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

Aerosoles Catalina FlatFranco Sarto Balica LoaferCalvin Klein Gabrianna PumpMarc Fisher LTD Zala Block Heel Pump

Fly London Yala Perforated SandalFericzot Buckle Mule – Zac Zac Posen Yancy Pointed Toe PumpSteve Madden Irenee Ankle Strap Sandal

Paul Green Cayanne Leather Peep Toe SandalTrotters Lizzie Herringbone OxfordECCO Soft 7 SneakerDr. Scholl’s Lucille Bootie

You can also wear long boots with your pants

Given that many of you may soon be heading from summer to fall, you may also want to consider pants you can wear with knee-high boots.

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

Söfft Sharnell II Waterproof Knee High BootNaturalizer Jessie Knee High BootVince Highland Knee High BootsBed Stu Glaye Leather Riding Boot

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

Shoes to wear with different pants - Karen wears animal print loafers | 40plusstyle.com

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?

Karen @styledbykaren above looks fabulous by making her shoes the statement piece of her outfit.

Get her look with this similar top, blazer, pants and loafers.

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.

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.

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.

Claudia @glamupyourlifestyle above (read her style interview here) opts for chunky white shoes with her ankle pants.

Check out this similar blouse, pants, oxfords and crossbody bag.

Ankle pants | 40plusstyle.com

Boden Hampshire 7/8 PantsPaul Green Cayanne Leather Peep Toe Sandal – Calvin Klein Gabrianna PumpMarc Fisher LTD Zala Block Heel PumpSteve Madden Irenee Ankle Strap Sandal

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.

Carelia @myevolvingstyle above (read her style interview here) wears pumps with her bootcut pants.

Recreate her outfit with this similar blazer (another option here), pants, pumps and clutch.

Bootcut pants and shoe styles | 40plusstyle.com

NYDJ Barbara Bootcut JeansPaul Green Cayanne Leather Peep Toe SandalCalvin Klein Gabrianna PumpMarc Fisher LTD Zala Block Heel PumpSteve Madden Irenee Ankle Strap Sandal

Boyfriend style pants

The best shoes to pair with boyfriend style 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.

You can wear your boyfriend jeans with heeled sandals and a blazer to elevate a casual look.

Greetje @no_fear_of_fashion above (read her style interview here) shows how you could wear your boyfriend jeans with sneakers.

Check out this similar shirt, coat, jeans, sneakers and crossbody bag.

Shoes for boyfriend style pants | 40plusstyle.com

Frame Le Garcon Ankle Slim Boyfriend JeansECCO Soft 7 Sneaker –  Trotters Lizzie Herringbone Oxford –  Calvin Klein Gabrianna Pump – Steve Madden Irenee Ankle Strap Sandal

Cropped flared pants

The best shoes to pair with cropped 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.

Psyche @economyofstyle above matches her boots to her pants.

Steal her look with this similar sweater, pants, boots and handbag (another option here).

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

FRAME Le Crop Flare PantsFly London Yala Perforated Sandal –  Fericzot Buckle Mule – Paul Green Cayanne Leather Peep Toe SandalMarc Fisher LTD Zala Block Heel Pump

Cropped wide leg pants

The best shoes to with cropped 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.

Eugenia @theeageofgrace above (read her style interview here) opts for pointy-toe pumps with her wide cropped pants.

Recreate her outfit with this similar blouse, pants, sandals and crossbody bag.

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

Boden Belted Wide Leg Crop PantsFly London Yala Perforated SandalPaul Green Cayanne Leather Peep Toe SandalMarc Fisher LTD Zala Block Heel PumpSteve Madden Irenee Ankle Strap Sandal

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).

Cathy @themiddlepageblog above (read her style interview here) shows how you could wear knee-high or over-the-knee boots with your skinny jeans.

Check out this similar top, blazer, jeans, boots, bag and belt.

Shoes and boots to wear with skinny jeans | 40plusstyle.com

NYDJ Ami Skinny JeansNaturalizer Jessie Knee High Boot –  Zac Zac Posen Yancy Pointed Toe PumpAerosoles Catalina Flat –  Dr. Scholl’s Lucille Bootie

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.

Beth @styleatacertainage above (read her style interview here) looks super stylish in her monochrome outfit.

Get her look with this similar top, pants, sandals, scarf, bag and earrings.

Shoes that go with straight leg pants | 40plusstyle.com

M.MLaFleur The Smith Pant – ECCO Soft 7 Sneaker –  Zac Zac Posen Yancy Pointed Toe Pump – Calvin Klein Gabrianna PumpSteve Madden Irenee Ankle Strap Sandal

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.

Tanasha @stylishheights above wears high, red stilettos. You could opt for a lower height in the same style if you have difficulty wearing heels.

Steal her look with this similar blouse, blazer, jeans, pumps and bag.

Shoes that go with wide leg pants | 40plusstyle.com

Boden Hampshire Ponte Wideleg Pants –  ECCO Soft 7 SneakerFly London Yala Perforated Sandal – Fericzot Buckle MuleSteve Madden Irenee Ankle Strap Sandal

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 that 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 @stealmystyle40 above shows how you can keep your look casual yet stylish with a pair of sandals teamed with utility pants.

Steal her look with this similar blouse, pants, sandals, tote and hat.

Utility pants | 40plusstyle.com

Kensie High Waist Utility Pants – ECCO Soft 7 SneakerTrotters Lizzie Herringbone Oxford – Zac Zac Posen Yancy Pointed Toe PumpSteve Madden Irenee Ankle Strap Sandal

Leggings

What shoes to wear with different styles of pants | 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.

Alison @wardrobe_oxygen above (read her style interview here) wears a classic combination of sneakers and a denim jacket with her leggings.

Recreate her outfit with this similar top, leggings, sneakers and belt bag.

Leggings | 40plusstyle.com

SATINA High Waisted LeggingsSöfft Sharnell II Waterproof Knee High BootAerosoles Catalina FlatECCO Soft 7 SneakerFly London Yala Perforated Sandal 

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 Tanasha @stylishheights

Sylvia

Sylvia is 40+style’s editor-in-chief and has been helping women find their unique style since 2011. An alumni of the School of Color and Design, she is devoted to empowering women of any age to look and feel their best. Read more about Sylvia and 40+style on this page.

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