12 Ways to Wear Skinny Jeans Without Looking Dated

If your head is spinning about whether skinny jeans are in or out, I don’t blame you. The answer is complicated. Gen Z declared them out on TikTok in February 2021. Along with that, emerging from the pandemic, skinny jeans felt too constricting after living in sweatpants, and for the first time in some time, straight-leg jeans had a surge in popularity over skinny jeans. 

At the time, folks who know fashion and jeans, including the CEO of Levi Strauss and Stacy London from What Not to Wear, said that even as fashion trends shift, there would always be a version of skinny jeans in the stores. They’re not going anywhere, they said. Sure enough, in the January and February fashion weeks, they were back on the runways. 

Meanwhile, there was an explosion of other jean styles in the stores, from kick-fit jeans to straight leg jeans, wide leg jeans, flare jeans, mom jeans, and bootcut jeans. The options are endless. 

But what if you love skinny jeans, and they’re a part of your personal style now? How do you keep wearing them without looking dated?

The answer is to wear them with current and classic shoes and tops.

In this post, I have 12 skinny jeans outfits to show you how to style them today. But first, let’s talk a bit about how we’ve styled skinny jeans in the past. 

How we’ve changed the way we wear skinny jeans in 10 years

How we wear skinny jeans has evolved from 10 years ago. 

Skinny jeans were huge back in 2012. You may recall wearing blue or colored skinny jeans with longer tunic tops. Partially, we did that because skinny jeans fit snugly. Loose-fitting tops create a balanced silhouette. Also, low-rise skinny jeans were everywhere. And with a larger rear, if I bent at the knees, my pants pulled down. We paired them with long shirts to make sure we didn’t flash people when we bent over. We even wore long shirts front tucked into low-rise skinny jeans. How did we even lift our arms overhead? I’m not sure how we did it without showing our stomachs. 

When it was chilly, we layered long cardigans over the top, with scarves wrapped around the neck, which I wore a ton. 

For shoes, we wore colorful ballet flats, platform and wedge sandals, and round-toe heels. And classic equestrian style knee-high boots with skinny jeans tucked into them. Also, wedge booties, lace-up booties, and booties with skinny jeans rolled up. Hunter boots were huge back then.

Fast forward to 2018. We wore stretchy skinny jeans and jeggings and started to see raw-hem jeans in the stores. We wore them with graphic tees, tunic sweaters, long turtleneck sweaters, plaid button-down shirts, hoodies, and sweatshirts. Oversized cardigans, duster and draped cardigans, puffer vests, teddy bear vests, blazers, and blanket scarves were popular. Mules, white sneakers, kitten heels, block-heel ankle boots, sock boots, and cut-out d’Orsay booties were favorites. 

Now, let’s talk about how to wear skinny jeans today to look current.

How to wear skinny jeans and look current

The proportions of today lean towards creating a short-waisted look with higher-rise jeans, if you can wear that with your body type. Generally speaking, high-waisted jeans with over an 11 or 12-inch rise are in the stores. Luckily, my current skinny jeans have a high rise, so my size 12 rear isn’t exposed anymore when I bend over. 

What tops do you wear with skinny jeans?

Today, longer tops still work proportionally with skinny jeans. Instead of longer tunic tops, you can update your look by choosing an oversized shirt like a button-down, cardigan, blazer, or sweatshirt. Since the skinny jeans of today are higher-waisted, hip-length tops and sweaters also work. And that’s one of the ways they were seen on the runway. 

What shoes do you wear with skinny jeans? 

For shoes, wear white sneakers or Adidas, loafers, classic neutral ballet flats, classic knee-high boots, pointed-toe or almond-toe ankle boots, and Chelsea boots. Western boots, combat boots, and over-the-knee boots are other options if they feel like you.  

Ready to take a look at skinny jeans outfits? Let’s dive in and look at some cute outfits!

12 skinny jean outfits

1. With a fair isle sweater and knee-high boots

There’s a good reason for wearing an oversized top with skinny jeans. An oversized sweater balances out the slimness of the jeans. For reference, I am a size 12 on the bottom, and my body shape is smaller up top. It makes your bottom half look smaller by comparison. Notice how this sweater ends above the widest part of my hips for a slimming effect. The fair isle detail around the neck of the sweater also draws the eye across, widening my smaller upper body, so my upper body and lower body look more proportional.

Sweater  | Jeans | Similar Boots

The best way to wear knee-high boots over jeans is with skinny jeans. Skinny jeans are some of the easiest to tuck in, and that’s reason enough to always have a pair in your closet. These knee-high boots with lug soles are my favorites and will always be in my closet. They’re the boots you want when you’re walking outside on a cold day.

2. With a hip-length cardigan and loafers

This cable knit hip-length cardigan is a bit chunky, so even though it has a slim fit, it still creates a fairly proportionate look with the slim-fitting jeans. These patent leather loafers create a fresh and on-trend casual look. My skinny jeans come down below my ankle, making my legs look nice and long.

Cardigan | Jeans | Loafers | Bag

In this picture, you can see how these tight-fitting jeans highlight my curves. It’s particularly noticeable on my straight leg. When I want to downplay my curves, I opt for straight-leg or kick-crop jeans. Both are stretchy and have a slim fit in the hips and thighs, but they’re a bit wider from the knee down, balancing out my hips.

Low-profile shoes that expose the top of the foot are the perfect combination with skinny jeans and are often easier to style than ankle boots. 

