Saddleback Leather Side Pocket Duffel Review & Giveaway (Winner: Nick S.)- $655

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[Congratulations to Nick S. for winning this beautiful Saddleback Leather bag out of 13,000 entries. He told me he would be using the bag for traveling and overnight trips!]

The Saddleback Leather Side Pocket Duffle is a redesigned weekender bag from Saddleback Leather. The very first thing I noticed when opened up the box was the rich, beautiful color. I own several SBL pieces in chestnut, but when I saw this one, my jaw dropped. It is positively gorgeous. I thought my other pieces were great looking, but it shocked me to see an exemplar of this idyllic hue in the real world. My other chestnut pieces are beautiful, but the color on SBL’s updated chestnut is somehow even richer.

For all of its beauty, however, there is what (initially) seems like a huge red flag: the strap containing the buckles that secure the side pocket flaps is fixed to the main pocket flap. It is just one long strap across the top of the bag that gets threaded through loops on the side pocket flaps and buckled to the side pockets themselves. This means that you cannot open the main pocket without the side pockets being unfastened. Either you travel with your side pockets unfastened, or you have to open three buckles every time you want to get into your main compartment. Opening the main flap all the way requires you to unthread that strap from the side pocket flaps. If you were opening the bag many times per day, this could get quite old.

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When I first saw this, I was surprised. Saddleback is typically very thoughtful in their designs.  SURELY, they know best and there is some brilliant reason for this that I will love once I figure it out. SURELY, they would not offer a bag with such an obvious design flaw. It seems that Dave uses his prototypes for something like 20 years to perfect them, sending a complimentary bag to Jesus of Nazareth by angelic courier via Jacob’s Ladder, and offering the remainder for sale to the rest of us.

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Then I remembered that this is luggage! The majority of my Saddleback Leather products happen to be everyday use items (like my backpack). But not so much with this one; you will put all your travel goodies in it and only open it up when you arrive.  More than likely, it will stay open on the hotel bed until you depart.

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As usual, you can see pictures and a 3D model of the bag on the Saddleback website, and you can see Dave handling the bag and commenting on it here: Also, as is par for the course, there are a number of reviews floating around on the web. The reviews on the site and on Amazon are standard SBL fare—the kind of glowing testimonials you would expect on an SBL piece.

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One issue that kept coming up is whether or not it fits into the overhead bins on various aircraft. One reviewer said it did not fit “easily” into an overhead bin on an aircraft flown by Southwest, though I assume that it ultimately did fit. Another said it fit easily into an overhead bin on a Jet Blue airplane, and a flyer in a Delta MD80 did not have any issues. In the video, Dave basically says it fits until it does not, in which case it fits below your seat. Based on the dimensions on Saddleback’s website (20.25” x 10” x 11.25”), it should be well within most airline carry-on size restrictions. If you are truly worried, you can lookup the dimensions acceptable to your airline for your upcoming flight at

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For all of my complaining about the top flap, the five straps do add more security for checking the bag if it is unable to be a carry-on, and the flap is generous enough to keep out heavy precipitation (the lack of which on my Rustic Leather mailbag—despite how much I love it—plagues me).

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Users also seem to disagree about the utility of the interior pocket. In the video, Dave explains that it is for muddy sandals, sweaty clothes, or seashells (basically, anything you’d rather keep separate from your other garments). I say brilliant. Cut it out if it truly bothers you. It’s supposed to be floppy, but, being constructed from that nice pigskin, the one in this bag is fairly rigid (for now).

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It’s nice to see that the interior pocket is merely pigskin, and not the leather/pigskin sandwich that used to be used for literally every panel and pocket everywhere. I have an older version of the backpack, which I love, but it is quite heavy. A lot of the pigskin is just unnecessary, and it seems Saddleback has become sensitive to that. This duffle, like the newer backpacks, is constructed using a more appropriate use of pigskin (for example, the side pockets are unlined), which keeps the duffel a bit lighter.

Another deliberate aspect of the design, which I was glad to have pointed out to me, is the flat handle. I love the round briefcase handle and wish my backpack had the same. For me, it is much more satisfying to hold the rigid, round handles than the flat ones. However, they can cause problems for a bag of these dimensions when being stuffed into an overhead bin.

