The Ultimate Guide To Hobo Bags

The hobo bag stands as one of the most enduring classic styles in the world of handbags. Known for its generous size, it effortlessly combines functionality with aesthetic appeal. What sets the hobo bag apart from other styles is its distinctive crescent shape and relaxed, slouchy silhouette.
This versatile accessory boasts a rich history and continues to evolve in the modern fashion landscape. In this comprehensive guide, you will delve into the origins of the hobo bag, explore the various types of hobo bags available, and learn to care for each kind.
What Are Hobo Bags?
Hobo bags are a popular style of handbag that typically features an unstructured design. They tend to collapse and fold over themselves, resulting in a soft, curved silhouette with a crescent shape that naturally conforms to the body when worn. Hobo bags are also known for being exceedingly spacious, boasting roomy interiors that can accommodate all your daily essentials with ease. Most hobo bags come with a single, adjustable strap that can be worn on one shoulder or across the body, offering the same comfort, convenience, and versatility as crossbody bags.
Although hobo bags traditionally exude a casual and laid-back style, they have undergone a transformation over the years. Nowadays, you can find a diverse range of hobo bags, including more structured and tailored designs, catering to different fashion preferences.
The Origin and History of Hobo Bags
The term 'hobo' was initially used to describe migrant workers in America at the end of the 19th century. These individuals were predominantly homeless and travelled on freight trains in search of work, carrying their belongings in a sack tied to a stick, a set-up commonly known as a 'bindle.' This bindle design served as inspiration for the relaxed silhouette of the modern-day hobo bag, with the first hobo bag dating as far back as 1936.
The hobo bag's popularity surged in the 1960s when it was embraced by the hippie movement. During this era, hobo bags were often adorned with tassels and other symbols of the time, making them a fashion statement for the flower children and their hedonistic lifestyle. As the counterculture movement waned, so did the hobo bag's popularity. However, in the late 1990s and early 2000s, bohemian influences gained prominence in haute couture, and celebrities such as Sienna Miller, Kate Moss, and the Olsen twins popularised the style as part of the larger boho-chic trend.
Today, the hobo bag is highly sought after for its stylish practicality. There are numerous modern interpretations of the hobo bag, ranging from sleek and minimalistic to petite in size. It's this adaptability and versatility that have ensured the hobo bag's enduring relevance in the world of fashion.
Types of Hobo Bags

Classic Hobo Bags
The quintessential hobo bag is characterised by its crescent shape, often made from soft and pliable materials. Its design is minimal, featuring complementary metallic hardware and a singular shoulder strap. Simple yet sophisticated, the hobo bag is favoured for its versatility; it effortlessly transitions from casual hangouts to upscale functions, exuding chic charm. With options available in different sizes and finishes, the classic hobo bag can be tailored to suit everyday needs and various style preferences.

Hobo Tote Bags
Combining capacious interiors with the laid-back hobo silhouette, hobo tote bags offer a functional yet stylish choice. You can keep things simple and sleek with elegant colourways and neutral finishes — they will complement any outfit and accommodate all your essentials for the day. For a more experimental silhouette, look for visually interesting details; metallic accents inject an edgy element, while belted straps add a polished touch.

Satchel Hobo Bag
Adapting the hobo bag into a cross-body style akin to a satchel, these iterations offer ultimate convenience and comfort. Noted for their classic belted look and utilitarian appeal, they strike a balance between looking casual and elevated.
In addition to the hobo bag's typical generous size, it also comes in small and medium sizes, adding a dainty quality that allows for versatile dressing, whether it's for a formal occasion or a casual outing. Furthermore, various alterations to the conventional satchel bag silhouette result in interesting pieces, such as those featuring a textured finish or a printed buckle.

Slouchy Hobo Bag
Arguably the most on-trend iteration, the slouchy hobo bag folds in on itself, creating deliberate crinkles and ruching. Its softer form enhances the feminine appeal of the hobo bag, making it the perfect off-duty accessory that strikes a balance between elegance and casual charm. The dynamic shape complements other offbeat details, such as a tubular trim or glossy finish, resulting in a standout bag that offers endless styling possibilities.

