Best Leather Hobo Shoulder Bag — Buyer’s Guide and Reviews -

Style come in, and style go out. However, some styles are so timeless that they never truly fade away. The hobo silhouette shoulder bag is one such style, and it is only accentuated even further with leather.

The top 10 most popular Leather Hobo Shoulder Bag based on sales on the website BestReviews.Tips. Updated daily.

1. The SAK Indio Demi Shoulder Bag – Most Stylized Leather Hobo Shoulder Bag


The SAK is a brand that draws its inspiration from a diverse set of south and southeast Asian influences. While this brand initially began with a fairly limited number of silhouettes, it has expanded well beyond those humble origins. This whimsical approach can trace its lineage back to the founders who saw the unique styles of Bali and brought them to western markets.

The Indio Demi exemplifies that evolution by providing a wealth of styles both classic and contemporary. From the 24 different styles offered with the Indio Demi many of them include either intricate embellishments, a vintage boho hippie bags style or a modern elegance and simplicity. Moreover, this leather hippie hobo shoulder bag is exceptionally inexpensive.
  • Offers 24 different styles to choose from
  • An exceedingly inexpensive leather hippie hobo bag
  • The thicker strap is more comfortable for longer periods
  • Has fewer compartments than preferred
  • Has a somewhat short shoulder drop
  • Is a fairly small leather hippie hobo purse

2. Heshe Leather Crossbody Hobo Bag – Best Satchel Leather Hobo Shoulder Bag


Unlike The Sak, Heshe is not a brand that can lay claim to an prestigious pedigree, but it still has been slowly working its way up the designer trail to become a well respected brand. While it does not own or supply traditional storefronts like most other designer shoulder bags, it still maintains a solid reputation through its various online outlets. That business model allows Heshe to offer their bags for a relatively inexpensive price.

For that modest cost, the Heshe provides one of the larger shoulder bags available. Moreover, that total volume is divided up into numerous main compartments as well as various smaller ones. In fact, this is one of the fewer shoulder bags to offer 3 main compartments instead of just one or two.
  • A fairly inexpensive leather hobo shoulder bag
  • A robust and large leather slouchy hobo bag crossbody
  • Offers an good sized shoulder and handle drop
  • The compartment distribution is inconvenient
  • Does not provides a wealth of styles to choose from
  • The leather is stiffer than one anticipates

3. The Sak Kendra Hobo Shoulder Bag – Best Baguette Leather Hobo Shoulder Bag


While the Sak Kendra does not boast the wealth of designs that the Indio Demi does, it still offers a fair number of designs in one of the most popular hybrid silhouettes available. With a short height but a long length, the Kendra manages to skirt the line between a traditional shoulder bag and a baguette. Of course, the extended strap with an almost 13” shoulder drop makes carrying this shoulder bag for an entire day much more comfortable.

Moreover, much like other Sak shoulder bags, this one is relatively inexpensive. Unfortunately, the baguette style does limit the overall volume of the Kendra, though this does not limit its ability to store away all your odds and ends in its numerous compartments.
  • A fairly inexpensive leather hobo shoulder bag
  • Provides a good number of additional compartments
  • Comes in 10 different styles
  • Has a relatively short shoulder drop
  • Is a somewhat small leather hobo shoulder bag
  • The lining is poor quality and not durable

4. Anuschka 433 Hobo Bag – Best Small Leather Hobo Shoulder Bag


Anuschka specializes in a more ethical approach to shoulder bag manufacturing. For one, all of their bags are handmade and hand designed. And while the designs may be somewhat few, they are some of the most elaborate and intricate available.

This shoulder bag in particular is on the smallish side, but that is by design. The combination of this petite bag with a decent shoulder drop makes for a delicate look to pair with a more casual look that makes it great for everyday leisure wear. Moreover, the wealth of compartments makes organizing the various carried items easy. However, this exquisite craftsmanship will cost you a fair amount.
  • Provides a decent shoulder drop
  • Offers a good number of additional compartments
  • Handmade both construction and embellishments
  • A fairly expensive leather designer handbag
  • An exceedingly small leather hobo shoulder bag
  • Genuine leather is the lowest quality

5. The Sak Sequoia Hobo Bag – Best Large Leather Hobo Shoulder Bag


Unlike many of the other Sak shoulder bags, the Sequoia lives up to its namesake and comes in at a relatively large shoulder bag. Oddly enough, this large bag is coupled with a somewhat short shoulder drop of only 11”. This means that taller consumers might not be able to carry this shoulder bag quite as comfortably, while smaller consumers may look dwarfed in comparison. Still, with 11 styles to choose from, the right person will love the oversized design.

