A good tweed blazer is like a retainer. Both are decidedly unsexy and conjure up memories of being in school—the former via your math teacher’s uniform and the latter via you, post-braces—yet once you have them, you’re likely to be wearing them for the rest of your life.

There are two types of tweed. There’s Chanel tweed, reminiscent of UES grandmothers who keep dogs in their purses and are either named Mary, Susan, or Mary-Susan. And then there’s full grandpa tweed. Boxy, more practical than fashionable, and complete with the distinct odor of cigar smoke.

Personally, I fall into the camp of full grandpa tweed enthusiasts. I love a good shoulder pad. I love a good masculine silhouette. And I love a good diner dinner at 4pm, which in my opinion is as essential to committing to the geriatric lifestyle as dentures are.

And when you’ve committed to dressing like the elderly, there’s no turning back. You may as well throw on a mom-jeans-and-turtleneck combo to make Steve Jobs bless you from above, because committing is a commitment and you don’t half ass looking like walking birth control.

Which is how I came to find myself prancing around the West Village, looking like your geometry teacher from Grade 9 who you could tell once had a dream but promptly killed it upon entering the public school system.