Even the simplest of handbag styles from Betsey Johnson is bound to have a quirky design feature somewhere on its exterior. I'd actually be shocked to see one without some sort of unexpected twist.

Enter the heart padlock detail on the front of the Locked In hobo. This otherwise relatively normal-looking purse is ...

The hobo has definitely undergone some changes in recent years. Once a crescent-shaped slouchy symbol of bohemian bliss, now it seems that anything goes!

The Charleze calls itself a hobo, but it's definitely not hippie-chic. There's a slightly relaxed feel, but this structured synthetic bag with its platform base has none of ...

Queens of class and sophistication, Gucci, have produced yet another subtle yet beautiful bag to accompany sexy gals through the day and well into the night.

This golden shimmery purse is actually incredibly simple of design. After all, the smooth soft golden leather isn't embellished in any way shape or form; the simple ...

A bright colorblock pattern is nothing new for a L.A.M.B. handbag, but I wouldn't call it the brand's signature style. However, the bold look fits right in with Gwen Stefani's strong fashion sensibility so easily seen in L.A.M.B.'s products.

Although the Darjeeling collection of handbags is by far my favorite colorful geometric ...

I've seen many designers attempt to reinvent the popular hobo handbag, but none have done it quite like Sondra Roberts.

The slouchy, relaxed profile we've come to expect is gone, replaced by a structured curved body. But the bohemian vibe isn't abandoned entirely, with natural canvas and twine fabrics woven together for ...

Rebecca Minkoff shows she knows how to do more than boxy bags with the new Darling.

This unexpected purse is more hobo than shoulder bag with its crescent shape and soft, slouchy silhouette. For a designer who favors structure, this bohemian look is a real surprise. But she embraces it, with tasseled ...

For once, cute surf-wear designer Roxy has produced a hobo that is more about simplicity than canvas.

Where usually the designer's signature logos and prints are all over the bag, this simple Where It's At hobo has only plain and minimalist white synthetic. Suddenly this casual designer is more than appropriate for the office, and ...

It's the season for plaid, and this classic print seems to be popping up everywhere. Like the Nine West Rory Cross-Body Bag, this Roxy Living It Up hobo handbag fits right in with the checkered scarves and coats that have now emerged from peoples' closets.

Although I tend to prefer red and ...

Nine West's recently released Vintage America collection is all about classic American style and timeless fashion combined with a little of today's trends. That's exactly how I'd describe this Cindy hobo bag from the line.

Its traditional hobo silhouette is both classic and predictable, yet some interesting details take the Cindy to a different ...

This All Over Studs Flap Over handbag from Melie Bianco has a bit of an equestrian vibe about it, which is a fashion trend I'm currently rather excited.

Although not a traditional saddle bag in its truest definition, this casual hobo's double buckled detail on the bottom of the front flap definitely reminds ...

The Mari Hobo bag is part of Big Buddha's fall 2009 collection, but I have to admit that I'm a bit confused by its placement there. It's not that I dislike the design. I'm just not sure it's totally fall-worthy with its fabric body.

That being said, the style of the Mari Hobo ...

It seems like every handbag brand has its take on the woven trend. But they don't all have to cost the prices of a Bottega Venetta. At $430, Linea Pelle's Juliana represents great value.

The price might not be exactly cheap and cheerful, but it's entirely reasonable for a woven purse crafted ...

No one expects genuine exotics for under $100. But if you hope to enjoy the look at a budget friendly price, this python-like hobo from Chinese Laundry is a decent option.

The traditional slouchy hobo shape is jazzed up by the snakeskin print, which is embossed on the polyurethane body. This blue ...

Canvas handbags might be on their way out for the new season, but tribal details aren't going anywhere. This Steven by Steve Madden Uptown Tribal Bucket Hobo has both features, which might not be the best option for the fall but is still a cute option for a wardrobe.

There's nothing overtly summery about this bucket ...

Here's another installment from B. Makowsky's collection of handbags named after famous cities around the world. There must be something about Havana and hobos, however, since both 7 For All Mankind and Hayden-Harnett have hobos by the same name.

There's aren't too many features that the other brands' versions share with this ...

Big Buddha gives the hobo a contemporary makeover with the Soho.

It features two of fall's biggest trends: fringe and pyramid studs. Yet by keeping the accents in check, the look is timeless rather than faddish. The fringing is short, ensuring the purse never looks like it's just stepped from the South. ...