Convertible Hobo Bag
With its minimal and laidback silhouette, the hobo bag is a truly versatile accessory that can be styled in numerous ways — especially when they are paired with various strap options. Adjustable shoulder straps effortlessly convert them into casual crossbody bags for convenient, hands-free carrying. For more formal occasions, chain-link straps add an element of elegance to the unstructured silhouette, transforming hobo bags into luxurious shoulder bags. With a plethora of strap options suitable for various looks, these convertible hobo bags seamlessly transition from day to night, ensuring effortless style.

Bucket Hobo Bag
While the hobo bag is renowned for its soft body, the bucket silhouette gives it a more defined shape. Bucket hobo bags not only provide a roomy interior but also exude a polished look — perfect for formal settings and occasions. Furthermore, sophisticated yet simple details elevate the style, such as a drawstring closure that ensures the security of your essentials while balancing the weight of the structured bottom.
Choosing the Perfect Hobo Bag
Selecting the perfect hobo bag is a decision that goes beyond mere fashion; it's about finding a companion that complements your lifestyle and personality. In this section, we'll explore the various factors to consider in your decision-making process, such as materials, sizes, strap lengths, closures, and colours.
Materials
First, let’s take a look at the different types of materials a hobo bag can be made from.
Leather
Genuine leather hobo bags undoubtedly represent a more luxurious and costly choice. However, if you seek an investment piece that will stand the test of time, opting for leather crafted from calfskin, lambskin, or nappa is a wise decision. These materials guarantee durability, ensuring your money is well-spent. With meticulous care, these bags can even transform into cherished vintage or sentimental items over time.

Fabric and canvas
Canvas and fabric materials are typically associated with tote bags, but that doesn't mean you can't find hobo bags made from these durable and lightweight materials. Canvas, with its distinctive neutral beige or off-white hue, creates a unique two-tone aesthetic, adding a casual vibe to the overall design.
Suede
Suede remains a popular material choice during transitional seasons, seen in cosy knee-high boots and soft-textured bags. Its thin, textured material will perfectly accommodate the fluctuating temperatures of early pre-fall and pre-spring. A suede hobo bag will kickstart your cold-weather wardrobe in fall and seamlessly transition into winter and spring without appearing out of place.
Straw / Raffia
A raffia or straw bag instantly evokes images of sun-soaked vacations and beachside relaxation. Its woven, weave-like texture adds a tactile and eye-catching element, making it a staple in our summer wardrobe. Why not consider the Winslet canvas hobo bag as your next warm-weather companion?
Nylon
Nylon bags are experiencing a resurgence in popularity. From cult classic designs to oversized and padded nylon hobo bags, they are highly sought-after for good reason. Lightweight, durable, and water-resistant, nylon stands out as a remarkably carefree material, making it perfect for everyday wear.
Synthetic Materials
For budget-conscious buyers, synthetic materials offer an excellent alternative. With a diverse range including croc-effect finishes, recycled polyester, faux leather, and faux suede, these hobo bag options provide a luxurious look and feel at a more affordable price – plus, they’re animal-friendly too!
Size
Hobo bags are available in a wide range of sizes, from petite options designed for essentials to generously spacious bags capable of accommodating all your needs. The size you opt for directly impacts the bag’s capacity and overall functionality, making it an important factor to take into consideration.
Strap Length & Handles
Choosing the perfect strap length and handle type ultimately comes down to your personal style and preferences. If you prefer a bold look, opt for sculptural acrylic handles or glamorous chain ones. Alternatively, if simplicity is your preference, a functional basic strap will suffice.
In today’s market, most bags come with adjustable straps. Therefore, choose a hobo bag with a detachable strap that aligns with your style. This adjustable feature allows you to customise the length and decide whether you want to sling it over your shoulder or wear it across your body. Either way, it keeps your hands free and offers great convenience.
Closure, Compartments and Pockets
It is important to pay attention to the details when selecting the perfect hobo bag for yourself. Even the smallest elements, such as the type of closure and the number of compartments, play a significant role. It is important to consider how these factors align with your specific needs and requirements.
For instance, for individuals who are constantly on the move, a larger hobo bag equipped with an inner pouch and a magnetic closure might be a better choice. This design ensures better organisation, allowing them to keep their belongings neat and sorted. Moreover, the magnetic closure offers quick and effortless access compared to a push-lock closure, enhancing the bag’s practicality and convenience.

