READ THIS NEXT: 5 Tips For Wearing Heels Over 65, According to Doctors and Style Experts. A kitten heel is a versatile shoe that you can wear from day to night without worrying about discomfort. “Pair them with classic bootleg jeans with a sloppy hem roll or clean, wide statement cuff to keep the look cool and current,” says Elizabeth Kosich, a New York City-based certified image stylist and founder of Elizabeth Kosich Styling. “If the kitten heels are slingback, wear them with a wooly turtleneck and peacoat for full coverage up top; if they’re closed-heel, show some skin with a V-neck sweater and cropped blazer.” These classic outfits can take you anywhere from the office to date night. ae0fcc31ae342fd3a1346ebb1f342fcb The block-heeled boot is a fall and winter staple. You can wear them with all types of jeans, including skinny, straight, and boot cut. Andie Sobrato, a personal stylist and image consultant, also suggests matching them with flared-leg jeans. “Because flares have a tendency to drag on the ground, wearing a nice block-heeled bootie is a great way to give you some lift and ensure the flare hits above the ground. Paired with a striped turtleneck, pussy-bow blouse, or blazer, we lean into the ’70s but continue to look classic and chic.” READ THIS NEXT: 4 Flattering Jeans for Women Over 50. Pumps look great with everything from dresses to jeans and all sorts of hems in between. “I love wearing my pumps with slightly cropped, straight-leg jeans,” says Sobrato. “The crop ensures that we’re seeing enough of the foot and a bit of ankle, keeping the look sleek and sexy.” In the summer, pair them with a fun going-out top and statement bag. In the winter, consider a black turtleneck. “Extra points if you layer with a camel or fun-colored overcoat—this is a very classic winter look,” Sobrato adds. There’s nothing more exciting than a statement shoe. Luckily, they can be paired with most jeans for a fun and flirty moment. “Boyfriend jeans and a statement heel are the ultra-fashion-forward pairings in this category,” says Tara West, a fashion stylist who serves clients in Connecticut, Boston, New York City, and Los Angeles. “Achieve this super stylish and comfortable look by rolling up your jean hem with one thick cuff and letting your heels steal the show.” A fitted turtleneck and cropped blazer complete the look. For more style advice delivered straight to your inbox, sign up for our daily newsletter. Platform heels are having a moment—and one of the easiest ways to style them is with jeans. “I would style a pair of wide-leg jeans with a pair of platforms pumps and a basic white button-down,” says Dawn Del Russo, an editorial stylist and fashion expert. The look is fun on the bottom and business up top. Add a cool necklace or statement ring and you’re ready for girls’ night.
