The Most Stylish and Comfortable Shoes to Wear Based on Each Style of Pants for Women Over 50

You’ve found the perfect pair of pants that fit you just right, paired it with your favorite top and now just need to figure out which shoes to finish off your outfit. But with so many different types of pants and so many different shoe styles, how do you know what goes with what? Which shoes look best with flare or bootcut pants compared to skinny jeans? Which toe styles complement the shape of each pant? Perhaps you’ve never put much thought into which shoes to wear with which your pants or maybe you’ve found yourself looking up outfit inspiration on Pinterest; Either way, we’re here to set the record straight on the best shoes to wear with different styles of pants, from bootcut to straight leg to tight pants, for women over 50.

What to look for in shoes for women over 50

First things first, no matter the style of pants, ensure you’re choosing shoes that are comfortable and supportive — especially if you’re over 50. As we age, we’re more likely to run into common foot aches and pains, from flat feet to plantar fasciitis to bunions. These problems can only exacerbate if you choose the wrong pair of shoes, so when you’re considering your pants and shoes sitting in the closet, keep the following in mind.

Shoes with arch support

If you suffer from flat feet, you’ll definitely want to look for supportive shoes that have adequate arch support. This arch support can help mimic a natural arch, which can lead to much less pain and the ability to be on your feet for longer periods of time.

Shoes with cushioning

You shouldn’t feel like you’re walking on a thin piece of cardboard when wearing your shoes. Instead, look for comfortable cushioning to support your feet. Sometimes, you may even want to opt for a cushioned footbed with heel cupping if you need extra heel support. If your feet are sore after only just an hour of wearing your shoes, that’s probably a sign they don’t have enough cushioning.

The 16 best shoes to wear based on different pant styles

Keep reading for our favorite shoes to wear with all of your favorite pants.

Shoes to wear with bootcut/flare pants

Journee Collection Haylinn Boot

A simple black bootie is a staple for fall, as well as your bootcut pants. Hence the name, bootcut pants make it easy to wear booties and shorter boots since they have a wider opening at the bottom. We like Journee Collection Haylinn Boot’s narrow square toe to balance out the wideness of the flare bottom.

Mix No. 6 Aliciana Sandal

A simple strappy heel looks cute with just about any pant style, but we especially love them with a bootcut or flare pant to dress up the outfit. This pair, Mix No. 6 Aliciana Sandal , is simple enough where they don’t overwhelm the flare, but still makes the overall look a bit more elevated. These sandals are also great to wear when going to a nice dinner or out for happy hour.

Crown Vintage Pimmy Bootie

We had to include another bootie option for bootcut jeans (it was only right). The olive green color of Crown Vintage Pimmy Booties is a classic fall shade, and goes with pants that are brown, black, tan and just about any other neutral hue. It has a lightly padded footbed, and we love the pointed toe style to balance out flare pants.

Sam Edelman Cleo Slingback Flat

These slingback flats, Sam Edelman Cleo Slingback Flat , are oh-so-sophisticated and chic, and work just as well for the office as they do dinner. Slingbacks are great because they help ensure feet won’t slip out of the shoe, aka there’s much more security with a slingback than, say, a slip-on mule.

Shoes to wear with straight-leg pants

Cole Haan Bellport Bow Drivers

Everyone needs a comfy pair of slip ons in their closet, and even better, a comfy pair of slip ons that you can wear to the office just as much as you can wear running errands. Cole Haan Bellport Bow Drivers are just that, a versatile shoe you can just slip on and go. The bow detailing makes them extra chic, and they have a fully padded foam footbed for peak comfort and a rubber outsole for extra traction.

Skechers Arch Fit Arcade

It can be difficult finding sneakers that go well with jeans — you don’t want them to look too sporty or gym-like, but you want them to feel as comfortable as gym shoes. Thankfully, Skechers Arch Fit Arcade has the best of both worlds: They’re fashionable and chic, while also making your feet feel good all day. Best of all, they have arch support, a removable insole that molds to your foot and a flexible outsole to make walking a breeze. Straight leg pants are one of the few pant styles that pair really well with sneakers — sometimes, sneakers with tight jeans or pants look too bulky, whereas the slightly wider silhouette of straight leg pants balance out the sneakers.

