The Importance of Getting Your Appearance In Order

My fashion sense in high-school consisted of the following 'outfit', which I wore with remarkable consistency: boring haircut, large glasses with smeared lenses, unshaven 'moustache', unibrow, faded, over-sized, plain black t-shirt (assorted stains and holes optional), cheap plastic watch, too-tight jeans, and cheap, ratty running shoes. My posture was horrible and I was unfamiliar with the concept of exercise until my last year of school. It was one of the many ways in which I was a mega dweeb.

Having half-decent grooming habits and some fashion sense is pretty much mandatory to doing better socially. Unless you are extremely cool as a person, people will have a hard time looking past a sloppy exterior. Putting more thought into your appearance is one of the easiest ways to improve your social prospects and the way people see you. And why not live up to your appearance's full potential?

Most people are pretty superficial and mentally lazy when they size others up. If you look like you have your act together, they can't help but assume you really do. The opposite is true too, if you don't look all that great, people will attribute all kinds of negative traits to you. But clean up your look, and suddenly you don't seem so bad, and they're more willing to give you a chance, even though you're the same person deep down.

A put together looking guy and an unkempt, badly groomed guy can both tell someone they like science fiction. When the good-looking guy tells them, people probably think something like, "Oh, good for him. I've read some of those stories myself. They're very thought provoking." When the dorky looking guy says the same thing, the response is, "Ugh. What an obsessive loser. He needs to get a life and start living in the real world." People suck that way, but we seem hardwired to judge people externally like this. May as well be on the right side of the fence and use this lazy thinking to your advantage.

Mental barriers to improving your appearance

If improving your look is one of the easiest ways to do better socially, why don't some people do it? Here are some reasons:

It's just not on the radar

When I was younger, the idea of putting effort into my appearance just wasn't in my mental airspace. Even when people made blatant suggestions to me, like saying I should shave my ratty, wispy mustache, or stop wearing the same clothes everyday, it just went over my head. My hair could have looked like a rat's nest and I literally wouldn't 'see' it. I was also clueless about what good grooming and fashion entailed because I never really thought about it. So if I put on a slightly less dorky t-shirt than I'd normally wear, or I bought a brand new pair of sweatpants, I'd walk around thinking I was looking so fine. Unconscious Incompetence at it's finest.

It's not worth the effort

Well sometimes I did realize I could be wearing better clothes and whatnot, but I didn't care. My priority in life was sitting in my basement by myself and playing RPG's, why did I care how I dressed or how my hair looked? I didn't have many friends and there was no one important I wanted to win over. Caring about your appearance is something that matters socially, and I wasn't the least bit concerned with that world.

Much more commonly, tons of people don't dress as well as they absolutely could because they can't be bothered to go shopping all the time, or keep up with the latest fashions. They settle for looking passable and half-decent. That's me most of the time too. Thankfully I don't look like a total slob anymore, but I'm hardly the most fashionable guy you'll ever meet.

Money is also a factor in the effort it takes to look better. I'd be lying if I said things like clothing, hairstyling and makeup aren't a significant expense for some people. If you know what you're doing though, you don't have to go broke to look half-decent.

Fear of change

I remember the idea of buying better clothes or changing my look in other ways as being vaguely scary and uncomfortable. It was so much easier to stay in my comfort zone.

A negative attitude towards caring about your looks

In high-school I saw the people who put effort into their looks as being shallow, as well as brainwashed consumers. It's easy to get sucked into the ideal that worrying about how you look on the outside is a superficial waste of time, and that what's on the inside is more important. It definitely makes you feel better about yourself. Realistically though, what's so bad about wanting to look your best? I appreciate it when other people take the time to look nice for me.

Not wanting to accept something you don't care about is important

How someone presents themselves externally is a factor in human relationships. It's just how the world is. When you don't naturally care about this area, and honestly wish you didn't have to devote mental energy towards it, it can be hard to accept it's important. You can just not want to admit it to yourself, and resist improving yourself in this regard because you wish life worked differently.

A poor or rigid self-image

I think I've resisted looking better at times because my poor self-image wasn't aligned with the idea of me being more attractive. I saw myself as being a dorky loser, and making myself look like more of a regular, well-adjusted guy on the outside clashed with that. My mind told me, "You're not really a cool guy who dresses well. You can't go out and buy better clothes. That's not who you are."

Stubbornness and bitterness

Been guilty of this one too. When you've taken your share of crap from people for not putting effort into your appearance, even if they're right, the last thing you want to do is listen to what they say. That would feel like letting them 'win'. That would mean conceding that those assholes were right and you were wrong. You can also feel like since the jerks who gave you a hard time care about how they look, then if you start paying attention to your looks, then you're selling out to become like the enemy.

A few basic tips for guys on looking better:

I think avoiding blatant grooming and fashion mistakes is much more important than possessing a bunch of high-end fashion knowledge. The blatant mistakes will actively turn people off you.

I'll list some basic tips and things to avoid here (geared towards guys, since that's all I know), but really, this almost isn't necessary. Once you start devoting even a little thought to how you look, you'll very quickly notice and correct all these yourself. On the other hand, if you're oblivious or indifferent enough to make certain mistakes, then having them pointed out directly probably won't make a difference:

Basic grooming

It feels condescending to write these out, but I suppose I should anyways:

Groom your facial hair. Avoid the patchy beard, long black moustache hairs, or chin pube goatee. Pluck your unibrow.
Brush your teeth.
Wash your hair.
Take care of your skin.
Trim your fingernails and toenails, and clean the dirt out from under them.
Wear deodorant.
Pay attention to little details like not having a mole with a single long hair growing out of it.

