Messenger Bag Process:
From Sketch to Finished Product

July 6, 2014 | 71 Comments


Ugmonk has always been about making products that I wanted to exist. Yes, there are thousands of different bags on the market to choose from, but I wanted to design a bag completely from scratch based around my wants while incorporating the Ugmonk aesthetic. The original idea for the bag started over 2 years ago but it was a long process to finally see the finished product through. Each new product is a learning process and brings on new challenges, but in the end it’s worth the work.

Concept Sketches

I started by sketching out a variety of concepts that incorporated the functionality that I wanted in a bag. I can’t emphasize enough how much it helps to start with pencil and paper rather than jumping right onto the computer. I also researched other bags, making notes of things I liked and didn’t like about each. The bag style that I eventually landed on is similar to a traditional postal messenger bag. One of the key things I noticed from those classic bags is how the shoulder strap attached to the back of the bag instead of the ends. This allows it to lay flatter against the body instead of bumping up against your hip while walking. These sketches helped me think through the various functionality and details.

Digital Mockup

I don’t have any sewing or pattern-making experience, but I knew it would be helpful to draw the bag digitally to get a more precise mockup to send to manufacturers. This also helped me figure out the dimensions and proportions for each part of the bag. Though some parts of the bag were altered during the actual prototyping process, this gave me a solid idea to work from.


One of the hardest parts of the entire process was finding the right manufacturer to work with. I wanted to find a place in the USA that not only specialized in this type of high quality bag making but was also willing to accommodate low minimums for the first run. I could have easily just found blank stock bags from a Chinese manufacturer and added some Ugmonk branding, but I wanted to produce a completely custom bag with the highest quality possible.

Since this was a completely different product than anything I have produced so far, I needed a place that would help guide me through the manufacturing process and give input based on their expertise. Many of the larger factories I contacted wanted a fully-designed bag to work from and didn’t seem to take a personal interest in helping me through the process. After contacting over 40 places I finally found a company in Portland, Oregon (with help from Maker’s Row) that specialized in making the type of bag that I was looking to produce. Moral of the story: don’t give up even when the search seems hopeless.


When researching materials to build the bag from I kept gravitating towards the combination of waxed canvas and leather. Waxed canvas is a rugged water-resistant material originally developed for fisherman and navy sailors back in the 1800s to keep them dry and warm. Not only is it durable and functional but it also ages beautifully with use and wear.

I’ve released a number of other Ugmonk leather products over the past few years and have learned about the different types of leather in the process. Most bags produced overseas use cheap bonded leather or faux-leather that breaks down quickly with use. If you’ve ever purchased a cheap wallet or belt and had the outer layer start to peel off and crack then you know exactly what I’m talking about. We chose to use full-grain vegetable tanned leather (similar to our other leather products) that is super durable and will hold up for many years of heavy use. The leather starts off a little stiff but softens over time and conforms to the individual use pattern. For example, if you tend to carry the bag on the same shoulder the strap will smooth out and form to that particular shape. Unlike most things, these materials actually get better with use and wear.

Early Prototypes

It’s hard to know exactly how the sketches will translate until creating the first physical prototype. After I had the first prototype bag in hand I noticed a number of things that needed to be modified and improved. For example, the original canvas that I chose was too thin and didn’t have enough structure making the bag feel too flimsy. Since I only had a sample swatch of the canvas it was hard to know that it wouldn’t work well for a whole bag, but that’s why it’s important to build out the whole product before proceeding with the full run. We also tweaked a number of other things like the length of the front flap, extending the back leather strip to help cinch the sides closed, and using more streamlined hardware.

Final Prototypes

After these revisions were made, some additional prototypes were produced to ensure the proposed changes and new materials fixed all of the issues. Each one of these prototypes takes time and costs money, but they are all part of the investment of creating a superior final product.

I could have easily cut corners along the way and used cheaper materials or simplified parts of the bag, but it was important to me that these bags were the best they could be. This means that our final production costs were much higher than anticipated. If our main focus was selling wholesale our retail price would have to be double what it is now but since we sell directly to the customer we are able to produce an exceptional product and still keep the costs as reasonable as possible.

