Hey Michelle! I like the look of dresses with opaque tights and booties in the same color.
I do prefer booties with that hit lower than the ones you posted, though. That high up on the ankle doesn't look right to me.
How about these?
http://www.zappos.com/clarks-d.....ck-leather

Sarah, you just reminded me that if I'm wearing black tights, the shoes should be black too right? Hmmm... How high do the Clarks booties you posted come up on the ankle? I'm wearing the Naturalizer ones right now and they basically enclose the ankle.

The Clarks look like they end before the ankle, so it doesn't cut off your leg line as much if that makes sense.
Ana reminded me that the same color tights and booties will also keep the leg line longer.

Hmm, so my current booties wouldn't work even though they're the same colour as my tights?

I don't know. I'm not a booties expert, but that's my personal opinion. Can you take a photo and post it for others to look at?

The booties that you have are very square heeled- like an oxford shoe is. To me, it is a look that is best paired with pants of some kind. The ones that Sarah posted are much more feminine looking- slender higher heel, button detailing, so could go with a dress. I don't see why you can't wear ballet flats with tights? Post some pics if you can.

Michelle, the booties you have posted a picture to look like trouser booties to me. The booties that Sarah posted a picture to are adorable for a dress. I would love to try those too. However it's all in the visual if you can post a picture we can better analyze.

I've tried on everything Sarah suggests. :) I've tried on those Clarks booties... SUPER cute, adorable really. The heel was way too high for my comfort, though. This could be just me because I've never worn heels before, though. But they're really good looking shoes and would look great with your cobalt dress (which I want to steal from you.)

I was at a Naturalizer store today and they have so many cute comfortable options.

Here are a few options that I loved and would look great with your dress:
1) A short boot:
http://www.naturalizer.com/Sho.....pg=3005867

2) A bootie: (I was drooling as a girl was trying these on with jeans... they looked really nice)
http://www.naturalizer.com/Sho.....pg=3006016

3) Super comfy mary-jane:
http://www.naturalizer.com/Sho.....pg=3005594

4) Zebra flat
http://www.naturalizer.com/Sho.....pg=3005915

Ok, I will absolutely not wear my current booties with that dress. The question remains about ballet flats, though. I have a black patent pair I'd consider wearing if it's acceptable to wear flats with tights (something I'm still not clear on). Corey (my boyfriend/resident photographer) isn't around at the moment, but I'll get a visual for you guys in the next day or two.

Yes! You can wear ballet flats with tights and hose.

The booties that Sarah posted are more like a shoe and less like an ankle boot which is why they’ll be more flattering with the cobalt frock.

However, tomorrow post is about "how to wear calf length boots" and I think you should investigate that option for dresses and for over skinnies as well – if you fancy the idea.

OOh- the Bf has a name! ;)

Michelle, one way I distinguish between appropriate bootie types is to change the name. The kind you have is more of an ankle boot, which I have too and plan on wearing in bad weather with pants, etc. The kind Sarah and Marianna linked are what I call shooties -- a combo boot/shoe. Those work great with skirts and dresses, and come in a million styles and heel heights.

Khris: Yes, he has a name!!! He'll be so honoured that "the people on the fashion site" now know who he is. :)
Angie's post today has given me an idea that maybe my slouchy boots will work. They're higher than I remembered. I'll try it out later and show you shots with both the boots and the ballet flats.