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Style Inspiration

The Best Shoes to Wear With Jeans

The most asked question of Real Life Style right now? The best shoes to wear with jeans. Yes, this blog will give you general answers to this sartorial challenge. But most importantly, you will find steps to follow to get your own personal answers. I can’t tell you how thrilled I am to bring you this long-requested blog! Now, I hand you over to the RLS denim expert, Kyle Dunphy!

Happy Shopping!

lani signature real life style

P.S. Next month will be Kyle’s 11 year anniversary with RLS!!!

Kyle with the perfect example of how to pair a wide leg pant or jean with a visually weighted boot. So cute and balanced!

The First Step

Have you ever heard the phrase “build your outfit from the ground up?” Your daily itinerary almost always affects the shoes you wear, whether it’s a car-to-door dinner or a day touring the city.

You must think about what footwear you gravitate towards the most before choosing your new favorite jean style. Love ballet flats or Rothy’s? Consider a tapered leg or a cropped bootcut jean. However, if you’re always reaching for a block-heeled bootie, a wide leg or flare style would be the best jean style for you.

Measure Twice, Click Once

After considering which shoes you’re going to wear, the second step is to consider where you want your jeans to hit. If you’re shopping online, this second step can be made more predictable by checking the inseam measurement listed in the fine print. I know that a 27″ inseam is going to be pretty cropped on me (Lani is laughing because that is the inseam of her entire leg!). However, an inseam 32″ or longer will need to either be reserved for 2″+ heels or be tailored. (The advantage of being more petite and needing to hem your jeans is the ability to choose exactly where your jeans hit your legs! Just bring your shoe of choice to your tailoring appointments.)

I took the liberty of listing out the inseam, as well as the rise and the leg opening whenever available, for all jeans shown in this blog. Try measuring the rise of your favorite pants and using the information to purchase new pants. I love knowing that how a 12″ rise hits at or above my belly button when I buy jeans online.

Are You a Rule Follower?

If you want to follow the so-called “fashion rules,” I will help you pair your shoes below. But here is a curveball to consider. The “wrong-shoe theory” is the styling trick that has been all over TikTok and Pinterest. Have you ever paired a sporty sneaker with a nicer sundress and thought it looked particularly fashion forward? The logic behind the wrong-shoe theory is that the juxtaposition of two completely different styles can feel so cool. So yes, balance and matching styles can and will look great, but don’t over think it! Any updated shoe in good condition can work with any of the new jean silhouettes, it might just take some extra styling to make it look intentional.

Happy shopping!

PS: Just another tip I want to share since it’s January. If you get cold wearing jeans in the winter, consider wearing Uniqlo HeatTech leggings underneath. The regular HeatTech fits underneath all of my jeans and keeps me warm, but not hot and sweaty.

Tapered Straight Leg Jeans

The tapered straight leg style is the first step for many women searching to modernize their look after skinny jeans. These are typically tight in the butt and thighs and then straight below the knee. Where a skinny jean might have a 10″ or 11″ leg opening diameter, a tapered leg will have a 14″ or 15″ leg opening. I like to find a pair that hits at or right above the ankle for my clients, as this feels the most modern and flattering.

If you love or own mostly flat shoes, this is a great style for you. Try these with a pair of ballet flats and a striped Breton shirt for a classic French-girl vibe. For boots, you will usually want your jean hem to cover the top of the boot or touch the top of the boot. I would avoid more than a 1″ gap between the top of the boot and the hem of the jean.

Re/Done 70s Stove Pipe High-Rise Crop Jeans, $275
27″ inseam, 11″ rise, 14.5″ leg opening

  1. A lace-up combat boot: Thursday Boot Company Coda, $190
  2. A slim profile retro sneaker: Gola Torpedo Sneakers, $125
  3. A ballet flat: M.Gemi Danza Square Toe Ballet Flat, $248
  4. A classic chelsea boot: Nisolo Eva Everyday Chelsea Boot, $228 $125

Other Jean Options

Good American Always Fits Good Classic, $159
27″ inseam, 12.5″ rise, 14″ leg opening

Favorite Daughter Valentina High Waist Crop Cigarette Jeans, $198
28″ inseam, 11.5″ rise

Cropped Wide Leg Jeans

A cropped wide leg jean is extremely versatile! Seriously! You can dress them up with sleek heeled boots and a blazer or you can keep them cool and casual with sneakers and a t-shirt. Your jean length can vary here, from right at your ankle without much skin showing, to a few inches above your ankle to showcase your shoes. I love wearing knee high boots under my full-length and cropped wide leg jeans. This helps me get more wear out of some of my favorite boots and keeps me warm in the winter!

Whether you choose a sneaker or a boot, look for a shoe with visual weight (i.e. a thicker sole, a lighter color, a wider toe box). This balances the wider width of the jeans. A slim shoe like a pointed flat or stiletto pump can work, but may require additional styling to achieve balance elsewhere in the outfit.

