Hobo Bags in Fashion

Designed to sit stylishly on your shoulder, our slouchy Hobo Bags are an everyday essential for a woman with a busy lifestyle and perfect if you like to be prepared in all situations. Our soft shaped leather hobo bags are not only on-trend but also incredibly practical – they are designed to be spacious enough to carry everything you might need, or to give you some extra storage on a shopping trip.

Crafted from the finest leather, we don’t compromise on luxury with our Hobo Bags, so you can showcase your laidback style with a wardrobe staple that you’ll return to season after season. Explore our full collection of timeless slouchy bags that are available in a range of wearable colours such as black, tan, burgundy, slate and grey. With various iconic styles and sizes for you to choose from, you’re sure to discover the perfect designer Hobo Bag to add to your collection.

What is a Hobo Bag?

A hobo bag is a type of handbag which is typically made from flexible materials, which when put down give the signature hobo slump or slouch look. The hobo bag is typically larger in size and features an oversized strap, this combined with the crescent shape help in delivering the perfect slouch. Many Hobo Bags come with an adjustable strap to allow for cross body use. However, in more modern hobo bags the fashion has changed and the most popular styles now feature a singular oversized strap that can be worn in the crease of the arm.

The hobo bag is a popular everyday bag of choice for many, this is because of the hobo bags casual and more slouchy style. Traditionally they are made from a relaxed, soft and flexible leather which allow the Hobo Bags shape to change throughout the day and ensures it fits to your needs, making them a very comfortable everyday bag to wear. Their popularity is only increased due to the spacious interior which will comfortably fit all your daily needs and also some extra storage (just in case!). Hobo Bags can come in many different designs, colours or sizes, the only aspect that qualifies them as a hobo bag is that they must be made from soft and flexible materials enabling the unique slouch.

Where did Hobo Bags originate?

The Hobo Bag was originally designed after a traditional hobo bindle, as seen in the nursery rhyme ‘The three little pigs’. A hobo bindle is a stick with cloth, or a blanket tied around one end for carrying items, the cloth is then secured around the stick and then the stick is carried over the user shoulder. Due to the weight of the bindle being transferred to the shoulder, rather than being carried by hand, allowed a longer lasting and comfortable grip, especially when it is a heavier load to carry. The idea of the Hobo Bag is that it can carry all of your things whilst still having room for more.

The term ‘Hobo’ was first used to describe homeless migrant workers in the late 19th century in America. George and Lennie from ‘Of Mice and Men’ were ‘hobos’ due to the fact they did not have a permanent resident and would carry all their belongings in a makeshift sack. All these traditions meanings were developed, and the fashion hobo bag was developed. The first ever Hobo Bag in the fashion industry was created in 1936 and was sold for only 35cents. Today is a different story, the hobo bag is incredibly popular and almost every fashion brand will have a hobo bag in their collection, a modern-day luxury hobo bag could go for as much as £3,000 a big difference from the first 35 cents.

Global Hobo Bag Trends

Whilst the first Hobo Bag was created in early 1936 it wasn’t until later that the trend spiked. In the 1960s hobo bags were the bag of the season, everyone wanted one and it completely took over the fashion world. A big spike in the hobo bag popularity was thanks to fashion icon Jacqueline Kennedy who began wearing a slouchy brown hobo bag with many of her outfits. The brown Hobo Bag gained huge popularity and truly shined a light on the hobo bag style. Women everywhere were wanting to get their hands on their own brown hobo bag. Gucci noticed how popular Jacqueline Kennedy’s bag was that they renamed the brown hobo bag ‘The Jackie’ in her honour.

The Hobo Bag popularity didn’t go unnoticed and Tom Ford launched their own bespoke design in 1999, Frieda Gianni also designed her take in 2004. Tom Ford’s revived hobo style bag quickly became the ‘it bag’ of the moment and it’s mass popularity led it to selling out everywhere. From here, more accessible fashion brands began creating their own takes so that the masses could also access this spiking trend. The hobo bag had its moment and it created a wave of bohemian styled fashion which only made the slouched hobo bag even more popular. The relaxed bag and the bohemian trend didn’t go unnoticed and many of the a list styled celebrities adopted the trend, Sienna Miller was a key style icon of the movement.

Whilst the Hobo Bag had it’s big moment in the mist of the bohemian trend in the 2000s, it is being revived and we are starting to see a lot more of the hobo bag again. However, the 2019 hobo bag revival has seen some adaptations to the classic, the addition of the adjustable and removable cross body strap has enabled a more hands free approach.

Since the early 2000’s the Hobo Bag has been a fashion staple. However, in 2018/2019 brands began to bring back the hobo style back, this time many bags had the added attachment of a detachable cross-body strap, as well as the shoulder strap. Presently, nearly every designer has a range of hobo bags. It’s unlikely that this style of bag will ever go out of fashion, as there are so many different shapes, sizes and colours it can be designed in. It remains just a popular as it is fun, strong, large, slouchy and relaxed as ever.

