What shoes to wear with different styles of pants

by Sylvia

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

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.

In this updated article with shoes you can shop for online right now, we de-mystify the most flattering shoe-pant combinations.

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.

Shoe Options | fashion over 40 | style | fashion | 40plusstyle.com

Rollie Oxfords – Fly Yala Wedge  – Ankle Strap Sandal  – Daria Bootie

Peep toe bootiesPointy Toe LoaferBallet flats – Gray Pointy Toe Pump

Orange Open Toe Slide Toms SneakersGray Pointy Toe PumpSlingback Pump

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.

Ankle pants | fashion over 40 | style | fashion | 40plusstyle.com

Ankle Trousers – Rollie Oxfords – Gray Pointy Toe Pump – Pointy Toe Loafer – Toms Sneakers

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.

Bootcut pants | fashion over 40 | style | fashion | 40plusstyle.com

Navy Bootcut PantsDaria Bootie – Gray Pointy Toe Pump – Pointy Toe Loafer  – 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.

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

Boyfriend style pants | fashion over 40 | style | fashion | 40plusstyle.com

Boyfriend Jeans –  Rollie Oxfords  – Gray Pointy Toe Pump – Toms Sneakers – 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.

Cropped flared pants | fashion over 40 | style | fashion | 40plusstyle.com

Cropped flare pants – Orange Open Toe Slide – Gray Pointy Toe Pump  – Slingback Pump – Peep toe booties

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.

We definitely do not recommend wearing ankle straps with this pant style, as you can bring too much focus on one part of your body. 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.

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

Cropped wide leg pants | fashion over 40 | style | fashion | 40plusstyle.com

Wide Leg Crop Pants – Orange Open Toe Slide – Gray Pointy Toe Pump  – Slingback Pump – Fly Yala Wedge

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).

Skinny leg pants | fashion over 40 | style | fashion | 40plusstyle.com

Black Skinny Jeans – Gray Pointy Toe Pump – Gray Pointy Toe Pump – Daria Bootie – Ballet flats

Skinny legs pants can also look great with open toe booties as the image below featuring Tania shows.

What shoes to wear with which pants | 40plusstyle.com


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 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.

Straight leg pants | fashion over 40 | style | fashion | 40plusstyle.com

Straight Leg Wool Suit –  Gray Pointy Toe Pump –  Daria Bootie – Ankle Strap Sandal – Toms Sneakers

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.

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

Wide Leg Denim Pants – Ankle Strap Sandal  – Slingback Pump  –  Orange Open Toe Slide – Gray Pointy Toe Pump

What pant-shoe combination are your struggling to master? What is your favorite combination?

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Feature Image: @taniadalton

{ 12 comments… read them below or add one }

1 Nancy

I am a real shoe addict. I have bought shoes that I have never walked on, but they are just simply beautiful to look at. I always think about where I have to go to and addapt my shoes on it.


2 Rita

LOL! I have shoes like that as well. I call them my curio cabinet shoes. I’ve never worn them out of the house, but I take them out of the boxes to admire how pretty they are. 🙂


3 Terrie

OMG it makes me feel so much better that there are people out there just like me that have pretty shoes they’ve never worn out in their closets 🙂


4 esther

very informative thank you


5 Mother & Daughter

i love shoes. I haven’t been able to wear any type of heels for awhile now. The last pair I wore I fell off of and broke my foot, but I still love them.


6 Rita

My “go-to” pairings are ankle pants with ballet flats or diminutive oxfords (slim vs. chunky), and straight-legged with ankle boots, oxfords, or loafers. If I wear boot-cut, I might go for a medium-height heel.

I am quite over the “skinny jean” trend. I just don’t find them comfortable or particularly flattering. For a few years, that was all that was available in most stores so I have a few pair, but they are in the give-away pile now.


7 Dee

I found this post very helpful! Most of the time I feel I have to get around on stilletos to look half way decent, (which I hate)! I’m glad the selection of shoes you have in this post, look great and look like they would be very comfortable!


8 Greetje

Thanks for the inspiration. I am going to try my distressed boyfriend jeans with my orange oxfords. Not something I usually go for, but hey.. let’s live dangerously .


9 Mademoiselle Coconath

Great tips! Thanks for sharing!
Mademoiselle Coconath


10 Sherry Edwards

I don’t have just one particular favourite style. I wear many different pant and shoe styles. However, I do like to mix it during the week. Skinny one day, wider another day. This way I don’t get bored and people who see me daily don’t have to know what I’m wearing tomorrow. I also like different lengths. How I choose has to do with weather, my daily agenda and what type of shoes I need to wear. Will I be doing a lot of walking, or sitting or driving.


11 Scotti

Great information! Like others, I have worn only flats for years now, so it’s nice to see that they can go with almost any style of pants.


12 Greetje

Very instructive. I have paid good attention the first time, as I think I am doing it right. Though I have bought wide cropped trousers since then, plus a straight pair which ends around my calf. Very challenging models for me. Reading this post makes me confident I made the right choices.


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