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Dark Grey - Brown
Dark Grey - Black
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 3 reviews
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.

Paul S
Perfect, go-to hat

This hat is perfect! The brim is perfect length, not too long, not to short. The crown is the perfect size, doesn't stand too far off your head (which I think looks silly on me). Love that it's hard felt, feel sturdy, won't lose it's shape like a soft felt hat might. For me the 59 size was spot on, it's not too tight or too loose. It's tight enough I can bend over to pick something up and it doesn't fall off, but loose enough that it's comfortable and I can fit a handkerchief underneath it when I want (in case I anticipate sweating a bit). I wear this hat all the time, even just chilling in the house, bought a second one cause clearly this is going to get a lot of use. I would love to see other colors but especially a true/dark black with dark gray as the accent color.


I purchased this hat for my fiancé who doesn’t really wear hats. He absolutely loves it! The quality of the hat is 10/10.
My fiancé is now a hat guy and will definitely be purchasing more hats from this brand!

Customer Reviews

Based on 2 reviews Write a review

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