How to Dress Well (12 Tips) – The Man’s Guide for Any Occasion





Last Updated: July 5, 2021

Imagine loose-fitting torsos, sagging jeans, and a pair of glasses that squeeze the sides of your temples as if they were trying to suffocate your skull. Often found in off-the-rack, fast-fashion cubby holes of terror, unkempt aesthetics seek to tempt you from every corner.

The reality is, many men are in this situation, where unfit clothing and a lack of grooming keep them from looking as polished as they can be. 

Don’t fear, our guide on how to dress well as a man is the secret sauce for your next glow up.

How to Dress Well

Get Clothes That Fit

It might sound simple, and yet it is an often forsaken piece of advice. Some men go for whatever is cheapest and quickest off the rack, but do yourself a favor and slow down.

If you need to go off the rack, look for items that fit nicely on your shoulders and waist. It is easy to alter the torso of a shirt or the sleeves of a pair of pants, but if you can’t get the critical points right, there is no hope.

Ditch the baggy shirts and loose-fitting jeans and get yourself something that fits to the natural shape of your body without sacrificing comfort.


Tailor Your Clothes

Your tailor has a purpose you might not know of, but I’ll let you in on the secret: they can alter the measurements of your clothes so that they fit nicer on your individual body. OOPS! Was that too much info?

But it’s true: they are there for your needs, always happy to oblige with new pant alterations, or even fix up that hole in your favourite jacket.

In any case, they are true, unsung heroes who can make you look your sharpest by tailoring your clothes to fit. So stop in from time to time and get measured; I guarantee they’ll help you look your best.


Express Your Personal Style

Incorporating your own sense of style into an outfit is never a bad idea. Not only does it help you stand apart, but it also helps boost your confidence.

Always be on the lookout for things that get you excited, and don’t be afraid to experiment. Did an intense new mint track jacket from Nike catch your eye? You get it and you get it right now.

However, if a piece is brighter or stands out a lot, try to keep the rest of your ensemble neutral.  A nice button up and a pair of tailored slacks with a track jacket is the kind of switch-up this world needs. And you can be the trendsetter to change their minds.


Develop Good Grooming Habits

Those snakeskin cowboy boots aren’t the only scaly, dusty piece of skin you need to take care of.

A regular grooming regimen of washing your face, getting some sun, and trimming the hairs on your head and face are absolutely necessary to maintaining a well-kempt look.

Prefer a scruffy beard and long, messy hair?

Fear not, even regular maintenance to these styles can keep them from growing out of control and make them easier to deal with. Not to mention, it also cuts down the amount of acne you may get.

And really don’t forget the sun. It isn’t about getting a tan, but absorbing enough vitamin D to keep a smile on your face and keep you looking well-rested and energized. 

Take your dog for a walk or try having your lunch break outside. The sun is a miracle, use it.


Buy Simple Underwear

This is a pretty easy concept to grasp, but we’re going to go through it anyway: underwear is not a good place to show off what you’re into.

No one looks good in Superman underwear. The only goal you’re achieving at that point is looking like a super dork.

Don’t opt for heavily branded underwear either. Literally no one is going to see your monogrammed Louis Vuitton boxers, and if they do, you either look sloppy, or are in a hot-n-heavy situation where underwear is not the focus.

Go for underwear instead that is comfortable, doesn’t ride up your backside, and gives your boys room to breathe. Comfort and fit is way more important than the look in this case.

You can find some great, comfortable underwear options online like these ones from Lululemon, or this adidas pack on Amazon


Invest In Accessories

Expensive watches, glaring sunglasses, and leather shoulder bags are staple accessories for a reason. 

They’re most often huge talking pieces, and elevate simple fits into the next level.

Always invest in high-quality pieces, especially your accessories. Having an expensive watch might not sound appealing, but it’s beauty and durability will pay off like nothing else.

You can even go simpler and opt for a pair of fun socks. They might not always be seen, but a man in a suit that sits down to reveal his flamingo socks is the definition of a fun time. 

This can even work in reverse, where wearing some matching and neutral accessories can really tame an outfit that is flamboyant. A black tie and shoulder bag make that patterned blazer into a uniform of profession.


Buy Some Classics

Leather jackets haven’t gone out of style for a reason; they’re always hot on anyone and never stop looking good.

Expressing your personal style is about embracing you, whereas flaunting classics is about embracing what works for most and helps achieve a sort of commonality.

Tailored suit blazers and bombers can give anyone a clean look and also add a sort of unseen professionalism to anyone. (If you’re unsure how to style a bomber jacket, check out our guide here). 

Certain clothes just make a person look distinguished and, if you really want to dress well, you shouldn’t shy away from that.

Classic pieces for men can include:

  • A leather jacket
  • Denim jacket
  • Structured blazer
  • A white dress shirt
  • Denim jeans
  • Plain white tee

Dress Appropriately For The Occasion

Wearing a suit to a night out with the boys? Probably not the most appropriate outfit. Wearing a sweater and some jeans to your sister’s wedding. Also probably not a good idea.

When it comes to how to dress well, knowing what you’re dressing for is just as important as the specific aesthetics you choose to wear. Content and context go hand in hand when it comes to dressing well.

Taking it slow is reiterated for a reason: it shows you care and makes you look good.

And dressing appropriately isn’t about conforming either, but offering some respect for organizers and others at the event, giving them a sense of belonging and of being listened to.


Stock Up On Basics

Being basic? It may sound like a bad thing, but this tip actually adds diversity to your loadout. An excess of camo gear can be cleaned up and make you look smart if paired with solid colors.

Basic black tees and navy pants aren’t showstoppers, sure, but they are necessary support for a wide range of outfits. They cannot be left out of the game unless you want the team to lose.

If your patterned raincoat is your quarterback, then a set of matching, plain black pants and shirt can offset the craze going on in one piece and offer a contrasting calm.

It provides the yin to the yang, a balance. That’s what basics are for: the ultimate balance in aesthetic power.


Invest In Your Shoes

There are tons of fast-fashion shoes out there, but what’s trendy now won’t last forever.

You’re most likely better off investing in some nice shoes that will be able to stick around for awhile. Look for high-quality, classic style shoes that are timeless, such as a nice pair of loafers and some classic sneakers

I’m not saying you can’t buy those funky pair of Nikes, I’m just saying you should also buy some more traditional shoes, too. 


Choose High-Quality Frames

If you wear glasses, the style of your frames can make or break a whole ensemble. That’s why it’s important to choose frames that will compliment any outfit, and make you look good while doing it.

Most of the time, more expensive frames dish out more style, and they’re usually better quality, too. The glasses you pick out might be your frames for the next few years, so take the time to pick a pair you really vibe with. 

Rectangle and round frames are always in style, so if you want a timeless look, opt for one of these shapes. If you’re not sure where to look, here’s a guide on where to buy the best prescription eyewear online.  


Wear Your Confidence

Our final tip on how to dress well is following your gut. Even though classic pieces and event-appropriate clothing can win you respect, wearing your personal style with confidence is sure to win you admiration. Once you have the basics down, don’t be afraid to break the rules every now and then by adding your own flair. 

A man wearing his style with confidence is one of the best ways to dress well without sticking to hard and fast rules. 


Final Fashion Reminders

  • Dressing appropriately for occasions isn’t about conformity, but respect.
  • Don’t be afraid to give your best suit a little of your own flair for your friend’s wedding.
  • Get your outfits tailored whenever you can, and get clothes that fit almost perfectly when you can’t.
  • Basics can offer a clean look when paired with flamboyant pieces.

UP NEXT: Ultimate Man’s Guide to Wearing a Bomber Jacket