Like any skill set, an eye for style involves a zillion tiny calculations, many of which are subconscious. You have a "feeling" about what will work, and what won't. But good news! Like other skill sets, when you're new to the game, you're in a great place because the learning curve is steep! A few small steps will net you big results. Start here.
  1. Go through your closet and get rid of everything that is too big, too small, has a stain, or that you haven't worn in 1 year.
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    If you're still holding on to Uncle Ralph's vintage bowling shirt, a lucky hoodie from the college days, and a pile of concert t-shirts with fond memories - and you never wear them but can't bear to part with them - do what I do: put them in clothing limbo. A large cardboard box. In another year, if you don't notice any effect on your life, give the whole box to the Salvation Army without looking in it.
  2. Ask around for a hair stylist recommendation
    Be prepared for sticker shock if you're used to 10 dollar cuts. Trust me, it's worth it.
  3. If you don't own a pair of dark blue indigo jeans, get one.
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    Levi's are fine. Try 514.
  4. Get a pair of Clark's desert boots. Brown.
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    Notice how they look with the dark jeans. Casual and classy.
  5. If you can swing it, get a pair of blue, grey, or black Chucks.
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    Bonus if they're leather.
  6. Get a white OXFORD shirt in the smallest size you can fit into.
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    Be sure the seams hit your shoulders. J.Crew, Banana Republic, Gap, Levi's are good places to look. Ebay is a great place to save some money.
  7. Get a knit tie from
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  8. Get a blue, red, or purple or black gingham shirt.
    See pic above.
  9. Finally, get either a blue or grey blazer... Or a thick, cuddly cardigan.
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  10. Prepare for a lot of attention.