Boxer Briefs

What’s This?

Boxer briefs are a type of underwear that’s in between boxer shorts and briefs.

Boxer shorts are loose shorts, briefs are ‘tighty whities’, and boxer briefs are close-fitting shorts that give you a happy medium.

Why Wear It?

Boxer briefs suit every body type. Tighty whities make you look like your mom still buys your underwear. You also need an awesome body to pull them off. Boxer shorts won’t flatter you either – the extra fabric will give you chicken legs if you’re skinny and a big butt if you’re heavier.

boxer briefsboxer briefs
A 2016 underwear survey by GQ found 65.6% of women preferred boxer briefs. Only 5% preferred briefs!

How To Wear It

Get pure cotton – synthetics can trap stinky sweat down there and cause chafing.

When To Wear It

Hopefully every day!

12. Cotton or Merino Wool Dress Socks

What’s This?

Dress socks are socks that you can wear with a suit, smart pants, or dress shoes. They’re thinner and smoother than most casual socks.

Why Wear It?

Wearing casual socks with a smart outfit is a huge rookie mistake.

How To Wear It

Don’t be afraid to wear bold and fun dress socks.

When you need to look extra serious, such as for an interview or new job, wear plain dress socks that match your pants (this also makes your legs look longer).

When To Wear It

Any time you’re wearing dress shoes and/or smart pants – but you can also wear them casually with jeans and sneakers.

13. Sports Jacket Or Blazer

What’s This?

The difference between a suit jacket, blazer, and sports jacket is simple: if it comes with matching pants, it’s a suit jacket. Blazers are one step down in formality – most common and versatile is a 2-button single-breasted navy blazer. Sports jackets are the most casual. They fit looser and come in rugged fabrics like herringbone, tweed, and corduroy, and almost any color and pattern.

Why Wear It?

It gives you a masculine ‘v’ silhouette, looks sharp, and can go from formal to casual.

How To Wear It

Ideally, you want a navy blazer and a sports jacket in a light neutral. Or for the best of both worlds try a knit blazer. It’s a more casual blazer, great for young men’s style – you can wear it with a t-shirt and jeans or dress it up.

man wearing blazerman wearing blazer

Make sure your pants are a different color from your jacket or it’ll look like you tried to fake a suit.

When To Wear It

Any time you want to look sharp but don’t have to wear a suit.

14. High Quality Winter Scarf

What’s This?

A knit scarf that’s long, wide, and thick enough to actually keep you warm.

Why Wear It?

Scarves are masculine – originally worn by flying aces to protect them from the cold in open cockpits, they’re associated with daring and adventure.

How To Wear It

Go for real wool in a neutral color for warmth and versatility. As with sweaters – if it’s a relatively thin and smooth knit it’ll work for smart or casual wear.

Click here to learn how to tie a scarf ten different ways.

When To Wear It

Any time it’s cold.

15. 100% Merino Wool Polo Shirt

What’s This?

A casual cotton knit shirt with a collar and several buttons at the neck.

Why Wear It?

It’s another versatile classic – you can upgrade your t-shirt to a short sleeve polo, wear a long sleeve polo as a sweater, or treat it like a shirt and throw a jacket over it.

polo shirtpolo shirt

How To Wear It

Pair it with jeans, khakis, or chinos – jacket optional.

When To Wear It

Any casual occasion. A polo with a sports jacket and jeans is a great first date outfit.

16. Wool or Cashmere Sweater

What’s This?

A good quality sweater is made of natural fibers like wool, cashmere, and cotton, and is well-fitted, not baggy.

Why Wear It?

It’s warm, tactile, and makes girls want to cuddle up to you. Plus it’s great for layering – even with smart outfits like this:

How To Wear It

V-necks look great with a collared shirt, but round necks are more versatile. Choose chunky textured sweaters for winter casual wear, and thin sweaters for smarter wear.

When To Wear It

Just about any time – you can even wear one to most offices with a sports jacket or blazer and dress shirt.

17. Peacoat (or Pea Coat)

What’s This?

A classic coat originally worn by sailors. The Peacoat is almost always dark navy or black and double-breasted with wide lapels.

man wearing pea coatman wearing pea coat

Why Wear It?

The naval heritage gives it a masculine vibe, and it looks MUCH more stylish than a windbreaker or hoodie!

How To Wear It

It goes great with jeans or smart casual wear, or with a suit in a pinch.

When To Wear It

Any time it’s cold outside.

Click here to see my Men’s Winter Jacket Infographic – the ultimate visual style guide for cold weather coats.

18. Leather Or Denim Jacket

What’s This?

Two of the most casual jackets in young men’s style.

Why Wear It?

These rugged classics build up your shoulders and give you a masculine silhouette. Plus leather jackets look sexy and badass.

man wearing leather jacketman wearing leather jacket

How To Wear It

You CAN wear a denim jacket with jeans – it just has to be a different color.

Get the best leather jacket you can afford. If the best you can afford is ultra-cheap, skip it – it’ll fall apart really fast.

When To Wear It

Leather when you want to look like a bad boy, denim when you want to look like a nice boy (but still ultra casual).

19. Cotton or Silk Pocket Square

What’s this?

A pocket square is the handkerchief in the breast pocket of a man’s jacket. It’s decorative – not for blowing your nose.

Why Wear It?

A pocket square matters in young men’s style because it shows you know how to dress – it’s also a good way to smarten up an outfit when a tie would be TOO smart. You can really express yourself with different pocket square colors, patterns, and folds.

man wearing pocket squareman wearing pocket square

How To Wear It

Learn how to fold a pocket square in a few different ways (the square fold is easiest to start with, and also the most formal.)

When To Wear It

Any time you wear a smart jacket (even if a tie would be too formal). For the smartest occasions, stick to plain white and a square fold.

20. Stylish Sunglasses

What’s This?

Sunglasses that you’ve dropped a few bucks on.

Why Wear It?

They just look cool – and the right sunglasses have a MASSIVE effect on your attractiveness, as well as making your whole outfit look better.

man in sunglassesman in sunglasses

How To Wear It

Get the right frames for your face shape. Aviators and wayfarers suit almost everyone.

When To Wear It

Only OUTDOORS when it’s SUNNY. Don’t be that guy.

21: A Classic Analog Watch

What’s This?

Analog is the opposite of digital – it’s a watch with hands.

wrist watchwrist watch

Why Wear It?

Sure, you’ve got the time on your phone, but young men’s style should include a watch. It makes your outfit look complete – and checking the time on your watch looks much more stylish than fumbling in your pocket.

How To Wear It

For your first watch, pick something that goes with everything. Most versatile is a plain dress watch on a leather band.

When To Wear It

Any time, but know how to match a watch to different dress codes.

Another essential a lot of young men neglect? Wearing clothes that fit. John Henric has you covered here – before launching, they talked to over 800 men about their bodies and did solid research on what they were missing in fit before launching their popular men’s sweaters and shirts. 

Read next: how a man in his 30s should dress sharp.

Worst Lies Society Feeds Young Men





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