Product Photography

It was an amazing feeling to finally have the finished bags in hand. The bags looked and felt incredible in person but I wanted to make sure that the same quality and detail really came through in the product photography. Too many people overlook this part when selling online and skimp on photography. This is the only interaction a potential customer will have with the bag and it’s vital that the photos reflect the quality of the product. I spent several days shooting the bags and designing the product page layout and flow. Scroll through the product page here to see all of the details.

Launching the Bags

After 2 years of work (on and off) it felt great to finally flip the switch and launch the bags in the shop. As with any product I never know what the response will be, but I was thrilled when the first run of bags sold out in just two weeks! I’ve learned a lot through the process (including how to be patient) and am looking forward to applying this knowledge to future products. Hope this gives you some insight into what happens behind the scenes to make these bags reality. Thanks to all of you who continue to support Ugmonk and help me bring new products to market!


Sign up for the Ugmonk Newsletter to be the first to know when we release new products and stay updated with all things Ugmonk.

  • Justin Newhouse

    LOVE. Keep doing what you’re doing my friend.

    • Jeff Sheldon

      Thanks Justin!

  • Chris_Krammer

    I’d really love to order a bag since I like how everything is looking. However I still struggle with the price. While I totally understand where it is coming from, I yet have to justify it for me. But I might order one soon …

    • Jeff Sheldon

      Thanks Chris. It’s definitely an investment but is built to last.

      • Josh Robertson

        True. Thank you Jeff for everything you do. I really love ugmonk & your passion! Continue doing what you’re doing!!

  • nicholos

    This is certainly a beautiful looking item. However, the first thing that came to mind when viewing the final product was that you would not want to use this in anything but sunny, beautiful weather. The size of the flap is a fair bit smaller than the storage compartment so there are openings on either end for rain or snow of any kind to pour right into.

    Can someone allay my fears in that regard?

    I will admit that I am likely not the target demographic for this, as my messenger bags need to be more cycling friendly, so perhaps those concerns are not important.

    • Jeff Sheldon

      Hey Nicholos, I understand your concern. The side straps help to minimize that gapping but it’s not 100% waterproof. I’ve been caught in the rain with it and has been fine, but might not be fit for cycling in a rain storm where you need something completely weatherproof.

      • Dave

        Hey there,

        Have any modifications been made to the bags based on customer feedback? I see concerns here about the size of the flap and also the inside rivets scratching laptops.

        The bag looks great by the way!


        • Jeff Sheldon

          Hey Dave. Yes, we changed the laptop closure strap to be sewn in instead of riveted to prevent any scratching. We couldn’t alter the flap shape or it would hit the shoulder strap when opening the bag, but you can cinch the sides with the leather adjusters to close up the gaps most of the way. It’s not 100% sealed but it’s kept my gear dry when I’ve been caught in the rain. Hope that helps. Let me know if you have any other questions.

  • JonathanBowden

    great work as always jeff!

    • Jeff Sheldon

      Thanks man!

  • Shia-leigh Sapir

    Want one now ! Really, really amazing… keep on, you rock!

    • Jeff Sheldon

      Thanks. Appreciate the kind words!

  • karine
  • Beth Rufener

    This is one amazing bag!

  • PS

    I think that closure should be placed opposite. Currently, buckles can unhook themselves under the weight of the bag.

  • Henrique Pinheiro


  • Quinn Milionis

    Received this as a graduation gift and I absolutely love it. Favorite bag I’ve ever had and I’m so excited to use it at college next year. I’ve always loved your design and attention to detail and quality. This bag is the perfect example of that.

    • Jeff Sheldon

      Awesome! Nothing better than hearing feedback like this. Glad you’re enjoying the bag and good luck in college next year :)

  • AJ

    Any posts/tips on accomplishing that type of product photography? I love how those products are shot. We’re they shot from above?

    • Jeff Sheldon

      Yes, most are shot from above. It’s all about lighting and shooting a lot. Sometime I’ll have to post a walkthrough of my product photography.

  • Austin Brown

    I love the bag! I got it in the mail and finally got around to using it this week. My only complaint is that I feel I need to keep my laptop in a sleeve in the bag. I feel like the metal bits inside the laptop sleeve are going to scratch my laptop.

    • Jeff Sheldon

      Thanks, glad you like it! And thanks for the feedback about the rivets. We’ll have to see if there’s a way to fix for future versions.

