I would wear these boots with almost anything...jeans, sweaters, leggings and tailored jackets...they are awesome!!!

I have a lovely sweater dress and tights that would look great with these boots.. maybe throw in a cute purple scarf! :)

I would wear these Boots with some tight faded wash Skinny Jeans and a One Shoulder Amazing Top. Some Tear drop earring and layers of silver chains.

I would wear those boots with the perfect jeans I have here and a nicely fitted sweater. Then when I finally take them off I have a feeeling my teenage daughter may "borrow" them she has some really cute outfits that the boots would be great with.

Hmm I would wear them with a scarf, mittens, hot pants and a t-shirt that says SASSY on it.

I would wear these boots with black tights and and a loose mini dress that is belted with a metal skinny belt. The colors and metal tone can vary. My nails would be cut short and painted Essie Clam Bake. I would wear a long necklace that has at least 5 loops around (statement necklace with this outfit would be just too much). To finish the outfit off, I would wear a military style black cashmere coat . I would also use the Green Patent Leather Elvie tote by Alexander McQueen

I would wear the boots with a cute little skirt

With beautiful buttersoft looking boots like these, the best outfit in my wardrobe would be a set of deep, dark washed jeans without any streaking or "designer distress", tucked into them, with a Heather gray to a charcoal gray wrap sweater, or sweater dress and a amber toned stone necklace with similar earrings. A brown wide belt could be worn with the sweater dress, or a wrap sweater with brown (preferably wooden) buttons would be a good accompaniment.

I would wear them with a long tunic and tight or super skinny jeans. Being pregnant these would be perfect to wear as there's no heel and would rock some maternity clothing.

I would wear these boots with my loong white sweater : )

I would wear these boots with just about anything. My clothes are always underplayed, and for the first time...i'd have something that is a wow factor when it comes to the plain clothes in my closet. Plus i dont wear heels being very tall, so i'd feel sexy without the need of heels :)

I'd wear it with an awesome black mini!

I would wear these boots with a great outfit for a trip away with my husband.

I have worn Stuart Weitzeman's shoes and have loved them for their style, quality and durability. Talk about a stylish boot! At 58 I'd be the talk of the town in these. :o)

I would wear these gorgeous Stuart Weitzman unbelievable boots with simple black tights and a loose sexy charcoal grey sweater dress that would be beautifully belted with a wide black belt, and would keep the hem just a few tantalizing inches above the top of the boot. So the outfit would accentuate the gorgeous boot and of course, my legs!

Stuart Weitzman's are the ONLY shoe brand that I buy without trying on, because they always fit me like a custom personalized shoe and let me wear sexy 3.5" heals all day without ever putting my feet in any discomfort. I ALWAYS get complimented on my shoes and outfit when i wear Stuart's, especially up here in Vancouver, Canada where most women pull out boring Uggs to weather the fall and winters...so wrong, so wrong.

Good luck to the winner! She will be envied indeed :)

Stuart Weitzman's "HiLo" over-the-knee boots are all about keeping a tall and lean silhouette. Going with that theme, I'd pair them with black skinny ponté knit jeans, a black sequined boyfriend-fit blazer, a washed black burnout tee. To add a splash of color, I'd top it off with a dark goldenrod clutch!