Wearing: Make sure you take a good look at how you look from the back with these boots. It is best for those with long slender legs since it creates the illusion of shorter ones.

Future: I'm not sure if these boots will make it to next years winter season, so if your on a budget stick to faux mukluks.

Get the look: ESKIMMO$149.95

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Wearing: Tuck your jeans into the boots and wear with a fitted top or a shrunken jacket.

Future: These boots look a bit more classic than the previous boots. If you purchase them you will be able to at least wear them next winter season to the grocery store without looking foolish.

Wearing: Uggs have been around as a trend since winter 2003. You can update your look by wearing funky socks higher than your boots. Letting a little sock show will look great when wearing a skirt.

Future: This trend is on it's down fall.

Get the Look: Sheepskin Style Boots $47.50

Wearing: Cowboy boots look best with skirts, long or short. When wearing cowboy boots with jeans its best to wear your jeans over them to avoid the too trendy look or even eighties depending on the top you choose.

Future: These boots are classics. They may go in and out of popularity but you can definitely bet that they will be back during some season sometime in the future.

Wearing: I saw a lot of girls wearing these in the East Village (NYC). They look best beat up so if you can find a vintage pair go for it. When tucking jeans in to boots try jeans that are a slim fit straight leg.

Future: They may be around for awhile, if not you can always wear your jeans over them, any way who knows you might take up riding!

Get the Look: Leather Riding Boot $120.89

Wearing: Slim jeans! If you are going to wear them, wear them with slim jeans or any tight fitting pants. Avoid Nicole Sheridan's frumpy look.

Future: I doubt it. They will scream winter 2004!

Get the Look: SNOBUNY $79.95

Wearing: For those who want to tuck jeans in, make sure your back view looks good!

Future: You never know.

Wearing: There is a fine line between classy and slutty with these boots. If you are wearing these with micro mini's check twice to make sure it doesn't look trashy. Your best bet, wear them over jeans or fitted pants, and skirts that come mid thigh length.

Future: Buy them in classic colors and styles and you can wear them forever.

Get the Look: I will let you know when I find the perfect pair!