Favorite Daughter Mischa High Rise Wide Leg Ankle Jeans, $198
29.5″ Inseam, 12″ Rise, 22″ leg opening

  1. A comfy clog: Birkenstock Boston Genuine Shearling Lined Clog, $170
  2. A lug-sole boot: Athlefit Women’s Chelsea Platform Ankle Boot, $49.99
  3. A trendy sneaker: Adidas Samba Sneaker, $110
  4. A sleek tall boot: 27 Edit Naturalizer Falencia Knee High Pointed Toe Boot, $260 $156

Other Jean Options

Madewell Perfect Vintage Wide Leg Crop Jean, $128
27″ inseam, 10.75″ rise, 18″ leg opening

Kut from the Kloth Meg Fab Ab High Waist Ankle Wide Leg Jeans, $99
28.5″ inseam, 11″ rise, 24″ leg opening

Full-Length Wide Leg Jeans

With full-length wide leg and full-length flare jeans, the length and the leg opening will both affect the shoes you wear. If you love a wide leg jean for everyday (like me!), it would be totally reasonable to have a pair that you wear with flats and sneakers, as well as a pair you wear with taller heels. My January uniform has been a pair of wide leg jeans with my Sunburst Mini Uggs I got on sale this season (however I really wanted to justify the Elder Statesmen collab pair below!). With Uggs and sneakers, I typically wear my Ayr Secret Sauce jeans in the regular length. The leg opening on these is only 20″, so they don’t feel too oversized with flatter shoes. My Citizen’s Paloma jeans that I got from Big Drop last year are only half an inch longer but are 4″ wider in diameter. I typically wear these jeans with shoes that have a slight lift, like a clog or block heel boot.

Citizens of Humanity Paloma Baggy High Waist Wide Leg Jeans, $228
32″ inseam, 12″ rise, 24″ leg opening

  1. A 70’s inspired clog: Dansko Britton Mule, $145
  2. A chunky sneaker: Nike Air Force 1 Sneaker, $135
  3. Your favorite cozy boot: Ugg The Elder Statesman Classic Ultra Mini, $325
  4. A knee high block heel boot: Blondo Tessa Waterproof Knee High Boot, $219.95 $149.96

Other Jean Options

Ayr Secret Sauce, $245
29.5″ Short Inseam, 31.5″ Regular Inseam, 11″ Rise, 20″ Leg Opening

Hint of Blu Happy Shaggy High Waist Raw Hem Wide Leg Jeans, $69
32″ inseam, 10 1/4″ front rise, 23″ leg opening

Cropped Flare Jeans

The cropped flare has been a favorite jean style for so many of my clients this fall/winter. They have the hourglass effect of a flare jean with the ease and fun of a cropped jean. Again, you’ll usually want your booties to have a higher shaft to cover your ankles and tuck underneath the flare of the jeans. If you want to wear your loafers or sneakers without your ankles being cold this winter, consider a fun sock.

Veronica Beard Carson Raw Hem High Waist Ankle Flare Jeans, $298
28″ inseam, 19.5″ leg opening, 11.5″ front rise

Other Jean Options

Pistola Lennon High Waist Ankle Bootcut Jeans, $158
27″ inseam; 17 leg opening; 11″ front rise

Paige Claudine High Waist Frayed Hem Flare Jeans, $229
28″ inseam, 17″ leg opening, 12″ front rise

Full-Length Flare or Bootcut Jeans

Flare jeans can be hard to pair with completely flat shoes (although I think the new pair from Ayr shows a great length for flats. Notice they don’t have a “break,” with fabric gathering on the top of the foot, and the back is about 2″ off the floor). A “flat” with a 1″ block heel is a great way to achieve the look of height underneath a flare. I also love the classic look of Converse with flares, even better if they have a slight platform. “Big” sneakers are a great solution to the height issue if you don’t wear heels. A lug-soled boot also works. If you don’t mind a boot with a bit of a heel, your legs will look 6 feet long in a pair of longer length jeans and a heeled boot.

Frame Le High Waist Flare Jeans, $238
34.5″ Inseam, 10.5″ Rise, 22″ Leg Opening 

Other Jean Options

NYDJ Blake Slim Flared Jeans, $99
33″ Inseam (or 30″ Petite Inseam), 10.75″ Rise, 18.5″ Leg Opening

Spanx Pintuck Flare Jeans, $178
30″ Petite Inseam, 32″ Regular Inseam, 35″ Tall Inseam

Wow!!! Thank you, Kyle! That was an incredibly thorough blog that I’m sure our readers will appreciate. And come back to for advice again and again. Please let us know what you think, as well as your favorite new, non-skinny denim style, in the comments below. -Lani

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