Basic dressing

Again, a list of stereotypically clueless mistakes. But I made a lot of these:

Don't wear white socks with dark shoes and vica versa.
Don't wear socks with sandals.
Don't wear T-shirts that are too big.
Avoid the socks with sandals, too big t-shirt, and khaki shorts combination.
Don't wear the same outfit two days or more in a row.
Don't wear a similar outfit every day (i.e., a dull black t-shirt with jeans.)
Don't keep wearing your clothes after they've become ratty or faded.
Don't wear clothes that are overly wrinkled.
Don't keep wearing something if you've dirtied or stained it.

Basic Appearance

If you have glasses, consider getting contacts. They're not as expensive or high-maintenance as you may think. At the very least, if you do wear glasses, make sure to get some hip frames that look good on you. Glasses suit some people, but just as many would be better off without them. They also unfortunately are associated with some negative stereotypes.

Get your hair looking good. Grow it out or cut it in a fashionable style. Good looking hair can be the cornerstone of an attractive appearance. Traditional dorky styles to avoid are long straight hair that parts in the middle and goes down to around the bottom of your neck, and that conservative generic look where it's buzzed short on the sides and left about an inch or two long at the top.

Stand up straight. One thing that helps is to always keep your mouth closed and breath through your nose if you currently don't do so. Besides from not looking like a slack-jawed yokel, you'll be forced to stand up straighter to create a better pathway for the air to travel from your nose to your lungs. When you breath through your mouth a more slouching posture is required for proper airflow. Having your back muscles in shape also helps.

Tanning is controversial but most people do look better when they're not pale. It's your call.

If you don't have great teeth, see what you can do about that. Of course this isn't something anyone can do in five minutes.

Get in shape, but don't think you have to get completely ripped. If someone is fit for their natural frame people subconsciously pick up on it and think you look better. Subtle differences in things like the size of your chest muscles, the width of your shoulders, or the V-shape in your torso show through. Don't think your only options are lifting weights or running on a treadmill. There are tons of activities you can do that will make you fitter. Take up rock climbing, or kick boxing, or dancing, or Ultimate Frisbee. Pick something you enjoy doing and that isn't an unnecessary hassle to take part in. If you truly don't like doing something, or it's just a pain in ass to do it, you'll quit before long.

Some advice on getting better clothes

Having decent clothes is one of the biggest factors in looking better. It's also a bit more complicated than vowing to take good care of your skin. The factors that make people resistant to improving their looks often come into play most strongly when it comes to clothing. Here's what my experience has taught me:

For me, the hardest part about getting better clothes is getting myself out the door and to the store. Once I've bought some nice outfits, I'm happy about it, but it seems like such a hassle to take a few hours to go shopping.
You may think you don't know much about fashion, but you likely have an idea deep down about what looks good. A rigid self-image can make it hard to admit to yourself that you can wear these attractive clothes yourself.
Go to a store that sells good clothes and start trying stuff on. You can use the staff's knowledge and style to your advantage by asking them to help pick out some good outfits for you (of course trust your gut and don't let them push or flatter you into buying something you're not keen about). I have some shirts that people often compliment me on. I got them by literally walking into a good store and asking the staff to help me, "pick out some nice shirts."
I have no idea where you live or what people dress like where you're from, so I won't recommend any specific stores or labels or anything (and I'm not enough of a clothes horse to be making recommendations anyways).
Don't judge anything until you try it on and see if it looks good on you. Many things look a lot better than you'd think from just seeing them hanging on the rack or sitting folded up on a table.
Your self-image and discomfort with change may make you think things like, "That's not me, I'm not the type of person who wears this stuff". Ignore these messages and push out of your comfort zone. I'm always surprised with how within a few days I'm totally comfortable in styles I initially dismissed as, "not me".
You may have some emotional baggage around certain styles, even though you think deep down that they look good. If you don't like the people who wear certain styles (e.g., jocks, preps, hipsters) the idea of dressing like one of 'them' may seem traitorous to you.

There are two broad ways you can go when it comes to getting better clothes. One is to just dress like everyone else (the ones who look good that is). This is cheaper and easier. Yeah you're not being a unique trailblazer, but you'll still come out looking a lot better than you did before. The problem is your clothes will soon go out of style and you'll have to get new ones.

The second option is to go to some hip, higher-end stores and buy some cooler, more unique items. This is more expensive and there's a higher risk that you'll accidentally buy something that truly isn't your style. On the upside, these clothes tend to just look better and attract more positive attention. They also exist outside of the short lived trends more mainstream styles are subjected to, so they take much longer before they're blatantly out of style.

Like anything there's a learning curve involved in picking out your own clothes. You get better at it with practice. As such, I'd recommend not blowing too much money your first few times out.
Personally, I don't have a problem with paying more for what I feel are good clothes. However, I totally understand if that's not your thing. It's totally possible to look good and not kill your bank account. I know well dressed guys who take pride in the fact that all their shirts cost less than $15.
If in doubt lean towards (relatively) plainer and conservative clothes over flashier ones. Flashy clothes can backfire and make you look like you're trying too hard if you don't pull them off properly.
One thing that's interesting is that the most socially successful guys often dress in a nice, but plain and simple style.
Don't forget about accessories like a nice pair of sunglasses or a cool watch, necklace, or wristband.
Get some nice shoes. Girls care about shoes.

Your external looks are influenced by your internal states

If you took two outwardly identical guys, but one was insecure and had a lot of other issues, and the other was self-assured, happy and confident, they would actually come across as quite different from each other. They would carry themselves differently and wear different expressions on their faces. One would literally be better looking than the other.

If you're insecure about your appearance, or some aspect of it, do everything you can to look better then stop thinking about it. Once you've done everything you reasonably can to improve your looks, there's no point in wasting any more mental energy dwelling on the topic. Stop thinking about it so much and stop doing things like looking in the mirror every few minutes to 'check up' on your supposed flaw.