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How To Dress For a Regatta, the Ultimate Preppy Tailgate

How To Dress For a Regatta, the Ultimate Preppy Tailgate: tfxc/Flickr Creative Commons

tfxc/Flickr Creative Commons

This weekend marks the 50th running of the Head of the Charles regatta. The legendary rowing event takes place along the Charles River in Boston. It began in 1965 and has grown into the world’s largest two-day regatta, attracting rowers of all ages and 400,000 spectators.

It’s also, to use the local dialect, a wicked awesome party. Technically, the Head of the Charles is about the rowers, and there are winners and losers and all that. But, it’s also an enormous preppy tailgate, a WASPy Freaknik, if you will.

Even though it’s a big party, you still want to look your best. Unless you are an actual oarsmen, we suggest you shy away from the rowing blazer. Instead, stick to the preppy classics. You’ll fit in with the Boston Brahmins in no time.

Here is our Head of the Charles style guide.


Fair Ends Cap
$48, fairends.com
Rowers love stripes. This soft brushed twill cap from Fair Ends allows you to rock that style without declaring any school allegiance.

Fair Ends

Fair Ends


Warby Parker Griffin Sunglasses
$95 (non-prescription), warbyparker.com
A classic shape and a timeless tortoise shell color make these the perfect shades for the event. They’ll also come in handy the following day, when you’re muttering to yourself, “Sunglasses and Advil, last night was mad real.”

Warby Parker

Warby Parker


J. Press York Street Oxford Shirt
$125, jpressonline.com
J. Press has been making clothes for Ivy Leaguers for generations. The new York Street line is designed by the brothers behind Ovadia & Sons and features the same great J. Press craftsmanship in more modern fits.

J. Press

J. Press


Polo Fair Isle Sweater
$285, polo.com
It doesn’t get much more classic than the Fair Isle sweater with its intricate woven pattern.

Polo

Polo


Barbour Heritage Liddesdale Jacket
$189, nordstrom.com
There’s a reason this jacket made it into our 50 must-have fall classics. It provides the ideal amount of warmth for fall and looks equally sharp over a suit or a sweatshirt.

Barbour

Barbour


Carhartt WIP Club Pants
$120, carhartt-wip.com
It’s hard to go to a construction site and not see a pair of Carhartt pants. With its WIP (it stands for Work In Progress) line, Carhartt blends its expertise in creating durable workwear with sleek styling.

Carhartt WIP

Carhartt WIP


Timberland 3-Eye Classic Lug Shoes
$130, timberland.com
The lug sole on these full-grain burgundy leather shoes is thick enough that you won’t mind tramping along the banks of the river, or through any party fouls.

Timberland

Timberland


Steiner Safari Ultrasharp Binoculars
$194.99, binoculars.com
Whether you actually watch the rowing or just want a closer look at that hot girl down the river, these compact waterproof binoculars with 8x magnification will do the trick.

Binoculars.com

Binoculars.com


Snow Peak Titanium Flask
$150, snowpeak.com
Aside from being an incredibly strong and lightweight metal, titanium also doesn’t produce any metallic taste so whatever booze you put inside will keep its flavor profile in tact. What to put in your flask? Well, we’ve got the perfect booze for you.

Snow Peak

Snow Peak


Justin Tejada is a writer and editor based in New York City. Follow him on Twitter at @just_tejada.

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