It doesn’t have a great deal of personality, but it does have a rather clean, simple look to it that I think a lot of women would find attractive, but it’s not too rigid and stuffy to be usable outside of an office setting. I’m pleased. Are you?

The leather might be soft, or it might be that deceptively slouchy stuff that actually feels like and elephant’s butt when you touch it, it’s impossible to tell from here. But it does look reasonably touchable and just casual enough, and the ruching is a nice touch to give the bag a bit of specialness that they could have easily skipped and still sold a decent number of bags. I can’t praise it too vocally, since it’s still kind of boring, but for the price I think it’s a nice effort. Buy through Saks for $395.

The Cole Haan Prudence Leather Hobo offers the same great woven leather design as the satchel, but more of it and with a few different colors. I was a huge fan of the grey leather used for the satchel, but I can also equally appreciate the chestnut and zinfandel colors offered for the hobo. The pebbled leather and tassel zipper pull both play off of one another perfectly. I am just wondering if with the hobo, the woven leather is too much. Yet whatever hangup I have, the bag itself is lovely, wearable and absolutely perfect for the cooler fall temperatures. Buy through Saks for $428.

Which is exactly what happened with the Cole Haan Sloane Woven Suede Tote.

Cole Haan calls this bag woven, but that doesn’t appear to actually be the truth. Instead, it looks patchwork, and kind of hastily so. I know that the edges are rough on purpose, but it doesn’t work for me. It looks old and rather inexpensive.

The distractingly wavy pattern and the unfinished materials detract from the beauty of the bag overall. Instead of looking rich and winter-y in chocolate suede and brown leather, it looks vintage (in a bad way) and previously worn. The embellishments are not done in a high-end way, and I can’t help but think that it ruins the bag. Buy through Saks for $398.

Just like the bag I covered yesterday, the Cole Haan Whitney Leather Hobo is an instant classic. The distressed chocolate leather is scrumptious and I absolutely adore the goldtone grommets. This particular shade of leather goes extremely well with the grommets. Plus, the shoulder strap looks like it will rest ever so perfectly on my shoulder. Again, I think Cole Haan has a fabulous hit on their hands and I am sure this is a bag that will hold up well. Buy through Saks for $348.

You know the kind I am talking about. It goes with anything, it is timeless and it is always faithful. This is the bag that can dress up or dress down an outfit based on what you need it to do. And of course, while you might have a black bag that you want to carry for years and years to come, you know that one day you’ll take a look at it and need a replacement.

So, what should that replacement be? I’m not here to tell you exactly what it should be, but I do think I came across a fairly promising option. The Cole Haan Kendal Drawstring Tote has classic elegance and daily usability down to a tee. The leather is supple and plush and the goldtone hardware shines. I am not always a fan of drawstring closures or tassels, but for some reason I really like both on this bag. Upon first look, I didn’t think these handles would fit over my shoulder, but the 16″ double rolled handles with an 8″ drop makes me think it might work.

Now that you’ve spent some time looking at the bag, what do you think? Is this the kind of black handbag you’d see yourself carrying and constantly going back to? Buy through Bluefly for $328.

And it’s even better when it’s combined with soft leather and a subtly slouchy shape, as it is in the Cole Haan Prudence Small Satchel. I’ve been a fan of this shape ever since Cole Haan introduced it last season, and it’s even better with the thick pieces of matte woven leather. These handbags are light as a feather but still made of thick, durable materials and the color and texture are perfect for cold weather (some of which I wish I was experiencing right now. I’m sure I’m not the only one). Buy through Bloomingdale’s for $495.

The reason this element is balanced out, I think, lies in the inherent slim shape of the bag. It’ll lie flat against your hip rather than bulging out and looking messy. The shape and mini-studs, plus the faintest shine in the grained leather, make this is fashionable bag. Even if you work in the most conservative of offices, that’s no reason to shun your stylish gear- simply sleekify your wardrobe with subtly sophisticated items such as this. Buy through Bluefly for $225.

You know the kind I am talking about: functionable, affordable and fashionable. However, I don’t want to pick up some random just “ok” bags. So, you might be able to imagine my excitement when I came across the Cole Haan Raleigh Small Triangle Tote. The color of the bag is breathtaking, the shape is sturdy and the over all feel is one I wouldn’t mind having on my arm. What do you think? Is this the kind of bag you could see yourself carrying day-to-day? Buy through Saks for $348.

Which is why I find the Cole Haan Raleigh Small Triangle Tote particularly impressive. There is little in the way unnecessary distraction in this bag’s design, but it’s nothing if not chic and well-realized. The lines are clean, from the construction of the gussets to the handles, and the bag’s rugged, pebbled leather provides just enough visual interest to keep the bag from being boring. The minimalist theme continues on the bag’s interior, where instead of a traditional cloth lining we see the blue leather’s soft suede underside and a few electronics pockets. If you’re looking for a simple, stylish bag, you can’t do much better than this. Buy through Saks for $348.

But in this case, I think it would be much better if this bag was a tote. A pattern like this, with this many colors, is going to be really difficult to match to an outfit in order to go shopping, out to dinner, etc. A person would have to wear an outfit with no patterns and very few colors, and what’s the fun in that, particularly if you don’t change your bag every day? It might have worked well, though, as a big tote bag. One that you could use for your laptop and papers for work or school. Bags that serve that kind of function have less of a need to go with every outfit that a person wears, so a crazy pattern isn’t so prohibitive. Buy through Nordstrom for $228.