How to dress
Please note that this guide is my personal opinion. I did not want to create a guide for all men (that would be way too much work). I just wrote what I like to do and what I think is cool. If you disagree, don’t do it. And don’t get mad.
That said, I am interested in hearing feedback.
Keep an open mind The number one thing that holds back men from dressing better is that they have created an “identity” for themselves that prevents them from dressing better. For example, for a long time I thought that guys who wore gel in their hair and leather jackets are douchebags. I still do. But now I realize that those things look good. You have to keep an open mind if you want to dress well. You need to realize that the shit that was appropriate to wear when you were 15 is different than when you’re 20, which is different from when you’re 25, etc... You also need to realize that women and other people oftentimes have a radically different opinion of how you dress.
Keep a couple girlfriends around to tell how to dress Women love dressing up guys so ask your girlfriends to go out shopping with you. You may disagree with their recommendations, but unless they want you to wear something fucking ridiculous, they are probably right. Remember, you don’t have a pussy so you don’t know what makes it wet, so your opinion of what looks like good on a guy is probably not worth much.
You need to look clean and well put-together This is by far the most important thing. It doesn’t really matter what style you dress, as long as everything is clean, organized, and looks like you meant to look that way. Every hair on your head should know its place and look like you thought about it. Make sure your body hair is evenly trimmed and taken care of and there are no weird splotches of hair anywhere, like your neck. Even if you dress grungy or goth, you should look like a fashion designer planned you to look that way. If you give your hair the “messy” look, it should be a planned messy look. Women spend a ton of time on their appearance, and they are impressed when a man does the same.
You should feel good How you feel about what you’re wearing is more important than what people see. Your clothes need to make you feel more confident, not less. If you feel silly or uncomfortable wearing something, don’t.
Your clothes should fit It’s amazing how many guys wear clothes that don’t fit. You need to realize that women have weird bodies with weird curves so its hard to fit clothes that “fit” them, so they definitely notice when a guy doesn’t wear clothes that fit. Your clothes should look like they were designed for your body. They don’t have to be custom designed, but they can’t look like you got them at a homeless shelter and just needed to put something on your body.
You should stand out It’s amazing how many guys dress to look like every single other guy in the club. You may have heard of “peacocking,” where a guy wears a ridiculous outfit to stand out. This was made famous by Mystery. I personally don’t like peacocking because I don’t want to feel ridiculous, but I do think that you should try to stand out. How? Bright colors, interesting patterns, weird combinations, etc...
Classy, but hip Dressing well involves a tension between being classy and being hip. If you focus too much on being classy and not enough on being hip you will just look like a boring businessman or office manager. If you focus too much on being hip and ignore being classy you may end up looking trashy or tacky. If you want to know what hip without classy looks like, look up most rappers nowadays (i.e., Future or Migos). Ideally, when you show up to a party you will look “nicer” than everybody else in the sense of formality, but you will also look interesting and unique. If given the choice, however, you should lean towards classy.
Create your own look The best dressed men have their own unique style. Your style should be an expression of what you like and who you are. For example, I would describe my own style as a mixture of hip hop and surf culture, but fancied up so I still look good in a preppy setting. If that sounds weird, that’s the point. A guy with a unique style will stand out.
Have a style role model Most guys don’t know the first thing about fashion or where to start, so I would suggest that you get a style role model, which is basically a guy that dresses well that you wouldn’t mind looking like. My style role model is a guy named Rameet Chawla, who is the CEO of Fueled. You can search him on Google images to see what he looks like. I basically just copy a lot of his looks and buy a lot of the stuff he wears. If you want something a little more “street” look up Pharrell Williams.
Be aware of the stereotype you are emitting Like I’ve said in other articles, people think in stereotypes, and will judge you as such. If you dress “hip hop” you need to realize that a lot of women will immediately associate with you the hip hop world, and assume you’re into drugs, violence, thuggery, etc... On the other hand, some girls are into that. But just be aware of the stereotype you emit. If you don’t believe people think in terms of stereotypes, read this article about Jezebel thinks that America’s Olympic uniforms are “WASPy bullshit.” http://themuse.jezebel.com/usas-olympic-uniforms-are-waspy-bullshit-1773596823. Whether or not you agree with Jezebel, you have to admit that when you see those outfits you immediately think “WASPY.”
Go to the gym How many times do you have to fucking read this before you realize that YOU HAVE TO DO THIS! Just do it asshole!!
Pants To be safe, go with black or blue dress pants or some slim fit jeans. The “baggy” look doesn’t look good, nor do you want to wear skinny jeans so tight it looks like you are constricting your nuts. Khakis and corduruys are fine, but lean a little to the basic side. You don’t want to look like a basic bitch. Leather pants, camo, and any weird bright colors (like red or white) are making a strong statement, so be careful. Pants should generally come to your ankles, maybe a tiny bit lower, but not much lower.
