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
113 months ago
Wow that is sharp!
Score: 2 Votes (Like | Disagree)
ActionableMango Avatar
113 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
113 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
113 months ago
The bag does look sharp!
Score: 1 Votes (Like | Disagree)
dingle19 Avatar
113 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
113 months ago
Oh wow, this looks amazing!
Score: 1 Votes (Like | Disagree)

Popular Stories

Mayday Calendar

Apple Acquisition Hints at Upgraded Calendar App on iOS 19 or Beyond

Friday May 9, 2025 9:13 am PDT by
Apple acquired Canadian startup Mayday Labs in April 2024, according to a European Commission listing, spotted by French blog MacGeneration. The acquisition had not received widespread attention from tech publications until now. Apple is legally required to report certain acquisitions to the European Commission, under the terms of the EU's Digital Markets Act. Mayday Labs founder Jeremy...
Nineth iOS 19 Feature

iOS 19 Beta is a Month Away With These New Features for Your iPhone

Thursday May 8, 2025 7:37 am PDT by
The first iOS 19 beta is just one month away, and there are already many new features and changes that are expected with it. Apple should seed the first iOS 19 beta to developers immediately following the WWDC 2025 keynote, which is scheduled for Monday, June 9. Following beta testing, the update should be released to the general public in September. Below, we recap the key iOS 19 rumors...
iOS 18

Apple Releases iOS 18.5 With New Wallpaper, Screen Time Changes, Carrier Satellite Support for iPhone 13 and More

Monday May 12, 2025 10:06 am PDT by
Apple today released iOS 18.5 and iPadOS 18.5, the fifth updates to the iOS 18 and iPadOS 18 operating systems that came out last September. iOS 18.5 and iPadOS 18.5 come a little over a month after Apple released iOS 18.4 and iPadOS 18.4. The new software can be downloaded on eligible iPhones and iPads over-the-air by going to Settings > General > Software Update. The iOS 18.5 update has a...
fortnite apple featured

Epic Games Submits Fortnite to U.S. App Store

Friday May 9, 2025 9:57 am PDT by
As promised, Epic Games today submitted Fortnite to the U.S. App Store, and if approved by Apple, it will mark the first time that the Fortnite app has been available in the United States since 2020. Fortnite will include options to purchase in-app currency from the web rather than through in-app purchase, which is what got the game banned to begin with. This time, though, Apple has been...
iOS 18

Here Are Apple's Full iOS 18.5 Release Notes

Tuesday May 6, 2025 2:17 pm PDT by
Apple today seeded the release candidate version of iOS 18.5 to developers and public beta testers, giving us a look at the final version of the update that will be provided to the public next week. With the release candidate, Apple provided release notes, so we have a more complete look at the new features that are included in the update, including those that weren't found during the beta...
AirPods Pro 3 Mock Feature

AirPods Pro 3 Just Months Away – Here's What We Know

Tuesday April 29, 2025 1:30 am PDT by
Despite being more than two years old, Apple's AirPods Pro 2 still dominate the premium wireless‑earbud space, thanks to a potent mix of top‑tier audio, class‑leading noise cancellation, and Apple's habit of delivering major new features through software updates. With AirPods Pro 3 widely expected to arrive in 2025, prospective buyers now face a familiar dilemma: snap up the proven...
iPhone 17 Pro Blue Feature Tighter Crop

WSJ: Apple Weighing Price Hikes for iPhone 17 Lineup Without Blaming Tariffs

Monday May 12, 2025 3:36 am PDT by
Apple is considering raising prices for its upcoming iPhone 17 models set to release this fall, according to people familiar with the matter cited by The Wall Street Journal. The company reportedly aims to pair the potential price hikes with new features and design changes to justify the increased cost to consumers, rather than attributing them to U.S. tariffs on goods from China. The...