You know, I would love to tell you that back when I was a high school kid, my fashion sense sucked.

But that wouldn’t be true. The truth is, I simply had no fashion sense. In the morning, when I decided what clothes to wear, I ran through the following checklist:



Are they clothes?

If the answer was yes, I put them on. I would wear that huge yellow t-shirt that was really comfy and made me look like I had woken up in a collapsed tent and never bothered to climb out of it. My hair was all over the place, and when I first grew facial hair, it was a fluffy mustache that I left untouched for months and months.

While all the other kids figured out how to style themselves, I oscillated between looking horrible and looking awful.

It took me years to get better. But when I did, I worked really hard to catch up on all the fashion, grooming and accessorizing I had missed. Today, I understand how to dress well, style myself and pick the right accessories to radiate class and personality.

And I’m happy to share what I learned with you!

Dressing with Personality.

First of all, I believe there’s a difference between just dressing well, and dressing with personality.

You see, I went through a lot of phases where I thought some fashion choices – black clothes, hats, a Freddy Krueger necklace, really big clothes, Huey Lewis and the News pins to name a few – were going to give me an edge, a special kind of character. Well, yeah, they did. It was the creepy-nerdy kind that screamed at girls, “avoid me at all costs!”

But that said, go into the business district of your city and look at all the suits and ties walking around. Does it feel like The Matrix? That’s because those business guys all look the same. I mean, yeah, there may be colour variations, and don’t get me wrong: even a black suit, white shirt and black tie do make you look very good.

But do they, alone, make you unique? No, they make you blend into a bank headquarters.

You and I want to dress to look both appealing and interesting. So let’s have a little crash course, shall we?

First, how to pick the right clothes to look appealing.

Then, how to pick the right style and accessories to look interesting.

Clothing Fundamentals.

Okay, fundamental rule number one:

You don’t have to be rich to look nice.

Why not try this:

Go to a fancy store, have the sales guy dress you up the sharpest possible (they know what they’re doing!), take notes. Then, go to H&M and buy the stuff you were shown for a fraction of the price.

Take an hour or two every other Saturday to sift through your town’s second hand stores. Buy clothes that fit your body type for peanuts. Then, take them to a tailor and have them fitted specifically to you.

The first is good if you want to quickly assemble one single great outfit on a budget. The second is if you want to build and expand your wardrobe over time.

Fundamental rule number two: I already mentioned it above…

Your clothes need to fit.

No, seriously. Are you wearing a beautiful button-down shirt and it’s three sizes too tall, hanging loosely over your body and/or bulging over the edge of your pants?

If so, please consider watching “Crazy, Stupid Love” and then come back. Go ahead, I’ll wait.

Tailors. Make friends with them. You won’t always find perfectly fitted clothes (glad if you do), but what you save on the price tag of a beautiful second-hand dinner jacket is well-spent on a tailor that makes it look really badass on you.

Okay, now we have this out of the way, it’s time for fundamental rule number three:

Your colors should match.

Are you wearing stinging red trousers and a sky-blue t-shirt? Aye. We have work to do!

You see, it’s not that you can’t combine blue and red. But please, for goodness’ sake, use tones that indicate some kind of coherence. I’d say, make them muted: a desaturated port wine kind of red for your trousers and jacket can work well with a dry, Greek-midsummer-sky-right-after-sunset kind of blue on your fitted v-neck sweater.

Think elegantly-rugged vintage. Avoid shrill, screamy colors. You’re not a traffic light.

Also, please only ever combine two tones. Plus, it’s always safe to make one of them black or white. Black trousers, black dinner jacket, pink finely striped shirt? Works!

On to…

Clothing Items.

Jackets. Are you a trench coat or leather jacket type of person?

Are you a trench coat or leather jacket type of person? Dinner Jackets. Walk into a Salvation Army or any other thrift store any time of the day and see how many elegant jackets are available! When I bought my first own dinner jacket, it was a plain, beautiful black one for about 10 bucks. Plus 15 bucks for the tailor to take in the sides a bit. And all it took me was to walk into the store, grab the jacket and go. They’re incredibly common and incredibly affordable.

Walk into a Salvation Army or any other thrift store any time of the day and see how many elegant jackets are available! When I bought my first own dinner jacket, it was a plain, beautiful black one for about 10 bucks. Plus 15 bucks for the tailor to take in the sides a bit. And all it took me was to walk into the store, grab the jacket and go. They’re incredibly common and incredibly affordable. Shirts. Button-down shirts or v-neck t-shirts. I wear most of my button-down shirts tucked into my trousers, but some work well over them. Mix and match, see what makes you happy.

