Thanks everyone for all the suggestions.
Now, here’s a nooby question: What is the difference between a button-down, an Oxford, a polo, or just a plain old collared shirt? Is there a website or book that lists all these terms? Halp me!
There are varying definitions of each, but manly a button down is any mens collared shirt that buttons from the top to the bottom, an Oxford has buttons to hold the collar down, a Polo is a pullover collared shirt with one to three buttons at the top and a plain old collared shirt is just that. There are some things about the cloth content too, but that’s the gist.
I shop almost exclusively in thrift stores, and not just because I’m poor or cheap (though I am both:p) I wear what appeals to ME. I could give a shit what anyone else wears, though I do sometimes admire an outfit and seek to emulate it.
One of the reasons I prefer used clothing is that so often, whatever is available new is just not to my liking. And I like the thrill of the hunt and having many different seasons of styles to choose from.
I am hardly a dedicated follower of fashion, but I do tend to get a lot of compliments on my clothes. I love to throw together something and get compliments and questions about where I bought it and be able to say, “thanks, I got the dress at Goodwill, the shoes at Salvation Army, the scarf at some other thrift store, I forget, etc…about $15 total.”
I think it comes down to what makes you feel comfortable and creative. And being comfortable with yourself in general. Look at Johnny Depp (oh, CAN we, please?:D) he can pull it all off, from grunge to vintage to looking like a hobo on his way to the laudrymat, lol. But well, of course, he’s Johnny Depp, right? If you looked like him, you could pull off a flour sack 
But seriously, he has a sense of personal style that enables him to rock just about any style (a few pretty awful suits aside, but that’s just my opinion) He is a trend-setter because he 1. doesn’t give a shit and 2. DOES give a shit and obviously puts a great deal of care into his wardrobe, even if only in the sense that he never throws anything away and wears stuff for sentimental value.
I’m not sure that can be taught or learned.
So yeah, check out the fashion mags and current trends, but never be afraid to put your own spin on things and pick and choose based on what YOU like. Get some sound, classic pieces that never go out of style and build around them.
If it flatters your figure and makes you feel good and confident, go for it.
Or, you could follow David Byrne’s advice: “If you always wear the same clothes, people will remember you better.”
Corrections:
A men’s dress shirt has a collar and buttons down the front from collar to hem. They are typically cotton, but can be poly/cotton, rayon, silk or a combination of those. They make them with short sleeves but that’s not recommended.
http://dress-shirt.com/arrow/dover-broadcloth/whitebroad1.jpg
A “button-down” shirt means a men’s dress shirt where the tips of the collar are also buttoned to the shirt.
http://www.ritabarber.com/prodimages/17822683613V0030100.jpg
An Oxford shirt is a men’s dress shirt (button-down or non-button-down collar) made out of Oxford cloth (a kind of cotton). If you ever had a light blue preppy sort of dress shirt, it was probably Oxford cloth. It doesn’t have to be blue; it’s more about the weave/texture:
A polo shirt is a knit/cotton shirt with a collar, a few buttons down from the collar, and short or long sleeves.
http://www.petermillarshop.com/DSN/wwwshoppetermillarcom/Commerce/ProductImages/mn1_000015.jpg
A Henley is like a polo shirt, but with no collar, and is much more casual.
http://mirror.altrec.com/images/shop/detail/swatches/TNF/4280.39904_d.jpg
Random thoughts:
French cuffs would be cuffs on a dress shirt that take cufflinks.
A non-button-down dress shirt can take stays to hold the collar stiff but these may be going out of fashion.
There are also collarless dress shirts but that takes a certain elan:
Oxford shoes:
Cap toe has a seam outlining the toe area:
http://www.tedsclothiers.com/productimages/dawson%20cap%20toe.jpg
Wing tip has scrolly seams on toe and heel and punch details throughout:
http://www.theshoemart.com/mas_assets/full/ALD_m_WING_TIP_BLUCHER_CALFSKIN.jpg
Spectator shoes are essentially wing tips, but with contrasting colors on vamp vs heel and toe (only **Robot Arm **can pull these off):
http://image.bizrate.com/resize?sq=160&uid=795621323&mid=55715
I hope it’s not rude to bump this and find out how the shopping is going?
No worries gigi. To be honest, due to my financial state (negative dollars), I haven’t really bought any new clothes. I have gone through my own wardrobe though, and found out what actually fits me and what doesn’t. I’ve also been going to the gym a lot and doing some research on what style I’d like to emulate. Also, nashitashii recommended me some great books on men’s style so going to the library and picking those up is also on my to-do list.
Geez, this being stylish and attractive thing is hard work!
Not for some of us.