How to Style Jeans and Heels: The Ultimate Style Combo for Effortlessly Chic Women

How to Style Jeans and Heels

If you’ve been an email subscriber or following the blog for a while, you know that I LOVE jeans! I wear jeans pretty much every day and I’ll try any style or trend that’s out there. They’re comfortable, easy to style, and can be dressed up or down. Plus, they just really work for my more casual lifestyle. You’ve probably also noticed that I love wearing heels too… I’m 5’4”, which technically means I’m petite. As a petite woman, I’m all about adding height where I can get it and making my legs look longer.

Together, an outfit with jeans and heels can instantly make me look and feel chic, modern, and sophisticated. I love the way the casual vibe of denim and the dressy feel of heels can give you the perfect elevated look. Since there are so many different styles of jeans and heels, it can be a little confusing. But I promise, it’s much easier than you think! The plethora of styles actually creates an endless list of outfit combinations to choose from. Below, I’m sharing 7 tips to help you style your jeans with heels AND 7 jeans and heels outfits to try…

If heels aren’t your thing, that’s fine! We shared 15+ comfortable FLAT shoes in this post.

Choose The Right Jeans

My first tip is to choose the right jeans…for you! Whether you’re a trend follower or not, picking a pair of jeans that fits and flatters your body is most important. For me, I love to wear high-rise (10+ inches) jeans with no more than a 32” inseam. The inseam length is important to note. Depending on your height and the heel height, different inseams may work better for you and your heels.

Because I do love trends, I prefer to wear baggy jeans, wide-leg jeans, flared jeans, or bootcut jeans. We’ll have a post all about this season’s most popular jeans trends coming next week so be on the lookout for that. While I love baggier denim styles, that doesn’t mean you have to wear them. If you still love your skinny jeans, wear them. If you love your skinny jeans but want to try a jean silhouette that’s a little more modern and will go with most heels, consider a pair of straight-leg jeans or even boyfriend jeans. There are so many options out there that it can feel overwhelming. But knowing what you look and feel good in is most important!

If you’re interested, I share more about baggy jeans for women, some great brands, and more in this post.

 

Choose The Right Heels

Next, is to choose the right heels. The best thing you can do is to make sure you have your basics. If you don’t know what wardrobe basics you need, we give out two FREE checklists (one for spring/summer and one for fall/winter) that have a complete list of what you need in your closet…including shoes, accessories, tops, bottoms, and more. Sign up for the newsletter here to get your free checklists. For the sake of wearing jeans and heels, I recommend a pair of classic pumps and heeled boots or booties. Some other options if you already have those basics might be wedges, block heel sandals, strappy sandals, embellished heels, etc.

Know What Works

Knowing what works and the perfect combination is where it can get a little tricky if you’re new to wearing jeans and heels. But…if you have your go-to jeans and your basic heels, it will be a lot easier! Because there are so many denim and heel styles, here are a few fool-proof tips to help you know which jeans work with which heels..

• Skinny Jeans – You can wear any style of heels. Depending on the shoes and the length of your jeans, you can tuck the jeans into the shoes, do nothing, do a small cuff, do a large cuff, or double cuff your jeans.
• Straight-Leg, Boyfriend, or Tapered Jeans – You can wear any style of heels. Depending on the shoes and length of your jeans, you can do nothing, do a small cuff, a large cuff, a double cuff, or a tapered cuff.
• Wide-Leg, Flared, or Bootcut Jeans – You can wear any style of heels with the exception of knee-high-heeled boots because they will show underneath the jeans. You don’t have to worry about cuffing or doing anything special because your heels will most likely be covered by our jeans.
• Cropped or Ankle Jeans – You can wear any style of heels and since your jeans are cropped, they’ll beautifully show off your shoes…No need to worry about cuffing or tucking!

If you want more detailed tips on how to wear boots and jeans, cuffing your jeans with booties, and more make sure you check out this post next.

 

Create Contrast

This is really a personal preference but creating contrast between styles can look really stylish when you wear heels with jeans. For example, wearing a pair of ripped jeans with pumps or sleek slingbacks can really elevate the look of ripped jeans and add some cool contrast. Similarly, wearing cropped wide-leg jeans with some strappy heels can elevate the more casual feel of wide-leg jeans. If this feels like too much, just stick to styling all of your jeans with classic pairs of heels to make it simpler.

Elongate Your Legs

This one is especially important if you’re petite but works for everyone because really, who doesn’t want to look of longer, leaner legs, right?! There are a few main things to consider and do when you want to elongate your legs while wearing jeans and heels…

• Match your shoes to your jeans OR skin tone – If you’re wearing dark-wash jeans, go for darker heels like black, brown, navy, etc. heels. Black jeans? Wear black heels, booties, etc. If you’re wearing light-wash jeans, try to match your heels to your skin tone or even clear sandals so your legs aren’t chopped up.
• Wear pointed-toe shoes – Wearing pointed-toe, closed­-toe shoes will easily make your legs looks 2” longer.
• Be aware of leg silhouettes – While you can still wear your skinny jeans, wide-leg jeans will make your legs look longer!