“With only one bag, you can change your outfit completely.”- Sonia Rykiel

Radley Hobo Bags for Women

Eaton Hall- Large Zip-Top Hobo Bag

Eaton Hall is a soft leather large hobo bag which is the perfect everyday accessory. The spacious interior holds enough space for all your everyday essentials and more and the fun metallic stripe design is so stylish you could easily transition it from day to night.

Patcham Palace- Medium Zip-Top Hobo Bag

A minimalistic hobo bag, the Patcham Palace offers a roomy interior compartment and a sleek design that will go with any and every outfit. This leather hobo bag comes in a variety of classic colours, from a dove grey hobo bag design, a simplistic black hobo bag and also a tan hobo bag which would be perfect for those summer outfits.

Oxleas- Large Zip-Top Hobo Bag

Oxleas offers an on-trend approach to the classic hobo bag. The tonal colour blocking intertwined with stylish faux snake skin means this animal print hobo bag is not only on-trend but also very versatile. The beautiful leather hobo bag offers plenty of interior space to hold all that you need day to night.

Pear St- Medium Zip-Top Hobo Bag

This practical black leather hobo bag will compliment your work wardrobe perfectly. The flapover front and internal zip pockets will help to keep you organised all the time.

Hobo Bags for Men

Whilst there are many handbag styles that are now aimed at men, the hobo bag is one that isn’t as transferable. The reason for this is more male focused designs tend to be much more structured which is the opposite of the hobo bag.

Different Types of Hobo Bags

Hobo Bags come in many shapes, sizes and styles; however, they all have the same common features in that they are typically large in size and crescent shaped to give a slouchy posture. Many of them have slightly different features which distinguish them from others.


A Hobo Bag that is embroidered is one that has been decorated with patterns sewn on with thread. This is done to give the bag a pretty and distinct pattern to make stand out from others. It gives the bag a more feminine touch, rather than just having the plain leather.


A Hobo Bag that is tasselled is one that has tufts of loosely hanging threads or cords knotted at one end and attached for decoration to soft furnishings, clothing, or other items. This is done to give the bag a trendy and smart look when carried.


This is the typical style Hobo Bag. The bag has either one or two straps that are long enough to be carried on your shoulder with the bag being tucked under your arm. The heavier the bag, the thicker the strap should be to help distribute the weight of it. Some hobo bags come with different materials of straps to the actual bag.


This is the other style of Hobo Bag that is become quite popular in more recent years. Instead of a shoulder strap, the bag has one longer strap, so that you can wear the bag cross-body, allowing you to be hands-free. Some hobo bags come with both the shoulder and cross-body strap, so that you get the option of what strap you prefer. These straps are usually detachable.


The most common material for Hobo Bags to be designed in is a soft, flexible leather. This is because it is a strong and durable material, that still allows the bag to slouch when set down. However, a hobo bag can be made from and flexible material, and wool is one of the other common ones. Woollen hobo bags are popular as they are usually cheaper than leather but give the same effect that the leather ones do. They are also more of a casual style than the leather bags.

How to choose the right Hobo Bag for you

What are you using it for?

If you are looking for a Hobo Bag that you can use in everyday life, then it is best to get a bag that is slightly bigger and has more compartments in it. This is so that you can carry more but also be able to separate and locate the contents of your bag with ease. If you are wanting a bag to take shopping then a smaller one may be better as it won’t be in your way as much. Some hobo bags that have detachable cross-body straps are good for shoppers who only want to take a couple of things with them and use their hands to look. They are also good for mothers who have children with them and need to hold their children as well as their essentials.

How much will you need to put in it?

The more you need to put in the larger it will need to be. If your bag it going to be heavy, it’s always better to go for a hobo bag which has a thicker strap on it. This is because the weight of it will be distributed more evenly across your shoulders and be a lot comfier for you.

Try it on

Take what you will carry in the Hobo Bag with you and try it on with everything inside. That way you can see how heavy the bag will be when it’s on your shoulder. You will also be able to work out if it is a comfortable fit on you.

Where are you taking it?

If you’re going to have your Hobo Bag outside, it would be better to go for one that is made of a waterproof or water-resistant material to protect it from rain or snow. Leather is the most popular choice for hobo bags, because it is a durable material.

How to wear a Hobo Bag

The best way to wear a hobo bag is on your shoulder so that the bag slouches to the shape of your body for comfort.

You could also wear a hobo bag on the crook of your arm for a more stylish look.

Holding the strap of the hobo bag with your hand gives off more of a relaxed vibe.

Some hobo bags also come with a cross body strap, therefore, for on-the-go, wear the bag across your body for a hands-free experience.

Fun Hobo Bag Facts

The name ‘Hobo’ comes from the term ‘Hobo Bindle’ because the bag’s slouchy crescent shape is similar to a bindle.

The hobo shoulder bag became very popular in the 1960’s after Jackie O was seen wearing one.

Hobo style handbags are a big favourite amongst bohemian fashionistas such as Sienna Miller, Nicole Richie or Vanessa Hudgens.

Hobo Bags are produced using flexible materials such as soft leather, microfiber or suede. As a result, this style of bag tends to slouch or fold in on itself.