Colour
Where colour is concerned, the options are literally endless. If you are searching for a hobo bag that offers unparalleled versatility and will complement everything in your wardrobe, classic hues like black and white are foolproof. Alternatives that are just as elegant and versatile include neutral colours like beige, brown, and cream.
On the other hand, if you are looking to inject a vibrant pop of colour into your wardrobe, bright, punchy hues such as orange, fuchsia pink, and lime green will do the trick.
With all these factors taken into consideration, one thing is for sure — you will find something that piques your fancy from our wide and extensive range of hobo bags.
Styling with Hobo Bags

Casual Everyday Look
With its signature slouchy silhouette, hobo bags effortlessly embody a casual aesthetic. Their laidback look complements any outfit, whether paired with a simple t-shirt, jeans, and sneakers combo, or styled with a light, airy sundress and sandals. Moreover, the bag's large capacity makes it the ideal companion for your everyday errands.
Boho-chic
Opt for a hobo bag with fringe details in natural, earthy tones if you're aiming for the Y2K boho-chic look. Pair it with a printed maxi dress or flared pants and a peasant blouse as the base outfit. Complete the look with ankle boots or open-toe sandals, and layered jewellery that will perfectly capture the relaxed bohemian aesthetic.
For The Office
Neutral-toned hobo bags with a more structured silhouette are the key to sporting this style in a professional setting. Crescent-shaped bags that hold their shape well offer the same casual feel as the classic slouchy bag we know and love. They pair perfectly with tailored pants, blouses and blazers to create a polished and sophisticated look.

Evening / Party
Create an eye-catching, party-ready ensemble by choosing a hobo bag in a vibrant shade or one with a striking metallic finish. Consider hobo bags with chain-link or metallic hardware details to add a glamorous touch to your overall look. Let the bag take centre stage by keeping the rest of your outfit more subdued — a little black dress paired with your favourite high heels will do the trick.
Weekend Getaway
When it comes to a short weekend trip, having a versatile bag tops the packing list. Opt for a practical and stylish hobo bag that can be transformed into a crossbody style when you need to keep your hands free or your bag more secure against your body. Additionally, choose a bag that offers ample space to accommodate all your belongings.

