How to Style Black Booties 3 Ways


As a Style Coach, I teach my clients the importance of choosing items that can be worn at least three different ways, and finding a versatile shoe, like the Ugg Tasman dupes, is important for any season of the year. No one wants a shoe or piece of clothing sitting in the closet collecting dust because of its lack of versatility.

The black bootie is a must-have staple in your fall/winter wardrobe. My personal favorite is from Rag & Bone with an oval toe and a stacked block heel. There are several ways this basic bootie can be styled and because of this, you may want to consider investing in a quality pair as you’ll be wearing them often.

Elements to look for when choosing a versatile bootie:

**Dips down in the front as opposed to straight across the ankle

**Stacked block heel

**Oval toe (looks more casual and can be paired with more styles)

**Pointed toe (dressier)

Below I share with you how to style them 3 different ways:

1. Dark Wash or Black Skinny Jeans: The most classic and often easiest way to wear black booties is with a pair of dark wash or black skinny jeans. When rocking your black booties you want to elongate the legs (unless you are very tall) and one way to do this is by keeping the color of the booties in line with the wash of the jeans for a longer, leaner silhouette. If your jean is more of a slim straight or straight leg jean the jean can go over the bootie. If the jean leg is more of a skinny or legging style jean then you can either have the jean tuck slightly into the bootie (it should NEVER bunch up though, if it does this they need to be hemmed) or you can do a slight cuff to the jeans. I share my cuffing jean method in this Instagram video HERE if you need a visual on how to properly do this. Last thing, don’t cuff your jeans in lieu of hemming them. If they are the right length then they will look more polished and be more versatile.

Black Skinny Jeans

2. Cozy Fall/Winter Dress: While black booties often look great with dark wash jeans, they also can look amazing with a cozy fall/winter dress. The most important thing to look for when selecting a versatile pair of black booties is a dip down effect as opposed to a straight across your ankle/leg cut. This will create a more flattering silhouette when pairing these booties with a dress, whether you go bare legged or wear black opaque tights. If you are quite tall and have long legs you can often get away with a straight across cut bootie, but for me and many femmes the dip down is best. Lastly, make sure that the casualness of the bootie matches the casualness of the dress. Pair your dressier dresses with a more sleek, dressier bootie.

Winter Dress

3. Black or Dark Wash Boot Cut Jeans:  You can never go wrong with black booties and a pair of black or dark wash boot cut jeans. Boot cut jeans are back and they look best when paired with a heel of some sort, never flats. The black bootie is most versatile when the toe is an oval or pointed shape as that looks best underneath a jean. Make sure to have the jeans hemmed to your black booties, and a good rule is to have them hemmed a thumb nails length off the ground.

Dark Wash Boot Cut Jeans

Want more style tips on how to wear your favorite basics? Check out my blog on “How to Wear a Denim Jacket 3 Ways” HERE.

Also, below you can download my handy, stylish guide on light layering for these cooler months (by clicking the image)! This is perfect guide for helping you create outfits with your fabulous black booties!

light layering guide


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