A Guide to Matching the Ideal Shoes with Every Pant Style

Love them or hate them, skinny jeans are back in style; however, this time around, they’re considered a dressier type of jean. A far cry from the chokehold they had on millennials who would wear them with every single type of shoe, nowadays skinny jeans are best combined with delicate footwear like T-bar sandals. ” … I can appreciate skinny pants with a narrower silhouette of shoe,” John Fluevog tells us exclusively.

A big reason why skinny jeans pair so well with delicate sandals is that — just like the narrow shoe — they also accentuate your legs. “They emphasize shape and lengthen the appearance of the legs,” stylist Cuinn Casey explained to Real Simple. “And with the right styling, they can work well with any outfit by creating balance when paired with flowy or structured tops.” So, if you have a pair of skinny jeans, pair them with sandals for the ultimate flattering summery combo.

A pair of classic jeans and white sneakers is a safe match for a reason — it’s easy, comfortable, and always looks good. “… if you’re in relaxed jeans, I would suggest a relaxed piece of footwear as well.” John Fluevog shares exclusively with Glam. And while there’s plenty of leeway when it comes to picking the style of relaxed jeans, we’d recommend going for mom jeans. 

“It’s such a classic, cool fit,” stylist Sheyna Imm told Shop Today. “The way that they are cut allows room for different body types to kind of make them their own, and they look really flattering on a lot of different shapes and sizes.” As for footwear, we’ve already declared that white sneakers are the one shoe that works with every pair of jeans, but with mom jeans, they are a tried-and-true combo.

If you’re someone who loves chunky boots, the best way to make them shine is by pairing them with tights. “I think tights with a tall lace-up boot like the John Fluevog Olivia Zip-Up Ankle Boot With Laces is classically cool (side zips are allowed),” John Fluevog suggests exclusively to Glam.

If tights aren’t your thing, you can achieve a similar look by going for simple leggings, as long as they don’t take away the attention from your boots. Chunky boots come in all shapes and sizes, and whether you prefer a tall heel and platform or a simpler look, there is a style of chunky boot out there for you. Just keep in mind that the more intricate your boot is, the better it works with classic tights, resulting in an edgy and bold look that literally takes minutes to style.

When it comes to a more sophisticated and timeless pairing, looking at classic trends staging comebacks in 2025 is a great place to start. “All the classic combinations are classic for a reason, but I love it when people do their own take on it,” John Fluevog shares exclusively with us. 

While there are numerous options you could go for, one that is timeless yet modern is undeniably the combination of suit trousers and Mary Janes. The suit trousers can be cropped or normal length, slightly baggy, perfectly tailored, or even skinny. And as for the Mary Janes — your personal preference is all that matters. Kate Middleton is known to be a big fan of trendy Mary Janes, so looking at her for inspiration is definitely worth it. And if you want to make this sophisticated combination a tad more modern, opting for a pair of Mary Janes in a bold and bright color is an easy way to create a statement. 

Kitten heels have been popular for years now — and for good reason. They easily add the elegance of classic heels while still allowing your foot to be somewhat comfortable, especially if you’re wearing them all night. “This style can work very well with different looks, especially if their wearer wants to play with proportions — they can pair very well with a cropped trouser, for example,” Colleen Hill from New York’s Museum at FIT told WWD. While sandals with kitten heels look amazing with midi skirts, we recommend pairing them with capris if you’re more of a pants person.

“Capris are having more than a moment; they evoke innocent sexiness — that’s rare in that it’s both timeless and now, once again, trend-forward,” celebrity fashion stylist Jenni Lee revealed to Real Simple. “They’re bridging the gap between casual cool and elegant sophistication. A summer must-have — without question.” Add a simple top and statement bag to the look, and you’re ready to seize the day (or night).

Wide-legged pants have been at the forefront of trends for years now, and it doesn’t seem like the craze is going anywhere anytime soon. “They provide more room and freedom of movement compared to skinny jeans,” stylist My Tran told Nordstrom. “This makes them comfortable to wear for various occasions, whether you’re running errands, lounging at home or going out with friends.”

When it comes to matching them with the perfect shoe, a variety of styles work. However, a classic choice that always looks good is a pair of ankle boots — extra points if they’re pointy so that they can peek at the bottom. “You want to buy boots that have a 2-inch heel, give you lift and leverage your style for work and the evening,” stylist Sandra Okerulu suggested to Today. The best part of ankle boots under wide-legged pants is that whenever you’re sitting and your pants naturally rise up a bit, the shoe will have its moment. Even though wide pants tend to have a reputation of looking best on tall people, don’t worry — you can still rock wide-legged pants if you’re short. 

Cowboy-boot looks can bring a fun edge to any ensemble, so if you have a pair at home, consider them a wardrobe staple that can easily turn a bland look into a fashionable one. As John Fluevog tells Glam exclusively, “Whatever you do, make a statement … try to be outstanding … because you are outstanding (whether you’re standing in pants or not).”

While cowboy boots look particularly cool with dresses, skirts, and shorts, you can also wear them with pants. Our recommendation is a pair of straight-cut jeans tucked into the boots. “This look feels very reminiscent of Lady Di mixing classic prep with the cowboy boots,” stylist Liz Teich explained to InStyle. “We’ll be seeing a lot of mixing genres/styles this coming season and this is a prime example of one that works, especially as a riding boot would feel expected.” And don’t worry about your jeans bunching up above the boots — that is part of the nonchalant look. “If versatility is your main priority, try a pair of black cowboy boots that will pair nicely with a range of outfits,” styling pair Danielle and Alix told Marie Claire. However, if you want your cowboy boots to be a statement piece, pick a pair in a bright color or a fun pattern.

