how to wear jeans over 50

A Fashion Guide: How to Wear Jeans Over 50

Please note that this post may contain affiliate links and any sales made through such links will reward us a small commission – at no extra cost for you.

Let’s talk denim! Regardless of body type, age, or personal style, jeans beat out all of the latest trends when it comes to truly ruling the fashion game. While there are some denim “rules” that we might all agree on (picking high-rise styles over low-rise jeans, taking our body shape into account, steering away from too-tight jeans), there are still a lot of options and nuances when it comes to denim pants. Whether you are after the most flattering jeans, an overall sleeker look, or different styles you haven’t tried before, there are plenty of places to start from. Let’s be honest – finding a good pair of jeans might be difficult, but it is definitely rewarding! 

With the help of our seasoned style advisor, I’m here to show you different outfits, styles, and tips for creating the perfect looks with this true fashion staple. 

over 50 style advisor

With the insight and opinion of Dr. Wood sprinkled throughout this piece, let’s get right into it! 

1. 90s jeans + cotton silk sweater + loafer + bag

how to wear jeans over 50

jeans | sweater | shoes | bag

A neutral look doesn’t have to be limited to just beiges, ivories, browns, and blacks. Featured in my spring capsule wardrobe for the upcoming warmer months, this baby blue color is a great option for those wanting to incorporate some color while still going for neutral outfits. 

When asked about her favorite way to style jeans, Dr. Wood gave us a few of her go-to options, including sweaters, cardigans, and sporty vests. In keeping with her taste, this blue cotton silk sweater is the perfect transitional piece to complete this look – especially for those who live somewhere where the temperatures take a little longer to rise! 

On the bottom, these 90s straight jeans support and lift with their vintage fit, making you look and feel great as you stroll out the door.

For shoes and a bag, these brown accessories go beautifully with the existing color of the look, enhancing and elevating the ensemble while still staying within the neutral palette. 

2. sweater + tee + crop jeans + leather belt + sandals

how to wear jeans over 50

sweater | tee | jeans | belt | sandal 

Blue is definitely the color most of us think about when the topic is jeans, but exploring other colors for this iconic style can be a great way to incorporate more of it into your wardrobe. 

This flattering white jean makes it possible to create looks like monochromatic outfits without giving up your beloved denim, keeping the fit and the structured look of this beloved staple. For this particular outfit, I’ve created a simple ensemble that is versatile for a number of different occasion within your week – and beyond! 

It can be tricky to style looks for different seasons, but Dr. Wood knows just what to do with jeans when the weather starts to turn sunnier: “I’d probably switch over to cropped jeans and wear them with cute sandals.”

Start with this pair of jeans that feature a mid-rise and a cropped length. Their crisp white color keeps your look fresh for the sunny days ahead, and premium fabric ensures zero see-through. 

On top, start off with this basic white tee for a simple, foolproof base. Layer this open bomber sweater over your t-shirt for chillier moments of the day, adding some warmth to both your look and your color palette. 

Bring it all together by matching them to the buttons on the jacket. In keeping with Dr. Wood’s suggestion, a black belt and a black pair of classic sandals are the ideal final touches to this look. 

3. turtleneck + toothpick jean + blazer + mule + top handle bag

turtleneck | jeans | blazer | shoes | bag

Skinny jeans have been around for decades, and still are many people’s favorites when it comes to integrating this style into everyday looks. 

This particular type of jeans might have its critics, but has stuck around for long enough to win the hearts of many! “I still love skinny and feel that they’re the most flattering. Boot cut jeans are cool though and serve a real purpose when wearing boots,” says Dr. Wood. 

If you also love your pair of skinny jeans, this look is ideal for when you want to look confident and put-together both in professional and personal occasions – there’s no need to go after new trends you don’t really see yourself in! 

Start with these super high rise toothpick jeans. Designed to offer support and elongate your figure as a whole, these pants will bring out your confidence with a flattering fit. For your top, this wool-blend turtleneck continues to elongate your silhouette and contribute an elevated, chic feel. 

Layer a classic black blazer on top, helping to tie both of your base pieces together and bringing some balance to the body-hugging fit of the jeans. For accessories, these heeled mules keep the look professional while still adding some style flair. A mini top handle bag is the ideal accessory when transitioning this look for the nighttime. 

4. cashmere top + straight jeans + suede mules + saddle bag

top | jeans | mules | bag

Jeans are the right style choice for a great spring day, making you look polished and fresh without requiring a ton of effort. 

For this casual elegant outfit, the jeans of choice and high-rise cheeky straight jeans from Gap.

When asked to talk to us about her favorite pair of jeans, Dr. Wood didn’t hesitate: “The Gap, but only because they fit me best. They’re very traditional.” If a traditional pair of jeans is what you’re after, you know where to shop! 