      • Austin Brown

        I just noticed these side pockets. Do you find yourself using those at all, and if so what for?

        • Jeff Sheldon

          Yep, not the best for small items since it’s hard to reach but those pockets work great for tall thin things like a flashlight or a super compact umbrella.

  • JAL

    Oh my god, I just received this today and I absolutely love it! Many thanks to my brother for telling me about Ugmonk!

    • Jeff Sheldon

      Awesome, glad you like the bag! Thanks for your support :)

  • DJ Waldow

    Okay. Adding this to my wishlist. LOVE IT @ugmonk:disqus. And thank you so much for all of the detail – text, sketches, pictures, etc – in this post. VERY cool to see the process.

    • Jeff Sheldon

      Nice, glad you enjoyed seeing the process!

  • catalogototal

    I find very creative design I like because everything always starts with a sketch, I liked the finish

  • Shawni

    Hello Jeff I thoroughly enjoyed this article and your insight….I am hoping to make my own line of bags(not messenger bags) and like you I would love to use a U.S. manufacture. Your sketches were great and final product was beautiful! I also searched and searched for factories and makers row is on my short list. I have sketches but I am not an artist so it looks more like doodling but my vision and creativity is there!! Any suggestions or feedback as to how to get professional sketches made? Also what was your experience with Makers Row…again great article very inspiring.-Shawni

    • Jeff Sheldon

      Thanks Shawni. Glad you enjoyed the post. I don’t think you need professional sketches as much as you need your ideas clearly defined to present to the manufacturers. If you’re looking to turn your “doodles” into more refined digital versions like I did above, you can hire a graphic or product designer to help do those in Illustrator. A good place to search for designers is and Hope that helps.

  • Leandro

    Muito bom trabalho! eu gostaria de ter uma dessas na cor preta como eu posso?

    meu e-mail é:

  • Leandro

    Very good job! I wish I had one of these in black as I can?

    my email is:

    • Jeff Sheldon

      We currently only make these in charcoal gray and army green colors, but we are considering adding a black version in the future.

  • Jerry Sievert

    looks great! just curious what the laptop case in the pictures is?

    • Jeff Sheldon

      Thanks! It’s by Byrd & Belle

      • Jerry Sievert

        thank you! two purchases soon!

  • tacticus

    Don’t suppose you’ve taken it through a solid bit of rain by chance? just a bit concerned about how the flap doesn’t sit over the entire opening.

    • Jeff Sheldon

      I’ll admit it’s not 100% waterproof, but I did get caught in the rain with it and everything stayed dry. Cinching the side straps even tighter helps.

  • Tanya

    Buying one for my boyfriend’s birthday!

    • Jeff Sheldon

      Nice, thanks! :)

  • Richard Lazazzera

    Hey Jeff, may I ask what your minimums were for your first run?

    • Jeff Sheldon

      Minimums can vary depending on the type of product, materials, and manufacturer, but we did 100 bags for the first run.

  • Yehuda Cohen

    I loved the process, the way you choose to present your dream has become a reality

  • Kyle Hotchkiss

    Nice bag. Would be good if rivets were covered (caught some scratches on the bottom of my laptop). I feel much more fancy walking into the coffeeshop. Would love to see you write some blog posts about the things you would stuff in your bag jeff

    • Jeff Sheldon

      Awesome. Thanks for the feedback. We’re looking at ways to cover those rivets in future versions. I’ll have to a “what’s in my bag” post sometime soon :)

  • Alex

    Jeff, the messenger bags are absolutely stunning except for one little thing, the backs of the buttons are exposed within the laptop area which can scratch it.

    • Jeff Sheldon

      Thanks Alex. We’re looking at ways to improve this for future versions.

  • fluxx

    Hi Jeff, I bought the bag over two months ago and just want to give you a constructive feedback what might be improved on the next iteration – but keep in mind its a great messenger bag as it is and I will never let it go :-)

    In the first few weeks I really struggled with the leather shoulder strap. Because of the fresh, natural leather it was losing so many leather fluffs it almost was no fun to wear. I still have to clean my darker clothes from time to time because of it. I don’t have an idea how you can solve this because otherwise the leather is great, but this was my main complain.

