Bally ups the sophistication factor of the traditional hobo with the Keli.

The crescent shape and relaxed form are pure vintage hobo, but there's a certain chicness here missing from those classic purses. This one's much more uptown girl than flower child, making it a more versatile choice for most fashionistas. The nappa leather and pleats bring that sophistication, while emphasizing that casual slouch.

I do worry about how sophisticated a purse of this size will look slung over a shoulder though. There's always the risk of overwhelming your frame with an oversized bag, and this one definitely fits that description. But at least there's the space to carry everything you need, and a few things you don't!

I'd have appreciated a few more color options, but it's hard to argue with the appeal of basic black. In this classic shade you could easily pair the Keli with a power suit during the day before toting it to the bar for a few martinis afterwards!

More Features of This Bally Pleated Hobo

• Jacquard lined interior
• Zip top closure
• A single shoulder strap with a 5.5 inch drop
• Measures 9.5 x 17 x 5.5 inches
• Comes with a dust bag
• Made in Italy

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I must admit that Anuschka's famous hand painted purses have never really tickled my fancy. They always looked a little homespun and folky for me. But by moving from its traditional tan leather to dark ebony, the brand may have just won me over.

A stunning example of the sophisticated new look is this Crsna Top Zip satchel. Anuschka's famous hand painted approach is just as whimsical as ever, with colorful butterflies and foliage. But it looks so much more stylish against the black backdrop.

The traditional satchel shape maximizes storage space. The brand goes above and beyond what we expect, with the traditional zip and slip pockets complemented by a handy key hook. There's also another zippered pocket discreetly placed on the back of the bag. It may not look as lovely as more hand painted butterflies would, but it is practical.

Not too big and not too small, the wide shoulder straps with their long 9.5 inch drop are more than up to the task.

This Crsna Top Zip satchel is just the sort of bag that should encourage purse lovers to take a second look at Anushcka.

More Features of This Hand Painted Anuschka Satchel

• Signature pink lined interior
• Top zip closure
• Measures 12 x 6.5 x 3.5 inches

Get this Anuschka Crsna Handbag:

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The name Phoenix conjures an image of a purse rising from the ashes as the savior of the fashion industry. This tote doesn't really live up to that grandiose mental picture, but it is a classy creation nonetheless.

It all starts with elegant black, buttery soft leather. The slightly flared shape adds interest, as does the lovely pleated pocket we also saw on the Phoenix hobo. It's this collection's trademark, one that combines good looks and practicality. The tiny Stone Mountain nameplates on the pocket and zipper pulls are the only bits of external branding, a welcome break from the loud logos of so many other designer purses.

The styling may be a little pedestrian for some tastes, but Stone Mountain's always been more about practicality and timelessness than cutting edge looks. The giraffe print lining hints at the brand's wild side, but the plethora of pockets you'll also remind us that a functional space is much more important than one which simply looks good.

At $110 retail, the Stone Mountain Phoenix tote represents excellent value. You're not likely to find many totes with such classic looks and high quality fabrics in this price range.

More Features of This Stone Mountain Leather Tote

• Front and back zip exterior slip pockets
• A zippered pocket and three slip pouches inside
• Silver-toned hardware
• Platform base
• Dual shoulder straps with an 11 inch drop
• Measures 8 x 8 inches

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This Martini wristlet from Alexis Hudson is quite the opposite of the similarly named Martini Glass zippered bag from SR Squared by Sondra Roberts. Whereas the Sondra Roberts version opts for a literal take on the name, Alexis Hudson's styling is much more abstract.

The Martini wristlet has a unique sculptural quality to it that gives it a sophisticated feeling. The chocolate brown leather keeps the style from being too formal, though. It isn't the type of bag you'd carry to the gym, but it's a great accessory for dressing up a cute girl's night or date outfit.

The large pleated detail on the front of the wristlet is soft and pretty, but it's the structured, wing-like wrist holder that's the real eye-catcher. I'm not sure how awkward it would look to carry the Martini bag as a clutch in your hands as opposed to with the wrist feature, though.

This Alexis Hudson design's zippered top opens to a twill-lined interior with a slip pocket for small items. The Martini wristlet retails for $295, which seems a little steep for a somewhat limited bag but worth it if uniqueness is your main goal.

More Features of the Martini Wristlet

• Measures 11.5 x 4.5 x 1 inch
• Leather material
• Zip top closure

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La Regale lives up to its reputation as a great choice for affordable, stylish, and unique bags for formal events with this pleated bow clutch with the style number 25068.

Now, I've seen some generously sized bows on various handbags, but this one definitely takes the cake. Instead of merely functioning as a decorative feature, this one practically takes over this clutch.

It seems a tad overpowering to the design but adds a sort of playful touch rather than looking out of place or tacky. While most satin clutches tend to be elegant and sophisticated, this pleated bow version from La Regale is cute and whimsical. It would be a great accessory for a dressy holiday event.

The large detail might make the clutch somewhat bulky to carry around in your hands, though. Thank goodness for the optional shoulder strap hidden inside the bag. Whatever drawbacks the handbag might have, it makes up for with a fabulously low price of $38.

More Features of the 25068 Clutch

• Measures 9.5 x 4 x 1.5 inches
• Optional shoulder strap with 21 inch drop
• Front flap with magnetic closure

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Lauren Merkin purses are red carpet favorites, but with the Tatum she's created a clutch that's more rock and roll than Hollywood glamor.

The secret is the patent leather finish, which is given an extra dose of attitude with bold mock croc embossing. The finish isn't likely to fool anybody into thinking you've snared a genuine exotic, but I'm not sure it's meant to. Rather than imitate the real deal, Lauren Merkin creates a cool, modern texture with her scaly skin. We've seen the Tatum's pleated shape before in raffia, but this modern polished finish makes the purse seem like an entirely different breed!