Jackets A good jacket makes all the difference in the world. I think every guy needs an actual jacket that keeps him warm, and a cool looking peacoat. Here is a good looking regular coat: http://amzn.to/1WLet0p. Here is a fancy peacoat: http://amzn.to/26XbPth. Leather jackets work too if you want be a little more daring and stuff.
Shorts Shorts generally look childish or too casual, but if you want to wear them make sure they look good and the rest of your outfit is on point. You can pull shorts off, but you have to be a BO$$. Pharrell pulls shorts off well.
Blazer A nice blazer is a must. I recommend a blue or white or something with a nice pattern. You can wear the blazer with a cool t-shirt or a nice collared shirt. Here is a cheap 20 dollar blazer from Amazon: http://amzn.to/1YaTcw2.
Sweaters A good sweater separates the men from the boys. I don't need to tell you how to do this.
Collared shirts I generally like long-sleeve collared shirts with an interesting pattern, but not trashy or hip hop looking. Bright colors, especially red and purple, are usually awesome. To get a conservative dress shirt, go to Brooks brothers: http://www.brooksbrothers.com/mens/dress-shirts/0203,default,sc.html?lid=topnav-menu. To get a little crazier, go to Express: https://www.express.com/. For anything crazier than that, your on your own. I kind of like LordWilly’s in New York, but its expensive: http://lordwillys.myshopify.com/collections/shirts?page=2. For something inexpensive, try Paul Jones casual shirts: http://amzn.to/1YaTkeZ.
Polo shirts I generally don’t wear them but I don’t have a problem with them. Just make sure they look good and stuff.
T-shirts I’m all about a nice t-shirt. I like to wear them with a blazer to class it up. Depending on the context, a t-shirt with a crazy pattern will really stand out. Because I’m into surf culture, I like to wear surf shirts, like this one from Volcom: http://amzn.to/1WLaSzA. But of course, you should buy whatever t-shirt you are into. When wearing t-shirts, remember that people think in stereotypes so you don’t want to give off a weird stereotype. If you wear a Dungeons & Dragons t-shirt, girls will probably think of you as the weird kid in their high school, not the football player they sucked off in the locker room.
Shoes The most important thing about shoes is to make sure they are clean and they look new. Women obsess over shoes and they will notice yours. Every man should have some shoes that look like this: http://amzn.to/1YaQg2i. John Varvatos is an expensive brand, if you want to go a bit cheaper, go for Steve Madden: http://amzn.to/1T3vR1a. If you’re going to wear sneakers, make sure they are either high-end, really cool looking sneakers. http://amzn.to/1T3t1Jz. Or they look high-end (I like the Puma black on black): http://amzn.to/1TuKa9k.
Flip flops I generally advise that you only wear flippies if you are going to an event wear its weird to NOT wear them, like a boat party or the beach. Women generally aren’t impressed by flip flops.
Socks Socks don’t really matter, but I like wearing crazy socks because it feels like I have a secret weapon that nobody knows about. It’s like a hidden confidence boost. You can find some awesome socks at http://www.happysocks.com. And of course, wear clean socks – nothing feels worse than taking your shoes off at somebody’s house knowing that your socks look like shit.
Underwear Same with socks.
Hats Don’t ever wear a fedora. Ever. Ever. I think fedoras are actually kind of cool, but they have been tainted with loseriness and never-get-laidness. Trucker hats and stuff are fine, depending on your audience, but just follow the above rules: make sure that it looks good and clean. Once again, I’m into surf culture, so I look surf-y hats like this one: http://amzn.to/1NZJHPT. Cowboy hats and shit are cool, I guess, but realize that you’re making a statement and you’re going to be pigeonholed into a certain stereotype.
Facial hair Nothing wrong with facial hair, just make sure it looks clean and taken care of. Make sure you get rid of ear and nose hair. Buy one of these if you have to: http://amzn.to/26X8CK8.
Hair Whatever you do, make sure it looks clean and on purpose. If you have long hair brush it or put it in a ponytail or man-bun or something. You want to look like Fabio, not like a homeless guy that can’t afford a haircut. If you have short hair, I advise you put gel in it. I used to hate gel and thought guys who wore gel were douchebags (I still do), but I realize that you will look a lot better with it. I recommend Lay-rite: http://amzn.to/1TuIigJ.
Hygiene Brush your teeth and rinse your mouth out with mouthwash every time you leave the house. Keep 2 or 3 mints on you in case you need to freshen your breath. Trim your pubes to a reasonable length and keep your dickshaft free from all hair. Make sure your balls are as smooth as eggs (I’m kidding about this one). Wear a unique smelling cologne but don’t over do it. Remember: spray into the air and walk into it; don’t spray it on yourself.
Accessories Women notice accessories A LOT, so focus on them. Get a cool looking IPhone case. Get a nice watch. Etc... I don’t wear jewelry, but I’m sure you can pull it off as long as it looks clean and organized.