Whipping Post Vintage Messenger Bag review

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When it comes to my every day gear bag, I’m very picky. It has to be the right size, right weight, right capacity and it has to look good. I’ve been carrying a Timbuk2 messenger bag for as long as I can remember, so I figured it’s time to broaden my horizons and try something new. First up is the Whipping Post Vintage Messenger bag.

Note: Images can be clicked to view a larger size.

Whipping Post’s back story

If you’re a regular visitor here at The Gadgeteer, you’ve probably heard of Saddleback Leather Company. They make incredibly rugged leather bags and accessories that are very popular. Ryan Barr, the founder and owner of Whipping Post mentored with SBL:

“I was getting started working with leather and actually started Whipping Post, Dave Munson of Saddleback took me on and mentored me, as I was getting my footing he actually let me work for Saddleback and learn the business. We have different styles, but he’s been very influential.

I do all the design work and we do manufacturing in Mexico as well.

The name Whipping Post is actually inspired by the song Whipping Post by the Allman Brothers. In the song it’s actually a metaphor for the way he’s been treated, but I like that a Whipping Post is designed to take abuse. We hope the products we make will be able to take whatever abuse you throw at them and stand the test of time :)”


Styled after leather postal worker bags from days gone by, the Vintage Messenger looks old and new at the same time. It has a classic look that I absolutely love. There’s nothing gaudy or flashy about this bag. It has a very simple style without logos plastered all over it. That doesn’t mean people won’t notice it. It’s hard not to notice (and smell) the gorgeous aged brown stained vegetable tanned leather that is both soft and supple.

The Vintage Messenger has an overall size of 18.5 x 11.5 x 4 inches and weighs in at 3.5 lbs empty.


Flip the bag around and you’ll see the simple grab strap that keeps the style of the bag lean and mean instead of adding a bulky grip handle to the top.


Also on the back of the bag is a large flat pocket which is large enough to hold magazines, newspapers or other flat documents.


The bag has an adjustable padded shoulder strap that is surprisingly comfortable except for the buckle that rubs against my breast bone when I wear it bandoleer style across my chest. Most people probably won’t notice this issue. I only notice it because don’t have any “padding” up there anymore due to the big C. It doesn’t bother me at all when I have jacket or thicker shirt on.

Even though this bag is more narrow than my Timbuk2 messenger bag, it is still able to stand up instead of falling over. Of course it would depend on what you put in the bag.


The bag has a large flap that can be secured with a leather strap which has a post and slot style design. I wasn’t sure if I’d like this type of closure “mechanism”, but for the times when I’ve used it, it is easier to deal with than a metal buckle. For the most part, I just let the flap hang loose.


The leather is soft enough that it’s easy to flop the flap behind the bag. When you do this, you reveal a nice sized flat pocket.


This pocket is large enough for a wallet, phone, small notebook, etc. I’ve shown a Field Notes notebook peeking out of the top to give you an idea of the size.


Inside is the main compartment which is just a large open space with a suede lined and padded laptop sleeve sewn into the back wall of the bag. The sleeve is large enough that it can accommodate up to a 15″ laptop. I tested both a 13″ Macbook Air and a 15″ Macbook Pro. Both fit fine.

You might also notice from the images, that the bag and flap are made of one layer of leather with cut raw edges. Some people might think this style of construction is too simple, but I like it. There may be some concern that the leather might stretch – especially when carrying a laptop. The laptop sleeve is made of multiple layers of leather and padding, so I don’t really think that will be an issue.


Attached to one side of the bag is a key clip on a narrow strap of leather. I don’t normally use these types of clips which seem to be attached to most bags.


The main compartment is roomy enough to hold a lot of gear, but the lack of other slots and pockets means all the items end up scattered at the bottom of the bag making it difficult to find your smaller items.


