If you love the way you look in something, rock it no matter what. Some of the best shopping advice I have ever received was to try everything on, no matter the size on the label says. Every style and every cut of clothing is made differently so it's very likely a size 12 women's top is not the same fit as a size 12 women's top at the next store over. A lot has to do with different materials used as well. For example, a jersey fabric will be a lot more forgiving than a structured blouse. This advice is best used in a secondhand shop because all of the brands are different and usually from different eras, so sizing will rarely be consistent. You should really look in every size area and try everything on that catches your eye. I'm not saying wear clothes that are extremely tight and ill-fitting - what I'm saying is don't limit yourself to a certain size, every article fits differently.
The top and the jacket I'm wearing in this post are borrowed from two different friends of mine. Neither of my friends are anywhere close to being my size but I took the pieces and I wore them how I felt comfortable. The size on the tag of the dress is either a 10 or a 12, which I'm definitely not, and it's actually meant to be worn as a dress but I love the way it fits me. It's just long enough on me that I can wear it with leggings and it fits perfectly around my stomach and chest. The leather jacket is a men's medium and doesn't actually zip up, but I feel like a rockstar when I wear it and it fits well when it is unzipped.
DRESS/ H&M* SHOES/ Spring* LEGGINGS/ Giant Tiger ACCESSORIES/ Various places
PURSE/ H&M COAT/ Thrifted* WATCH/ Michael Kors
* - BorrowedAll pictures were taken by Michael Tundo and Laura Kidd.