10 Basic Rules of Dressing Up For Young Men


Want to dress well but don’t know where to start? Here’s some step-by-step advice for guys on how to dress for success without being too flashy or blasé.

Boys, there’s a secret to living a fulfilled life that I don’t think many adults ever get around to teaching you because very few of them understand it themselves. The basic idea is that if you want some peace of mind in your life you’ve got to stay grounded in something consistent. For most people this is their values, although most people who aren’t religious don’t take the time to reflect on what these are. Without this, they end up bouncing around like a pinball, falling in line with whatever seems cool with the people who are currently agreed upon as the popular ones. This is a monumental waste of energy and a surefire path to anxiety and at least mild depression. Trust me; this pretty much sums up the decades of my teens and twenties.

Why Dress Nicely?

Being grounded in something consistent is just as important in how you dress. In this case it’s not values that will ground you but aspects of men’s fashion that will never look bad. I know as teenagers you guys are constantly looking around to figure out what’s “cool” at the moment, or alternately, trying to do exactly the opposite to make some kind of brash statement. Either path is wasting mental and emotional energy because your sense of self-worth is dependent on others’ opinions of you, which are out of your control and prone to tons of fluctuation day-to-day. You’re either trying to get acceptance by going along with the crowd or trying to get attention for being boldly “different.”

Consistently classy yet under-stated (meaning “effective yet hard to notice right away”) clothing choices will always win out in the long run over the latest popular craze at school, like bright-colored soccer socks with khaki shorts and a blazer, something I saw at a boys’ school recently. The only reason that look isn’t completely dumb is because a small number of popular kids started it. Things like that never last. Stick with the basics and you’ll never go wrong.

Why dress nicely, though? Seriously, what will you get out of it? First off, you’ll start noticing the adults in your life treating you differently. They’ll give you their trust in small doses as a result, rewarding you for taking the time and energy to attend to the details. And it definitely doesn’t hurt in the romantic relationship department. I don’t care if you’re into girls or boys or both, if you look like a slob or a Johnny Same-As-The-Other-Guys, you’re communicating that either you can’t take care of yourself or that you’re a mindless sheep, two things that are almost always strikes against you in the world of dating.

How to Get Started

Two important things before we begin: One, in case you haven’t been told this yet, males have a much higher chance of being partially or fully colorblind from birth, so this may make things difficult for some of you. Being colorblind means you see colors differently than most people and sometimes have a hard time distinguishing between certain ones, like red and green. This makes it hard to know if you look bad.

If you’re not sure you’re colorblind, go online and take a simple test that’ll take less than three minutes. If you are, then you’re just going to have to find a trusted advisor in an older sibling or friend, preferably a female with at least a basic amount of social status. Whether or not they’re culturally conditioned or biologically predisposed to this skill, women and girls in these social circles are often very good at eyeing winning color combinations.

Last thing: I’m well aware that one of the major downsides of having a penis is that we’re constantly being assessed by other people with a penis for whether or not we’re gay. It’s weird and exhausting and pointless, and I bet some of you are worried that what I’m about to say is going to bring your masculinity into question.

If so, don’t worry. Take a close look at the celebrities I mention at the end of the article. Even if these men are gay or come out later, they’re some of the manliest dudes you’ll come across. Being gay and being manly are different things. You can be both. Always remember this.

The 10 Basic Rules

All right, I’m going to let you take care of the casual-wear decisions for now but nail these basics of dressing up as soon as possible in order to expand your autonomy with adults and start getting noticed by the right people. Here we go:

1. Never, ever wear pleated pants. I truly have no idea why these even still exist. I don’t care if you saw American Psycho and think Christian Bale looked cool in them or if you recently read some blog post that “pleated pants are back!” They look profoundly ugly and make a man’s crotch look unnecessarily weird. Always go with “flat-front” khakis or suit pants.

2. Always wear a belt. Your waistband just looks weird with belt loops doing nothing. The only exception would be if you’re going to try to pull off suspenders, but that’s a pretty advanced choice. Keep it simple for now.

