In the first part of this two-part series, we tackled how long and short the hems of 9 types of pants should be. The other side of the equation is the constant challenge of what shoes to wear with what pant style. Exactly what shoes should you wear with different styles of pants?

In this updated article featuring shoes you can shop for online right now, we demystify the most flattering shoe-pant combinations. How do you match your shoe styles with your pants?

Shoe options

Below are shoe styles ranging from peep-toe booties to brogues, sandals to slip-ons, which can all be combined with a number of pant styles.

The shoes you have in your closet will very much depend on your style personality.

What shoes to wear with different styles of pants | 40plusstyle.com

Rollie derby lace-up flat shoeFly London ‘Yala’ perforated sandalNaturalizer ‘Vera’ ankle strap sandalSole Society ‘Candrah’ bootie

Sam Edelman ‘Felicia’ flatSteve Madden ‘Gemmy’ loafer flatMarc Fisher LTD ‘Yulunda’ pumpNaturalizer ‘Everly’ pump

Sam Edelman ‘Laurna’ muleTed Baker London ‘Mhalil’ slingback pumpClarks ‘Un Capri’ step platform wedge sandalJSlides ‘Hippie’ laser platform sneaker

You can also wear long boots with your pants

Given that we are heading into winter, you may also want to consider pants you can wear with knee-high boots.

Knee high boots to wear with pants | 40plusstyle.com

Naturalizer ‘Sterling’ knee high bootSam Edelman ‘Kerby’ knee high bootBella Vita ‘Braxton’ buckle knee high bootSöfft ‘Sharnell’ water resistant knee high boot

What to consider when choosing shoes to wear with different styles of pants

Now that you’re thinking about different shoe and boot styles, and which ones you are drawn to, what should you consider when putting these shoes together into a stylish outfit with your pants?

Are there right and wrong options when you choose shoes to wear with different styles of pants?

Think about balance

Melinda wears pointed shoes with her skinny pants | 40plusstyle.com

Just as with the rest of your outfit, matching your shoes to your pants is all about balance. For example, if you are wearing wide, flowing palazzo or wide pants you can wear chunkier shoes, while if you have narrow pants, you may wish to mirror this with your shoe or heel style.

Melinda (above) opts for pointed toe flats with her skinny pants.

Recreate her outfit with these similar pants, flats, shirt, blazer, clutch bag and earrings.

Start from the bottom up

Bev wearing white mules with black pants | 40plusstyle.com

You may find it easier to think about your outfit in a different way. Start with your shoe selection and think about which pants will go best.

Rather than considering what shoes to wear with different styles of pants, you’ll then be looking at it from the other way around.

This can be a great way to think of different outfit combinations if you find that you’re bored with everything in your closet and you’re looking for outfit inspiration.

Bev (above) wears on-trend white mules which she matches to her shirt.

Check out these similar pants, sandals, shirt, handbag and necklace.

The best shoes to pair with every type of pants

Below you will find plenty of examples of which shoes will go with the pants in your closet.

There isn’t only one style of shoes which will match each style of pants, so there are a selection of options for you to choose from.

Ankle pants

The best shoes to pair with ankle pants | 40plusstyle.com

It’s important to remember that ankle pants look best when worn immediately above or right on your ankle bone.

When selecting the right shoes, pairing ankle pants with high vamp shoes (booties, loafers, etc.) is the most flattering approach.

Whether flat, medium, or high-heeled, we certainly recommend trying a diversity of styles, as ankle pants tend to work well with a number of shoe styles.

Nuria (above) styles her ankle pants to perfection with a pair of classic pumps.

Steal her look with these similar pants, pumps, top, cardigan, handbag, belt and necklace.

Ankle pants | 40plusstyle.com

Wit & Wisdom plaid ankle trousersSam Edelman ‘Laurna’ muleTed Baker London ‘Mhalil’ slingback pumpRollie derby lace-up flat shoeJSlides ‘Hippie’ laser platform sneaker

Bootcut pants

The best shoes to pair with bootcut pants | 40plusstyle.com

Bootcut pants are one of the most versatile styles of pants. They look best when they almost touch the floor, yet do not completely cover the entire shoe.

Depending on whether or not you’re going for a dressed up or casual vibe, you have a diversity of options with bootcut pants.

Pointy-toed pumps tend to look very chic when paired with bootcut pants, as do mid-heel height boots and loafer style flats.

Petra (above) opts for pointed animal print shoes with her bootcut jeans.

Check out this similar pair of jeans, leopard printed pumps, belted coat and handbag.

