Ok folks, OP here. I went around and around and finally ordered the first Merrell's (the 'mad max' rock n' roll looking boots). They are waterproof and not too dressy so I figured, let's give this a try. I have realized that I needed more of a utilitarian boot (almost a work boot) than something dressier. And yeah, I can totally wear them to work (again, I wear furry boots - my office is 'jeans are ok any day' casual).

They are great. And in person, the sole is very minimal, so they look a lot less badass than they appear in the pictures online. They fit nicely in the ankle and calf - I have super skinny calves so it is great that they aren't flopping around! I'm off to write my Zappos review...

The Born are made of leather so I think the others are better for rain/snow.

Read the reviews of the Keen Berns. Lots of people are saying that the soles split after a few months.

First two (Merrell Captiva and Keen Bern) are not cute. They have that ugly running shoe-boot combo look. Mad max sounds pretty fair.

Second set are both much more attractive. I personally prefer the Born as I prefer a more tradiitonal sole on a boot. I do not like the Merrell Angelic's sole although think the leather part is pretty.

I like the first pair you posted. With that style though, note where they hit on your calf...some boots hit lower and can make even the most fit legs look chunky.

The first two look appropriate for work if your job is as a rock n' roll roadie or stomping people.

Huh. I don't love any of these. And I can't imagine wearing them to work anywhere. Also, if what you're wearing now are Ugs, I doubt these will be an acceptably comfortable and warm substitute.

I saw some of the Athleta boots in person over the weekend and was shocked at how much better they looked on the web site. Just a warning. I do not like any of the boots pictured above. I like both merrells posted by the OP.

I like the born shoes much better than these recent merrells you posted. But the circumference looks like it might be too big.... I like the very first boots you posted!

You might like some of the boots on the Athleta website.

I don't like them. Sorry. I looked up boots by 13.5in on zappos. What about these:

Anonymous wrote:I would not wear the first pair to work, they are too casual for even a business casual office.

It depends on where you work. I work in IT and it would be perfectly fine to wear these on a Friday, and even a Tuesday. Most companies in my space are full of young progressive leaders that put more emphasis in what you product vs when you wear to the office (if you even decide to show up at the office).

To the OP-I prefer the second links you sent you. For what you describe, comfy and waterproof, these seem to fit the bill. I'm more inclined towards FRYE, you get all of the above with some style slpashed in.

waterproof

Maybe look at some La Canadienne styles. I believe most are waterprooof and they are very comfortable.