Reader Request: Style Advice

Reader Emily, a Midwest Transplant from California send me a question asking my opinion on some shoe choices her is Emily's question and my response:

What do you think of:
1)Sportos http://www.zappos.com/sporto-aroostic-black-tan
2)Sperry Top-Sidershttp://www.zappos.com/product/7609984/color/4697

I can't decide if they are cool or ugly (if you think they're ugly please tell me!) but I'm seeing them EVERYWHERE! It took me a little while to finally break down and get sheepskin boots, and now I have Hunters, Uggs, and Old Navy sweater boots (but don't get me wrong, I do own plenty of other "regular" shoes) and I'm wondering if I need these additional weird (?) shoes in my collection.

I love your blog and trust your style!

-Emily

Thanks for reading the blog Emily! Here is my response to her question:

Thanks for reading my blog! I am honored you would want my advice!
SO here's my take on the shoes. I rarely wear flats, they just don't flatter me. Flat boots and sandals are exceptions.

The first pair I am not into at all. The second pair reminds me of of boat shoes, which I love. And wish I could pull off a nice Hampton-esque look of shorts, a v-neck and a collared shirt poking out, rocking some boat shoes. Or I can picture them paired with a blue and white striped sweater, so Polo and like Classic American. The pair you linked isn't my favorite, I would prefer something a little plainer like this version http://www.zappos.com/sperry-top-sider-bluefish-2-eye-ivory-1 but if you are looking for rain shoes maybe the others would be better.

So my take is I love the look of boat shoes, I know I can't pull them off. Maybe one day when I get some rocking legs.

Hope that helps! Thanks for reading the blog!
-Amber
Looks I am imagining:

Image from Vogue Issue unknown

Image from Shopbop.com

Let me now what you think and I'm sure Emily would appreciate any Midwesterners opinions as well, as I don't have to dress for Midwestern weather! And you would like my opinion on any style advice or a question about anything else feel free to shoot me an e-mail at Ambersnotebook@gmail.com.