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From a practical standpoint, this bag should have enough space for the average adult to comfortably pack for a 2-3 day trip, minus any speciality equipment or bulky warm clothing. That said, you can fit your blueprints, map tubes, or harpoons right underneath the top flap of this bag and still fasten it closed, if you run the top strap through slits designed for this purpose. The side pockets can fit about three cans of beer.

BestLeather conclusion

This is a nice bag that is excellent for travel, but does not seem designed for the everyday grind (unless yours is at 35,000 feet in between investment property visits). Aesthetically, it is a knockout and the construction is the standard robust Saddleback Leather fare.

Check out the Side Pocket Duffel on Saddleback Leather’s website here.

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About Author

A love for the symbolism of quality motivates me to enjoy the excellence of these products. I hope my labors are helpful to you. Most photos are shot with a Canon 6D and L glass and are not edited for color. What you see is what you get.

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170 Comments on "Saddleback Leather Side Pocket Duffel Review & Giveaway (Winner: Nick S.)- $655"

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Mark Levengood

Thanks for taking the time to post this review. I’ve often wondered about the side pocket closures and your explanation makes a lot of sense…


[…] Enter this Giveaway at Best Leather […]

Anne Marie Carter

I would keep this bag for myself if I won it.

Lauren S.

I would use this bag for everything! It would be great for work, and for weekend trips.


I would use this for weekend road trips


I would probably keep it on me 24/7


I would carry this baby with pride!

Jessica Arena

I’d use this bag for travel; it’s so elegant and beautiful.


I’d definitely make it my go to carry on bag, as well as a prepacked bag for unexpected travel needs.

Kyle Pierce

Beautiful bag – thanks for the opportunity.


I would use it for carrying stuff to the coffee shop to work remotely.

Amy M

I’d use it as a weekender, for sure, but I think it would also become my everyday city bag. It’s a beautiful, beautiful bag, and I love that it’s made with a sense of pride and a sense of humor.

Nick Tefoglou

I would use it as a travel bag

Diane Estrella

I would love to use this for myself. Gorgeous!

Kim Williams

Love it!


Oh I love how this looks with so many uses.

Janice L.

Great overnight bag!

Emily Morelli

Saddleback makes the highest quality, most luscious leather bags in the universe!

David Todd

I want this bag for travel with work.

Teri Melton

This bag is so beautiful. I can almost smell the leather.


If I win I will use this bag as a handbag.

Susan D

I am almost at the point where I need a replacement carry-one travel bag for trips, so I would use it as my new travel bag


Replace our current leather duffel bag, which is well past its prime after many miles and years of service, with this new one




hubby will use it on trips

Julie Scow

I would keep this bag for me.. but I’m sure my husband would be VERY jealous. I’d use it for work to keep my books/papers and for travel.

damien crawley

everyday great bag

Catherine Haynes

I would use it for work.

roberta wade

I would probably give it to my son, but which one?

Farrah King

I love everything about this saddle bag! My fingers are crossed and would love to be your lucky winner!

Lois Jones

I would use it for weekend getaways with my friends! Perfect size for it!

Ross Olson

I would use this great bag as a weekend traveling bag. Thanks!

jo ann

Beautiful bag…thanks for giveaway!

Melanie Rhodes

I would love to win this bad. It is a very high quality bad, and looks like a true luxury!

Bri Galloway

What a beautiful bag 🙂 Love it!!

Daniel Hinzman

Travel bag

April Paik

I would use it as an overnight bag or a school/work bag! Thanks for the giveaway!


Beautiful bag

Tamika Taylor

I would use it as an everyday bag for work.

Mary W

I would use this while traveling for my job.

Leora Totton

I’d take this bag with me every time I leave the house.

Susan Moseley

This is beautiful bag. I would certainly make good use of it. 🙂

Linda Kish

I don’t know what I’d use it for but I would definitely use it.

Sharon Siqueiros

This would be my everything bag! It’s sooo gorgeous
Thanks for the opportunity to win it!

rae ramos

i would use this everyday, everywhere

Esther Chanie Dushinsky
Esther Chanie Dushinsky

Thank you for the in depth review.
How do we enter the giveaway? Thanks


I would give it to my father, he would LOVE this!

Rosa Espinal

on my trips

Alison Cowart

I would use this bag for lots of things–it is quite versatile. My husband will probably try to steal it , though. I like that it has a very rugged, yet polished look to it. It makes it work for everything from work to travel to casual things–it really is a great bag!