3. Exactly match your colors in two places: Belt & shoes, socks & pants. The idea here is that it actually looks worse to have two colors that are of slightly different shades in your outfit than two very different ones. Eventually you can try taking some risks and wearing funky socks or matching a minor color of your belt with your shoes but start with this for now. I cringe every time I see a dude wearing a light brown belt with dark brown shoes or light tan khakis with slightly darker tan socks. Don’t be that guy.

This is such an easy rule to follow that it’s harder not to do it than to just get it done. Squint your eyes if you can’t tell right away. Open the shades in your room during the day and hold them up to natural light to double-check. Take the time to get this right.

To be crystal clear, I’m not saying to make all four of these things the same color. I’m saying match your shoes and your belt exactly then match your socks and pants exactly.

4. Save up for quality dress shoes. They say the shoes make the man and I totally agree, most especially with dress shoes. Saving up probably won’t be easy for those of you who have to work an after-school job to buy your own clothes like I had to, but I don’t think you’re going to find the right level of durability, quality and style unless you drop at least $200.

Nordstrom Rack and Designer Shoe Warehouse are great stores to look for significantly reduced, awesome-looking dress shoes, so start there if you want to save sometimes up to 100 bucks.

Your first purchase should be dark brown wingtips:


By ASuitableWardrobe (Own work) [CC-BY-3.0 (http://creativecommons.org/licenses/by/3.0)], via Wikimedia Commons

Next purchase should be black oxfords (below). Those two pairs of shoes will go with 90% of possible dressy outfits, from khakis to a suit.

Crockett & Jones men's dress shoes, type Dalton, black calf leather 01

By OlafJanssen (Own work) [CC-BY-SA-3.0 (http://creativecommons.org/licenses/by-sa/3.0)], via Wikimedia Commons

5. Speaking of dress shoes — rounded toe! Your dress shoes should not be square-toed nor should they look like what Aladdin might wear to a wedding, all curled up at the end and pointy. Find the middle ground between boxy and pointy and you’ll never go wrong. The two pairs above in Rule 4 are great examples of this balance.

On the other hand, here’s an example of terrible-looking, square-toed dress shoes with thick stitching:

Photo credit: Flickr / South Granville Live (http://www.flickr.com/photos/southgranvillelive/6098069354/)

Photo credit: Flickr / South Granville Live (http://www.flickr.com/photos/southgranvillelive/6098069354/)


And another:

Photo credit: Flickr / Dana Lookadoo - Yo! Yo! SEO (http://www.flickr.com/photos/pixelposition/5171308132/in/set-72157625352821808/)

Photo credit: Flickr /
Dana Lookadoo – Yo! Yo! SEO (http://www.flickr.com/photos/pixelposition/5171308132/in/set-72157625352821808/)

I don’t care if your dad wears shoes like this or if 80% of the men you see on the street wear them. They do not look good. They look average and safe. That’s not what we’re going for here.

6. Buy fitted dress shirts. Most dress shirts for men have always been made such that they fit the same at the armpits as at the waist, straight down. This usually leads to billowy, excess material that starts to poke out of men’s waistbands as their shirts ride up in the back and sides from moving around. It just makes guys look disheveled and dumpy.

Maybe you’re in middle school and you’ve yet to have that teenage growth spurt so you’ve got a bit of extra fat around the waist. I should know; I was shopping in the “Husky” section of K-Mart and J.C. Penney until I was in 7th grade. Fitted dress shirts that feel comfortable may be a bit tough to find for you boys, but keep trying. The main thing here is to avoid that unnecessary material overflowing over your belt when you put your hands over your head.

7. Wear skinny ties. Not ridiculously skinny ones you might find at Aldo or Urban Outfitters that are only an inch wide or less. Go for ones that are about two inches wide.

8. Stick with light-colored dress shirts. You should always avoid dark- or bold-colored dress shirts, at least while you’re learning the ropes. Ketchup red or royal blue or bright purple… Yuck-Town.

The sub-rule here is to make sure that the main “background” color of your tie is always darker than your shirt. Once again, squint your eyes as you hold the tie up to the shirt to double-check. Advanced fashion guys can get away with light-colored ties on dark shirts, but it’s hard to do without looking really bad.

9. Match a “secondary” color in your tie to your dress shirt. This is the simplest way to pretty much never go wrong with tie matching, which can get complicated. Let’s say your tie’s main background color is dark red but it has a light blue, diagonal stripe throughout. Find a shirt that’s the same color as that blue stripe, or at least “goes” with that color. Then make sure the main red color of the tie doesn’t visually clash with the color of the shirt.