This is the first all leather bag that I’ve reviewed which I have ended up loving. Unlike other bags, this one isn’t bulky or heavy, even when loaded it down with all my normal gear. I found the Whipping Post Vintage Messenger bag comfortable to carry and large enough to hold all my stuff. It’s made very well and looks fantastic. The only area for improvement would be to add some interior slots and pockets to help organize the gear. I like this bag so much that I have plans to modify it to add my own organization panels and snap them into the sides of bag. I’ll report back with some pictures after I do. Until I modify it, I’ll be using it as is because it’s a definite keeper and I can’t wait to see what they come up with next.


Product Information

Manufacturer:Whipping Post
  • Classic style
  • Not too heavy
  • Soft leather
  • Grab handle
  • Not enough pockets to organize your gear

37 thoughts on “Whipping Post Vintage Messenger Bag review”

  1. Gadgeteer Comment Policy - Please read before commenting
    1. @Dmitriy The laptop sleeve part of the bag is more robust than the rest of the bag. It’s slightly padded and made of more than one layer of leather. I think the bag will keep its shape just fine. I will edit the review to add this info.

  2. This is a beautiful bag, but I cannot get my mind around why someone would name their company “whipping post.”

    1. We were right… here’s the scoop from Ryan:

      The name Whipping Post is actually inspired by the song Whipping Post by the Allman Brothers. In the song its actually a metaphor for the way he’s been treated, but I like that a Whipping Post is designed to take abuse. We hope the products we make will be able to take whatever abuse you throw at them and stand the test of time 🙂

  3. I’ve owned & used a Whipping Post vintage messenger bag since January 2013, and it has held up just fine.

    I’ve also owned a Saddleback medium classic briefcase since June 2008. The Saddleback bag is definitely heavier duty – thicker leather, more & heavier hardware, etc. I’m really happy to have and use both bags, but for everyday use, I find the Whipping Post bag *much* more comfortable. If it turns out my kids don’t fight about it the same way when I’m dead – Saddleback’s slogan – at least my shoulders and back will be happier in the meantime.

  4. Julie, just a quick note, that strap is so long that you could easily get a leather worker to shorten it for you. Shorten the side with the buckle by a few inches, and I’m sure it would be low enough to not dig into a bone.

  5. it looks Great and much lighter than Saddleback. I did get caught up in the Saddleback fever, had 7 at one time. Realty hit me one day that they were just to heavy. Sold them all, went to Timbuk2
    and lost all that weight.
    This looks much lighter and basic, and I agree it needs more pockets inside and out.

    However, the price has turned me off. Since its made in Mexico, I’m seeing about 65.00 materials and labor and importing cost.

    That leaves a unreasonable 200:00 profit, definatly following the Saddleback thinking of more profit is better when it comes to selling to got to have it fools.

    For that reason I will not be buying one. I just do not see the value.


  6. Julie, I have considered buying a Saddleback bag for a while, more because of the quality than the styling. I really like the styling of this messenger bag but I’m curious if there’s a compromise in quality vs Saddleback bags. Could you tell me your thoughts on the materials and craftsmanship as compared to the Saddleback bags you’ve seen? I can certainly judge styling from photos but things like leather quality, stitching, etc are hard to judge without handling them.


    1. @Bryan Comparing the Whipping Post bag to Saddleback bag is like comparing apples to oranges. They are not the same types of bags. Saddleback bags are made of thick leather that is not soft or what would be considered supple. Their bags are rugged, bulky and heavy. Some people like that that though. Whipping Post bags are softer and are not going to survive a tug of war with an alligator or anything like that. But they are made very well and should last for years and years… but probably not 100 years like SBL.

  7. @Julie, thanks for the comparative info. I just ordered this messenger bag and I’m looking forward to it arriving! I like the idea of a softer, lighter bag that’s still well made.

  8. I’ve seen the Whipping Posts’ products and am convinced that the quality can’t be beat. Those bags are made in Mexico, but when those expert leather workers are paid a fair wage, plus top grade material, I don’t think his profit is outrageous at all. Quality things cost more, but I bet it will last longer than most, too.