Other issues that the Sequoia demonstrates is a poor inner lining. While it is made from polyester, it seems to rip fairly easy. Moreover, the lining itself is not always sewn into the seams quite as well either. Unlike many of the Saks, the Sequoia does not come with numerous compartments.
  • A relatively inexpensive leather hobo shoulder bag
  • One of the larger leather hobo shoulder bags
  • Comes in 11 different styles
  • Has a relatively short shoulder drop
  • Does not offer many additional compartments
  • The lining is poor quality and not durable

6. Coronado Concealed Carry American Hobo – Best Self-Defense Leather Hobo Shoulder Bag


All too often, accessories are often judged more on form and less on function. The style and silhouette predominate the decision, leading to a multi pocket shoulder bag that ultimately fails in one respect or another. Of course, sometimes manufacturers make the conscious effort to cater to a consumer that seeks a specific function over all else.

The Coronado is rare bird in this respect as it is explicitly designed for concealing a firearm for self-protection. However, the compartment designed for this purpose is not without its flaws. For one, it will only fit smaller handguns. Moreover, the lining, while a sturdy ballistic nylon, will often catch either the velcro holster or the firearm itself.
  • A somewhat inexpensive leather hobo sling bag
  • Provides a decent shoulder drop
  • Full grain leather is the highest quality
  • A somewhat small leather hobo crossbody sling bag
  • Does not offer a large number of compartments
  • The conceal zipper secret pocket leaves a bit to be desired

7. FRYE Melissa Hobo Leather Handbag – Best Tote Leather Hobo Shoulder Bag


Frye is a brand far more well-known for its high quality footwear than its shoulder bags–specifically boots. However, most of their products are also made out of leather–moreover the leather is fairly high quality. In this instance, the Melissa leather hobo handbag is made out of luxe Italian leather.

In terms of the bag’s overall qualities, the Melissa does offer a decent shoulder drop–though it is not truly long enough to be worn cross body for most people. The handle drop, however, is also a good size as well. Moreover, this is a fairly large shoulder bag. Unfortunately, it does not offer many compartments which makes it solid as a tote hybrid.
  • Is a fairly large leather cloth hobo crossbody bags
  • Provides a good sized shoulder and handle drop
  • Made from high quality luxe Italian leather
  • An exceptionally expensive leather hobo shoulder bag
  • Has few additional compartments
  • Snap closures are one of the least secure

8. HOBO Sheila Oversized Crossbody Handbag – Best Bowling Leather Hobo Shoulder Bag


As the name indicates, the HOBO brand is a manufacturer that hangs its hat on the hobo bag style. However, while that is not the exclusive style the brand produces, it is definitely the most prominent. Moreover, even when the bag made is not a true hobo silhouette, there are still features that tie it to the namesake.

What wiki says about hobo bag.

For instance, the Sheila is just as much a bowling silhouette as it is a hobo–perhaps more so. With the two handles as well as the adequate 17” shoulder drop, this bag does not carry the traditional slouchy hobo style. Also like a bowler, this bag is fairly large and includes a decent number of compartments for organization.
  • Is a fairly large leather hobo brand bag
  • Offers a decent shoulder drop
  • Provides an adequate number of additional compartments
  • Comes in 3 different styles: biege, green and black black hobo bag
  • A fairly expensive hobo leather crossbody bag
  • The zipper can be a bit finicky
  • Is a somewhat heavy leather hobo shoulder bag

9. Michael Kors Fulton Large Shoulder Tote – Best Tablet Leather Hobo Shoulder Bag


Michael Kors is a giant of the fashion industry. All styles and all genders are welcome. However, when it comes to shoulder bags, the brand likes to skirt the line between edgy and elegant. That is why the Fulton displays a number of unique characteristics all in a relatively compact size. Unfortunately, that size is exceedingly small, even for smaller hobo tote bags.

