hey,
my brother's facing senior year in Harvard without ever having being kissed and needs major coaching!

I'm starting with a makeover and tips for his posture. We don't have much money and almost his entire wardrobe is unfashionable in my opinion.

He feels really insecure because of all the rich preppy kids.

What priorities in Style do you think we should set?

a) invest in a few preppy clothes and have him walk around in the same few outfits (like black, grey, dark blue basics, so it's not so obvious?)
b) invest in urban basics, cheap to mid price range so he has the full range of clothes (shirts, polos, sweaters etc. each in a few colors)
c) peacock - have bright colors or a totally individual style, so he stands out and doesn't fall into the same category as the other kids

(if c, then how? examples?)

this is a serious question!
thanks for your advice!

Or d) none of the above. You be much better off with taking your brother to the mall and have him look at clothes that he finds appealing to him. Trying to have him fit in or totally stand out is not going do him any favors. A lot of those rich kids at Harvard don't have much money of their own. They live off daddy's and mommy's money.

yeah, I think everyone should develop ones one sense of style and feel comfortable.

Problem is, I've done that before and he's SO LOST and helpless.

He has no clue what's hot, what not, what fits him, which jeans have the right fit for him, even when he tries the stuff on and compares.

Every time we shop I end up basically end up choosing the clothes. He'll say yes to like 90% of the stuff I preselect.

But now he's become more skeptical because of all his insecurities.

I think getting him a new wardrobe is the least of his problems right now. Trying to have him fit in with the crowd I doubt will help him any. He needs to work on his insecurities. Getting him a new wardrobe just so he can fit in will more than likely make things worse for him.

I wouldn't worry too much about the money thing. We all start out small. Peyton Manning once never threw a football, Michael Jordan sucked at basketball in his younger days, and even many/most PUAs sucked with women before they found out seduction.

If you only have money to buy a shirt and pants, just go out and buy that. It's not like you have to change overnight. Be on the lookout for deals and whatnot, but buy things you like and are quality. I spend $20 on my shirts. I bought a pair of shorts for $40 and just bought an overshirt for $30. It's alot of money but I like them alot and to me it's money well spent. Also I get lots of compliments and that's something you can't put a price on.

Also I agree with jurupa, you shouldn't just get him a wardrobe just to 'fit in'. I'm changing the way I dress because I want to, so should anyone else. If he's going to be wearing something other people like but he doesn't, it's going to make him feel uncomfortable and be more detrimental to his inner game than anything else.

buy what you FEEL COMFORTABLE in dont buy things that just look good because if you dont feel comfortable in it you'll feel conscious of it and your energy will drop

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I would say something along the lines of b). Go for something(s) current, stylish, and cheap (and not having to wear the same outfits over and over again is the best).
Hit up the clearance racks. That is where you will find the cheapest clothes, and go for the good ones. (good = the ones that impress the hot babes, first and foremost)

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Femme85,

Clothing is a small part of improving yourself.

I would suggest him to take a look at this forum and take a look at the fasion threads here and make him pick out some cool items. Copy them and he will feel more secure.

But i think that problem lies not with clothing though, it's like you said: He is insecure. I think if you want him to appear more confident you should give him challenges in the inner game directions and in the meanwhile build up a wardrobe.

You know why Johnny Depp, Brad Pitt, George Cloony and all the guys woman love always appear confident... not because of their cloth. Even in rags would George Cloony think he is great. It's because they have great inner game (or are great actors to hide insecurity).

Try to improve his inner game.

Riqueza.

If your brother is facing Senior year, then he is going to want to change his clothes in preparation for the work force anyway, so getting new clothes is going to happen regardless. You dont have to buy expensive new clothes, look for clearance rack stuff, and sales, that way you can spread your money out. A lot of upscale clothing stores have big sales often (Mens Wearhouse, Joseph A. Bank, etc.), so be on the lookout for those. I think the key when starting a new wardrobe on a budget is versatility. Buy clothes that can be worn at work, or when going out to bars and clubs (obviously, not everything works for both). Jeans are versatile, as are polo shirts, khaki's and dress button downs. Find things that can be mixed and matched. This also doesnt have to happen overnight, and can be worked on throughout the year. But, as others have said, clothes will only help his insecurities so much, and he needs to find his own sense of style, and be comfortable with it.

Make sure that you get an amazing pair of brown shoes.