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Yep, it's true. I too went down a 1/2 size somewhere in and around 20 - 21 years old. I couldn't keep up to my metabolism and lost a bit of weight. The 1/2 size apparently went with it, all thanks to being broke. I wouldn't really concern yourself with that though. It's the risk you have to take, if you're gonna step it up.
 
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You'd be surprised. I think I went up a full size from ages 16-20 and then down half a size and up a width from like 25-30 (which is where I am now). Furthermore, if you're 16 I'd place savings ahead of long term shoe investments. Your style and needs will change a lot. I always thought it was a good idea to wait until you fully enter the workforce/career before dropping a lot if money on clothes. You'll fall into a long term personal sense of style. For now, experiment with the cheap. Thrift stores, eBay, etc. Figure out what you like.

Oh and don't wear fedoras/dress hats outside of school projects until you're about 40. ;)
Yeah, I won't have much choice what I wear when I go to college (if I get in where I want to) because I want to go to West Point...
 
For your age I suggest buyng from palces like target, H&M or JC Penney. Yeah, thats right, JC Penney. Stafford dress shirts are no joke and they go on sale for $18. That way you dont break the bank on stuff you might still grow out of.

Shoes: desert boots are an easy win for this. also some lug sole wingtips. The lug sole keeps them high school appropriate so you dont look like you are palyign dressup. Also cant go wrong with classic Chucks or Vans.

Tops: Plaids, tatersal, gingham, oxford cloth button down shirts are all long sleeve staples. You can still have style without going dressier on the formality scale. A simple henley or thermal as an undershirt instead of a basic tee will elevate a chambray or corduroy work shirt. Summer time, go with some linen shirts and maybe a light weight seersucker. Use shortsleeve henleys instead of palin tees. A good polo is popular but I personally cant stand them on me.

Pants: Chinos are a staple and come in all kinds of colors, but stay away from loud stuff. Olive, tan, grey, a dark wine or cranberry, camel. Cords are a step up from jeans so good job there. In the summer stay with at the knee chino shorts if you wear shorts. No cargos. You get more freedom with colors on shorts. Mix in some seersucker for texture if you want. Seersucker comes in all kinds of colors too.

Outerwear: blazer at public high school might be going to the overdressed level but it is whatever you feel comfortable with. Cardigans and vnecks are solid sweater options. Also consider a pea coat, field jacket, mac coat, chore coat, denim trucker, or safari jacket. All classic and better than the puffer or baseball bomber stuff that is so common these days.

Accessories: I am a big believer in just watches. I dont wear any other jewelery but a nice clean watch can make an outfit. Doesnt have to be pricey. Timex Weekender with a few different bands to slip in there is perfect. Canvas and leather are available all over the web for cheap.

Hats: I only use a hat if it is functional. My grandmother always told me a gentleman takes his hat off indoors so I only wear them when I need it for the elements.
 
I recommend you be somewhat subtle with your changes. Just a little bit every now and then. Ridicule over a drastic change can be disheartening and sometimes embarrassing. You can avoid this by taking things slow and being subtle, without anyone noticing at all. Suddenly, one day, someone blurts out "Hey, nice jacket".
 
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For your age I suggest buyng from palces like target, H&M or JC Penney. Yeah, thats right, JC Penney. Stafford dress shirts are no joke and they go on sale for $18. That way you dont break the bank on stuff you might still grow out of.

Shoes: desert boots are an easy win for this. also some lug sole wingtips. The lug sole keeps them high school appropriate so you dont look like you are palyign dressup. Also cant go wrong with classic Chucks or Vans.

Tops: Plaids, tatersal, gingham, oxford cloth button down shirts are all long sleeve staples. You can still have style without going dressier on the formality scale. A simple henley or thermal as an undershirt instead of a basic tee will elevate a chambray or corduroy work shirt. Summer time, go with some linen shirts and maybe a light weight seersucker. Use shortsleeve henleys instead of palin tees. A good polo is popular but I personally cant stand them on me.

Pants: Chinos are a staple and come in all kinds of colors, but stay away from loud stuff. Olive, tan, grey, a dark wine or cranberry, camel. Cords are a step up from jeans so good job there. In the summer stay with at the knee chino shorts if you wear shorts. No cargos. You get more freedom with colors on shorts. Mix in some seersucker for texture if you want. Seersucker comes in all kinds of colors too.

Outerwear: blazer at public high school might be going to the overdressed level but it is whatever you feel comfortable with. Cardigans and vnecks are solid sweater options. Also consider a pea coat, field jacket, mac coat, chore coat, denim trucker, or safari jacket. All classic and better than the puffer or baseball bomber stuff that is so common these days.

Accessories: I am a big believer in just watches. I dont wear any other jewelery but a nice clean watch can make an outfit. Doesnt have to be pricey. Timex Weekender with a few different bands to slip in there is perfect. Canvas and leather are available all over the web for cheap.

Hats: I only use a hat if it is functional. My grandmother always told me a gentleman takes his hat off indoors so I only wear them when I need it for the elements.
Thanks! I do have a pea coat (which I love and wear when it's cold eg. Now) and I agree on the watches (I have a digital one for vacation where I don't want to risk a nice watch, a black metal banded one, a gold/silver Disney metal banded one, and a mechanical pocket watch)
 
Check out dappered.com for some tips and also links for sales, deals, etc. It's a pretty cool site. If you want watches for style and are cheap.. Check out dappertime.com, I have 2 watches from them and a third on the way.
 
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Might I also suggest:

a) Dark jeans - classic wash. You can wear just about anything with a good pair of dark denim.

b) If you want to do some button-front shirts with a bit of extra color, don't lock into button-down collars/oxfords. Get yourself some tailored-fit poplin and linen-weave cotton shirts in madras or gingham plaids with a regular tab color. Close to the body, but not tight.

c) Shoes - chukkas, desert boots, Chelsea boots. Classic, classy, and suitable for moderately fancy dates as well as every day wear.

d) and yeah, a soft-bodied corduroy jacket in a medium or tobacco brown is a great idea.
 
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