Your Cart is Empty

If you need an exchange to get the right fit or hat, we'll cover the shipping!*


The Damnson Guarantee| Risk-free confidence

Orders ship in 7-10 business days

Dark Grey - Brown
Dark Grey - Black
Thanks for signing up for restock notifications!
There was an error signing up for restock notifications. Please try again.

Sign up for restock notifications

Notify Me
Note: This hat is one of our most popular styles, but it tends to fit more shallow than some of our others. If you have a larger head, or like your hats to fit further down on your head, you might prefer the Waterloo. It's a similar shape, but fits a bit deeper.

You might see "Old City" and think that this fine felt fedora hat is about playing checkers in the park, reading the newspaper and catching an early dinner at the Sizzler. While we enjoy a good board game with chums, sports page and steak-'n-shrimp special as much as the next guy, the Old City isn't about that at all.

As a matter of fact, this hat's namesake has more culture, history and depth per square inch than probably any other place on US soil. Like the man that places the Old City on his head, the real magic is behind what you see, told in the stories and etched in the volumes. Can't be faked. Can't be bought on its own. It has to be earned.

No, this hat ain't Vegas. It's Old Town Philly.


The Old City quarter of Philadelphia hasn't stuck around this long just because. It was built to last, built to mean something. Old City, the hat, was built in a similar way. Made almost entirely by hand with 100% Australian wool, this hat knows that details matter and that what matters most isn't its creation, purchase or even unboxing — it's what comes in the months, years and decades after.

This Old City features a thin 3/8" black band, but we also have an Old City that rocks a 1 1/4" golden brown grosgrain band.


Brim: 2 1/2"
Crown: 4 1/2"
Band: 3/8" nylon grosgrain with knot


Side note: This hat fits true to size.

All sizes are measured in centimeters circumference.

55 57 59 61 63
Inches 21 1/2" 22 1/4" 23 23 7/8" 24 5/8"
Fitted Size 6 7/8 7 1/4 7 1/2 7 5/8 7 7/8

Customer Reviews

Based on 7 reviews
Hat is great; exchange process was slow

Took several weeks to do the exchange. Replacement hat fits better

Victor H
A Touch of Class

I love Styles I'm on my third order possibly 4th

Jonathan Lockett
My first Fedora

I've been wanting to purchase a Fedora since I saw a picture of my grandfather wearing one. When I saw the Old City it reminded of that picture and I knew it was the one for me. It looks good, feels good and I feel both wearing it. I definitely plan on buying another from Two Roads.

dean sharp
more than a hat!

So, i have numerous straw and summer weight fedoras…all shapes and materials…but my winter wardrobe almost always consisted of toques or the like. when i decided to up my winter/fall game my research brought me to 2ROADS for price/quality/style…no brainer as stetsons were 2x and 3x the cost.
what i didn’t realize was the customer service made this more than a hat purchase…i feel like it became a relationship. when i had a sizing issue, it was met with great and constant communication…the exchange was a breeze. when it came to a shipping issue, i barely had to say anything and the problem was solved AND THEN SOME!!! With hardly anyback and forth.
i’ve NEVER had this experience with any other company. to say i love the hat would be an understatement…i love the company!

David L
Love the new addition to my hat collection.

Love the quality, craftsmanship and look and feel of the new addition to my hat collection. For over 20 years I been buying from another hat company, they used to have stores here in LA but have closed them down, I would have to travel to SFO to visit a store or San Diego on only Thurs-Sun. Two Roads can improve on the shipping practices and not wait a week before shipping out.

Hey David, thanks for the feedback. Happy to see that you love the hat, but thanks for letting us know about the shipping. We were slightly backlogged a couple of weeks ago due to some big promotions, but we're back on track and running smoothly.