Perforated leather, in my opinion, can either go really well or look a little off on a purse. Personally, I tend to prefer it as a detail rather than the main material of the handbag body, but this Just Cavalli Flower Bag's use of the feature has me intrigued.

The small perforations ...

Burberry is a label that, honestly, I sort of thought of as a one-trick pony until a few years ago. Its one trick being the trench, of course. In the past couple years, though, the line has really stepped up its fashion game. And Prorsum has taken it one step further with ...

There are some things that are OK in modern society, and some things that aren't. Leather, for the majority of the market, is OK. In a similar vein, eel skin shoes and handbags are acceptable to modern values, whereas fur ... fur is not. With so many alternatives for real fur, many of ...

Patchwork isn't always a handbag design feature that I love, but the look can be stunning when it's done well. Without a doubt, some of my favorite patchwork leather bags come from designer brand Miu Miu.

The price range of Prada's younger sister company isn't for everyone, though. Although Steve Madden's line ...

The design of the Treesje Kingsley hobo shares quite a few similarities with the trendy features of the Botkier Uma satchel with its slouchy ruched body and zippered detail. Actually, the two designer brands really aren't that far apart in their overall styles.

The main difference between the Uma and this Treesje handbag is ...

Ralph Lauren combines casual cool and British charm to create this chic Houndstooth Hobo.

The fabric finish gives this bag a relaxed style, but it's a little different to the boho vibe we associate with hobos. The shape's a lot more structured, and that houndstooth print creates a preppy private school feel. ...

I usually think of Whiting & Davis as a go-to brand for classy formal clutches and minaudieres, and it certainly has its fair share of shimmery bags that fit those categories. However, this long-standing fashion brand also has a wonderful selection of hobo bags that simply refuse to be overlooked.

Just like their ...

When Valentino himself retired from designing his eponymous line, I was a little concerned. Who, after all, can replace an icon? The current designers, Maria Grazia Chiuri and Pier Paolo Piccioli, however worked under the man himself designing accessories, and their designs haven't disrupted the continuity of his legacy, at least in ...

Well, I'm back to grommets again. The classy Bulga Cava Tote must have gotten me on a kick for them. There's something so interesting yet casual about the detail that makes it a great addition to a handbag.

This is not the first time that Cole Haan has used grommets on a ...

Stuart Weitzman gives the hobo style a girly makeover with this pleated leather bag. The Ruche Hobo brings sophistication to this traditionally casual style.

The classic crescent shape and relaxed slouch is maintained, but it's given a little more structure than usual thanks to the striking pleats. This vertical ruching is the ...

Stella McCartney is one of those rare fashion designers who puts her morals where her mouth is. She is a militant vegan, and none of her designs use any animal products or even any PVC-based synthetics. All her designs are made from eco-friendly and totally plant-based materials. And, they're also amazing.

I'm basically ...

Jessica Jensen takes the hobo back to basics with its Artisan bag.

The style is simple and chic, without all the accents we tend to see. Forget fringing and studs: this is minimalism at its most pure. That might not suit the season's taste for embellishments, but the Artisan isn't about catering ...

Miu Miu, the hip younger sister line to Prada, is always on the cutting edge of what's new and hot. Miuccia Prada, the designer of the line, has been rumored to say that she thinks in Prada, but she dreams in Miu Miu.

This Quilted Nappa Hobo is a great example of Miu ...

This is a fantastic back-to-school bag for so many reasons. Kenneth Cole New York is a great youth brand; its bags are stylish and fun, and good quality for the affordable price. This is also a classic style that would serve a high school or college student well. Plus it has an ...

Cole Haan is known for its leathers, so it makes sense that the brand would create a Soft Collection designed to showcase its "supple leather fabrication." And, as I always find it silly to make super soft bags too structured, a drawstring hobo like this one seems like the perfect shape for ...

Tartan might not be a look that suits everyone's taste, but I happen to love this checkered fabric when it is done well. It's not a fabric pattern that you want to include in every outfit you wear, unless you're part of a Scottish clan; however, it's a fun addition to a ...

This Francesco Biasia Lucky Seven hobo brings together sophisticated simplicity and modern convenience in one beautiful package.

If you like the understated elegance of brands like Linea Pelle or Joe's Jeans, then this handbag is probably right up your alley. The Lucky Seven hobo offers women a hint of an equestrian-inspired ...

Although the Bally Joletta handbag looks like a simple hobo at first glance, there are some first-rate details on it that make it worth your consideration.