I shared 15 petite styling tips to help you look taller in this post that’s a must-read!

 

Wildcard: Tuck It In

This is a bit of a wildcard but it’s very on-trend so I wanted to share it in case any of you fashionistas want to give it a try! On the runways and in street style, we’re seeing more women tucking their baggy jeans into their boots or booties…yes, even knee-high boots. I tried it out in the photo above and I really love the fashion-forward look but I know it’s not for everyone!

14 Jeans And Heels Outfit Ideas

Below, I’m sharing 14 outfit ideas with different leg silhouettes, different types of heels, and different occasions. You’re sure to find an outfit idea you want to recreate!

Wide-Leg Jeans & Platform Booties

First up, I’m sharing 3 options for wearing those on-trend wide-leg jeans. In this outfit, I’m wearing a pair of Mother jeans that have a dramatic flared leg and flattering high waist. I styled them with a gorgeous white blouse by L’Agence that has pretty lace details at the cuffs, covered buttons, and a flattering v-neckline. On my feet, I’m wearing a pair of platform booties by Veronica Beard. I could really wear any sort of heels I want with these jeans since they would be covered up. But since these jeans have a 32” inseam, I knew I’d have to wear higher heels…which is all part of knowing your body and what works for you!

Cropped Wide Leg Jeans & Brown Boots

I also wanted to share a cropped pair of wide-leg jeans in case that’s what you have in your closet. But don’t worry, I’m sharing more about what heels to wear with cropped jeans below. These are from Sezane and are such a nice fit. You could wear these jeans with pretty much any heels but I styled them with a pair of brown suede booties for fall. If you’re going to wear booties with your cropped jeans, just make sure that you can’t see any skin between the bottom of your jeans and the top of your booties. I completed the look with a chic striped sweater, a brown belt, and a classic navy blazer.

I shared even more about these jeans and everything else I’m wearing in this post with even more French-inspired wardrobe basics.

White Wide-Leg Jeans & Wedges

The two previous outfit ideas for wide-leg jeans were more fall-ready. But if you’re not quite ready for fall yet, this is a great spring/summer look. This is something I’d wear on date night or out to dinner. I’m wearing a pair of white wide-leg jeans by DL1961 that are super comfortable, flattering, and not see-through at all. They have a 31” inseam so with a 4.5” heel, they are completely off the ground…which I prefer for white jeans so they don’t get too dirty! I wore these Stuart Weitzman wedges on repeat this summer and know they’ll be heavy hitters year after year. I completed the look with a chic black one-shoulder top but you could wear any black top you have in your closet that’s more body-skimming. When you wear wide-leg jeans, avoid tops that are too billowy to balance out proportions.

If wedges aren’t your style, consider a pair of block heel sandals instead. I love these Valentino shoes that look good with every denim style. I did a full review of them here.

Straight-Leg Jeans & Mules

If wide-leg jeans are a little outside of your comfort zone, don’t worry. The next three outfits are featuring one of the most classic jean silhouettes…straight-leg jeans! In this look, I’m wearing a pair of straight-leg jeans by Frank & Eileen that are such a good basic to have in your closet. These have a 27” inseam which may be too cropped for some of you taller women, but they’re perfect on me. I paired them with some Vince mules in a beautiful neutral beige tone that kind of blends in with my skin. I kept the rest of the look simple by throwing on a white button-down shirt for a chic but simple jeans and heels outfit!

Straight Leg Jeans with Sock Booties

Next is a pair of straight-leg jeans that aren’t cropped. This pair of Mother jeans have a high-rise (of course!), a 31” inseam, and a nice fit. They do run a little small so I recommend sizing up one size in these. I paired them with some Stuart Weitzman sock booties I’ve owned for years and wear all. the. time. during fall/winter. Sock booties are a great piece to have in your closet. You can wear them with EVERY jean silhouette, dresses, skirts, and pants. They’re a really versatile piece and they take the guesswork out of what shoes to wear. I completed the look with a fun pop of color. This pink lace L’Agence blouse is no longer available but I linked a similar option below.

Straight-Leg Jeans & Block Heel Ankle Boots

Because I’m petite, I tend to gravitate toward cropped jeans if they’re straight-leg, skinny, or tapered because it just makes it easier to wear them for me. So…here’s another pair of cropped straight-leg jeans by Agolde that are a wonderful basic to have in your closet. I styled them with a pair of black Jenni Kayne booties that have a very small heel on them. But I still wanted to show you how easy it is to style your jeans with ankle booties! These exact booties are sold out but I linked a similar pair below. On my top half, I’m wearing a classic Jenni Kayne sweater but you can wear any sweater you have in your closet to recreate this look…it’s such a great, classic fall look!