Dress up your flattering pair of high-rise straight-leg jeans with a delicate and refined cashmere top that features padded shoulders and a mock neck. Though subtle, these design details bring sophistication to this otherwise casual look. 

For accessories, a smaller bag is great for carrying on your shoulder and keeping your essentials safe. Match the tone of the bag with this suede mule that will keep your feet comfortable as you stroll through town. 

5. high-rise jeans + button-up shirt + sunglasses + leather loafers + shoulder bag

jeans | shirt | sunglasses | shoes | bag

This almost French-inspired look truly embodies some of what we love most about elevated casual wear. Though simple on their own, these staple pieces come together to form an effortless ensemble that is perfect for a lot of different occasions throughout your week!

Begin with these high-rise 90s jeans, featuring a straight fit and a gorgeous blue wash. On top, this oversized button-up shirt balances out the casual feel of the jeans with something a little more elevated, while still keeping things laidback. 

Here’s where styling magic comes in! Just a few small tweaks in how you wear a particular item of clothing can drastically affect the final outfit. Tucking your shirt in, wearing it slightly open at the top, or rolling up your sleeves are all things you can try until you land on your ideal final look. 

Here, the accessories make this outfit. These polarized sunglasses keep your eyes comfortable while adding undeniable chic flair to your look, while this quilted leather shoulder bag contributes some classic edge as well. For shoes, lug sole loafers bring some current (but still traditional!) style into the mix. All black, these pieces tie together seamlessly, balancing the outfit and finalizing it beautifully. 

6. kick out jean + rib t-shirt + belt + shoulder bag + platform mule + chain necklace 

jeans | shirt | belt | bag | shoes | necklace 

If you are lucky enough to be dressing for warmer temperatures, few things are better than having a truly great and simple go-to denim look. While jeans are great to dress up, they are also ideal options for any day of the week, getting you quickly pulled together to check some items off of your to-do list. 

It is important to note, however, that a basic outfit doesn’t have to be boring! Picking high quality pieces and accessories can totally change the feel of something as simple as a t-shirt and jeans. 

Kick off this look with these full-length jeans that flare out at the bottom. Mid-rise, these pants are also made from premium material that offers great support, keeping you comfortable in more than one way. 

Pair your blue jeans with this simple black t-shirt for a sleek and flattering foundation. Accessorize with a skinny black leather belt and a large leather shoulder bag that keeps you organized and prepared.

For shoes, these platform mules welcome sunnier days while keeping this look grounded. For a final delicate touch that complements the gold hardware on the belt, this gold chain is a good choice. 

7. baby boot jean + funnel neck top + leather loafer + necklace + hoop earrings

jeans | top | shoes | necklace | earrings

We certainly love our traditional blue jeans, but black denim gives us the option of easily bringing sophistication to a comfortable look that is quickly pulled together. 

These mid-rise jeans fit snuggly through the thighs and hip, and feature a discreet slight flare at the bottom. Not only does this style make for a flattering fit, but it also looks great with slightly larger, more structured shoes. 

A standard black loafer keeps this look understated and casual while also lending it an air of elegance. On top, this black turtleneck continues to steer this look in the right direction with its chic silhouette.

For accessories, small silver hoop earrings and a silver necklace bring some texture to the final look, adding a feminine touch. 

8. boot cut jean + wool-cotton sweater + ankle boot + faux leather bag

jeans | sweater | shoes | bag

Remember Dr. Wood’s brief mention of boot-cut jeans? Well, I couldn’t agree more! When it comes to wearing boots and jeans, this style serves a real purpose when it comes to both functionality and aesthetics. 

These blue boot-cut jeans are inspired by the late 1970s, blending traditional and modern designs to create the perfect pair of jeans. Made from organically grown cotton, these pants feature a high-rise fit that makes for flattering results. 

On top, this simple wool-cotton sweater keeps things casual while also elevating the look with its quality material, perfect fit, and gorgeous neutral shade. 

Accentuate the brown tone of the top by bringing in some brown accessories. For shoes, these square-toe boots make great use of the boot-cut structure of the jeans, while a brown shoulder bag brings the pieces together simply. 

9. oversized button-up + crop jean + sneaker + shoulder tote + drop earrings 

shirt | jeans | sneakers | tote | earrings

When asked about a favorite shoe style to wear with jeans, Dr. Wood didn’t hesitate, saying “I know you’re supposed to wear at least a small heel, but I would say sneakers and boots because they’re more comfortable.” 

For a piece as popular and sought-after as jeans, shoe options shouldn’t be limited to aesthetics, but should instead take all important factors into consideration! Heels can be great for certain occasions, but sneakers and boots absolutely belong with denim – and this look is here to prove it! There’s no need to sacrifice on either the style or the comfort front to make an outfit work. 

These kick out crop jeans are a great length to rock when the weather begins to warm up, and also go perfectly with a larger shoe as they avoid awkward bunching up in unwanted places. If you fall under the category of petite women, cropped jeans are also a great choice for you! 