The Joletta's impressive quality comes with a hefty price tag, however, as you might expect from the brand. While a $1,165 retail price will probably keep ...

With the temperatures around the globe beginning the depressing nosedive into winter, the time has come to look for a classy and elegant bag with a hint of the cool and icy about it. This surprisingly spacious cool gray tote from the G by Guess range is just the cool-as-a-cucumber hobo that I ...

Spiegel keeps it simple with this lovely jersey-knit hobo bag.

At first glance, one could easily accuse this handbag of being boring. It's got no bows or buckles to attract our attention. Black is a color too conservative to wow us. And jersey-knit doesn't have the same appeal as an exotic skin ...

If you know B. Makowsky's style fairly well, you could probably spot this one as one of the brands' designs from a mile away. Though there's nothing particularly stunning about it, the Kingston hobo has the label's signature look written all over it.

Like most B. Makowsky handbags, the Kingston is crafted ...

Melie Bianco has a special knack for creating on-trend handbags that don't cost the earth. While the label has been known to "borrow" inspiration from Jimmy Choo and Valentino, it's just as capable of coming up with must-have fashion items all its own. The Franny is this season's head-turner.

The ...

Origami has been one of the most enjoyable trends sweeping fashion circles this year. From beautifully executed folded dresses through to paper jewellery, this Japanese paper art has hit all aspects of fashion face on. New technology means that origami style doesn't have to be made from paper, as this wonderfully structured ...

Lucky Brand's slouch hobo combines the casual profile we expect from these bags with a new sophisticated attitude.

Slouchy relaxed leather is a hobo trademark, and this purse delivers on that score. But by keeping the design simple, this Lucky Brand bag is more sophisticated than most of its hippie-chic peers. There ...

Dolce & Gabbana's young, hip line of the business D&G is usually ahead of the curve when it comes to trends. This contemporary Katri hobo is no exception to that.

With its modern-looking styling and one-of-a-kind details, the Katri has an undeniable urban feel to it. Of course, if brands like Kate Spade ...

Hobos aren't a handbag you traditionally associate with private schools and Ivy Leaguers, but that's exactly what I'm reminded of when I look at the Vanessa Bryn Mawr from Kate Spade.

That's not to say the purse oozes the sort of luxury most of us could only dream of. The leather and ...

Jimmy Choo gives the hobo a little rock and roll edge with the Rania.

The punk attitude comes from two rows of gleaming grommets that embellish the top of the bag. They've become somewhat of a Jimmy Choo trademark, utilized in iconic bags like the Ramona, Riki, and Rio. ...

Inge Christopher is famous for feminine evening bags which channel old Hollywood glamour. So it's surprising to see the brand creating something as edgy and contemporary as the Greta.

This hobo has the crescent shape we expect, but it's a lot less slouchy. The structure comes from decorative seams dotted with edgy ...

One of the best ways to get a top-end designer handbag with a twist is to choose a handbag crafted from unusual yet economical materials. Straw bags are a great idea for this, as the material is cheap yet the designs are very ... well ... designer!

If the vintage style classy straw bag ...

There's something about this B. Makowsky Lucca hobo that reminds me of a Marc by Marc Jacobs handbag. I think it must be the combination of buttery soft leather with unique design details.

Like the Totally Turnlock Quinn and the Softy City Bag, the Lucca's bold color choice accentuates the lightly pebbled texture of ...

Many designers have attempted to cash in on the fringed trend, but few have done it with the style and sophistication of Gucci.

The Babouska is a bag that stays true to the bohemian style synonymous with the hobo, while adding an injection of elegance. The traditional crescent shape and long flowing ...

SR Squared by Sondra Roberts doesn't have any particular signature style but is one of those brands that merely mimics big trends like ruffles and patchwork. It was just a matter of time that they came out with a studded handbag since the trend has been making the rounds with designers ...

Metallic trim on every inch that isn't coated in sequins, the Coach Sequin Spotlight Bag will certainly shine a light on your sartorial choice. It's a bag to love or hate on sight, but has some details worth a closer look.

If the glare is too blinding for you to delineate features, I'll tell you that ...

These days a hobo is rarely just a hobo. The original crescent-shaped, bohemian-chic bag has given way to purses that are less slouchy and more sophisticated. The Essex is Etienne Aigner's elegant interpretation of the traditional hobo handbag.

Despite its slouchy top, the Essex has more structure than the average hobo. Its ...