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
120 months ago
Wow that is sharp!
Score: 2 Votes (Like | Disagree)
ActionableMango Avatar
120 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
120 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
120 months ago
The bag does look sharp!
Score: 1 Votes (Like | Disagree)
dingle19 Avatar
120 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
120 months ago
Oh wow, this looks amazing!
Score: 1 Votes (Like | Disagree)

Popular Stories

iOS 26

When Will Apple Release iOS 26.2?

Monday December 1, 2025 4:37 pm PST by
We're getting closer to the launch of the final major iOS update of the year, with Apple set to release iOS 26.2 in December. We've had three betas so far and are expecting a fourth beta or a release candidate this week, so a launch could follow as soon as next week. Past Launch Dates Apple's past iOS x.2 updates from the last few years have all happened right around the middle of the...
ios 18 to ios 26 upgrade

Apple Pushes iPhone Users Still on iOS 18 to Upgrade to iOS 26

Tuesday December 2, 2025 11:09 am PST by
Apple is encouraging iPhone users who are still running iOS 18 to upgrade to iOS 26 by making the iOS 26 software upgrade option more prominent. Since iOS 26 launched in September, it has been displayed as an optional upgrade at the bottom of the Software Update interface in the Settings app. iOS 18 has been the default operating system option, and users running iOS 18 have seen iOS 18...
maxresdefault

iPhone Fold: Launch, Pricing, and What to Expect From Apple's Foldable

Monday December 1, 2025 3:00 am PST by
Apple is expected to launch a new foldable iPhone next year, based on multiple rumors and credible sources. The long-awaited device has been rumored for years now, but signs increasingly suggest that 2026 could indeed be the year that Apple releases its first foldable device. Subscribe to the MacRumors YouTube channel for more videos. Below, we've collated an updated set of key details that ...
iphone 17 cyber

iPhone 17 Demand Is Breaking Apple's Sales Records

Tuesday December 2, 2025 9:44 am PST by
Apple's iPhone 17 lineup is selling well enough that Apple is on track to ship more than 247.4 million total iPhones in 2025, according to a new report from IDC. Total 2025 shipments are forecast to grow 6.1 percent year over year due to iPhone 17 demand and increased sales in China, a major market for Apple. Overall worldwide smartphone shipments across Android and iOS are forecast to...
iOS 26

Apple Seeds iOS 26.2 and iPadOS 26.2 Release Candidates to Developers and Public Beta Testers

Wednesday December 3, 2025 10:33 am PST by
Apple today seeded the release candidate versions of upcoming iOS 26.2 and iPadOS 26.2 updates to developers and public beta testers, with the software coming two weeks after Apple seeded the third betas. The release candidates represent the final versions of iOS 26.2 and iPadOS 26.2 that will be provided to the public if no further bugs are found during this final week of testing....
Touchscreen MacBook Feature

Here Are the Four MacBooks Apple Is Expected to Launch Next Year

Monday December 1, 2025 5:00 am PST by
2026 could be a bumper year for Apple's Mac lineup, with the company expected to announce as many as four separate MacBook launches. Rumors suggest Apple will court both ends of the consumer spectrum, with more affordable options for students and feature-rich premium lines for users that seek the highest specifications from a laptop. Below is a breakdown of what we're expecting over the next ...
Photos App Icon Liquid Glass

John Gruber Shares Scathing Commentary About Apple's Departing Software Design Chief

Thursday December 4, 2025 9:30 am PST by
In a statement shared with Bloomberg on Wednesday, Apple confirmed that its software design chief Alan Dye will be leaving. Apple said Dye will be succeeded by Stephen Lemay, who has been a software designer at the company since 1999. Meta CEO Mark Zuckerberg announced that Dye will lead a new creative studio within the company's AR/VR division Reality Labs. On his blog Daring Fireball,...
iphone air camera

iPhone Air's Resale Value Has Dropped Dramatically, Data Shows

Thursday December 4, 2025 5:27 am PST by
The iPhone Air has recorded the steepest early resale value drop of any iPhone model in years, with new data showing that several configurations have lost almost 50% of their value within ten weeks of launch. According to a ten-week analysis published by SellCell, Apple's latest lineup is showing a pronounced split in resale performance between the iPhone 17 models and the iPhone Air....
chatgpt logo

Sam Altman Declares 'Code Red' for ChatGPT, Delays OpenAI Advertising Plans

Tuesday December 2, 2025 3:30 pm PST by
OpenAI is deprioritizing work on advertising as it focuses on improving the quality of ChatGPT, reports The Information. OpenAI CEO Sam Altman declared a "code red" on Monday, and told employees that the company needs to improve ChatGPT so it doesn't fall behind competitors like Google and Anthropic. Altman said that OpenAI needs to work on personalization for each user, image generation,...
Sad Siri Feature

Apple AI Chief John Giannandrea Retiring After Siri Delays

Monday December 1, 2025 2:16 pm PST by
Apple AI chief John Giannandrea is stepping down from his position and retiring in spring 2026, Apple announced today. Giannandrea will serve as an advisor between now and 2026, with former Microsoft AI researcher Amar Subramanya set to take over as vice president of AI. Subramanya will report to Apple engineering chief Craig Federighi, and will lead Apple Foundation Models, ML research, and ...