The Measure

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What to Pack for the Perfect 3-Day Weekend: A Gentleman’s Guide

We've got the essential kit for a weekend in Chicago, Montauk, or Lake Tahoe.

October 2nd, 2015

Labor Day is upon us, boys. That’s right: The three-day weekend is here!

Some of us will head to the outdoors while others will be seeking some R&R in the city.

Whichever direction you’re headed, we want to make it easy for you to pack. Don’t be the guy who asks to turn the car around to get his lucky Cubs baseball cap.

First things first, we need something to put all this gear into. Grab yourself a weekender bag. We like the vintage Dolce & Gabbana bag shown above. If you can’t find a bag just like this, look for something simple, classic, and not too big. Remember, you’re packing for a three-day weekend, not two weeks in Europe.

Basics are a man’s best friend, so pack a couple v-necks, a couple changes of socks and your go-to sweater for when it gets a little chilly. Let’s not forget a few button-ups to show the guys that you still have some type of class.

And definitely grab a camera to document the trip. Sure, you could use a smartphone. But isn’t it more fun to use a camera that actually takes awesome photos?

Now, what you pack will be a little different depending on where you’re going. To help motivate and inspire you, we’ve got packing lists for three classic weekend destinations.

Oh, and just because there are no pants in these pictures doesn’t mean you should forget those!


You never know what’ll happen over the course of a long weekend, so throw in a tie and even that double ring belt to dress things up a bit, in case you find yourself heading to a fancy restaurant. And don’t forget that Cubs hat!


Chicago items:  Cubs hat, V-neck in white, Dolce & Gabbana bag, Broadway in Blue & Coral, Single ring belt, Canon AE-1, Mcallister tie in green, Bi-fold wallet in brown, Card holder in brown, Piedmont blazer, Broadway in Blue & Olive, Fulton tie in black,  Coleman sweater in Dark Indigo, Andy Pratt notebook, Walk over shoes, mechanical pencil, fifth avenue playing cards.

Montauk, New York

If you’re heading to the seashore, grab a towel — it isn’t something you should share at your age. You’re also going to need some flip flops so you don’t get your shoes all sandy. And you’re going to want some shade from the sun, so pack a hat.


Montauk items: Abruzzo Blazer, beach towel, Dolce & Gabbana bag, fedora, double ring belt, Coleman sweater in black, V-neck in white, Bi-fold wallet in brown, Vernon in green, Vernon in Blue, Camino, Mcallister in navy, Rainbow sandals.

Lake Tahoe, California

If you’re headed to the lake, button up your chambray shirt, pull on some Red Wing boots, and grab a lantern and a camp cup for your outdoor evening adventures. But don’t forget a map! You too can become a modern day – not to mention very stylish – Indiana Jones.


Tahoe items: Vernon light grey, Crawford in navy, double ring belt, zip wallet in brown, Everitt, Mitani blazer in dark khaki, Dolce & Gabbana bag, lantern, coleman camp cup, Red Wings, V-neck in white, journal, mechanical pencil, Lombard tie in burnt red, map of Lake Tahoe.

Hopefully this list of essentials has helped make things a bit easier for you moving into the last glorious 3-day weekend of summer. Now grab yourself a beer and kick back – it’s time for some well-earned R&R.

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