Timberland: Beckwith Side Zip Chelsea
Ugg: LaVelle
Born: Trinculo

I have never been a shoe person. Do you know how many pairs of flip flops I own? Me neither but it’s a lot (well, used to be a lot until I cleaned out my closet…again). Enter Zappos. The more I’ve been trading in the yoga pants and t-shirts the more I’ve been shunning the flip flops. They’re easy and comfy-ish but they’re not that…cute. Gasp. I can’t believe I just typed that. Who would have thought?

Not me. You know what else I wouldn’t have thought? That I would ever wear booties. It started with flats. And, I still love my flats but then the weather got a little too cold to live in footless tights (that trend seems to be going out so I’m caring gently for the ones I have left because in or out, I still love them), I decided it was time to turn to real shoes. I’m over my oh so comfy and oh so ugly Uggs (I do wear them here and there still- I mean they’re comfy!). So, we arrive at my search for the perfect bootie and unlike the jean dilemma, I actually found several pairs that I love. Heck, I’ll be honest, I think I love them all.

I think I have been wearing the wrong size shoe for a very long time. Or my feet shrunk. Either way, all of a sudden shoes are comfortable like they never have been. I don’t need to live in flip flops because I have found many pairs of versatile shoes that are actually comfortable. And, I don’t know if you figured it out yet but comfort is a big deal for me. My point is, if you’re having a problem with your shoes- get measured because it may not be your shoes at all, it may be the fit.

Now, heres the low down. I like all of these. But, my new mantra is to wear what I love and return the rest. That’s how two pairs of booties made it into my closet (and my trusty Rockports, not pictured, that I pretty much have been living in with dresses as you may have noticed). Which two? The tan Sofft booties and the deep leather Timberlands. Why are those the winners? Well, first, the other pairs J bought for me as a gift in the wrong size. They came in damaged and Zappos didn’t want them back (which is why I’m trying to sell them for charity but that’s a topic for a different post- both why I love Zappos and my hopefully soon to be registered charity!). Second, I fell in love with the other pairs and like I said, that’s what fashion is all about for me right now. Trying things and figuring out what is me and what isn’t so me.

Let’s talk Sofft. I like that they’re different. There are a lot of black booties, a lot of tan ones, a lot of brown ones. But, there are not a lot with the staining quite like this. They’re comfortable. I put these boots on and feel like they’re made for my feet. I have never been one to spend a whole lot on shoes and I will probably never be in the red soled heel category, however, you get what you pay for. Yes, I could find a pair of $30 booties and they probably would look okay. But, would my feet hurt after a day running after little monsters? Probably. In these mid priced shoes, you really get what you need in a pair of shoes that’s going to last you (I hope anyway). Good structure, great style, and comfort for a long day on your feet.

Here come the Timberlands. I don’t think you could have told me I’d be buying Timberlands a year ago. The thought of Timberlands brings to mind big clunky boots on hefty male rappers. Maybe that’s a 90s image but it’s what’s stuck in my head. These booties? They’re solid that’s for sure but they’re also elegant. I love the shape at the ankle and the leather is exquisite. They were a little stiff the first time I put them on but I’m glad I decided to give them a chance because they softened right up. If you decide to give them a try, know that it is hard to get your foot in these- read the reviews, it says so. But, they have stretched out comfortably and I can walk in them all day now without a twinge (again- not a shoe person- I’m used to lots of twinges).

Have you jumped on board the bootie bandwagon yet? It’s not too late, according to my weather app we have a few cold days yet.

Jeans: Level 99

Shirt: Loft

Booties from top:


Sofft (unavailable)

Ugg (In black)