1. Is the item in good shape.
2. Does the fit flatter my figure and fit appropriately
3. Can you update the piece or make it look modern by adding a jacket, belt or other accessories to change the look.
4. If you are using or wearing Vintage pieces: Wear only a couple vinage items/accessories in your overall outfit and pair them with modern/timeless or classic pieces to avoid looking like you are wearing a "costume".
I tried this with several articles of clothing but my favorite had to be a striped dress I recieved. Black and white vertical stripes, knee length and I was not so sure I liked the neckline. But I instantly was inspired to play off of the potential of a nautical look with the stripes. I put on a brown belt ( yes you can mix brown & black -they are both neutrals) added a kaki safari inspired jacket and my favorite: red sling back, platform peep toe pumps!
I loved it! In fact I wore this outfit to church Fourth of July weekend and a lovely woman passing by me in the hallway complimented my outfit and said I was "rocking it!"-Which made my day! Not long ago I would have passed over this dress and would not have even thought I could change the whole look of the outfit just by pairing a few accessories with the dress. I have grown in my creativity and expression, and think a little more outside the box now. A couple years ago, I would have never pair brown with black and would have opnly thought to add a black or maybe a red belt--it would have been alot more "matchy matchy". It goes to show that anyone can grow in the area of style and evolve their own style if they put some thought into it.
What do you have in your closet that you can ad a new modern twist to? Use some creativity and give it a try! You never know, it may be your next favorite outfit!