One of my fashion goals for 2014 was to try new things and break out of a rut, including new silhouettes (above-the-knee shorts, straight leg/skinny jeans, boyfriend jeans). So far so good there!

However, as I take the tags off off my first pair of slim jeans my first thought is how is this going to impact my footwear choices for the upcoming season?

I have gear shoes (including winter snow boots that can be used as commuter shoes in the worst weather) covered. I also am carrying over a pair of dark red water resistant sneakers from last season, a pair of olive green Klogs, and a pair of dark red short boots. I also have a pair of black and white heeled oxfords that I wear as dress shoes, but aren't cushy enough for everyday.

The Klogs are the oldest and still look fine but are up to be retired soon.

I mostly wear jeans and anticipate that this year I will have two pair of bootcuts, two pair of slim or skinny pants, and a pair of BF jeans. I also have two pair of trousers (in different weights) that I need to occasionally wear with winter boots but aren't everyday clothes. That also goes for my black ponte pencil skirt. I've also considered adding a dress for winter.

I am planning on adding 2-3 pairs of shoes/boots. However, with so many different silhouettes to cover I'm confused by exactly what to add. I wear both cognac leather and black leather.

In my earliest searching, these two pair appeal the most:

However, I'm wondering if those pair (along with my existing 2-3) cover enough bases?

What would you ladies recommend? Something different? What am I missing?

Thanks so much for your time and expertise : )

P.S. I've put pictures of all the shoes in my finds attached to the post, my oxfords are black not brown, though (several seasons old, couldn't find the exact color).