Booties are key for a well edited closet. More versatile than their knee high sisters, booties will take you through all four seasons.  As the temperature continues to drop, we take these booties beyond jeans and leggings pairings and venture into skirt and dress territory as well.

Yes, it is easy to rely on old faithful styling and not run the risk of creating a disproportionate look with the wrong dress-booties combination. However, we’ve got you covered with twelve looks covering pants, skirts, and dresses.  The key is to make sure they flatter your legs and lend a lean and chic look to your ensemble.

Booties with pants

Booties with pants, jeans, and trousers | 40plusstyle.com

Booties with jeans or trousers are quite possibly the easiest style choice. However, there are some guidelines to follow so you don’t create a disproportionate and unflattering silhouette.

The key is to select booties that can carry a tune on their own and don’t mind being the star of the show (because they will definitely be on display).

Monochromatic looks (blue booties with blue jeans or black booties with black trousers) also create a longer and more flattering look. Select a slim or straight leg that hovers right above the top of the boot. Jeans (or even trousers depending on the occasion) can be styled with a cuff to add a more casual chic look.

Shop the above looks below.

Booties with skirts

,Booties with long and short skirts | 40plusstyle.com

The general rule regarding skirts with booties is “the shorter the skirt the taller the boot”.  Of course, this rule can be broken depending on styling and body shape. Longer skirts can get away with shorter booties (such as with the longer Anna Sui skirt above).  You can also promote a more lean look by keeping the bottom monochromatic (like the black tights and black booties look above). Showing more of the ankle also allows you to get away with a shorter boot, as does a heel to elongate the leg (like the peep toe booties above paired with the showstopping Vivienne Westwood skirt).

Shop the above looks below:

Booties with dresses

How to wear booties with skirts | 40plusstyle.com

Like skirts, pairing booties with dresses can sometimes be a tricky endeavor. The key here is to once again pay attention to getting your proportions right and promoting a long look that does not chop your body in half. An easy style tip is to go for a monochromatic look that creates a lean look.

Booties are short enough to not shorten your leg (especially when paired with a shorter dress and leggings). Also, wearing booties outside of the black color selection (like the gray or brown pair featured above) creates a more complementary look.

Shop the above looks below:

Ready to add more versatility to your closet with the four season boot? Shop some of our favorite selections below.

How have you been wearing your booties this season?

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How to wear booties | 40plusstyle.com