[How To] Update Boring Clothes

I try to keep my closet pretty organized most of the time. I regularly clear out things I haven't been wearing or don't feel expresses my style anymore. Sometimes I have pieces that I really like, but something is just off about them. Maybe its a dress with a really cute print but an odd boxy silhouette? A pair of shorts that are comfortable and fit really well but sort of look like pajamas? Or a vintage silk button down that's just downright boring? 
What do you do with clothes that you aren't wearing, but can't bear to part with? Don't donate that top you've only worn once quiiiiite yet. Fix the problem!
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I loved the bow print of this dress, but the shape was boxy and unflattering and looked like an awkward hospital gown. I cut the sleeves into a tank and took in the sides of the bodice. A little snip and a couple of stitches completely changed the shape of the dress! It still sort of looks like a slip, though, so I may still add some buttons or trim.
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I got these shorts at Forever 21 a couple of years ago. I adore the hearts and pinstripe print, and the fact that they have pockets! These shorts are also soooo soft and comfortable, but whenever I wore them, they translated as pajamas, which I wasn't really going for. I sewed pom pom trim along the hem, and now my shorts are festive and summery, without looking like sleepwear.
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I found this simple black and white striped button down at Salvation Army and for a while, I was content to wear it as it. The 100% silk fabric is so nice, but I was bored with the 90's feeling of the fit. To give this shirt an update, I added cutouts to the shoulders. I folded the shirt in half, matching the points of the shoulders together, and then cut half ovals across the folds of the fabric to make sure they matched. I wanted large cutouts, so I cut longer, deeper ovals, but for a less dramatic look, cut more shallow ovals. Fold over and sew. It was a little bit difficult to sew the silky fabric, but a regular button down should be much easier!
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Is there anything in your closet that you aren't wearing, but can't give up? How have you updated pieces to make them more wearable? Leave a comment and let me know!