Button-down shirts or v-neck t-shirts. I wear most of my button-down shirts tucked into my trousers, but some work well over them. Mix and match, see what makes you happy. Ties. Always a good idea. I think you can break the two-color rule here if you know what you’re doing: for instance, the black-and-pink combo I mentioned above may well work with a white tie. Otherwise, I really like shades of the same colours: a red satin-type tie can look amazing on a red shirt if the hues differ just a bit.

Always a good idea. I think you can break the two-color rule here if you know what you’re doing: for instance, the black-and-pink combo I mentioned above may well work with a white tie. Otherwise, I really like shades of the same colours: a red satin-type tie can look amazing on a red shirt if the hues differ just a bit. Trousers: pick the kind that makes your ass look sexy. Fitted, remember? Make them long enough to cover your shoes, but not so long that you walk on them. When you sit down and cross your legs, do they still reach your shoes? Yes? Good, you’re golden. Style: I recommend three trousers to begin with: one brown tone (these work nicely with those buttoned pockets attached on the legs), one black, one dark blue jeans with some features (stone-washed). Remember: plain blue jeans are, well, plain. Do get jeans, but make sure they have character.

pick the kind that makes your ass look sexy. Fitted, remember? Make them long enough to cover your shoes, but not so long that you walk on them. When you sit down and cross your legs, do they still reach your shoes? Yes? Good, you’re golden. Style: I recommend three trousers to begin with: one brown tone (these work nicely with those buttoned pockets attached on the legs), one black, one dark blue jeans with some features (stone-washed). Remember: plain blue jeans are, well, plain. Do get jeans, but make sure they have character. Shoes: you may be surprised how important those are. People (especially women) do notice your shoes. Do they fit into your overall color theme? Safe bet for starters: get a pair in dark brown or black, leather or leather-like substances, no laces. Think sleek, elegant, classy, shiny.

you may be surprised how important those are. People (especially women) do notice your shoes. Do they fit into your overall color theme? Safe bet for starters: get a pair in dark brown or black, leather or leather-like substances, no laces. Think sleek, elegant, classy, shiny. Socks: Please, please match the colors of your shoes and trousers. White socks peeking out between black shoes and trousers suck.

Please, please match the colors of your shoes and trousers. White socks peeking out between black shoes and trousers suck. Underwear: wear underwear.

Now, all these are basics. Ultimately, you want to go for an overall look and it needs to be your personal one. There’s only so much I can tell you here without knowing you, but let me suggest some overall styles you may want to adopt:

Classy, sophisticated (James Bond)

Athletic

Rocker dude

Casually elegant (Doctor Who)

Adventurer (Indiana Jones)

So now we have the clothing down.

But…

Remember when I said clothes aren’t the whole deal, and there’s more you can do to truly bring out your personality? Well, here’s the trick:

Accessories.

See, here’s where you can really set yourself apart. Think of accessories as your “decoration”. Ideas:

Hats. Are you a sportive guy? Nothing wrong with wearing a baseball cap. Other nice options are the Jason Mraz hat (thin brim, summery – google it), or a classy fedora. Or a French cap.

Are you a sportive guy? Nothing wrong with wearing a baseball cap. Other nice options are the Jason Mraz hat (thin brim, summery – google it), or a classy fedora. Or a French cap. Glasses: if you’re wearing glasses, check out what styles are available. What works for you? Sportive aerodynamics, narrow elegance? Same goes for sunglasses: nothing wrong with investing some extra dough to get really nice ones. I like the ones Brad Pitt wears in “Fight Club,” and then there’s always the Morpheus glasses from The Matrix. Inspired yet?

if you’re wearing glasses, check out what styles are available. What works for you? Sportive aerodynamics, narrow elegance? Same goes for sunglasses: nothing wrong with investing some extra dough to get really nice ones. I like the ones Brad Pitt wears in “Fight Club,” and then there’s always the Morpheus glasses from The Matrix. Inspired yet? Vests: a great way to add character and layers to your clothing outfit.

a great way to add character and layers to your clothing outfit. Pocket squares: what you put into the front breast pocket of your dinner jacket. If square, they peek out the top as a thin line adding contrast and character. But they don’t have to be square… You can fold them into all kinds of shapes and e.g. have them protrude from your pocket like a flower.

what you put into the front breast pocket of your dinner jacket. If square, they peek out the top as a thin line adding contrast and character. But they don’t have to be square… You can fold them into all kinds of shapes and e.g. have them protrude from your pocket like a flower. Bandana. Consider it.

