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 pant styles?

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

Here are shoe styles ranging from peep-toe booties to brogues, sandals to slip-ons, which can 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 sandalNine West ‘Pruce’ ankle strap sandalNaturalizer ‘Dora’ bootie

Tory Burch ‘Minnie’ ballet flatCC Corso Como ‘Jatiba’ loafer1901 ‘Perrin’ sneakerSam Edelman ‘Dori’ pump

Bella Vita ‘Kathy’ open toe muleNaturalizer ‘Azalea’ slingback sandalMarc Fisher LTD ‘Zala’ pumpSchutz ‘Kayla’ metallic sandal

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

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.

Start from the bottom up

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.

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.

Melinda (above) shows how ankle pants can work perfectly with sneakers.

Get her look with this similar blouse, blazer, pants and sneakers.

Ankle pants | 40plusstyle.com

Eileen Fisher ankle pantsRollie derby lace-up flat shoe1901 ‘Perrin’ sneakerCC Corso Como ‘Jatiba’ loaferSam Edelman ‘Dori’ pump

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 these belted jacket options from Halogen and Vince that you can pair with these similar jeans and leopard print pumps to recreate her look.

Bootcut pants | 40plusstyle.com

Mavi Jeans bootcut jeansNaturalizer ‘Dora’ bootieNine West ‘Pruce’ ankle strap sandalCC Corso Como ‘Jatiba’ loaferSam Edelman ‘Dori’ pump

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.

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

Sallyanne (above) mixes casual and formal elements to great aplomb.

Steal her look with this similar puff shoulder top, jeans and pumps.

Boyfriend style pants | 40plusstyle.com

Citizens of Humanity boyfriend jeansRollie derby lace-up flat shoeNine West ‘Pruce’ ankle strap sandal1901 ‘Perrin’ sneakerSam Edelman ‘Dori’ pump

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.

Bev (above) chooses a white-on-white look.

Get her belted vinyl coat from Topshop and pair it with these similar pants and booties.

Crop flare pants | 40plusstyle.com

Topshop flare trousersMarc Fisher LTD ‘Zala’ pumpNaturalizer ‘Dora’ bootieBella Vita ‘Kathy’ open toe muleSam Edelman ‘Dori’ pump

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.

Patricia (above) opts for block heel sandals.

Recreate her look with this similar top, wide leg pants and slingback sandals.

Crop wide leg pants | 40plusstyle.com

Loveappella wide leg crop pantsFly London ‘Yala’ perforated sandalNaturalizer ‘Azalea’ slingback sandalBella Vita ‘Kathy’ open toe muleSam Edelman ‘Dori’ pump

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

Greetje (above) opts for pointed-toe pink pumps.

Get her trousers from ME+EM and pair it with this similar sweater and pumps.

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).

Kristen (above) wears a pair of flat slingbacks.

Check out this similar blouse, skinny jeans and slingback flat.

Skinny pants | 40plusstyle.com

BOSS slim ankle pantsCC Corso Como ‘Jatiba’ loaferNaturalizer ‘Dora’ bootieTory Burch ‘Minnie’ ballet flatSam Edelman ‘Dori’ pump

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.

Gail (above) opts for heeled sandals.

Steal her look with this similar blouse, faux leather straight leg pants and sandals.

Straight leg pants | 40plusstyle.com

Vince Camuto belted slim leg pantsNaturalizer ‘Azalea’ slingback sandal1901 ‘Perrin’ sneakerNine West ‘Pruce’ ankle strap sandalSam Edelman ‘Dori’ pump

Wide leg pants

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.

Greetje (above) opts for a pointy green pump.

Wide leg pants | 40plusstyle.com

Entireworld wide leg trousersNaturalizer ‘Azalea’ slingback sandalMarc Fisher LTD ‘Zala’ pumpFly London ‘Yala’ perforated sandalBella Vita ‘Kathy’ open toe mule

Utility pants

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.

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

Joie slim utility pantsSchutz ‘Kayla’ metallic sandalSam Edelman ‘Dori’ pumpNine West ‘Pruce’ ankle strap sandal1901 ‘Perrin’ sneaker

Sara (above) wears her utility pants with her sneakers.

Get her look with this similar shirt, pants and sneakers.

Leggings

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.

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

Abi (above) tucks her leggings into her booties. Recreate her look with this similar coat, faux leather leggings and booties.

Leggings | 40plusstyle.com

Commando velvet leggingsRollie derby lace-up flat shoeFly London ‘Yala’ perforated sandalNaturalizer ‘Dora’ bootie1901 ‘Perrin’ sneaker

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. Wide Legged Pants: How To Wear Them And Where To Buy The Best Ones

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

Feature Image by @the_fashionstalker

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