Bootcut Jeans & Pumps

Next up…bootcut jeans! Technically these L’Agence jeans are called straight-leg jeans but they fit me more like bootcut jeans. I wear these jeans all the time and can style pretty much any type of shoe with them. But in this look, I’m wearing pair of heels. I styled this outfit for the holidays last year and went with pair of pumps that have a fun metallic color but if you wanted a more classic look you could go with black or nude pumps. Or spice it up with a pop of color! For the holidays I wore a cute sequined cami but you could make this more fall-ready by wearing a classic black cami and a chic blazer.

Bootcut Jeans & Heeled Sandals

In this look, I’m wearing a pair of Mother Hustler cropped bootcut jeans. I love these jeans so much that I’ve bought them in multiple washes! The length and fit are so perfect on me and many Team Busbee members have said the same thing after trying these on. Another wonderful thing about these jeans is that they go with SO many different shoes. In this look, I’m wearing them with a pair of pretty white heeled sandals but you could wear these with heeled ankle booties, mules, wedges, etc….the possibilities are endless! I’m wearing a white blouse and white handbag but to make this more fall-ready, swap the heels for some black booties, the white bag for a black bag, and throw on a black blazer.

Ankle Jeans & Slingbacks

These are another pair of Mother Hustler jeans in a different color. I love these because they’re such a dark, deep blue that they look black. They are a cropped flare jean but similar to the last pair, they can be worn with any kind of shoe. In this look, I’m wearing them with some chic black slingbacks by Reiss. On my top half, I’m wearing a classic white cami and a black cardigan (that doubles as a dress). I could wear this look with sneakers or loafers for a more casual vibe but I love the way the slingbacks really elevate this outfit!

For more ways to style this black cardigan dress, make sure you check out this post next.

Ankle Jeans & Statement Heels

Did I mention I own these jeans in multiple washes?? Yes, these are the Mother Hustler jeans again but this time in white! Can you see how versatile they are yet? No matter what wash you buy these jeans in, you’ll be able to wear them with almost every pair of shoes you have in your closet! In this look, I’m wearing the jeans with statement heels by Cult Gaia. I love that with cropped or ankle length jeans you can really show off a cool pair of gold heels like these!

Cropped Black Jeans & Black Booties

In this look, I’m wearing a pair of black Rag & Bone jeans that are such a good pair of basic black jeans. They are cropped but you can pull off this same look with any style of black jeans. I’m wearing them with a pair of black western-inspired booties with a cool cone-heel shape and silver accents. If the Western look isn’t your style, opt for a pair of classic black pointed-toe boots instead to achieve the same look. On my top half, I’m wearing a pretty printed blouse by ba&sh that’s no longer available, but I’ll link a similar option below.

Tapered Jeans & Wedges

The final three looks all include tapered jeans. I chose not to include skinny jeans in this roundup because tapered jeans are very similar and you can wear all of the same shoes with them. In this look, I’m wearing a pair of tapered Moussy Vintage jeans. Moussy Vintage is one of my go-to denim brands because the washes are really cool, the fit is amazing, and the length is always perfect for me. I styled the jeans with a pair of metallic espadrille wedges and love the way the shorter, tapered leg silhouette shows off the show. These wedges became a heavy-hitter for me this summer but I also love my See by Chloe wedges I’ve had for years. I linked them and an affordable option below. Keep the rest of your look simple by adding a classic button-down shirt and you’re ready to go!

Tapered Jeans & Knee-High Boots

Another simple way to wear your tapered or skinny jeans is to wear them tucked into knee-high boots. You can also try this with baggy jeans as I mentioned earlier in the tips, but this is a really classic option that looks chic, sophisticated, and streamlined. In this look, I’m wearing another pair of Moussy jeans with my favorite knee-high boots by Schutz. Schutz makes beautiful shoes at accessible price points that are a great mix of classic and trendy. To keep the look streamlined, I’m wearing a black cami and a double-breasted blazer, but you can make this more casual with a simple sweater on its own too.

Tapered Jeans & Block Heel Booties

Chunky block heel booties and lug soles have been “in” for a while now and it’s safe to say that these were my most worn boots of 2021 and 2022. AND…they continue to be a best-seller each month this year. I’m wearing a pair of chunky lug-sole booties by Steve Madden. They come out with a new, updated version each year but they’re essentially the same…super comfortable, super lightweight, and super versatile! I love the way these boots look styled with tapered jeans. But I’ve also worn them with flared jeans, wide-leg jeans, bootcut jeans, and even dresses and skirts!

What is your favorite way to style jeans and heels? Let us know in the comments below!

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