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
110 months ago
Wow that is sharp!
Score: 2 Votes (Like | Disagree)
ActionableMango Avatar
110 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
110 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
110 months ago
The bag does look sharp!
Score: 1 Votes (Like | Disagree)
dingle19 Avatar
110 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
110 months ago
Oh wow, this looks amazing!
Score: 1 Votes (Like | Disagree)

Popular Stories

Apple iPhone 16e Feature

Apple Announces iPhone 16e With A18 Chip and Apple Intelligence, Pricing Starts at $599

Wednesday February 19, 2025 8:02 am PST by
Apple today introduced the iPhone 16e, its newest entry-level smartphone. The device succeeds the third-generation iPhone SE, which has now been discontinued. The iPhone 16e features a larger 6.1-inch OLED display, up from a 4.7-inch LCD on the iPhone SE. The display has a notch for Face ID, and this means that Apple no longer sells any iPhones with a Touch ID fingerprint button, marking the ...
iphone 17 pro asherdipps

iPhone 17 Pro Models Rumored to Feature Aluminum Frame Instead of Titanium Frame

Tuesday February 18, 2025 12:02 pm PST by
Over the years, Apple has switched from an aluminum frame to a stainless steel frame to a titanium frame for its highest-end iPhones. And now, it has been rumored that Apple will go back to using aluminum for three out of four iPhone 17 models. In an investor note with research firm GF Securities, obtained by MacRumors this week, Apple supply chain analyst Jeff Pu said the iPhone 17, iPhone...
apple launch feb 2025 alt

Here Are the New Apple Products We're Still Expecting This Spring

Thursday February 20, 2025 5:06 am PST by
Now that Apple has announced its new more affordable iPhone 16e, our thoughts turn to what else we are expecting from the company this spring. There are three product categories that we are definitely expecting to get upgraded before spring has ended. Keep reading to learn what they are. If we're lucky, Apple might make a surprise announcement about a completely new product category. M4...
iPhone 17 Roundup Feature 2

iPhone Design to Change 'Significantly' This Year

Monday February 17, 2025 7:09 am PST by
Apple is set to "significantly change" the iPhone's design language later this year, according to a Weibo leaker. In a new post, the user known "Digital Chat Station" said that the iPhone's design is "starting to change significantly" this year. The "iPhone 17 Air" reportedly features a "horizontal, bar-shaped" design on the rear, likely referring to an elongated camera bump. On the other...
apple launch feb 2025

Tim Cook Teases an 'Apple Launch' Next Wednesday

Thursday February 13, 2025 8:07 am PST by
In a social media post today, Apple CEO Tim Cook teased an upcoming "launch" of some kind scheduled for Wednesday, February 19. "Get ready to meet the newest member of the family," he said, with an #AppleLaunch hashtag. The post includes a short video with an animated Apple logo inside a circle. Cook did not provide an exact time for the launch, or share any other specific details, so...
Generic iOS 18

Here's When Apple Will Release iOS 18.4

Wednesday February 19, 2025 11:38 am PST by
Following the launch of the iPhone 16e, Apple updated its iOS 18, iPadOS 18, and macOS Sequoia pages to give a narrower timeline on when the next updates are set to launch. All three pages now state that new Apple Intelligence features and languages will launch in early April, an update from the more broader April timeframe that Apple provided before. The next major point updates will be iOS ...
iOS 18

iOS 18.4 Coming Next Week With These New Features for Your iPhone

Friday February 14, 2025 6:18 am PST by
The first iOS 18.4 beta for iPhones should be just around the corner, and the update is expected to include many new features and changes. Bloomberg's Mark Gurman expects the iOS 18.4 beta to be released by next week. Below, we outline what to expect from iOS 18.4 so far. Apple Intelligence for Siri Siri is expected to get several enhancements powered by Apple Intelligence on iOS...
Apple 2025 Thumb 1

Two of Apple's Oldest Products Are Finally Getting Updated This Year

Friday February 14, 2025 6:03 am PST by
Apple released the HomePod mini in November 2020, followed by the AirTag in May 2021, and both still remain first-generation products. Fortunately, rumors suggest that both the HomePod mini and the AirTag will finally be updated at some point this year. Below, we recap rumors about the HomePod mini 2 and AirTag 2. HomePod mini 2 In January 2025, Bloomberg's Mark Gurman said Apple is ...