10. Avoid black dress pants, unless as part of a full, black suit. So many men wear these with dress shirts that by looking around you’d think it’s fine to do this, but resist the urge. They’re just too dark to look good with most dress shirts, and in the most basic sense, they’re just such a common choice for men that you’d best avoid them in order to distinguish yourself a bit.

Light grey, dark grey and tan khaki are three pant colors that should be the first you buy. After that you can try to branch out into maybe navy blue, but beyond that you don’t need much.


There’s your basics, boys. Stick with these and you’re ahead of probably at least 80% of grown men, which is something to be proud of. As a way of illustrating a lot of the things I just mentioned, let’s take a look at my fashion evolution from 8th grade until my adult years. Hopefully this article will avoid you having to do what I did, slowly and painfully learning this stuff over the course of 15 years.

Here’s me at my middle school graduation:

Photo courtesy of the author

Notice the god-awful pleated khakis, bold blue dress shirt that’s way too big for me and three inch wide tie. That’s breaking three rules already. The only thing I kind of did okay was match my tie to my shirt, although the tie pattern is pretty horrible. (Forgive me, it was 1993.) Do you see how limiting that blue colored dress shirt is? It looks really bad with those khakis. And it would look bad with black khakis too, and even grey trousers. It’s just an inflexible choice.

And now here I am 16 years later, at age 29:


See the difference? My shirt fits properly and it’s a lighter shade of blue, so it’s not so jarring to look at. My tie is skinny but not too skinny and it’s not only a darker blue than my shirt but it’s minor “accent” color is the same shade as my shirt. My pants are flat-front and light grey. I’m not saying I’m perfect in the fashion department, but as my dad always says, “No brag, just fact.” I’m looking pretty above-average here, boys, and the ladies agreed that night too, if I remember correctly.

Once all these guidelines become second nature you can try to branch out and take some risks. The best way to do this is to watch at least a handful of episodes of Mad Men. (Ask a parent or guardian first if you’re in middle school. Some of the content might not be appropriate in their eyes).

If you haven’t heard of this show, I bet your parents have. It’s won more Emmy awards than I can count, and it’s an absolute goldmine for finding advanced, subtle color combinations. The first five seasons are available on Netflix Instant Download. Or you can borrow it for free from the local public library on DVD.

Pretty much anything the three main male characters wear at the office looks totally awesome (that’s Don Draper, Roger Sterling and Pete Campbell, in order of their importance on the show). Don’t worry at first about all the accessories they wear like tie bars and pocket squares folded like origami. Just keep an eye out for the colors of three things: their suit, their tie and their dress shirt. Start learning to see how these colors “flow” together visually, even though they may be very different. That’ll be the first step in branching out from the basics and really wowing people. I’d also take a good look at how their clothes fit. Snug, but not too much. Most men wear dress clothes that are way too big with too much extra material.

One important thing I’ll say about Mad Men, though: It’s generally for white dudes. This might pose a problem for those of you who are of other ethnicities, although I’d say that there’s a significant amount of their style that will look good on anyone, regardless of race or culture. But, if you’d like other options to explore, here are some other well-dressed icons you can look to in today’s culture to find some guidance.

If you’re African American, try first looking at Jamie Foxx, Nick Cannon, Barack Obama, and Idris Elba. If you’re of Asian descent, try Daniel Dae Kim, Harry Shum Jr. and Bruno Mars (even though technically Mars is American-Hawaiian). If you’re Latino, try Jay Hernandez, Adam Rodriguez or Edgar Ramirez. These are all men who don’t try to get too flashy and just consistently nail the basics I’ve outlined above. Regardless of who you take after, keep in mind to look for that “flow” between the colors of the suit, the tie and the shirt as well as the fit of their clothing.

Good luck, young gents. Dressing well is one of the most worthwhile pursuits a man can master. Start now and you’ll be on an upward trajectory that will keep you looking awesome the rest of your adult life.

Lead photo credit: Flickr / Sonia Belviso

The post 10 Basic Rules of Dressing Up For Young Men appeared first on The Good Men Project.

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