Shoes to Wear With Dress Pants That Aren 39
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.
Aerosoles Catalina Flat – Franco Sarto Balica Flat – Calvin Klein Gabrianna Pump – Marc Fisher LTD Zala Block Heel Pump
Fly London Yala Perforated Sandal – Louise et Cie Fionnah Mule – Zac Zac Posen Yancy Pointed Toe Pump – Steve Madden Irenee Ankle Strap Sandal
Paul Green Cayanne Leather Peep Toe Sandal – Trotters Lizzie Derby Flat – Superga Cotu Sneaker – Marc Fisher LTD Vincent 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.
Söfft Sharnell II Waterproof Knee High Boot – Trotters Kirby Knee High Boot – Bed Stu Jacqueline Knee High Boot – Bos. & Co. Jade Waterproof 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?
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
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.
Vince Coin Pocket Stretch Cotton Chino Pants – Franco Sarto Balica Flat – Superga Cotu Sneaker – Marc Fisher LTD Zala Block Heel Pump – Steve Madden Irenee Ankle Strap Sandal
Bootcut pants
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.
Mavi Jeans Marcia Crop Bootcut Jeans – Paul Green Cayanne Leather Peep Toe Sandal – Calvin Klein Gabrianna Pump – Marc Fisher LTD Zala Block Heel Pump – Steve Madden Irenee Ankle Strap Sandal
Boyfriend style pants
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.
Frame Le Garcon Ankle Slim Boyfriend Jeans – Superga Cotu Sneaker – Trotters Lizzie Derby Flat – Calvin Klein Gabrianna Pump – Steve Madden Irenee Ankle Strap Sandal
Cropped flared pants
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).
Vince Crop Flare Pants – Fly London Yala Perforated Sandal – Louise et Cie Fionnah Mule – Paul Green Cayanne Leather Peep Toe Sandal – Marc Fisher LTD Zala Block Heel Pump
Cropped wide leg pants
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.
Sweaty Betty Cruise Culotte Pants – Fly London Yala Perforated Sandal – Paul Green Cayanne Leather Peep Toe Sandal – Marc Fisher LTD Zala Block Heel Pump – Steve Madden Irenee Ankle Strap Sandal
Shoes for skinny jeans and skinny leg pants
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.
AG Farrah High Waist Skinny Jeans – Bos. & Co. Jade Waterproof Knee High Boot – Zac Zac Posen Yancy Pointed Toe Pump – Aerosoles Catalina Flat – Marc Fisher LTD Vincent Bootie
Straight leg pants
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.
Anne Klein Clean Front Pants – Superga Cotu Sneaker – Zac Zac Posen Yancy Pointed Toe Pump – Calvin Klein Gabrianna Pump – Steve Madden Irenee Ankle Strap Sandal
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.
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.
Socialite Washable Satin Wide Leg Pants – Superga Cotu Sneaker – Fly London Yala Perforated Sandal – Louise et Cie Fionnah Mule – Steve Madden Irenee Ankle Strap Sandal
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.
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.
Wit & Wisdom Ab-Solution Utility Pants – Superga Cotu Sneaker – Trotters Lizzie Derby Flat – Zac Zac Posen Yancy Pointed Toe Pump – Steve Madden Irenee Ankle Strap Sandal
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.
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.
Zella Renew 7/8 High Waist Leggings – Söfft Sharnell II Waterproof Knee High Boot – Aerosoles Catalina Flat – Superga Cotu Sneaker – Fly 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.
shop all items above here:
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:
- The Most Comfortable Heels That Look Hip AND Are Comfortable To Wear
- Best Shoes With Arch Support – Comfortable Walking Shoes To Walk In All Day!
- How To Wear Jeans Over 40 – Guidelines And Lots Of Ideas
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Feature Image by Tanasha @stylishheights
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