On top, this striped button-up shirt brings in some understated color and pattern to this fresh look, without dressing it up too much. An elevated tote adds interest by contributing to the neutral color palette but continues to keep the feel casual with its large size and looser structure. 

For shoes, these white sneakers blend chic and laid-back for a perfect combination. Add in a pair of gold drop earrings to bring together all of the gold touches of the look! 

10. pintuck denim trouser + peplum top + knee-high boots + hoop earrings + ring

jeans | top | shoes | earrings | ring 

For something of a more elevated outfit, this look takes the cake. Composed of just a few intentional pieces, this ensemble takes advantage of small but intentional design choices that give the garments personality and charm. 

Starting off at the bottom, these black pin-tuck denim trousers work to elongate your figure with their design details and silhouette. 

On top, this ponte peplum top lends a modern touch to the look with its twist detail in front, while still keeping this look sophisticated and sleek.  

The jeans’ below-the-ankle length and wide-leg fit make this design perfect for these classic knee-high boots, while dainty silver accessories are the closing accents of the look. 

11. boot cut jean + sweater blazer + tee + ballet flat + tote + stud earrings

jeans | blazer | tee | shoes | bag | earrings

We love monochrome looks, neutral outfits, and black accents – so why not bring it all together in this final outfit? 

A relaxed fit bootcut jean gets us started on this look. Featuring a straight fit before it flares, these gorgeous nude jeans bring depth to the look without distracting from the other pieces, still maintaining the classic structured denim look we all love. For those who are looking for a softer color that’s not white denim, this shade is a great option. 

A white tee shirt keeps things simple on top. Layer this sweater blazer on top, adding even more subtle structure to this ensemble for a sophisticated end result. 

In order to tie the rest of the pieces in with the jacket, make sure to intentionally add some more gold accents throughout the look! For this look, go with a large black leather tote with some gold hardware, as well as some gorgeous curved studs. 

For shoes, these ballet flats are the way to go, finishing this look off in true classic fashion. 

The Hunt for the Perfect Pair of Jeans

It’s not hard to see how denim has become a staple for all kinds of people, independent of their individual taste: from boyfriend jeans and mom jeans to new trendy styles and classic designs, there are very few jeans you’ll be hard-pressed to find.

While having all of these options at our fingertips is fun, it can also make the process of finding and styling the right jeans a lot more stressful than it needs to be. That’s where this post is here to help!

So, have you found your new favorite jeans yet? I hope so, but if not, no need to worry! There are hundreds more where these came from, all you have to do is be persistent and know what you want. If you are still on the hunt for the ideal pair of jeans, here’s a quick check-list to help you continue your search: 

The Fit:

  • Prioritize the right fit: one that flatters your body shape and feels comfortable. Experiment with different cuts like straight, skinny, wide-leg pants, or bootcut jeans to find what suits you best. 

Waistband Comfort:

  • Pick a waistband that sits comfortably on your hips or waist without digging in. A well-fitted waist ensures both comfort and style! The type of denim used to make jeans also has a great impact on how much support and comfort it provides. 

Inseam Length:

  • Consider the inseam length. Whether you prefer ankle-length, regular, or long lengths, make sure the length complements your height and desired look. Size charts are always available online! 
  • It’s also important to be aware of your proportions when shopping for jeans, rather than only focusing on your height. Having either short legs or a short torso, for example, can really change the way your jeans fit. 

Quality Construction:

  • Examine the stitching and overall construction. High-quality jeans with reinforced seams are more likely to withstand regular wear and washing.

Wash and Color:

  • Decide on the wash and color that suits your style. A darker wash is often considered more appropriate for formal occasions, while distressed jeans or faded styles add a casual touch.

Brand Reputation – Invest in Quality

  • Consider reputable brands known for quality denim styles. While exploring new brands is fun, established names often have a track record of producing reliable and stylish jeans. When asked how women over 50 look best in jeans, Dr. Wood says it best: “In general, I think if they splurge on a good pair, that fit well, they’ll look good. And I would say no sequins or other fru-frus.” Keep it simple and high-quality! Looking for vetted brands to get shopping? Wood recommends Gap, Talbots, Mother, and J.Crew. (And one of my favorites is Madewell!)

Now that you’ve got the perfect pair of jeans and you know how to wear jeans over 50, it’s time to ensure you have the rest of your investment-worthy pieces for your wardrobe: 6 Investment Pieces To Have by the Time You Turn 50


Founder and editor of My Chic Obsession, Carolyn is your trusted fashion maven. Carolyn's drive to help others achieve a classic and timeless wardrobe fuels her posts, making a go-to resource for style seekers worldwide. Beyond the wardrobe, she resides in the heartland of the Midwest, dreaming up new ideas and raising her two lively boys - her biggest fashion critics.