    The clip for the keys is not so useful: It’s too short to be used with keys on and long enough to get in the way if you don’t need it. Its also above the bag where I keep my phone and I always fear to scratch it. Speaking of scratches… the notebook compartment is also a dangerous place.

    In the first weeks the bag was very hard to open and even harder to close. As the leather worked, it’s quite fine now but a different closing mechanism might be better.

    But these are only little nitpicks. Its a wonderful bag, I love the look, the materials, how it keeps its form when its open, how it ages. I also find it inspiring to see your design process, thanks for sharing. You’ve done wonderful work here, keep it up!

    • Jeff Sheldon

      Thanks for the feedback! This is really helpful and I appreciate you taking the time to post. The leather will eventually stop shedding and smooth out. We are working to reduce this from happening, but it’s one of the side effects of using raw leather. Same with the stiffness. The straps should loosen up nicely with some use and make it easier to open and close. If you are still having trouble, you can slightly widen the holes with an exacto knife. We’re also modifying the laptop compartment in this next batch to prevent any potential scratching. Feel free to email me with any other feedback or suggestions. jeff at Thanks!

  • chrish16

    You’re hugely inspiring. I’m happy for your success!

    • Jeff Sheldon


      • Sk Hiron

        Hi Jeff
        My self Sk Hiron from Bangladesh, I am really appreciating your talent. but dear I need help ,Could you please help me by giving permission to make your samples as per your design and specifications ?
        If you do that, than I can make samples in my own factory,and will try to getting order from different buyers. or if my sample would be okay than you could manage order for me?
        I am asking because I have a little production units in Bangladesh. but there are no designer in my factory; and I do not want to copy others design without their permission.


    Loved the behind-the-scenes look at the making of this bag. Keep it up! Great leather bags on the horizon.

    • Jeff Sheldon

      Thanks Paul.

  • Patrick Branigan

    Awesome as usual! Keep it up Jeff. Even when I can’t really afford a product of yours, I still rep it like hell because of insight like this :)

    • Jeff Sheldon

      Thanks Patrick. Appreciate it :)

  • Luke Fisher

    Hey Jeff, love the bags and the whole process demonstrated. Was just wondering what software you use for your digital mockups?

    • Jeff Sheldon

      Thanks Luke. I did the digital mockups in Illustrator.

  • DarkSysop

    I see they went up to $235 from $219 which is fine, but are they going to stay at this price now? Also, will they be a permanent item because I want to buy it but can not afford it yet. Thank you.

    • Jeff Sheldon

      Yep, we’re planning to keep them at that price. We underestimated our material and labor costs in the beginning so we had to adjust, but this is the price point they’ll remain at.

  • Paul Minors

    The bag looks awesome. I can see that a lot of thought has gone into it :)

  • Dr. Paul

    Beyond impressed. Attention to detail and outstanding quality is evident. I only feared a stiff feel to the leather, but it is more supple than expected right out of the box. Closures appropriately tight. One shoulder or cross body carry is equally comfortable, the bag hugs me perfectly thanks to the geniusly placed strap hooks. I eagerly look forward to banging this bag up and adding to its already rich character. It not only feels custom made, but made just for me. Thank you for creating such a superb bag.

    • Jeff Sheldon

      Thanks! So glad to hear you’re enjoying the bag. It definitely gets better with use as everything softens up and conforms to how you carry it. I love how each bag is unique depending on who uses it :)

  • disqus_e9t5H3mkJg
  • farizal

    you inspiring me….i love bag,just like a bag freak.this a few month i was thinking about why not i make my own bag…but i dont know how to sewing it.because too love bout bag,today i just register to sewing class…i hope someday i will put out something.when i read what you wrote…it give me a spirit and thinking” this is it,i should do it”….thank you by the way.goodluck what ever you do man.

  • Bree Smith

    What digital mockup software did you use?

    • Jeff Sheldon

      I use Adobe Illustrator

      • Bree Smith

        Thank you so much! I really want to follow in your footsteps but have no experience so research is keeping me going!

  • Antonio Iturra

    Beautiful Jeff. As Chris states, price is always a but, I hope to be able to make it before they run out. I loved the post, as I like to see the process and I see you put a lot of effort into it. I’m a big fan of bags, so I really hope I can get a hold of one in the near future.