Bootcut pants | 40plusstyle.com

Joe’s high waist bootcut jeansNaturalizer ‘Vera’ ankle strap sandalSteve Madden ‘Gemmy’ loafer flatNaturalizer ‘Everly’ pumpSole Society ‘Candrah’ bootie

Boyfriend style pants

The best shoes to pair with boyfriend pants | 40plusstyle.com

The epitome of chic comfort, boyfriend style pants look best with a cuff that hits at mid-calf.

Though the pants can be loose and relaxed, you can create a well-tailored look by selecting a more structured flat or heeled shoe. Jennifer Aniston, for example, often wears her boyfriend jeans with high heels.

Oxfords create an on-trend menswear inspired look and dress up the look. We also recommend pointed toe flats and low key sneakers.

Gail (above) wears her boyfriend jeans with heeled sandals and a blazer to elevate a casual look.

Check out this similar pair of boyfriend jeans, sandals, shirt and blazer.

Boyfriend style pants | 40plusstyle.com

AG boyfriend slim jeansNaturalizer ‘Vera’ ankle strap sandalNaturalizer ‘Everly’ pumpRollie derby lace-up flat shoeJSlides ‘Hippie’ laser platform sneaker

Cropped flared pants

Shoes to pair with crop flare pants | 40plusstyle.com

The right fitting cropped flared pants should hit anywhere from mid-calf to right above your ankle bone.

When selecting shoes to wear with these pants, we recommend ensuring that you go with a lengthening look (best done with a monochromatic tone) and/or select a shoe that minimizes the flare to create a leaner bottom.

Our top shoe selections are block heels, mules, ankle boots (make sure your pants hit right at or below the top of the boots) and pointed toe heels.

If you go with boots for this look, a matching boot (black-on-black, nude-on-nude, etc.) is the best option to create a streamlined look.

Kim (above) looks stunning in her leather cropped flare pants with strappy sandals.

Steal her look with this similar pants, sandals, shirt, coat, necklace and bag.

Crop flare pants | 40plusstyle.com

DL1961 high waist crop flare jeansSteve Madden ‘Gemmy’ loafer flatFly London ‘Yala’ perforated sandalTed Baker London ‘Mhalil’ slingback pumpClarks ‘Un Capri’ step platform wedge sandal

Cropped wide leg pants

What to wear with crop wide leg pants | 40plusstyle.com

Cropped wide leg pants (like cropped flared pants) are quite on trend this season.

Though they can be a challenge to style, the payoff for getting it right is great. The goal is to avoid adding more volume to your bottom.

It’s usually best not to wear ankle straps with this pant style, as it may shorten the leg further. But, if you want to draw attention downwards or you have beautifully slim ankles, this could work, particularly if you choose shoes in the same color as your pants or your want to go for a more edgy look.

Select more dainty looks, such as structured pointy toe pumps, a loafer, and minimal mules.

Monika (above) styles her wide crop pants with heeled pumps.

Recreate her outfit with this similar pair of pants, pumps, blouse and clutch.

Crop wide leg pants | 40plusstyle.com

Halogen wide leg crop pantsFly London ‘Yala’ perforated sandalNaturalizer ‘Vera’ ankle strap sandalClarks ‘Un Capri’ step platform wedge sandalJSlides ‘Hippie’ laser platform sneaker

Shoes for skinny jeans and skinny leg pants

The best shoes to pair with skinny pants | 40plusstyle.com

The key to selecting the right pair of skinny leg pants is to remember that the less they bunch around the ankle, the easier it is to create a well-tailored look.

Go for a pair that hits right around or slightly above the ankle bone. Once you have the perfect pair selected, you also have the option of pairing skinny leg pants with a countless number of shoe styles.

Some of our favorite options are strappy sandal heels, pointed toe heels, flats, shorter ankle boots (make sure they fit a bit snugly around the ankle, and you could also opt for knee-high boots).

Sallyanne (above) shows how skinny jeans can be worn with knee-high boots.

Steal her look with this similar pair of skinny jeans, boots, blouse and sunglasses.

Skinny pants | 40plusstyle.com

rag & bone high waist skinny jeansSam Edelman ‘Felicia’ flatSam Edelman ‘Laurna’ muleSole Society ‘Candrah’ bootieSam Edelman ‘Kerby’ knee high boot

Straight leg pants

Shoes to pair with straight leg pants | 40plusstyle.com

Most shoes will flatter the straight leg, so the choice ultimately falls on the tone of the look you’re going for and the type of top you are wearing.

They are fuller than bootcut style pants, and some styles can cover the shoe more so than bootcut style pants.

