I have green motorcycle-esque boots from last winter. They are Blowfish from DSW and I love them so much I went back and got them in black. I wore them with jeans tucked in, with tights or leggings, or just barelegged with cute little dresses (we had a pretty mild winter, plus alcohol keeps you pretty warm, ya know?) I also have nice grey Steve Madden boots with a braid up one side. The only thing missing is pretty brown boots...Or fancy black boots. Or crazy colored fun boots... Or ugly brown boots...
Frye Owen Lace Boot - UO, $298
Love love love them. I guess they might be a tad impractical, but I would love to wear these out in the fall with cute little dresses. Oh, and maybe leather jackets...

Frye Paige Cuff Boot- UO, $398
More Frye... Love the color - it's 'Slate'. I've never had boots this high... I usually stick with the ankle or mid calf height..

Canvas Cuff Boot - UO, $48
I usually stick with flat boots, so for me to get a boot with a heel, it's got to have something special going on. I like the cuff of this boot. Oh, and the price.
C2 Dragon Boot - UO, $114.99 (on sale)
Now this one just looks neat. I guess you couldn't really do jeans tucked in, but it would look cool with tights, no?

Frye Paige Canvas Boot - UO, $149.99
They have this boot in black too, but I think the brown looks much prettier. This would be a great casual boot, with tucked in jeans, flowy blouse, giant sweater... This one is definitely a contender...

Angles Motor Boot - Free People, $298
Love it when the boots come with dirt already on them. Saves me the trouble of stomping around in the mud to get that worn in 'yeah, I walk in dirt, so what?' look.

Marc by MJ High Heel Belted Bootie - Shopbop, $695
I honestly have no idea why I want these booties so bad. They have a heel. They're freaking purple. But... Marc makes girls do crazy things.
Some more reasonable, although probably more uncomfortable, options.
American Eagle Maddie Ankle Boot - Payless, $37.99

American Eagle Riley Slouch Boot - Payless, $39.99
I like this one a lot. Good job, payless.

DV by Dolce Vita Jordon Boot - Nordstroms, $179.95
This one reminds me of a kinder, gentler version of those crazy Balenciaga boots the Olsen's wore. And you know how I feel about anything even close to something MK would wear....
And here is where I get a little crazy with the price tags. But they're oh so pretty, aren't they?
Miu Miu Strappy Bootie - NeimanMarcus, $790
Wow, I hope grey is as big of a color this fall/winter as it was last... Love it!
Chloe Strap Wrap Open Toe Boots - Intermix, $895
Mmm I love everything about these boots, even the heel. Someday, I will own Chloe shoes... someday...
Peace and boots for everyone!,
TheFashionHead