Today's Everyday Fashion: Similar Styles

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When JJ saw this new dress he said "do you already have something like that?" He's got a good memory because it's similar to this silk beige top from last Christmas. He inspired me to put the shirt into a spring look to help decide if I want to keep the dress (which one would I reach for first? are they different enough?). Shirt dresses are pretty awesome, but I don't want too many similar things in my closet, either! In your opinion, how similar is too similar? Do you buy multiples or mostly "new" styles?   

Dress: Express, $47
Belt: Gap, $10 (similar)
Shoes: Steve Madden/Macy's, $59 (same)
Purse: Michael Kors/Macy's, $111
Hat: Francesca's, $10 (similar, similar)
Necklaces: My Stella & Dot 1, 2, 3
Approx. dates: Belt is 5 years ago. Purse, hat and shoes are last season. Dress is new.

Top: Banana Republic, $32 (similarsimilar, similar)
Shorts: Forever 21, old (similar, similar)
Shoes: Nine West c/o Macy's (similarsimilarsimilar)
Purse: Michael Kors/Macy's, $111
Hat: Francesca's, $10 (similar, similar)
Necklaces: My Stella & Dot 1, 2, 3
Approx. dates: Shorts are 6 years ago. Shoes are 2 years ago. Hat, purse, top are last season.

H&M  /  Gap  /  Wallis  /  Limited
Jones New York  /  Express  /  MissGuided  /  Mango
MissGuided  /  Forever 21  /  Sanctuary  /  River Island