With pretty much all denim styles and silhouettes trending right now, it can be overwhelming to figure out what shoes work best with each one. A few years ago, I wrote this post about what shoes to wear with all types of jeans, so I thought I’d update it for Fall/Winter 2024. I even created an infographic of sorts to make it easy to reference.
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If you’ve been struggling with what shoes to wear with all types of jeans this fall, this should help! It isn’t an exhaustive list of denim and shoe pairings, but it’s a good place to start. (CLICK HERE for a printable PDF.)
What Shoes to Wear With Straight Leg Jeans
MOTHER Rider Straight Ankle Jeans (29) // Dolce Vita loafer mules (7.5) // Vince sweater (S)
Straight-leg jeans come in lots of variations, from relaxed and slouchy to sleek and slim-fit; and they can be cropped, ankle length, or full length.
Slim Straight Ankle Jeans
Slim straight ankle jeans are highly versatile and universally flattering, and they’re my favorite style to wear with loafers and loafer mules, as shown above. They also look good with fashion sneakers, sandals, pumps, Mary Jane flats and ballet flats, clogs and mules, and ankle boots.
AG Mari Straight Ankle Jeans (29) // similar boots // Pistola Monroe Crop Cigarette Jeans (29) // P448 John (39)
In fact, it’s hard to find a shoe that doesn’t work with slim straight ankle jeans, although ankle boots can be a bit tricky. The key with pairing straight leg jeans and ankle boots is finding the right combination of denim length and width, and boot shaft height and width.
HINT: A taller, slender boot shaft works best when wearing ankle boots under straight leg jeans. You can read more in my post, How to Wear Ankle Boots with Straight Leg Jeans.
Relaxed Straight Leg Jeans
Straight leg jeans also come in more relaxed silhouettes, which are usually full-length or slightly tapered at the ankle. (The trendy barrel leg jeans would fall into this category.)
Relaxed straight leg jeans can be worn casually with a thermal top and a low profile fashion sneaker such as the Vince Oasis, as shown on the left. Or you can dress them up with a heeled boot and a sweater for a more grownup take on this trend-driven silhouette, as shown on the right.
Madewell The Perfect Vintage Wide-Leg Jean (8) // Vince sneaker (8) // thermal top (S) // AGOLDE Lana (29) // similar Marc Fisher boots (8) // old cardigan
Shop my favorite straight leg jeans:
What Shoes to Wear with Bootcut & Flare Jeans
MOTHER Fray Hem Flare Jeans (29) // Blondo boots (8) // Treasure & Bond sweater (XS) // PEI Shoulder Bag
Bootcut jeans and flares are pretty much interchangeable when it comes to shoe pairings, so I’ve lumped them together for the purposes of this post. Like straight leg jeans, bootcuts and flares come in crop, ankle, and full length styles. I like to have some of each in my closet, but I’m gravitating more towards full length flares these days. That seems to be where trends are headed, although pretty much anything goes right now.
Full Length Flares
Traditionally, flares and bootcut jeans look best with a heel or a platform sole, preferably with a pointed toe. This helps offset the width at the bottom and helps to elongate the line of the leg. These days, though, we are often seeing flares paired with flat shoes, and I kind of like the look.
STYLE TIP: To keep proportions in check, wear a shorter top when wearing flares and bootcut jeans with flat shoes.
Below, I am wearing my FRAME Le Easy Flare Jeans with a 2″ heel on the left, and with flat Birkenstock slides on the right. They both look good to my eye, but the look on the right is decidedly more casual.
FRAME Le Easy Flare (29) // Vince sandals (8) // Birks (39) // sweater (S) // black top (S) // sling bag
Likewise, I wear these MOTHER Fray Hem Flare Leg Jeans with my low profile VEJA sneakers as shown on the left, as well as heeled ankle boots as shown on the right.
MOTHER Weekender (29) // Paul Green sneakers (8) // sleeveless hoodie (M) // Aquatalia booties (8) // Naadam sweater (S) // Andrew Marc Coat (S)
I feel like the secret to making sneakers work with the flares is to stick with a low profile silhouette, rather than a chunkier trainer or retro runner. In the graphic above, you can see that I paired the trainers with kick flares and the retro runners with straight leg jeans.
As far as the heels go, it’s fine if the hem of your jeans isn’t sitting a half-inch above the floor. Wearing them slightly shorter is a more modern look, and allows you to wear the same jeans with both flats and heels.
