With so many super cute winter boots available on Styleshack {from Sundance} we find that it not only becomes difficult to choose a pair, but THEN you have to style the pair(s) you choose! If you're anything like us, you want to style your winter boots in unusual ways {e.g. not JUST with leggings and chunky sweaters!} To gain outfit inspiration, we have picked some of our favorite boots, from the Styleshack closet {available to shop, here} and have paired them with fashionable looks that bloggers and celebs are wearing NOW!

Check out these fashionable and functional looks!

BEARPAW boot. This boot has 'SNUGLY' written all over it! This boot is ideal for the streets of Aspen as an after-ski-boot. Pair them with denim, an oversized sweater and super trendy beanie! For extra pizzazz, layer on some necklaces or add a textured coat and you'll make heads turn, for sure!

TOMS boot. We own this boot {in black} but we are highly debating nabbing it in other colors! Just look at all of the super cute ways to dress these TOMS wedge booties! We probably would never have thought to pair these sole-winners with a dress, but after seeing the pics…it is definitely a fashion risk we are willing to take {when the weather warms up a little…}

3. SOREL boot. We wore these boots for our Moosejaw campaign with leggings. It seemed pretty standard. However, how chic to these Sorel boots look with a riding blazer and tights!? We die for this unconventional winter look!

4. FRYE boot. We have proclaimed our love for Frye, and this is why! Though we own the fringe version of this boot and we have tried it with denim dressed both up, and down…Blake Lively shows us how to really play with these boots! A maxi plaid skirt with a belt and button down achieves the perfect boho look, with some edge! 

5. UGG boot. The UGG lodge boot is similar to our Penelope Chilvers boot, which we love! While these boots are more affordable they, like the boots we own, also come in a variety of colors. We love how they look paired with a poncho and slouchy knit hat for the weekend! Chic and carefree…what's not to love?!