Impossibly Cool

An edit of 39 vintage tailored jackets just in time for Fall.

Tailoring is best when it looks effortless—Jack Nicholson’s rumpled houndstooth jacket, Alain Delon’s silk scarf-tied nonchalantly over his tweed blazer, Sofia Coppola’s men’s tuxedo jacket with nothing underneath. Each image captures the art of looking like you didn’t try, but somehow getting it exactly right. It’s impossibly cool.

This edit is inspired by that sensibility— jackets you can throw over a tee and jeans, walk out the door, and still be the best dressed wherever you go.

I’ve organized the edit into 5 categories with 39 links to vintage blazers (mostly men's, some women’s) you can scoop up today to elevate your fall wardrobe. Sizes range from 36-48 and prices start at $29.

**Also I should note- I use images of mens style all over my mood boards even though I’m a womenswear designer. I’m really only ever thinking of women wearing similar looks. When I look at these images of Jack and Alain, I imagine a really chic woman wearing the same look. A man wearing these looks today would also be really chic. So there’s something for everyone really. **

Let’s get into it.

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No.1 - The Black and White Herringbone Blazer

I’ve been feeling more and more for heritage patterns these days. I styled a shoot earlier this year with a vintage black and white herringbone jacket that I borrowed from a costume house in LA and have been dying for one ever since.

Rediscovering this image of Basquiat looking effortlessly cool wearing a similar black and white herringbone jacket was just the push I needed to start digging for something similar on eBay.

**The rest of this post is for paid subscribers. If there was ever a post to try out paid I think this is it. And to all my paid subscribers, thank you so incredibly much for the support. You guys just made me a Substack Best Seller today and I still can’t believe it. Thank you!!** Onwards!