Consider it. Jewellery: rings, necklaces. The latter don’t have to be silver or gold (actually, I advise against gold: it’s pimpy). They can be leather or wood, with or without pendant. Surfer pendants are cool, but then be a surfer (or very sporty). Rings: wear one or two that you find cool. Silver or stainless steel. They’re not expensive and you will find them sold at outdoor festivals, markets, or by street merchants.

rings, necklaces. The latter don’t have to be silver or gold (actually, I advise against gold: it’s pimpy). They can be leather or wood, with or without pendant. Surfer pendants are cool, but then be a surfer (or very sporty). Rings: wear one or two that you find cool. Silver or stainless steel. They’re not expensive and you will find them sold at outdoor festivals, markets, or by street merchants. Wristbands/bracelets: again, they could be silver or gold, but I think leather works better.

again, they could be silver or gold, but I think leather works better. Piercings, earrings: yup, if they float your boat.

yup, if they float your boat. Tattoos: if you get one, make it personal. Have a story or philosophy attached to it. No barcodes or random tribals… You’ll wear that stuff for the rest of your life, so make it about the essence of your character, values, convictions.

Needless to say, you don’t have to (actually, really shouldn’t) add all of the above to your style. But consider which work for you as an individual!

Grooming and Styling.

The last thing I’d quickly like to talk about is your grooming. The question here is, how are you designing your body itself? While girls can paint their fingernails or wear make-up, you, as a guy, you have some really simple and cool options, too.

Hairstyle. Obvious, right? When I was young, I used to think of hair as something that needs to be cut now and again. Only later did I realize that not only is there a lot you can do to give your hair a certain look, but also, your hair has a very individual type that lends itself to very individual styling. I quite recommend seeking out a very professional hairdresser and asking them what’s best to do with the hair you have. Find one by asking really good-looking guys who they’re frequenting. Some hairdressers are real artists, shaving your hair short and then drawing tribals into it. You’ve seen it, right? Looks awesome. Whatever works for you and your daily environment, though. One general pointer: care for your hair. Don’t hesitate to use conditioner, nutritious sprays. Apply styling products (gel, wax) to shape it. People notice the difference when you care for your hair.

Obvious, right? When I was young, I used to think of hair as something that needs to be cut now and again. Only later did I realize that not only is there a lot you can do to give your hair a certain look, but also, your hair has a very individual type that lends itself to very individual styling. I quite recommend seeking out a very professional hairdresser and asking them what’s best to do with the hair you have. Find one by asking really good-looking guys who they’re frequenting. Some hairdressers are real artists, shaving your hair short and then drawing tribals into it. You’ve seen it, right? Looks awesome. Whatever works for you and your daily environment, though. One general pointer: care for your hair. Don’t hesitate to use conditioner, nutritious sprays. Apply styling products (gel, wax) to shape it. People notice the difference when you care for your hair. Nose and ear hair. Keep it short. Also, trim your eyebrows.

Keep it short. Also, trim your eyebrows. Fingernails. Clip them. There are places on a woman’s body you want to touch without ripping them open with your long, unkempt fingernails.

Clip them. There are places on a woman’s body you want to touch without ripping them open with your long, unkempt fingernails. Beard: there are more things you can do with a beard than shave it off completely or let it grow uncontrolled. Chin beard, goatee, ‘stache, sideburns… Be a designer, an artist! Check out the Seneca Crane character from “The Hunger Games” or Tony Stark from “Iron Man” for some extremely cool examples.

Smell.

I know this doesn’t really belong into the “looks” category, but I really want to point this out before I leave you for today.

Dude, the way you smell is incredibly, incredibly important. Bad breath and sweat are deal breakers for anybody coming close to you.

Mouthwash. Toothbrushes. Chewing gum. Deodorant. Shampoo. After shave. Eau de toilette. Keep them close. I mean it. There’s no excuse for smelling bad.

All right, here we are! With the knowledge from above, you can go out right now and browse your town’s boutiques. Speak to the sales people, tell them a bit about who you are and what you’re into. See what they come up with for each of the items I described to you.

From now on, I recommend you start watching people: in the streets, supermarkets, at work, in movies and TV shows, in advertisement: how are they dressed? How are they groomed? What items are they wearing, how do they fit together, what stories do they tell?

What are your clothing choices? What would you add or do differently? Let us know in the comments!