Color Coordination
When in doubt, create a colour-coordinated look to instantly elevate your style. Match your hobo bag’s colour to one element of your outfit, such as your shoes, to create a polished and put-together look. Alternatively, accessorise your outfit with a hobo bag in a complementary colour (an opposite hue on the colour wheel) to add visual harmony to your ensemble.
Caring for Your Hobo Bag
To prolong the durability and preserve the appearance of your hobo bags, exercise proper care. The care routine may vary based on the material of your hobo bag, requiring specific attention and methods. To ensure your CHARLES & KEITH bag remains in excellent condition, adhere to these product care tips.
A vital aspect of hobo bag care, especially due to their slouchy shape, involves preserving the bag's form and preventing creases in leather. One method is to stuff the bag with recycled tissue obtained from online orders or other packages. This will help it maintain an upright position when not in use. Alternatively, rolling sweaters and placing them inside the bag can aid in retaining its shape too.
It's essential to avoid hanging the bag, as this could distort the shape of the handle and cause it to age prematurely. By following these care practices, you can ensure your hobo bag stays stylish and functional for a long time.
Canvas
Although canvas hobo bags are durable, regular care and maintenance can maximise its mileage. Here are some tips on how to do so:
- Regular Maintenance: Gently brush off any loose dirt or debris from the surface of the bag. You can use a soft brush or a lint-free cloth.
- Spot Cleaning: For small stains or spots, use a mild detergent mixed with water. Dip a clean cloth into the soapy water, wring it out, and gently blot the stained area. Avoid rubbing, as it can spread the stain.
- Hand Washing: If the entire bag needs cleaning, wash your bag by hand. Fill a basin with lukewarm water and a mild detergent. Gently submerge the bag and agitate the water to create suds. Let it soak for a short period, then gently scrub with a soft brush or cloth. Rinse thoroughly with clean water and hang to air dry.
- Drying: Always air dry canvas hobo bags in a well-ventilated area away from direct sunlight and heat sources. Avoid using a dryer, as it can cause shrinkage or warping.
- Storage: When not in use, store your canvas hobo bag in a cool, dry place. Avoid hanging it on hooks for extended periods, as this can distort the shape.
Faux Leather
Faux leather, also known as synthetic leather, requires careful maintenance to keep its appearance and texture intact. Here are some important care tips to bear in mind:
- Spot Cleaning: For small stains, use a damp cloth with mild soap or a specialised faux leather cleaner. Gently wipe the stained area, then wipe again with a clean, damp cloth to remove any soap residue.
- Avoid Harsh Chemicals: Avoid using harsh chemicals, alcohol-based cleaners, or acetone on faux leather, as they can damage the material's finish.
- Conditioning: While faux leather doesn't require conditioning like genuine leather, you can use a small amount of non-greasy, water-based moisturiser to maintain its suppleness. Test in an inconspicuous area first.
- Protection: If you live in a humid environment, consider using a water-resistant spray to protect your faux leather tote from moisture and stains.
- Storage: Keep your faux leather tote in a cool, dry place, away from direct sunlight and heat. Use a dust bag or pillowcase to prevent scratching if you're storing it with other items.
Genuine Leather
Genuine leather hobo bags are a classic and reliable choice, but they require special care to maintain their appearance and durability:
- Regular Cleaning: Wipe down your leather hobo bag with a soft, dry cloth to remove dust and dirt. Regular cleaning prevents particles from accumulating and scratching the leather's surface.
- Avoid Water and Moisture: Leather is sensitive to water and moisture, so avoid exposing your bag to rain or spills. If your bag does get wet, blot it gently with a clean, dry cloth and let it air dry naturally at room temperature. Avoid using direct heat sources like hairdryers.
- Conditioning: Leather can dry out over time, leading to cracks. Apply a leather conditioner every 6 to 12 months or as needed to keep the leather moisturised and supple. Choose a conditioner specifically designed for the type of leather used in your bag.
- Spot Cleaning: For small stains, use a damp cloth with mild soap or a leather cleaner. Gently blot the stained area, then wipe with a clean, damp cloth to remove soap residue.
- Avoid Direct Sunlight: Prolonged exposure to direct sunlight can cause leather to fade and become brittle. Store your leather hobo bag in a cool, dry place away from sunlight when not in use.
- Storage: When not using your leather hobo bag, store it in a dust bag or pillowcase to protect it from dust and light. Avoid using plastic bags, as they can trap moisture.
- Avoid Sharp Objects: Be cautious not to scratch or puncture the leather with sharp objects. Avoid placing your bag on rough surfaces that could damage the bottom.
- Professional Cleaning: For deep stains or extensive cleaning, consider taking your leather hobo bag to a professional leather cleaner. They have the expertise to clean and restore leather without causing damage.
- Maintain Shape: To help your leather hobo bag maintain its shape, avoid overloading it with heavy items for extended periods.
- Patina: Over time, genuine leather develops a unique patina that adds character. Embrace this natural ageing process as it's a sign of quality leather.
Remember that preventive care is essential for all kinds of hobo bags. By keeping them clean and protected, you'll help maintain their appearance and extend their lifespan. Always refer to any care instructions provided by the manufacturer for specific guidance.
We trust this hobo bag guide will come in handy in helping you select one — or even a few — that aligns with your needs and aesthetic preferences. Styling with hobo bags offers endless possibilities, from everyday casual to polished office looks. By carefully coordinating your hobo bag with your outfit and the occasion, you can effortlessly enhance your everyday style.
Read Next
Everything You Need To Know About Mules and How To Wear Them
When it comes to versatility and wearability, few shoe styles would rival the mule. Now considered a modern classic and style staple that is a must-have in every woman’s shoe collection, mules are loved for their comfort and convenience. Thanks to their popularity, it is likely that there would be a pair of mules for any occasion, personality and mood.
In this comprehensive guide, you will learn about what mules are, their history and the details that differentiate them from sister styles like clogs and slides. You will also be introduced to the various types of mules, from flat mules and heeled mules to loafer mules and sneaker mules. Lastly, you will find useful tips on how to style mules for different settings and seasons.
What Are Mule Shoes?