This prestige lends itself to a stylish look but a sizable cost to match. Moreover, the Fulton also has one of the shorter shoulder drops. Because of this, the Fulton is truly designed for a more a petite person. Oddly enough, this purse also comes equipped with a wealth of different compartments all of them inside the bag.
  • Provides a bevy of additional compartments
  • Made from high quality Venus leather
  • An exceptionally durable leather hobo shoulder original handbag
  • Best selling hobo bag
  • A somewhat expensive leather hobo shoulder bag
  • Has a somewhat short shoulder drop
  • Is an exceedingly small leather hobo shoulder bag

10. Rebecca Minkoff Isobel Hobo – Best Handbag Leather Hobo Shoulder Bag


While Michael Kors may pride itself on hinting at edgy, Rebecca Minkoff blows the doors wide open. That is why it is a bt odd that the Isobel definitely strays more towards the conventional than it does truly creative. Moreover, however small the person the Fulton was designed for, the Isobel requires the wearer to be even more pint-sized.

This is due to the 8” shoulder drop which will definitely make the bag not sit properly on taller or larger people. Moreover, the number of compartments are few, though the overall size is somewhat decent. However, the Isobel is definitely one of the more expensive women’s hobo bags available, but additional touches like exquisite lining to make up for that somewhat.
  • One of the larger leather hobo shoulder bags
  • Fabric lining is more luxurious
  • Exceptional convenience makes it an everyday bag
  • A somewhat expensive leather hobo shoulder bag
  • Has a fairly short shoulder drop
  • Does not provide many additional compartments

Buyer’s Guide:

Outer Material:


Even though leather is often seen as a universally luxurious material, there are actually various grades of leather. Moreover, unlike with some other products, the “highest grade” of leather is not always seen as the best when it comes to shoulder bags. While there are numerous variations, the three main types of leather used are genuine, top grain, and full grain.


Genuine is the lowest grade of leather that can still technically be considered leather. This grade of leather is actually made from numerous thinner strips of leather that have been joined together by some type of adhesive. While this type of leather is the least expensive it is also the least durable. Though, different brands that use genuine leather can demonstrate different degrees of durability depending on the adhesive and treatments used.

Top Grain

Top grain leather is made out of the uppermost layer of the animal’s skin. While top grain is technically the middle grade of leather used for shoulder bags, it is often considered the best kind of leather to use for this purpose. This is because top grain leather is softer and more pliable than full grain leather. Moreover, top grain leather is also lighter and less expensive. However, full grain leather is more durable than top grain.

Full Grain

Full grain leather uses all the layers of the animal’s skin. While this is technically considered the highest quality of leather, many people do not prefer it for various fashion and accessory purposes. This is because full grain leather is meant to withstand long years without losing its beauty. However, this also means that full grain leather is generally much heavier and thicker than other grades of leather. This heft also makes full grain leather less pliable not to mention more expensive.


Because the process of adding a texture to leather generally involves removing various layers of the animal’s skin, textured leather is generally top grain or below in starting grade. Suede would be an example of high quality textured leather that uses top grain leather. However, various types of textured leather will often use the layering of genuine grade leather where only the top most strip is textured. Other textured leathers will layer embossing or wax over top the leather to achieve the textured look.


Because a shoulder bag is to carry pretty much everything a person would need to have with them on the go, they will often contain many items that are of differing size. However, if all of these items are simply put in a single compartment, it can be difficult to find something exactly when you need it. That is why having a large number of different types of compartments is so convenient. The different types of shoulder bag compartments can be broken down into pockets, slips, and mains.


These are the most common and preferred type of compartment. While not as large as mains, they are far more secure than slips. A pocket will include a closure whether snap, zipper, clasp, or velcro. These compartments are often larger than slips and are designed to hold items which might otherwise find themselves at the bottom of a main. Gum, change, and other assorted items that are easy to fall out of slips should be placed in a pocket.


These compartments are noted for their open design without a closure. They appear both at the inner and outer section of the bag. While they are fairly convenient, they are also the most likely to spill their contents should the bag suffer rough treatment. Item that are needed regularly like keys or a phone are often placed in a slip. While useful, these are generally less desirable than pockets–at least in abundance.


Most of the time, a bag will only have a single main, though a double main is not uncommon. Less common, though by no means rare, are bags with three main compartments. However, a bag with more than three main compartments is fairly rare–unless one of the “main” compartments is actually a large, exterior slip compartment.


