For the last few weeks, MacRumors has been running a special giveaway event, highlighting high-quality luxury bags from manufacturers like Pad & Quill, Intrepid Bag Co, Whipping Post, and Saddleback Leather Company, and now our event is coming to an end with one final giveaway from Intrepid Bag Co.

This week, we're giving away Intrepid Bag Co.'s Wayfarer Leather Messenger Bag, which is superbly designed and undeniably stylish. Made from a thick full grain coffee-colored saddle leather, the Wayfarer Messenger Bag is big enough to hold a 15-inch MacBook Pro and it boasts the most pockets out of any of the bags we've given away while also being the most compact.

wayfarer1
Measuring in at 16 inches wide by 12 inches tall by 4.5 inches deep, the Wayfarer Messenger Bag has a magazine pocket at the back, a large full-length front pocket, and an interior area featuring a padded MacBook pocket, two deep interior pockets, a main compartment, a pen pocket, a phone pocket, and a pocket with a clasp. The whole bag closes up with two front buckles so the contents stay secure during travel.

With all of the pockets and space inside the Wayfarer Messenger Bag, there was room to hold almost any Apple device and accessory I own (MacBook Pro, Retina MacBook, iPad Pro, iPad mini and iPhone), with leftover space for a lightweight hoodie, a water bottle, loose papers, two notebooks, three small books, and other small bits and bobs.

wayfarer2
The Wayfarer Messenger Bag is super rigid and stiff when it arrives, but it should loosen up and wear in with usage, gaining its own unique, lived in look. Along with the aforementioned outside buckles, there's an adjustable shoulder strap and a separate hand strap for carrying it around.


Intrepid Bag Co's Messenger Bag was one of the neatest and sharpest I took a look at, with careful stitching, a herringbone lining, and copper accents. Intrepid Bag Co normally prices its Wayfarer Leather Messenger Bag at $469, but one MacRumors reader will win one for free.

To enter to win, use the Rafflecopter widget below and enter an email address. Email addresses will be used solely for contact purposes to reach the winner and send the prize. You can earn additional entries by subscribing to our weekly newsletter, subscribing to our YouTube channel, following us on Twitter, or visiting the MacRumors Facebook page.

Due to the complexities of international laws regarding giveaways, only U.S. residents who are 18 years of age or older are eligible to enter. To offer feedback or get more information on the giveaway restrictions, please refer to our Site Feedback section, as that is where discussion of the rules will be redirected.

The contest will run from today (September 23) at 11:00 a.m. Pacific Time through 11:00 a.m. Pacific Time on September 30. The winner will be chosen randomly on September 30 and will be contacted by email. The winner will have 48 hours to respond and provide a shipping address before a new winner is chosen.

Top Rated Comments

strayts Avatar
119 months ago
Wow that is sharp!
Score: 2 Votes (Like | Disagree)
ActionableMango Avatar
119 months ago
Man, this is a beautiful bag. Am i the only one that refrains from entering every contest except for the ones I could really use or really want, so that i build up the "lucky karma" for not spamming and diluting every contest with my entries?

No? Just me? Alrighty, then.
I am fully supportive of this idea. In fact, I suggest everyone else also not enter any giveaway that I'm in. ;)
Score: 1 Votes (Like | Disagree)
sp3k0psv3t Avatar
119 months ago
Nice bag....

No shot at winning it but still nice bag!

Love the leather/suede/canvas combination; very durable.
Score: 1 Votes (Like | Disagree)
guychicago Avatar
119 months ago
The bag does look sharp!
Score: 1 Votes (Like | Disagree)
dingle19 Avatar
119 months ago
Man, this is a beautiful bag. Am i the only one that refrains from entering every contest except for the ones I could really use or really want, so that i build up the "lucky karma" for not spamming and diluting every contest with my entries?