Our favorite looks are strappy sandals, pointed toe pumps, boots (keep the shaft a bit taller to avoid a bunching look), and low key sneakers.

Psyche (above) opts for multi-colored strappy sandals with her straight navy pants.

Check out this simila pair of trousers, top, sandals, belt and earrings.

Straight leg pants | 40plusstyle.com

BOSS straight leg wool pantsSteve Madden ‘Gemmy’ loafer flatTed Baker London ‘Mhalil’ slingback pumpMarc Fisher LTD ‘Yulunda’ pumpNaturalizer ‘Everly’ pumpJSlides ‘Hippie’ laser platform sneaker

Wide leg pants

shoes to wear with wide leg pants | 40plusstyle.com

Wide leg pants will always look best below the ankle bone and/or skimming the floor. Completely flat shoes can be paired with this pant style, but we definitely recommend ensuring that if you go that route you keep it well tailored.

A very slouchy look is not flattering on all body types, and the casual chic vibe can quickly turn into a sloppy and unflattering look.

Whether you select a very minimal 1-inch heel or 3-inch heels, a bit of height will help create a longer silhouette.

For this look, we recommend block style heels, chunky heels, wedges, and strappy sandals. Pointed toe pumps can work great, as well, just make sure the pants are not so long that the toe of your pump continuously gets caught on the material.

Ashley (above) opts for a stylish pair of slightly-rounded toe silver loafers with her wide-legged pants.

Recreate her outfit with this similar pair of pants, shirt, cardigan, loafers and necklace.

Wide leg pants | 40plusstyle.com

Faherty paperbag wasit linen chambray pantsFly London ‘Yala’ perforated sandalNaturalizer ‘Vera’ ankle strap sandalRollie derby lace-up flat shoeJSlides ‘Hippie’ laser platform sneaker

Utility pants

The best shoes to pair with utility pants | 40plusstyle.com

If you prefer a more casual look, you don’t have to opt for jeans. A pair of utility pants could also give you the look you want.

You have lots of shoe choices which will go with utility pants. You can choose a casual shoe such as a sneaker or chunky boot. Or you could opt for a dressier shoe to contrast with your pant style.

Abi (above) styles her utility pants with sneakers and mixes formal and casual with a Chanel-style bouclé jacket.

Check out this similar pair of utility pants, sneakers, shirt, jacket, bag, necklace and earrings.

Utility pants | 40plusstyle.com

Wit & Wisdom utility pantsMarc Fisher LTD ‘Yulunda’ pumpNaturalizer ‘Everly’ pumpNaturalizer ‘Vera’ ankle strap sandalRollie derby lace-up flat shoeJSlides ‘Hippie’ laser platform sneaker

Leggings

The best shoes to pair with leggings | 40plusstyle.com

It’s hard to find a more comfortable pant style than a pair of leggings.

There are plenty of ideas here on how to wear your leggings.

But what shoe style should you opt for?

Statying within a sporty style with sneakers and brogues often works well.

Booties are also a great option with leggings as are ballerinas.

Nic (above) opts for a classic casual look styled with white sneakers.

Steal her look with this similar pair of leggings, sneakers, shirt, jacket, crossbody bag, hat and sunglasses.

Leggings | 40plusstyle.com

Zella high waist leggingsSam Edelman ‘Felicia’ flatClarks ‘Un Capri’ step platform wedge sandalJSlides ‘Hippie’ laser platform sneakerNaturalizer ‘Sterling’ knee high boot

Best shoes to wear with jeans

How about the types of shoes you should wear with jeans? Do you need to think about this any differently to wearing shoes with pants?

The short answer is ‘no’. You’ll see above that I’ve featured both jeans and pants. The key is to consider the shape of your jeans in the same way as any other pair of pants. So, think about whether they are skinny, straight, bootcut, boyfriend, wide or cropped and then apply the shoe guidelines to the shape.

You can wear anything from formal shoes with jeans to more casual shoes for women with jeans. The looks you can create are endless.

You’ll find more jeans inspiration in this article on the most flattering jeans for women over 40.

What pant-shoe combination are your struggling to master? What is your favorite pair of shoes to wear with different styles of pants?

Continue reading:

  1. The Most Comfortable Heels That Look Hip AND Are Comfortable To Wear
  2. Best Shoes With Arch Support – Comfortable Walking Shoes To Walk In All Day!
  3. How To Wear Jeans Over 40 – Guidelines And Lots Of Ideas

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What shoes to wear with different styles of pants | 40plusstyle.com

Feature Image by Sallyanne

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