Cuffed jeans provide an easy way to show off the shoes you’re wearing, and while ankle booties or fun high heels work well, our top choice for them is a pair of ballet flats. Channeling the popular balletcore aesthetic, the shoes — which were a staple in the 2000s — have experienced a resurgence and are now one of the shoe trends everyone is trying in 2025.

“They are a great investment because they are a timeless style that never dates,” Cassie Smart from Matches Fashion told Harper’s Bazaar. “You may wear them one year and not the next, but you will certainly always go back to them.” Smart went on, “It works hard in your wardrobe. It is a very flattering shape and can be styled with everything from denim to dresses at every length.” If you’re new to ballet flats, opting for a sleek and comfortable black pair is the safest option. And trust us: They will quickly become your favorite footwear choice for summer!

Traditionally, baggy pants are styled with a more relaxed shoe, like sneakers or flat sandals; however, if you want to make them into a fun statement piece, consider combining them with a strappy high heel. The contrast between the relaxed pants and dressy heels creates a fun look that plays around with mixing different styles for a unique aesthetic.

“Baggy or relaxed-fit jeans sit at your hips, held by the waistband, but with no restrictive tightness,” stylist Elizabeth Cardinal Tamkin explained to InStyle. Because of this, they are some of the comfiest bottoms you can wear, but they can also easily swallow you if not paired with pieces that are more structured and body-fitting. “They have an ability to cross through generational gaps,” Grace Na from Pistola Denim added. “They make a look — dressed up or down — feel effortless and versatile. They’re the epitome of casual cool.” Strappy heels help add some of that sensuality back into the look, preventing the baggy pants from looking too casual. 

Barrel-leg jeans have been an on-trend denim silhouette for a few years now, yet many are still intimidated by the style. “It felt very forward at first, but when people realize how flattering the right fit can be — they’re in,” Grace Na explained to InStyle. “Pair with a great belt and a fitted top. With more volume on the bottom, you want to pair it back up top.”

As for shoes, we recommend going for pointed-toe heels, as they help add some visual length to the look. Of course, if high heels aren’t your thing, you can always opt for pointed-toe kitten heels or even flats. It is the pointed-toe that complements the barrel-leg jeans perfectly, which is why we recommend sticking to it, regardless of the heel size. However, one thing to keep in mind with pointed-toe shoes is that your toes should be comfortable in them and not squished, so sizing up half a number might be necessary.

White bottoms aren’t everyone’s cup of tea, but that doesn’t change the fact that they are extremely chic. In fact, white trousers are the European summer staple, which means that rocking them can help you achieve that trendy old-money aesthetic.

Even though white pants work with virtually any shoe, we recommend pairing them with a loafer. Designer Danielle Kalish explained to Today that these “slip-on shoes, usually with a polished, leather-like look” often also have “a menswear-inspired strap detail but there are tons of modern variations with a feminine look and feel.” The white pants and loafers combo provides a classic look while allowing you to be as comfortable as possible. Stylist Enrique Melendez added that when it comes to creating a look, you should “try to match the color of your loafers with a corresponding jacket or bag to tie in the whole look.” If you want your look to be more casual, opt for a pair of white jeans with a subtly distressed bottom instead of dressier white trousers.

If going for a retro vibe is your thing, flare pants and jeans should definitely be a part of your wardrobe. “Flared jeans can be worn with everything from a casual T-shirt to a blazer,” stylist Kelly Jorgensen told Nordstrom. “There really is no wrong silhouette here. Oversized sweaters, cropped tops, you name it — it works!”

While the choice of flared bottoms is entirely up to you (you can even go edgy with a pair of faux-leather flare pants), the shoes you should be pairing them with need to have a platform. Now, whether that be platform heels or platform sneakers is, again, up to you, as long as your feet are slightly lifted from the ground. This allows the flared portion of the pants to shine without potentially getting dragged across the ground. Besides, a platform is always a fashion power move, so they will add some instant edginess to your appearance.

Distressed jeans can sometimes be difficult to style, especially if you want to offset their messy aesthetic, but you don’t want to go for a predictable pair of high heels. In 2025, distressed jeans are once again back in fashion; however, stylist Naina Singla explained to InStyle, “This time around, the look feels more effortless and intentional rather than overly ripped and casual.”

If you’re ready to bring this trend back, we recommend teaming them with a pair of simple and comfortable clogs. Whether you opt for your mom’s old Birkenstock clogs or a more modern pair with a thicker platform and animal-print leather, the shoe is the perfect choice to balance a pair of ripped jeans. Top the look off with a long trench, and you have just gotten yourself a combination that says you love fashion but aren’t willing to sacrifice comfort for it.

There’s a reason why loose silk or satin pants are so popular — they create an effortlessly chic look and are a cool-girl way to keep it light in the summer. However, styling them can be tricky, especially if you’re worried about them looking too much like pajamas. To avoid this, we recommend pairing them with a classic cotton top and a pair of buckle sandals. “It is a shoe that captures the essence of the modern woman – someone who appreciates comfort without sacrificing style,” Ganni creative director Ditte Reffstrup explained to Stylist. Black satin pants are a classic choice, but if you want a more daring look, opt for a pair in a vibrant color.

With this pant and shoe combination, you will be ready to walk all day, and your outfit will still look stunning in pictures, making this a great combination for sightseeing and vacations. Now, if you want more pairing inspiration, make sure you check out the most fashionable shoe choices to wear with your dresses.