For the next few weeks, MacRumors is running a special giveaway event, which will see us highlighting and giving away high-quality luxury bags from manufacturers like Pad & Quill, Intrepid Bag Co, Whipping Post, and Saddleback Leather Company. We've got all of these bags on hand so we can give clear details on construction, quality, utility, and more.

For today's giveaway, we've teamed up with Whipping Post to give away one of the company's all leather suede-lined Vintage Messenger Bags, designed to pay homage to antique postal bags. Compared to each of the bags in the giveaway, Whipping Post's Vintage Messenger bag is the softest and the lightest, but still with enough structure to hold all of your gear.

whippingpostvintagemessenger
Measuring in at 18.5 inches by 11.5 inches by 4 inches, it is large enough to hold a notebook as big as a 15-inch MacBook Pro, and it even has a dedicated MacBook or iPad section inside the bag. There's a big magazine pocket at the back of the bag, a smaller front pocket, and an inner pocket divided into two parts.

It's thin, which I liked, but it also expands outward once it's filled with stuff, and due to its malleability and its ability to expand, the Vintage Messenger Bag holds a lot of stuff (but it never looks overly bulky). It fit my MacBook Pro, two iPads, several notebooks and loose papers, a water bottle, and a bunch of various accessories and sundries.

whippingpostvintagemessenger3
The inside laptop flap clasps with a leather strap, as does the front flap, keeping both securely shut. The straps are, however, designed in a way that makes the bag easy to open and get into quickly, something I appreciated. There's a thin handle at the top so it can be held like a briefcase, and there's also a padded shoulder strap that can be adjusted to several different sizes with a set of buckles.


The Vintage Messenger Bag comes in a nice chocolate red color, which is pristine out of the box, but I suspect it will wear nicely and gain a lot more character once it's broken in. Whipping Post typically charges $295 for its Vintage Messenger Bag, but one MacRumors reader will get 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 9) at 11:00 a.m. Pacific Time through 11:00 a.m. Pacific Time on September 16. The winner will be chosen randomly on September 16 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

Jimmy James Avatar
99 months ago
Nice bag. I'm going to change citizenship and enter the draw.
Score: 3 Votes (Like | Disagree)
jonnysods Avatar
99 months ago
That's one tasty looking bag, but there's no chance because I live in maple syrup land.
Score: 2 Votes (Like | Disagree)
macrumorsuser10 Avatar
99 months ago
I don't get the name of this company. Why would anyone name a company after a sadistic ('https://en.wikipedia.org/wiki/Pillory'), racist ('https://3chicspolitico.com/2015/02/11/black-history-the-slave-whipping-post/') tool for torture?
Score: 2 Votes (Like | Disagree)
indiekiduk Avatar
99 months ago
bit saggy looking, not enough padded protection
Score: 1 Votes (Like | Disagree)
Anonymous Freak Avatar
99 months ago
This is not "vintage". Vintage means something old, not a newly-manufactured product. Same idiots who call any vaguely old-fashioned looking bar a "speakeasy". Can we stop letting millennials name things?
Exactly. While I think the style of the bag is okay, (and I'm definitely entering the contest) don't use "vintage" as a part of a name for a new product. It's like saying "buy our new Antique Furniture!" You can call it "retro" because that doesn't explicitly mean "old" the way vintage does. You can even use in the description "vintage-inspired" if you want to be all hipster and draw people in, but don't use the word "Vintage" right in the name of the product - unless you have actually found a stock of old items you're selling off.
Score: 1 Votes (Like | Disagree)
ignatius345 Avatar
99 months ago
This is not "vintage". Vintage means something old, not a newly-manufactured product. Same idiots who call any vaguely old-fashioned looking bar a "speakeasy". Can we stop letting millennials name things?
Score: 1 Votes (Like | Disagree)

Popular Stories

reset password request iphone

Warning: Apple Users Targeted in Phishing Attack Involving Rapid Password Reset Requests

Tuesday March 26, 2024 4:34 pm PDT by
Phishing attacks taking advantage of Apple's password reset feature have become increasingly common, according to a report from KrebsOnSecurity. Multiple Apple users have been targeted in an attack that bombards them with an endless stream of notifications or multi-factor authentication (MFA) messages in an attempt to cause panic so they'll respond favorably to social engineering. An...
maxresdefault

Apple to Launch New iPad Pro and iPad Air Models in May

Thursday March 28, 2024 11:07 am PDT by
Apple will introduce new iPad Pro and iPad Air models in early May, according to Bloomberg's Mark Gurman. Gurman previously suggested the new iPads would come out in March, and then April, but the timeline has been pushed back once again. Subscribe to the MacRumors YouTube channel for more videos. Apple is working on updates to both the iPad Pro and iPad Air models. The iPad Pro models will...
Generic iOS 18 Feature Purple

iOS 18: What to Expect From 'Biggest' Update in iPhone's History

Wednesday March 27, 2024 11:10 am PDT by
At least some Apple software engineers continue to believe that iOS 18 will be the "biggest" update in the iPhone's history, according to Bloomberg's Mark Gurman. Below, we recap rumored features and changes for the iPhone. "The iOS 18 update is expected to be the most ambitious overhaul of the iPhone's software in its history, according to people working on the upgrade," wrote Gurman, in a r...
maxresdefault

Apple Announces WWDC 2024 Event for June 10 to 14

Tuesday March 26, 2024 10:02 am PDT by
Apple today announced that its 35th annual Worldwide Developers Conference is set to take place from Monday, June 10 to Friday, June 14. As with WWDC events since 2020, WWDC 2024 will be an online event that is open to all developers at no cost. Subscribe to the MacRumors YouTube channel for more videos. WWDC 2024 will include online sessions and labs so that developers can learn about new...
apple maps 3d feature

Apple Maps May Gain Custom Routes With iOS 18

Tuesday March 26, 2024 3:10 pm PDT by
Apple may be planning to add support for "custom routes" in Apple Maps in iOS 18, according to code reviewed by MacRumors. Apple Maps does not currently offer a way to input self-selected routes, with Maps users limited to Apple's pre-selected options, but that may change in iOS 18. Apple has pushed an iOS 18 file to its maps backend labeled "CustomRouteCreation." While not much is revealed...
General iOS 17 Feature Orange Purple

Apple Releases Revised Versions of iOS 17.4.1 and iPadOS 17.4.1 With Updated Build Number

Wednesday March 27, 2024 5:59 am PDT by
Apple on late Tuesday released revised versions of iOS 17.4.1 and iPadOS 17.4.1 with an updated build number of 21E237, according to MacRumors contributor Aaron Perris. The updates previously had a build number of 21E236. The revised updates are available for all iPhone and iPad models that are compatible with iOS 17 and iPadOS 17, but they can only be installed via the Finder app on macOS...
applephilschiller

Apple's Phil Schiller Works 80 Hours a Week Overseeing App Store

Wednesday March 27, 2024 2:03 pm PDT by
With the App Store and app ecosystem undergoing major changes in the European Union, The Wall Street Journal today shared a profile on App Store chief Phil Schiller, who is responsible for the App Store. Though Schiller transitioned from marketing chief to "Apple Fellow" in 2020 to take a step back from Apple and spend more time on personal projects and friends, he is reportedly working...