Dear Fashion Kitty, How Do I Wear …

I have two pieces in my closet that I’ve owned for a long time now and I still haven’t figured out how to wear them. I was hoping you could help me out.

The first is a black/ white polka dot blazer (as opposed to the picture, mine has is cropped in the length and the sleeves- 3/4 sleeved).

The second item is your black all black Chuck Yaylor converse. I know they are a classic shoe but I can’t help but think they look so regular and boring with jeans, but so unflattering with skirts/ shorts. Thanks in advance!
Don’t you hate that?! When you have clothes that you love but sit in your closet because you can’t figure out how to wear the. It happens to the best of us, it even happens to me. Let me see if I can help you out with this fashion situation …

I will start with outfits for your Chuck Taylors …

You can go edgy-80s with a motorcycle jacket, feathered skirt, fishnets, and spikes. Totally fun but only if you think you can pull it off.

Or you can go can also mix a dressed up pieces with dressed down pieces for a super hip look.

And now onto the blazer …

I would go with a pair of cute skinny jeans (you could do plain, ripped, gray, or colored) with cute flats. Go simple with the jewelry … one giant cocktail ring will do the trick.