Jack McConnell hat

Hat Style and Wearability | Modern Millinery

Millinery Operations with Kristin Silverman

I’ve been thinking about wearability of hats. Outside of racing fashions and other fancy events, many people are nervous about wearing hats.

I recently acquired a vintage hat that is crazy and gorgeous … and absolutely not what you would see someone wearing today (at least not here in the U.S.). Here it is:

Jack McConnell hat
Vintage “red feather label” hat by Jack McConnell.

Well, maybe you’d wear it if you’re a vintage style blogger or an actor or someone with a unique style who is very confident. (I won’t wear it myself, and I’ll probably end up selling it. But I do enjoy how spectacular it is.)

My last post was about my personal top 10 Instagram accounts for hat lovers. One of the people who almost made the final cut is the amazing Style Crone. She is a perfect example of how to wear a hat: with joy and confidence.


There’s a sweet spot between ultra casual hats (knit caps, baseball caps, etc.) and fancy hats (racing fashions, wedding fashions, etc.). This is it. This is the type of hat I adore. And many of these hats can even be worn with jeans and a t-shirt!

I wrote at more length on my personal blog about How to Wear a Hat. Check it out — or just enjoy the eye candy above.

Happy hat-wearing!

Share The Love

Want More of the good stuff?