Hobo Bags Are Back - Here's How To Style The Slouchy, Retro Vibe

Out with the itty-bitty, cant-fit-a-tube-of-lipgloss bags, and in with bags that are stylish yet spacious enough to fit all our essentials. If you commute to work or school regularly, you know there has to be room for everything you use during the day — books, wallet, laptop, and maybe tampons. The need for more bag room is why, even though bags like the tote and the bucket bag may leave the trend table, they always remain in style for their versatility and spaciousness. It's no surprise that a relative of the tote is back on our radar, and it is none other than the hobo bag.

While it doesn't have the best name, the travails of the Great Depression inspired what we now know as the hobo bag. As Monpiel explains, many migrants were homeless and seeking employment while carrying their few precious belongings in a cloth with two ends tied to a stick or pole. This practical, minimalist combo inspired the hobo bag's crescent shape and slouchy feel. However, the bag has come a long way from a symbol of the Depression to a modern-day go-to for carrying items necessary for our daily activities.

We know you might be eager to cop one right now, and so to help, here are a few ways you can style the hobo bag.

As Laflore Paris explains, the Parisian chic style combines casual, simple, elegant, and modern. And the hobo bag is the perfect bag for such a style. Combine a shirt in a neutral color like beige or grey with some nice structured pants or jeans, and a fancy beret, and top it all off with a crossbody or shoulder hobo bag like the Marley Hobo from AALLYN from AALLYN.

The hobo bag might be simple, but it is full of character, which is why it's an excellent choice for dressing down, making an outfit more modern, or wearing with many layers of clothing. You can style your large hobo bags during cold days by wearing them with your layered winter jackets and a beanie/head warmer. Maria Alia does this fabulously by wearing a black Proenza Schouler bag with a black leather jacket and corseted layers undeath, allowing the bag and the jacket to merge and create one eclectic yet uniform look.

Think the hobo bag's only fit for play? Wrong! This is your sign to pair it with chic corporate clothing and hit the stage — or perhaps your cubicle. A small to medium hobo bag, like the Trudie Woven Hobo Handbag from Pilar, works great when worn on the inside of your elbow. Pair that with a lovely pencil skirt or, as Lane Crawford recommends, a square jumpsuit and some leather pumps, and you've got yourself a fabulous work fit.

Now don't get it twisted. Hobos are far from boring, and the many hues they come in prove that. When you're looking to spice up a monochromatic look or an outfit with many neutrals, try a bright-colored hobo like Bottega Veneta's Mini Jodie in Cranberry. Also, your look does not have to be monochromatic for your bag to be the focal point. Take it from Shanai, who styles her colorful knee-length cardigan with a bright mustard yellow hobo bag from JW Anderson.

While the hobo bag works well as a pop of color, it does even better when it matches your outfit. So style your hobo bag, whether a mini or a large one, with a button-up shirt in a similar shade for work or a dress in the same shade for a picnic. For some inspo on how to do this, Buka pairs an olive green shirt with a hobo bag in the same color.

Now that you know how to make your hobos the focal point by adding some layers underneath or wearing it as a pop of color, you should also know that you can wear it for play. Whether it's a large tote hobo or a miniature shoulder version, Brahmin says to go minimalist casual by pairing your hobo bag with denim pants and a white button-up shirt. Try a crossbody hobo bag like Selene Midnight Hobo from Han Wen for a more relaxed vibe.

Size matters, but only a few bags allow you to play with that element. Hobo bags, however, do. As Reecee explains, you can experiment with sizes depending on your mood and the occasion. A large hobo bag seems more whimsical and practical, and a smaller one is suited to more formal gatherings. Either way, play around it and have fun, just like Maria Alia with her bubble blue hobo bag. Get into it.