Nine West Rowen Slingback Dress Pumps

There’s nothing like a fun statement heel to instantly dress up any outfit. Nine West Rowen Slingback Dress Pumps are the perfect pair for summer and spring, with their bright floral pattern. They have a short heel, so you’ll get a bit of height sans the pain, and an ankle strap to keep your foot in place. The pointed toe design works well with straight leg pants to elongate the silhouette. Plus, they contrast beautifully when worn with light-wash, straight-leg jeans.

Bertuchi Made In Spain Leather Multi Strap Ballerina Flats

Ballet flats are still trending, and for good reason. They’re so comfy and you don’t need to worry about any aches and pains from heels. The gorgeous red color of Bertuchi Made in Spain Leather Multi Strap Ballerina Flats make them the perfect flat for fall. The straps will help ensure feet don’t slide out, which can easily happen with ballet flats.

Best shoes to wear with tight pants

Kelly & Katie Flomis Bootie

A bootie looks fabulous with tight pants or jeans with a rolled cuff. Kelly & Katie Flomis Booties are a staple pair of boots, with their rich chocolate brown that pairs beautifully with creams, whites, tans and beiges — making them great for fall. They’re not too bulky where they’ll overwhelm the tight fit of the pants.

Express Thin Mid Heel Mule Sandals

These heeled mules, Express Thin Mid Heel Mule Sandals , are so easy to slip on and instantly take your outfit to the next level. They go with just about anything with their beautiful neutral off-white hue, and they have a padded footbed for comfort. Heeled sandals go well with tight/skinny pants because, just like the other shoes mentioned above, they don’t add too much bulk. Since skinny jeans don’t have a lot of fabric, you want to match that with your shoes.

LOFT Horsebit Loafers

If you’re looking for a loafer that goes with tight pants, opt for a simple, thin loafer, rather than a platform or chunky loafer. An option that fits that criteria? LOFT Horsebit Loafers .These are lightweight and perfect to wear with your skinny dress pants for the office.

Cole Haan Addie Multi-Strap Heeled Sandals

Another sexy strappy moment, Cole Haan Addie Multi-Strap Heeled Sandals are as comfortable as they are chic. You can never go wrong with a classic pair of black strappy heels, especially with tight pants. This pair has a fully padded foam footbed, so you can wear them all day or night without pain.

Best shoes to wear with wide-leg pants

Kelly & Katie Pesla Pump

Breaking news: Cheetah print is back and better than ever. We’re obsessed with these 90s-style cheetah print, pointed-toe heels, Kelly & Katie Pesla Pump , which go perfect with a pair of wide-leg jeans or pants. Pointed-toe styles are typically the best choice for wide leg styles, as they balance out the width and help to optically create an elongated frame. We like how this pair has a short heel to make it easy to walk in and an ankle strap for added stability and security.

Vionic Alameda Mary Jane Flat

For flats for wide leg pants, opt for a pointed-toe or a square-toe design, like Vionic Alameda Mary Jane Flat . Flats can be hard for some women as many don’t have arch support, but this pair does. Podiatrists all over the world recommend Vionic, so they’re an excellent choice for women over 50.

LifeStride Sienna Bootie

Look no further than pointed-toe booties for your wide leg pant boot. LifeStride Sienna Bootie has a minimal, yet still interesting design with vertical line detailing at the back of the shoe. What’s more, they have a foam footbed and short heel for all day wear.

Cole Haan GrandPro Max Platform Sneakers

Platform sneakers look so chic with wide leg pants. Since wide leg pants have a lot of fabric and have a wider fit, you can get away with wearing a chunkier shoe. Cole Haan GrandPro Max Platform Sneakers are not only stylish, but are also great for women over 50 with their cushioned footbed and durable outsole (read: you can actually walk miles in these shoes!).