I’ve been obsessed with old things for most of my life. When I was 5, my mother said I would sing along to oldies she knew growing up. To her disbelief, I knew the words better than she did. And as I’ve grown up, my love of old movies, doo-wop songs, vintage items, and classic style has only become more prominent. But somehow, to my disbelief, I’ve never worn any vintage clothing!

As I said before, I prefer clothes with classic waists (high and cinched), heels that remind me of old dancing shoes, and glasses with a bit of a cat-eye. I sport a trench coat whenever it’s appropriate (I wear it a lot on the blog!) and try to find hats that are timelessly chic. So it’s only a matter of time before I dive into a few vintage clothing items! I think, for me, the real challenge in adopting any lonesome piece into my life, is how quickly it feels like mine. I’ve always been uncomfortable borrowing clothes or wearing someone else’s shoes for the sheer fact that it feels and smells different. The cut maybe wouldn’t fit nicely, or it was a color I wouldn’t have picked, so I was always aware these items didn’t belong to me, that they were borrowed. I think that’s my fear of buying vintage. It has to feel like it seamlessly fits into my wardrobe and becomes a part of my life. As if I were acquiring a new item for the first time.

So I’m hoping to break through my hesitation, and buy my first vintage clothing item this winter! Whether it’s a chic little pillbox hat or a dress that makes me feel as fabulous as a 1953 housewife, I’m keeping my eyes open for a new piece of old style!

Do you wear vintage? If not, would you give it a try? Also, the images above are from the awesome Etsy shop Mill Street Vintage! Check out her shop, or find each of the dresses I’ve featured here: 1, 2, 3, 4.