3. With an oversized sweater and chunky lug sole loafers

This oversized, slouchy sweater is quite long and cuts me across the widest part of my hips, drawing the eye to the thickest part where the hem falls. Instead of leaving it long and out, I prefer to side-tuck it to create a higher waistline. A front tuck would also work here. With a long sweater that you partially tuck in, the fold of fabric across the belly helps to hide a tummy.

Sweater | Jeans | Loafers | Bag

For shoes, I’m wearing chunky sole loafers to balance out the chunkiness of the sweater.

4. With a trench coat, striped button-down shirt, and loafers

The combination of a trench coat and button-down shirt creates a classic look when paired with these skinny jeans. Of all the jean styles, when wearing a longer coat with lots of volume, it’s the perfect time to embrace the fitted silhouette of skinny jeans, creating a streamlined and visually appealing balance. In contrast, wearing wide-leg jeans with a long coat can overwhelm the body. 

Shirt | Similar Trench Coat | Jeans | Loafers | Bag

These patent leather loafers are classic yet trendy.

5. With a ruffle neck turtleneck, black double-breasted blazer, and ankle wrap pumps

Here’s another classic look. I’m wearing a ruffle neck turtleneck, a black double-breasted blazer, and ankle wrap pumps for a chic outfit. The black blazer hits right below the thickest part of my hips. Whenever you pair a black blazer with a white or cream top, your eye is drawn to the vertical column of white between the lapels. Anytime the eye is drawn up and down, it creates a slimming effect. Pointy-toe heels lengthen the look of the legs. You could also wear an oversized blazer for a trendier look. 

Necklace | Turtleneck | Blazer  | Jeans | Heels | Bag 

It’s such a great look for dinner dates.

6. With a black cardigan sweater and cap-toe ballet flats

These days, you’ll see cardigan V-neck sweaters worn buttoned up like a shirt. I’m pairing one with my Chanel-inspired, classic tan and black cap-toe ballet flats. With skinny denim jeans, wear slim shoes with slim-fitting tops so your feet don’t look like concrete blocks in comparison. 

Necklace | Cardigan | Jeans | Flats | Bag 

7. With a striped ruffle neck blouse, black sweater vest, and black pointy-toe flats

This striped ruffle neck blouse is a little bit elegant yet preppy. Wear it under an oversized sweater vest for a fresh look with skinny jeans. Black pointy-toed flats are a great way to elongate the leg line.

Shirt | Vest | Jeans | Flats | Bag 

8. Black and white striped lady sweater and cap-toe flats

Breton stripe Chanel-inspired lady sweaters are super on-trend. Because of the short length of the sweater, they are perfect with wide-leg denim with a high waist. But you can also pair them with your favorite skinny jeans to modernize them. The stripes draw the eye across, visually widening the upper body to create a more proportionate upper and lower half. Since I’m smaller up top than on the bottom, that’s a good thing.

Sweater | Necklace | Jeans | Flats | Bag 

You could wear this sweater with black skinny jeans or white skinny jeans.

9. With a Houndstooth blazer, navy sweater, and Chelsea boots

When trying on ankle boots with skinny jeans, try unexpected combinations. When I wear my taupe block heel ankle boots with skinny jeans, I feel like the combination has been done repeatedly, and it feels stale and a little boring to me. The same thing happens when I pair low-shaft flat or block-heeled ankle booties with skinny jeans. Chelsea boots are a classic yet trendy option that creates a fresh look with skinny jeans. Ideally, when wearing ankle boots, your skinny jeans hit above the ankle, so the hem hits within an inch or two of the top of the boots. My jeans are longer, so I tucked them under to shorten the length. My kick-crop jeans or straight jeans are the perfect lengths for ankle boots, and the width at the hem means the ankle boots easily fit right under the hem of the jeans. These days, I tend to reach for them instead of skinny jeans.

Similar Navy Top | Blazer | Jeans | Boots | Bag | Necklace

Wearing Chelsea boots with this classic Houndstooth blazer and navy top creates a classic look.

10. With an oversized black and white striped sweater and black platform Chelsea boots

This is another oversized long sweater that I’ve deliberately side-tucked rather than leaving long and hanging out. It’s long enough that even when it’s side tucked, there’s fabric coming down that helps to conceal a bit of a tummy. These chunky platform Chelsea boots with a bit of a heel balance out the oversized sweater and are a little edgy.

Sweater (from a matched set) | Jeans | Boots | Bag | Necklace

11. With skinny corduroy jeans, a sweater, a quilted barn jacket, and knee-high boots

Kate Middleton provides a great example of how to style skinny jeans with knee-high boots in a classic way. She often wears brown flat lug-sole boots with black or blue jeans, a neutral sweater, and an olive green jacket. This is my nod to her. If you live in a cold climate, skinny corduroy jeans are amazingly warm and cozy. I will always keep a corduroy pair of skinny jeans in my closet for that reason. Here, I’m pairing navy cords with a white sweater, brown knee-high boots, and an olive green quilted jacket. 

Sweater | Skinny Cords | Similar Jacket | Similar Boots

12. With a white sweater and white sneakers

Here’s that same white sweater again, but this time I’m wearing it with dark wash jeans and my favorite Stan Smith sneakers for a casual outfit. White sneakers are a great choice. They have a minimalist feel that’s timeless and classic and never goes out of style.

Sweater | Jeans | Stan Smiths | Bag

Your clothing choices are deeply personal. Select styles that feel like you, boost your confidence, provide comfort, and complement your body shape.