Mules are a type of shoe characterised by a backless design. Loved for their effortless wearability and enhanced breathability, this slip-on shoe style offers the perfect blend of comfort, convenience and style. As mules come in a wide range of designs — from heels to flats and even sneaker hybrids — there is truly a pair of mules to complement any outfit and any occasion.
History & Evolution Of Mule Shoes
Dating back to Ancient Rome, mules were first referred to as mulleus calceus, or ‘purple shoes’. They were worn exclusively by the three highest elected officials and were fully covered by design. In the sixteenth century, French women wore mules within the privacy of their bedrooms. As mules gained favour with esteemed members of the court, they started to appear in public. The mules of the seventeenth and eighteenth centuries typically featured pointed toes, low heels and embroidered patterns, amongst other adornments.
In the twentieth century, mules became popular in the United States — actresses Joan Fontaine and Marilyn Monroe wore mules in their movies. The material shortages of World War II meant that mules had to be made with less delicate materials, such as synthetic hemp and plastic, which made them more appealing to the masses. Their open-back design made it easy to slip them on and off, and the low heels gave wearers a height boost without the discomfort. As more designs became available in the latter part of the century, mules evolved into a versatile silhouette that could work for both casual daytime wear and elevated evening occasions.
Difference Between Mules, Slides & Clogs



It is fairly common to mix mules up with similar styles like slides and clogs. Paying attention to the key differences can help you tell them apart. Clogs and mules may both be backless in their construction, but clogs typically have thicker platform bases that follow the contours of the feet. Clogs are also usually made with sturdier materials like wood. Mules, on the other hand, feature a thinner base, and may come with flat soles or heels of varying heights.
Slides are another backless style, but their open-toe design differentiates them from mules. They typically feature vamp straps that hold the foot in place, while mules are designed to keep the toes completely covered.
Types of Mules
Flat mules

As the name suggests, flat mules are shoes with flat soles or very low, wide heels, often resembling a pair of bedroom slippers. Depending on the design and style you choose, flat mules can easily be dressed down for a super casual look or dressed up to suit a more polished and elevated ensemble.
Heeled mules



Heeled mules are the effortless alternative to regular pumps — offering polished elegance combined with ease of wear, all while providing a stature boost. With a plethora of heels to choose from, there is truly one to suit every height and style preference. For a sleek and streamlined option, kitten heels and stilettos are the way to go. For those who still want a modest lift that is easy to walk in, block heels are ideal.
Platform mules

Playing up the proportions with exaggerated, chunky soles — whether in the form of towering block heels or thick flatform soles — platform mules offer the best of both worlds in providing a flattering height boost without compromising comfort or stability. Exuding a more casual and laidback aesthetic, this makes them a great choice for off-duty days and relaxed office dress codes.
Loafer Mules

