Chocolatey swag over the years

Published on 20 June 2020

I have been involved in the Chocolatey project in one way or another for a lot of years, and in that time, I have collected a lot of Chocolatey swag.

It wasn't until I was clearing out a few things, and looking at other collections of swag that I had, that I thought it would be a good idea to collect all of it into one place.

I might get the order of the creation of these wrong, or where they were given out, but I am hoping that Rob will be able to help out here to put them in the correct order, and also to provide more details.


Chocolatey Experience

This was the first official Chocolatey t-shirt which was created as part of the Chocolatey Kickstarter.

Chocolatey Experience - White

This t-shirt was also available in white (I chose to go for the black version). A photo of the white version was provided by Jan Karger.

Chocolatey Automation

Following on from the Kickstarter design, this became the default Chocolatey t-shirt for a long period of time.

This was a slight variation on the default t-shirt. colour

I don't think many of these ones were made, but it is one of my favourites.

Chocolatey Fest Front

Chocolatey Fest Back

This was the official t-shirt of the inaugural Chocolatey Conference, Chocolatey Fest, in 2018.

Grey Polo Shirt

Navy Polo Shirt

These ones are polo-shirts, which are only available to Chocolatey Employees and Contractors.

PSH Summit

This was given out to attendees of PSH Summit in 2019.


This t-shirt was given out to attendees at ChefConf in 2019, both here in the UK, and in the USA.


This t-shirt was given out at the AnsibleFest conference in 2019.

Chocolatey Strawberry Front

Chocolatey Strawberry Back

This was a limited edition run, featuring the "Config Management Strawberry Dipped in Chocolatey", created by Adil. This was given out in very limited numbers to attendees of both AnsibleFest and Puppetize. There aren't many of these in the wild, so definitely a collectors item if you have one!


This was given out to attendees of Puppetize in 2019.

Arc Reactor Blue

Arc Reactor Grey

Arc Reactor Black

This is another Adil design, and it is available in blue and grey, and it is inspired by the arc reactor from Iron Man. I believe I am right in saying that the blue and black ones are only available to Employees and Contractors for Chocolatey.

11th Birthday Colour

11th Birthday White

These t-shirts were created as part of the 11th Birthday celebrations for Chocolatey. Full praise goes to Steph for the creation of this design!



This was available to some Kickstarter backers, depending on what level you backed the project with.



Inspired by the Microsoft MVP Jacket, there is an official Chocolatey Jacket available to Chocolatey Employees and Contractors. This is an amazing quality jacket!


Hat Back

Hat Front Right

Hat Front Left

This was created by my colleague Stevie, and I absolutely love it! These were made in a very small quantity, and you should count yourself very lucky if you have one. This is my go to hat!

New Hat Front

New Hat Rear

Following on from his original creation, Stevie then created another amazing hat! This is my new go to hat!



Oh yes, in addition to creating a Package Manager for Windows, we have also created some Chocolate. This was given out to attendees at Chocolatey Fest in 2018.


Chocolatey Sticker

We have literally given out 1000's of these at various conferences over the years!

Chocolatey Fest

This sticker was given out to all attendees at Chocolatey inaugural conference Chocolatey Fest, in 2018.

Chocolatey Golden Ticket

In keeping with the Willy Wonka theme of Chocolatey Fest, the Chocolatey Golden Ticket sticker was created.

Chocolatey Strawberry

Chocolatey Strawberry Large

This is a reasonably new design created by my colleague Adil. It can be found in a couple different sizes.

11th Birthday

Similar to the t-shirts there were made for the 11th Birthday celebrations, a limited run of stickers were created.

Holographic Arc Reactor

Holographic Logo

Sponsorship Swag


WinOps Lanyard

WinOps Lanyard

As a sponsor of the WinOps events, Chocolatey has appeared on their lanyards at least a couple of times.

Chocolatey Fest Lanyard

If you attended Chocolatey Fest, you may well have kept a hold of yours as well!

KCDC 2018

Attendees of KCDC in 2018 were lucky enough to get one of these!


WinOps Bag

WinOps Bag

The Chocolatey logo has appeared on a number of WinOps bag which are given out to all attendees.


PowerShell Summit

If you attended the PowerShell Summit in 2018, you will find the Chocolatey Logo on the back!


The Chocolatey Logo appears on pretty much all the WinOps t-shirts!

Unofficial - but still awesome


Chocolatey and Boxstarter

Created by Manfred Wallner (a Chocolatey Community Member), this is a t-shirt showing the combination of Chocolatey and Boxstarter, which was the topic of his talk at the WinOps Conference.


Chocolatey Boxstarter

Manfred also took the time to create a sticker version of the t-shirt design that he created.

Rob The Founder

This was created by Stevie and Adil for the Founder of Chocolatey, Rob Reynolds.


Choco Poster

Inspired by some posters that I saw Patrik Svensson have made, I reached out to Bartek who created them, and had him make one for Chocolatey. This poster takes pride of place on the wall in my office!

If you have made it this far, thanks for reading. If you are aware of any other Chocolatey Swag, please let me know, I would love to hear about it!

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