It's certainly not an oversized clutch, but there’s enough space inside for party essentials. Just be sure not to cram in more than the Tatum can easily carry. The thick patent leather is bound to show bumps and bulges if pushed beyond capacity.

This orange Tatum is the most outrageous of the range, but I think it suits the purse's punk-rock personality. Black has the same rock and roll edge, although it's taken down a notch. If this still screams too loud, you might like to opt for the subdued gray clutch.

More Features of This Lauren Merkin Croc Embossed Clutch

• Inside zippered pocket
• Frame closure
• Signature striped shimmer lining
• Measures 13.5 x 7 x 2 inches
• Made in New York City

Get this Lauren Merkin Tatum Handbag:

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Hobo International accessories tend to be smart, but just a little boring. This Solano breaks the mold, combining sophistication and style.

Tiny pleats at the top of the bag create diamond shapes, providing a unique alternative to traditional quilting. There's texture here, but it's not predictable. These tight pleats give way to softer, subtler folds down the tote's body. They make the luxurious goat leather appear even more tantalizing and tactile. It's a relaxed look, but one that wouldn't look out of place in most offices or on a dinner date.

Hobo International bags are always practical, and the Solano is no exception. A secure zippered compartment is complemented by a whopping four multifunctional slips. Two pen holders ensure you're always ready to get the digits of your next crush. If the storage options inside weren't enough, there's another zippered pocket on the back of the bag.

I only wish this fashion-forward purse came in some more inspiring colors. Black, mocha, aubergine, and sage are sophisticated but a little too sensible for many tastes. Some more original choices, like bright blue or orange, would have made all the difference.

More Features of This Hobo International Pleated Tote

• Antique brass hardware
• Magnetic closure
• Fully lined interior
• Dual braided shoulder straps with a 9 inch drop
• Measures 18.5 x 13.5 x 2.5 inches
• Comes with a sleeper bag

Get this Hobo International Solano Handbag:

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Cross-body bags tend to be big and bulky affairs. There's convenience in that oversized approach, but not a lot of style. Elliott Lucca delivers a daintier option with the Trieste.

This is one smooth operator, with its inverted pleat design and chic braided strap. The textured leather is incredibly soft, and surprisingly considering the $98 price tag, the real deal. I guess by keeping the size down, Elliott Lucca could afford to give us the genuine article! The poppy red is a real show-stopper, while this boysenberry bag is so dark it could easily pass as a neutral.

The dimensions are closer to a small clutch than a cross-body bag, so it won't suit everybody. There's a long zippered pocket for change, which I'd use instead of taking my wallet. That frees up the main compartment for carrying your cell phone, keys, and a tube of gloss. A zip top keeps the essentials in place, leaving you free to get on with your day.

The Trieste refuses to follow the trend for oversized bags, which is what makes it such an intriguing option! This is an affordable and stylish purse for those who don't want to follow the pack.

More Features of This Elliott Lucca Leather Cross-Body Bag

• Brass hardware
• Canvas lined interior
• A single shoulder strap with a 23 inch drop
• Measures 5.5 x 5.5 inches

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This Jessica Simpson handbag design is a simple but interesting change of pace from a brand that can sometimes includes a few too many trends on one purse, in my opinion.

Granted, I have appreciated a few of Simpson's recent releases, such as the Jimmy Satchel and the Runway Tote. Now this Downtown Tote can now go on my somewhat short list of Jessica Simpson successes. It isn't the most stunning of handbag designs, but there's a certain appeal to its shape and texture that makes it a little unique.

The tote definitely has a downtown feel with its contemporary quartet of square studs on both sides and slightly square silhouette. There's just a hint of a slouch to the shape due to some soft pleating but not enough to give it a truly relaxed appearance. It's a nice mix of slightly structured and a little casual.

The Downtown handbag is, of course, faux leather like most of Jessica Simspon's purses. However, this one has a series of vertical lines or slashes that cover the material to add some visual interest and break up the synthetic look.

The double handles are rather short for the vertical shape of this tote and not exactly the most practical choice. Thankfully, the brand provided an optional longer strap for more convenience. As with other Jessica Simpson styles, I'm not entirely sure if this faux leather purse is worth its price tag, this one retailing for $118, but it does have some nice qualities that make it worth at least considering.

More Features of the Downtown Tote

• Measures 15 x 13.5 x 6 inches
• Double handles with 4.25 inch drop
• Zip closure
• Detachable strap

Get this Jessica Simpson Downtown Bag:

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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 Havana N/S hobo bag, though, beyond only slightly similar body styles. This option has a very distinct B. Makowsky flair to it that cannot be denied.

As I'd expect from the label, the hardware is bold and noticeable and the design details are numerous. It's not quite as flamboyant as some of the brand's other styles, but there's a definite "notice me" stamp given to this purse. The already slouchy shape is emphasized by a front pocket with ruching all along the top edge, and strap details call even more attention to the front. Even the sides of the hobo are adorned with silver studs and rings. It's a little strange how empty the back of the Havana is in comparison to the rest of the bag. Only a small coin pocket dresses up the back, which seems a little underwhelming.

The lipstick red color is certainly not for wallflowers, though, and it's not your only option for standing out in a crowd with the Havana hobo. For an even bolder look, you might go for this B. Makowsky bag in metallic pewter or bronze instead. The style also comes in subtler colors like black and brown. This N/S style of the Havana handbag retails for $298.

More Features of the Havana N/S Hobo

• Measures 15.5 x 11 x 4.5 inches
• Single strap with 7.5 inch drop
• Magnetic closure
• Signature leopard-print lining

Get this B. Makowsky Havana Bag:

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