Loafer mules toe the line between casual and formal — it is the perfect in-between style that nails the smart-casual aesthetic. They feature a covered-toe, high-vamp silhouette with a distinctive open-back design which makes them less formal than a classic pair of fully covered loafers. Easy to slip on and off, they are made for the on-the-go woman.
Sneaker Mules

If you thought sneakers were the epitome of comfort, sneaker mules take things up a notch with their backless, slip-on design. Retaining a sporty-chic aesthetic, sneaker mules typically feature a lace-up design and covered-toe silhouette combined with the familiar support of cushioned footbeds and flatform soles that promise maximum comfort for the wearer.
How to style mules for any occasions
Easy to wear and style, yet undeniably chic, mules are the ultimate go-to footwear. Here’s how to make them work for every occasion.
Casual Everyday


When dressing for casual, everyday moments, it’s all about comfort and ease. Mules are perfect for activities like running errands, brunch outings and more. Pair them with jeans or flowy bottoms for a relaxed yet effortlessly put-together look.
Office & Workwear


In workplaces with a more relaxed dress code, mules can be an acceptable footwear choice. Opt for heeled styles to create a polished, sophisticated look, and stick to neutral colours to maintain a professional appearance. When in doubt, speak with your HR team or refer to your company’s dress code guidelines to ensure mules are appropriate for your workplace.
Evening Wear / Wedding


While mules may not be ideal for a black-tie dress code, they are perfectly suitable for casual evening parties. Choose a high-heeled pair with sparkly gem embellishments to dial up the glamour. From weddings to girls’ nights out, they will carry you through most dressy occasion in style.
How to wear mules for every season
While the backless design of mules may suggest that they are not suitable for the colder seasons, the truth is quite the opposite. With a few clever styling tricks, you can wear them all year round.
Spring
Mules are a great footwear choice for transitional seasons like spring — their versatility would serve you well when the weather is unpredictable. A covered pair will keep your feet warm on chilly days while remaining breathable enough for warmer weather. Style them with a midi floral skirt for a cute spring look.
Summer
The easy-to-wear design of mules makes them a perfect choice for summer. Opt for a pair that is made with a lightweight, breathable material, such as mesh, to stay comfortably cool on hot summer days. Pair them with a breezy sundress to create a relaxed, effortlessly stylish look.
Fall/Autumn

Like spring, fall is a transitional season with unpredictable weather — this means that mules are a great option during this time as well. To give them a more autumnal feel, go for shades that align with the season’s colour palette, such as neutral, earthy browns.
Winter

Wearing mules in winter may be tricky, but it’s not impossible. Firstly, steer clear of thin, lightweight materials that will do little to insulate your feet from the cold. Instead, go for mules that are made with warm, cosy materials like shearling — not only will they keep you feeling toasty on frosty days, but they will also complement cold-weather ensembles perfectly.
You can also pair them with woollen socks or tights for extra insulation but always use your discretion. On the harshest winter days, it’s often safer (and wiser) to reach for sensible heavy-duty boots.
How to wear mules with socks


These days, wearing socks with mules is not only common, but also considered cool. The key is choosing the right colour and length. Crew socks in classic, solid colours, like black or white, are a failproof choice. However, there are no hard and fast rules. If you are a maximalist dresser, feel free to pair your mules with bold, statement socks that show off your personality.
Just don’t forget to consider the season when choosing materials — go for breathable cotton during the warmer months, and switch to cosy woollen socks when the weather turns chilly.
Mules are the reliable workhorses of a modern woman’s wardrobe. Traditionally seen as casual shoes, mules are now acceptable footwear for a wide range of occasions. Whether you are going to the office or a wedding, there is a pair of mules that will serve you well — you just have to choose wisely.
We hope this guide has helped you gain a better understanding of how to wear mules of different types and designs. By picking the right materials and styling them appropriately, you can wear mules all year round, through all four seasons. If you are looking to add a pair of mules to your shoe collection, check out our extensive range here.