Demi Boot & Crop Flares
Cropped and ankle length bootcut jeans and flares are great for showing off your shoes and the slimmest part of the leg. Sometimes you will see these called demi bootcut or crop bootcut or kick crop jeans.
MOTHER Hustler Ankle Flare (29) // Sam Edelman booties (8) // Andrew Marc Coat (S)
When it comes to ankle length and crop flares, ankle boots are a great option, but you have to play around with the combination of inseam length and shaft height. Just like with straight crops, you don’t want your jeans getting hung up on the back of the boot.
MOTHER Hustler (29) // similar clogs (8) // J.Crew vest (S) // Jenni Kayne sweater (S) // Citizens Isola cropped boot (29) // rag & bone Retro Runner (9) // old vest
Crop or ankle length flares also look great with block heel mules, loafer mules, and all types of fashion sneakers. And clogs almost always work.
STYLE TIP: These pairings look best when they allow some ankle to show, and that’s what allows you to get away with a chunkier shoe.
Shop my favorite bootcut and flare leg jeans:
What Shoes to Wear with Wide Leg Jeans
KUT from the Kloth Meg Wide Leg Ankle Jeans (6) // Blondo boots (8.5) // Rails jacket (S) // AllSaints tee (M)
Wide leg jeans also come in full length, crop, and ankle lengths, and this is the most current silhouette for everyday women.
KUT from the Kloth Meg Wide Leg Ankle Jeans (6) // Sam Edelman slingbacks (8) // Sanctuary sweater (S) // PAIGE Anessa Wide Leg Jeans (29) // Franco Sarto booties (8) // Nordstrom sweater (S)
Wide leg jeans, much like flares, tend to look best with a bit of a heel or a pointed toe. But once again, I’m seeing them paired with everything from ballet flats and Mary Janes to sneakers, and somehow it seems to work.
I haven’t played around much with wide leg jeans for fall, but I’ve worn wide leg ankle jeans a lot this summer with flat sandals and sneakers, as shown below.
KUT from the Kloth Meg Cuff (6) // Birks (39) // Faherty pullover (S) // Frank & Eileen Gaucho Jeans c/o (29) // Paul Green sneakers (8) // KUT from the Kloth Kara (M) // Frame tee (XS)
I’m also really excited to wear these full length MOTHER The Hustler Roller Skimp Jeans this fall and winter. (They call them flares, but they’re more of a wide leg silhouette, to my eye.) They look great with boots, and I can also see myself wearing them with the Sam Edelman slingbacks and other heels.
MOTHER The Hustler Roller Skimp (29) // rag & bone Walker Chelsea Boots (8) // muscle top (M)
Shop my favorite wide leg jeans:
What Shoes to Wear With Skinny Jeans
PAIGE Gemma (29) // LOCI sneakers (8) // Andrew Marc Coat (S)
Skinny jeans have been taking a backseat to more relaxed styles for the past few seasons, but there are rumblings that they’re already on their way back. I think it’s important to note that the “skinny jeans” we are seeing on some of the Hollywood style icons are more of a slim cigarette leg silhouette, and the overall look is elegant and leveled up. These are not the skintight legging-like jeans we were wearing with tunics and open toe booties five years ago.
To keep skinny jeans looking current, pair them with one of the latest shoe trends, such as a Mary Jane flat, low profile fashion sneaker, loafer mule, or pointy toe slingbacks. I don’t have a lot of personal photos to share because I’m not really wearing skinny jeans right now. I feel like bootcut jeans and flares are more flattering on my body type, and I’m enjoying the wide leg silhouettes, as well. They may not be my best silhouette, but they’re fun for a change.
In Summary
It may seem like anything goes at the moment, and I would say that’s kind of true. Almost any denim silhouette can look current if it’s styled in a current way, and a lot of the traditional “style rules” are being challenged. At the end of the day, you have to play around in your closet and try on different combinations to see what works best for you, but hopefully this helps you narrow down your options.
YOU MAY ALSO LIKE:
- Women’s Pant Styles and Hem Lengths Demystified
- How to Wear Retro Sneakers Without Looking Frumpy
- What Shoes to Wear With Flares
- How to Wear Loafers and Flats with Straight Leg Jeans
- How to Wear Ankle Boots with Straight Leg Jeans
And if you want more info, see all my posts about 2024 Fall Trends!
