The Tweed Ride: Cycling, Vintage Fashion & Hats!

The Tweed Ride: Cycling, Vintage Fashion & Hats!

What-ho, Hatty Folks! 

Have you ever pined for days past when gentlemen and ladies could be seen in dapper morning dress perched atop whimsical penny-farthing bicycles, or swanky Gatsby era tweed plus four suits donned for afternoon bicycle rides to a picnic in the park? 

You’re in luck, because your love of bicycling, vintage style, and hats all come together in a fantastic pageantry of delight in the Tweed Ride events held world wide!

But What Exactly is a Tweed Ride?

While there have no doubt been several vintage biking social groups spread throughout the world, the first coined “Tweed Run” came about in London during the winter of 2009, and has remained an annual event that has grown every year–even inspiring Tweed Rides in cities throughout the world! 

Washington DC has even hosted their own Tweed Rides since later that same year–brought to fruition by Eric Brewer, with the latest being November 2022, organized by the Dandies and Quaintrelles social club. The Tweed Ride has become such a hip event, they have even opted to start doing a Spring event dubbed The Seersucker Social. Fantastic!!

Tweed Rides, no matter where they are hosted, tend to be leisurely, social events. Packing for tea or a picnic is generally recommended, and it’s a refreshing way to see the city or bike paths one might usually take in a new fashion. There might be charity events tied in, but not always–so we recommend checking out the hosting groups and event pages you may find to get an idea of just what to expect. Either way, it’s sure to be a unique and entertaining time. 

What Do You Wear to a Tweed Ride, though?

Well–you know… Tweed. At the very least in one piece or so. There is never a really strict dress code to these events, and they hope participants have a bit of fun with it, but if you’re wanting to stick to traditions of the event, you can’t go wrong with 1920s day fashion like the tweed plus four suits or for the ladies likened trim functionality in day suits fitting to the period. While 1920s fashions seem to be the main point of focus, it isn’t uncommon to see dapper gents and ladies in Victorian morning dress attire with top hats, bowlers, and fascinators or pinned hats–some all the more fantastic with a Steampunk edge! If there’s competition for Best Dandy and Best Dame fashion, be sure to put your best foot forward! But most importantly, have fun with it!

Topping of Your Look

So you’ve put together an outfit you wish to wear, but something seems to be missing–maybe it’s time to top it off with a hat to really cinch the look together! This is where we come in, and boy, do we have quite the range in selection for you to find your perfect Tweed Ride Ready topper!


Tweed Caps

It's likely a good ol' tweed cap was the first hat to come to mind thinking of the Tweed Ride, and they are without doubt the easiest to try and pair with most any type of attire, event or everyday, and versatile enough to be considered both a man's cap and woman's cap. (An added bonus for the ladies: they come sized!)

Two main styles of caps you'll want to look into are newsboys and flat caps, so let's get started!


What better cap for Gatsby era attire than a style of hat who is also referred to as the "Gatsby"? With their roomy eight panels and classic profiles, newsboys give a nod to vintage style no matter what you pair them with. 

Wigens Shelby Green herringbone newsboy cap

The Wigens Shelby is a prime example of wool herringbone tweed with a sporty classic cut, and is lined inside for added comfort during wear. If you're there to wow your fellow riders, the Shelby has pop! with that rich green to set you apart.

Similarly, we also have the more barleycorn tweed styled Belfry Dunbar with its gray base and beautiful bright flecks of blues, yellows and reds, as well as the Belfry Grimsby for those that wish to have a more earth toned hat to work with. 

Flat Caps   

With their sleeker profile given by usually single panels atop the cap that are tacked down along the bill, flat caps, or here more specifically Ivy Leagues, fit just as readily into 1920s styled attire, and make a staple addition to any wardrobe well after any event you might wish to wear them to. 

Keeping to the more classic flat cap styled cuts for these, may we suggest the Wigens Oliver for a tartan-styled tweed that isn't afraid to show off some color?

Wigens Luke alpaca plaid cap

Or perhaps the soft grays of the Wigens Luke with it's soft-to-the-touch blend of alpaca and wool?

For more flexible options, we also offer the Wigens Georgie in a neutral barleycorn tweed, and the beautiful, terracotta rust of the Belfry Geofredo in a plain twill that still impresses. 


Though most of the remaining hats we'll recommend might not be tweed themselves, they'll surely pair well with any such attire to keep you looking sharp. With their classy (and classic) styles and shapes, they will add the perfect final touch to your Tweed Ride look. 

Berets and Tams

For the discerning dame wanting a touch of Parisian feminine flair to their vintage inspired look, tams and berets are the perfect grab and go that will hold on through your cycling adventure!

Hand painted burnt orange beret

The Belfry Verrazza  may be cute, but this tam doesn't hold back with its meticulous hand painted floral design. 

In counter, should you find the Tweed Ride you have your eye on is during the chillier part of the fall or winter, might we suggest the Belfry Emma? This knit beret will keep you warm while still being a delight in its cheerful teal with felt accents. 

Top Hats and Bowlers

Should you fancy taking a trip further back in time than the 1920s, or even alternative history where steam power and clockwork are all the rage, it's perfectly suitable to top off your look with a fashionable top hat or bowler to fit any Victorian and Steampunk silhouette.

Classic Opera Top Hat

The Belfry John Bull is a classic felt top hat with a slightly flared crown to fit any Victorian gent as he dons his morning dress to take on the day, but if you want a bit of a more rounded profile, the Belfry Tammany is a perfect bowler alternative! Both of these hats are also a perfect blank canvas for any Steampunk alterations you may have in mind as well, so the sky's the limit! 


Drifting casually back into styles more fitting for the 1920s, what about the romantic cloche? 

That said, a nice added bonus to the cloche is that it tends to hug closer down on the head to frame your face, so there should be little worry about the wind in this lovely brimmed style. Win, win!

Belfry Demaria brown cloche hat

Some to consider are the Belfry Demaria blocked into very flattering asymmetrical wool cloche style, and available in two colors (you heard us right, ladies!) You might fancy the Belfry Tortona, an updated wool mod cap with color-blocked style and feminine bow accent. 



Caps not really your thing, but still wanting to pull off a 1920s look? There's nothing wrong with opting for a fedora for the right touch of pizazz! 

Plaid tweed fedora

We even happen to have a tweed fedora to substitute for a tweed cap should you like, called the Belfry Danilo.

If a full felt fedora is more where you'd like to focus, the Belfry Bartolo comes in a treated wool to keep you covered rain, snow, or shine, and our Stetson District and Chapman are fur felt alternatives for those who may be sensitive to wool that could come in direct contact to their skin, and they feel absolutely amazing to the touch.  


What we consider the classic hat for the warmer seasons, boaters have been a hat for leisure since the late nineteenth century, and a staple for many of our ladies and gents that go to events in the spring and summer. We absolutely had to include the boater for anyone thinking of finding a Seersucker Social to go to!


Made of handwoven Panama straw, the Belfry Venice has a classic navy and red band, but if you want to really accent your look, the Belfry Brooks comes in a beautifully warm putty color with flashes of bright stripes on its band. Pairing off either of these with a trim seersucker suit will have you fit to flaunt at any park for a mid-ride picnic or tea!


There are so, so many more options available for you to peruse with us at Hats in the Belfry, but we hope we helped get you started. We look forward to seeing your pics if you do attend a Tweed Run or Tweed Ride, so please always feel free to tag us on any of our social media platforms (we love to see or #BelfrySelfie tag used too)!

Until next time!