So here is an idea that I like to play with every now and then, so I hope you can take this process and enhance your closet on your own!
Find an outfit or look that you really like. I found this on the internet of a real girl in NYC- I think the style is super cute, easy, and a lot of different body types can wear it.
There are a ton of shops that replicate trends, provide easy go-to pieces, and similar "knock-offs" of expensive brands. I took a quick look around at different internet shops and I found some very similar pieces at affordable prices to complete this look.
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For the motorcycle jacket, Forever 21 is selling a faux leather jacket for $32.80.
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I found a similar boy-friend style sweater at Target for $27.99 in a dark blue. They also have super similar shoes for $29.99.
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I didn't see a dress or tunic exactly like she's wearing but this one from Wet Seal ($24.50) is super cute and pretty darn close (plus I love stripes!).
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Then to top it off throw in a skinny belt ($4.80 Forever 21), a cream colored scarf ($5.49 Ebay) and a cute little necklace ($5.80 Forever 21).
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So there you go! This whole outfit can be bought for $131.37, and it is super interchangeable with other items. Hmm... this is really cute. I may have to buy it.