The type of closure your shoulder bag should employ will depend heavily on on what you are doing. For instance, if you are travelling on a plane, the closure of the purse needs to be more secure than if you are simply going to the beach. The three most common types of closure in order of security are magnetic, clasp, and zipper.


In terms of security, there is not another type of closure more secure than a zipper. It is the only closure commonly used for a shoulder bag that will completely seal the bag. However, the quality of the zipper will often depend on a couple things. First, the stitches keeping the zipper in place need to be thick and preferably reinforced. Second, the actual zipper itself needs to be well-machined–YKK zippers are the top choice in this regard.


Clasps are the next most secure closure and, depending on the construction of the shoulder bag, can either perform somewhat similarly to zippers or serve more as a minor closure. Clasps do often have the benefit of allowing you to reach inside the shoulder bag without having to actually undo the clasp. This can be convenient, but it is also inherently less secure. Moreover, a clasp is the most time consuming closure to undo.


Magnetic clasps are the least secure, but they are also by far the most convenient and lend themselves to quick retrieval from the shoulder bag. If you are going somewhere that will require you to constantly go into your bag, then this may be the preferred closure for that setting. However, dropping a shoulder bag with a magnetic closure is liable to cause the contents to spill out.


Since different heights ultimately means that the same shoulder bag will sit differently for different people, the drop of the bag is important for both style and comfort. Ideally, the base of the bag will sit on the top of the hip, though each person may have a slightly different sitting position depending on the contours of their body.


Another important factor to consider is the types of straps the bag has. Some shoulder bags only provide handles, while others will provide a longer proper strap. With handles, the drop is much shorter and may not be comfortably worn on the shoulder by all people. Straps on the other hand may sometimes be so long that they are designed to be worn cross body.


The shoulder drop of a shoulder bag should be at least 9” but can be as much as 25”. However, a 25” shoulder drop will pretty much always be worn cross body, otherwise it will dangle well past most people’s’ hip. Conversely, a 9” shoulder drop will often sit above the hip, unless the wearer is somewhat petite.


Technically, shoulder hobo bags do not have “hand drops,” however, plenty of shoulder bags do not necessarily provide a drop long enough to be worn on the shoulder by every person. Moreover, when a bag provides a strap designed to be worn crossbody, the bag may also provide a pair of handles with a much shorter drop. In the latter case, the handles should drop anywhere between 4” to 6” with 6” only being comfortable for smaller people.

Forbes Gallery Chic ’70s Hobo Bags


Depending on what you want, the best leather hobo shoulder bag will differ. For instance, if you are looking for a style to suit you, then The Sak Indio Demi is sure to catch your eye with one of its 24 styles in both classy and casual approach. Though, the Anuschka is breathtaking with a handmade construction and hand painted design.

However, if you are looking for a more functional bag, the Heshe offers a wide variety of compartments to ensure that all of your belongings stay organized. Of course, the Coronado is ideal for those looking to pack a little heat.

Hobo Bag NameSize, inchColor 
The SAK Indio Bag miniThe SAK Indio Bag
Review & Video
11 x 8 x 424Check Price
Heshe Leather Vintage Handbag miniHeshe Vintage Handbag
Review & Video
15 x 12 x 56Check Price
The Sak Kendra Hobo Bag miniThe Sak Kendra Hobo Bag
Review & Video
12 x 7 x 310Check Price
Anuschka 433 Hobo Bag miniAnuschka 433 Hobo Bag
Review & Video
8 x 10 x 46Check Price
The Sak Sequoia Hobo Bag miniThe Sak Sequoia Hobo Bag
Review & Video
11 x 12 x 411Check Price
Coronado Self-Defense Hobo miniCoronado Self-Defense Bag
Review & Video
11 x 6 x 44Check Price
FRYE Melissa Hobo Bag miniFRYE Melissa Hobo Bag
Review & Video
13 X 13 X 510Check Price
HOBO Sheila Handbag miniHOBO Sheila Handbag
Review & Video
14 x 10 x 53Check Price
Michael Kors Fulton Tote miniMichael Kors Fulton Tote
Review & Video
13 x 10 x 35Check Price
Rebecca Minkoff Isobel Hobo miniRebecca Minkoff Isobel Hobo
Review & Video
13 x 13 x 3
5Check Price