Most versatile style of boots?

[twowhat?]

How I have boots on the brain. I've never owned a pair. I'd like to get one pair of tall boots that are versatile (can dress down for casual wear or dress up for work). They need to be flat (or close to flat - I could probably handle a low wedge). Boots are appealing to me for (sadly) practical reasons - never have to worry about matching socks to shoes/trousers or not wearing socks, easier to walk in than pumps, etc. For work, when traveling for meetings I have seen co-workers wear boots with skirts or pants and a nice top, and that's acceptable. It's not a super conservative industry.

What style would be most versatile, i.e. work for jeans, pants, skirts. Most versatile color: brown or black? Riding boots? Slouch boots?

And for those of you with boots, does that mean you have to buy pants specifically to wear with the boots? I have mostly trouser-cut pants in my wardrobe. Nothing skinny (because I don't like the shape of my legs which are sort of bowed). Though I did buy a pair of dark wash stretch skinny jeans from BR this past weekend because it was my size, and on final clearance for $17.

Oh and one last question - do people typically only wear boots in the fall/winter?

[arivecchi]

Riding boots by far are the most versatile. I have these boots and wear them to work with skirts and tights and on weekends with leggings or cord pants. I wear boots from Sept. through April - May.

http://media.lawrence.com/img/photos/2005/11/07/pmo_tall_brown_boot_xout_BIG_cl_t440.jpg?9e2a24ba4 4807f8f9b96aad7c4082bf6ded075dc

[ahrimie]

I second riding boots. They are slimming too. I think slouchy boots make your legs thicker; I think it's almost too trendy... just my opinion.

[elektra]

I agree with arivecchi. You will get the most bang for your buck with riding boots. They can be dressed up or down, and the flat heel makes them more comfortable than heels generally.
You will need skinny jeans or leggings though. Straight leg jeans can work too but they tend to get loose/bunchy at the knee which doesn't look as good.

These are mine:

http://theshoemarket.files.wordpress.com/2010/01/frye_dorado.jpg

There are a bunch of riding boots out there- I looked at tons before finally getting these.

[tarahsolazy]

I agree with the riding boot suggestion. Mine are Frye Veronica Slouch, although they really aren't slouchy on me at all, just not super fitted at the ankle.

[ray7694]

I wear my boots with leggings, skirts, jeggings. I really don't like it when the jeans bunch at the knees. Leggings are so comfy. I like express and gap leggings.