No? Just me? Alrighty, then.
Score: 1 Votes (Like | Disagree)
Traverse Avatar
119 months ago
Oh wow, this looks amazing!
Score: 1 Votes (Like | Disagree)

Popular Stories

iOS 26

iOS 26.1 Coming Soon: New Features for Your iPhone and Release Date

Monday October 27, 2025 7:55 am PDT by
The upcoming iOS 26.1 update includes a handful of new features and changes for iPhones, including a toggle for changing the appearance of the Liquid Glass design, "slide to stop" for alarms in the Clock app, and more. Below, we outline key details about iOS 26.1. Release Date Given that Apple has yet to seed an iOS 26.1 Release Candidate, which is typically the final beta version, the...
maxresdefault

Apple TV 4K Could Still Launch Before 2025 Ends: All the Rumored Features

Monday October 27, 2025 4:51 pm PDT by
Apple is designing an updated version of the Apple TV 4K, and rumors suggest that it could come out sometime in the next couple of months. We're not expecting a major overhaul with design changes, but even a simple chip upgrade will bring major improvements to Apple's set-top box. Subscribe to the MacRumors YouTube channel for more videos. We've rounded up all the latest Apple TV rumors. ...
iOS 26 Maps Glass

Apple Reportedly Moving Ahead With Ads in Maps App

Sunday October 26, 2025 6:22 am PDT by
Apple Maps could feature integrated ads as soon as next year, Bloomberg's Mark Gurman reports. In his latest "Power On" newsletter, Gurman said that Apple's plan to bring more ads to iOS is moving "gaining traction," with the Maps app being next in line. The project will apparently give restaurants and other businesses the option to pay to have their details featured more prominently in...
iOS 26 Battery Glass Feature

iOS 26.1 Beta Liquid Glass Battery Drain Test: Tinted vs Clear Mode

Friday October 24, 2025 2:30 pm PDT by
In the fourth iOS 26.1 beta, Apple added a "Tinted" option that reduces the translucency of Liquid Glass for those who prefer a more opaque look. I saw some comments wondering whether the setting might preserve battery life, so I thought I'd do some testing. Test Settings I did four separate tests using the iPhone 17 Pro Max, and I kept the parameters as similar as possible. Here are the...
M6 MacBook Pro Feature 1

M6 MacBook Pro: Release Date, Pricing, and What to Expect

Monday October 27, 2025 9:15 am PDT by
Apple this month refreshed the 14-inch MacBook Pro base model with its new M5 chip, and higher-end 14-inch and 16-inch MacBook Pro models with M5 Pro and M5 Max chips are expected to follow in early 2026. However, these machines will represent the final update to the current design, with Apple reportedly developing a completely new version of the MacBook Pro packed with next-generation hardware...
iOS 26

6 New Things Your iPhone Can Do in iOS 26.1

Wednesday October 29, 2025 4:22 am PDT by
Apple is about to drop iOS 26.1, the first major point release since iOS 26 was rolled out in September, and there are at least six notable changes and improvements to look forward to. We've rounded them up below. Apple has already provided developers and public beta testers with the release candidate version of iOS 26.1, which means Apple will likely roll out the update to all compatible...
iOS 26

iOS 26.1 Coming Soon With These 8 New Features for Your iPhone

Wednesday October 22, 2025 6:15 am PDT by
The upcoming iOS 26.1 update includes a handful of new features and changes for iPhones, including a toggle for changing the appearance of the Liquid Glass design, "slide to stop" for alarms in the Clock app, and more. iOS 26.1 is currently in beta testing. The update will likely be released in the first half of November, and it is compatible with the iPhone 11 series and newer, but some...
iOS 26

Apple Seeds iOS 26.1, iPadOS 26.1, and macOS Tahoe 26.1 Release Candidates

Tuesday October 28, 2025 1:07 pm PDT by
Apple today provided developers and public beta testers with the release candidate versions of upcoming iOS 26.1, iPadOS 26.1, macOS Tahoe 26.1, tvOS 26.1, watchOS 26.1, and visionOS 26.1 updates for testing purposes. The RCs betas come a week after Apple released the fourth betas. The new betas can be downloaded from the Settings app on a compatible device by going to General > Software...
swift for android

Developers Can Now Make Android Apps With Apple's Swift

Sunday October 26, 2025 4:23 am PDT by
The first preview release of the Swift SDK for Android was published this week, allowing developers to build Android apps in Swift with official tooling and making it easier to share code across iOS and Android. The SDK enables Android apps to be built in Swift using officially supported tooling rather than community workarounds. In June, it was announced that Apple's Swift programming...