  9. I have had the Saddleback messenger bag which I really loved when I got it, but it just became impractical for me due to how heavy it was and its bulkiness. I am very interested in this bag as I like that you found it to be lighter and less bulky and I love the style and look of it. I look forward to your update after you have used it for a bit before I decide to pull the trigger or not. Thanks for taking the time to review this.

    1. @Vin I switched back to my Timbuk2 for the time being only because I don’t want to ruin the Whipping Post bag due to my specific habits. I carry my lunch in my messenger bag – this is almost always a 2 cup glass Pyrex dish with a lid. Inside is frozen leftovers. I just put the bowl in plastic grocery bag and then put it in my messenger bag. Depending on the weather, that dish will start to defrost and sweat. That condensation sometimes transfers to the bag. I don’t care if this happens to my T2 bag because it’s made of nylon with a water proof liner. If the WP bag gets wet, it might discolor the leather.

  10. Thanks for the update Julie. Other than that specific issue with the condensation would you say that the bag would hold up to normal to rough daily use? Does the leather seem to scratch up and develop character over time similar to the way Saddleback products do? If you are done with the Whipping Post bag do you want to sell it?? 🙂

  11. I’ve had mine for a week now and I like it so far. It doesn’t hold as much as my medium Timbuk 2 messenger bag but it fits my 15″ work laptop and my small lunch bag just fine. It smells great and I like the styling. It’s only seen daily use transporting my work laptop to and from work so I haven’t asked much of it but it’s worked fine so far. I haven’t any complaints.

  12. So I’ve had my messenger bag for another 2 months and have continued to use it daily to carry my small load for work. It rarely sees more than a 15″ laptop and a small assortment of items like snacks, small bottle of water. It’s continued to hold up well and looks essentially the same as when I’d bought it. The leather is breaking in a bit but still holds it’s slightly floppy shape. The laptop carry section that is partitioned off from the rest of the bag is lightly padded so I wouldn’t want to throw the bag around too much with the laptop in it. I could see someone wanting a bit more volume to the bag since I can’t imagine packing 2 days of clothes in it like I could with my medium Timbuk 2 messenger bag, but it’s fine for a laptop bag for my needs. Overall, considering that my intent is to use it to haul my computer, lunch, maybe a few file folders to the office every day, it meets my needs nicely and I’m quite happy with it.

    I just noticed that whipping post released a new leather duffel bag in a military styled design and it looks mighty appealing to me 🙂

  13. Hi, I was considering purchasing this bag, and I was wondering how it has held up since your original review. Have you had any problems with it? Has it held its shape?


    1. I’ve had mine since my original post back in 2013. Since then it’s seen daily use as a laptop bag. That’s not been a terribly demanding role since it’s basically carried from my car to my desk daily and rarely contains more than a laptop and maybe a small lunch. It’s held up great and looks better than when it was new as it’s gotten some typical character marks. I’m not sure the strap would hold up to filling it with bricks and carrying it around daily but for usage like mine, it’s great and has held up wonderfully.

  14. @Julie and @Bryan: thank you both for your responses. I’m choosing between this one and a thicker bag from Satchel & Page. Whatever bag I get, it’s definitely going to face robust wear (carried several times a day for full commutes, sometimes on a bike, and carrying a laptop, charger, 2 notebooks, and some papers). But if you haven’t noticed any stretching of the strap or the bag itself, that’s a great sign.

  15. @Julie and @Luke, I figured I’d try including a photo of how my bag looks now after roughly 2 years of daily use as a laptop bag.

  16. Hey can someone please suggest if they is a way to get it cheaper ? I really like the style but cant afford this price ?

    Are any websites out there who sell it for a discount ? Or an online place where users might resell it ?

    I am in Australia so will have to get it shipped. Cost (US$285) plus shipping (US$60) = roughly over 400 AUD, which is a bit too much.

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