The skinny jean controversy seems to be a hot topic these days. Something happened in 2020 between TikTok taking off, and Gen Z making a name for themselves in the fashion world, Millennials have somehow been thrown to the fashion wolves, if you will. It felt like overnight that Millennials and our skinny jeans became cheugy and dated. And while I think some variations of a skinny may need to be purged from our closets, not all of them have to be. For me, many styles of denim really stand the test of time when in a classic wash, with no major distressing, and a mid-high rise. It’s more about what’s flattering for your body type. But while Gen Z tells us to dump our skinny jeans, I’m here to tell you that you don’t have to.
There are definitely great skinny jean styles that still work for right now. Plus, many ways to style them. But here’s the kicker. The way we were styling them back in 2012 when they took over our lives, has to change. No more riding boots with skinny jeans topped with a tunic and a cardigan. We’re refreshing them for the present times to give them a more trendy and contemporary look. And if you need a few more closet swaps from 2012 to 2022, you have to check out my Millennial Style Guide here.
What To Wear With Skinny Jeans
Before we dive into all the things you can wear with a pair of skinny jeans, I want us to keep in mind a few styling notes and tips. Proportion. Balance. Your skinny jeans are just that, skinny. Tight. Instead of pairing it with more tight things, we want to balance things out and also keep proportions in mind.
We’re Not Doing This
All of these looks have a few things in common. Lots of tight things paired with them. So very tight. And lots of elements from 10 years ago that just feel a bit dated. Big blanket scarves, flannels tied around the waist (just wear it! that’s the easiest swap to update these too) and Hunter boots when you’re not taking care of horses. Let’s make some updates.
But We Do Approve Of These Skinny Jean Styles As Our Base To Get Started
Add More Oversized Pieces To Balance Out The Skin Tight Jeans
This is rule #1 for me. I am no longer wearing a fitted tee tucked into my skinny jeans. This was a look I wore a lot back in the day on repeat. Now it’s more about balance and adding something a bit more oversized, and even cropped, to create proportion and balance.
Rule Of Thirds
When we get dressed, we want to create visually appealing looks. But that really starts with the rule of thirds. If you’re cutting your body in half with your clothes it can make your look feel a bit off. To create a more appealing look, think of your body in thirds. And items should hit in one of the third sections. For example. Let’s think of our high rise skinny jeans. On top, we can add a cropped oversized boxy tee and that hits about the 1/3 part, leaving the jeans to be the 2/3. And vice versa. If you want to do a longer top, try one that hit’s a bit lower than your hip, maybe mid to upper thigh, to hit the top 2/3 mark. These are just general rules of thirds, and they tend to be a good guide when putting outfits together.
Add A Third Piece
Instead of just a tee and skinnies, add a third piece to pull everything together. This can make or break the look. Whether it’s a cool belt, great jacket or coat, or even a silk kerchief around your neck, this instantly updates your skinnies and makes them feel super elevated and put together.
Add Something That’s Currently Trending
As I head into the third pieces and shoes to try, these are all items that are trending much more right now, than 10 years ago. Items that are not really classics and are instead trendy. Whatever you are loving right now with the hot trends, try to add that in!
Go All Black
When in doubt, just wear all black. But use some of these pieces like oversized blazers and chunky sneakers to make it work. There’s just something so chic no matter what to an all black head to toe look. I’d do a leather jacket with a lug sole loafer and black silk button down or tee. This is also when I think a black riding boot can still work.
Third Pieces To Try
The perfect pairing in my book is adding an oversized blazer or boyfriend-style blazer to your skinny jeans. This would be great with a pair of black skinny jeans for a business casual look too. Think a slightly longer blazer too. A fitted, slim blazer is a hard no here.
Oversized Silky Pajama Shirt
A silky pajama shirt that’s oversized is great to pair with a pair of blue skinny jeans or even white ones for spring and summer. Add a simple leather slide for a little vacation look. Or a kitten heel for a more office friendly look. Silky pajama shirts are ultra chic right now.
Graphic Pullover Sweatshirt
My go-to for a casual look is adding a graphic pullover sweatshirt or hoodie. This is a cool and casual way to wear skinnies to run errands or for a casual lunch. I like to style this combination with my Madewell Trainers, just a chunky trendy sneaker. Any will do! Trend on trend!
Oversized Leather Jacket
While I love my leather jacket, there’s something super cool about an oversized one paired with skinnies. I’ll still allow a more fitted leather jacket so long as you pair with a lug sole boot of some sort or chunky sneaker and an oversized top.
Cool Chunky Cardigans
Probably the #1 most asked item on how to update for Millennial style are cardigans. It all depends, friends. But I think a chunkier and cropped cardigan is very cool with skinnies paired with a heavier shoe on the bottom.
This is the update to all our favorite utility jackets. A cool shacket (that’s a shirt meets jacket combo like this) to be your oversized piece. There are so many to choose from that you can find one for any personal style.
Oversized And Longer Coats
Add a long and oversized coat to your look. This is perfect for fall and winter. You can add a chelsea boot, sneaker or heel. Any will do!
Boxy Tucked In Tee
For tops, I really love a boxier or roomier tee that’s tucked into jeans. Bonus points for it being a slight crop top if your jeans are more on the higher rise. This creates more proportion and balance. Gone are the days of a really long tunic top tucked in the front and flowy in the back. This paired with a ballet flat, or loafer, along with any of the third piece options above, would be a great outfit combination.
Button Down Shirt Tucked In
The same goes for a button-down. Having one tucked in with a sleek belt feels very Parisian chic. I’d avoid a really slim fit button down though. Think one that can blouse a bit so you’re not tight on top and tight on the bottom.
You could also do a cropped cardigan that you can front tuck a bit for a slight blousing effect. These are having a big moment right now and you can find them just about anywhere.
Oversized Untucked Button Down Shirt
This has been my personal go to. A really big oversized and longer line button down shirt over skinny jeans create the perfect balance of fitted and loose. You’ve seen this look here.
And if it’s cropped, even better. But a looser oversized fit is great. I really love a cropped sweater so you can tuck the front into your high-waisted skinny jeans. But an oversized larger sweater works too and would be nice with some of the shoe options below.
Types Of Shoes
Chunky Fashion Sneakers
A good balance to the skinny jeans for a shoe option is a chunky fashion sneaker. A simple swap is a classic slim Converse for the platform ones. That’s my go to. Any cool Dad sneaker or chunky New Balance like these are great. They add balance and feel updated.
Lug Sole Boots
The lug sole trend is super popular right now and they are the perfect way to add some chunky weight to your skinny jean look. Lug sole boots come in so many styles too from flats, to heels and knee highs. These would be a great swap for your beloved riding boots.
The ultimate boot that Gen Z has brought back into style again. While I feel like these never go out of style, they’re definitely more popular and mainstream right now. These add the chunky sole, heavier look and edge to your look. PS read my full Dr Marten’s boot review here.
To add just a little height, and they’re super chic, a kitten heel is great to pair with your skinnies. These would work great with a beautiful oversized sweater, pajama shirt, or a great blazer.
High Top Sneakers
A high-top sneaker is super cool and edgy. Try a pair of Converse or Nike for a classic yet updated look.
Knee High Boots
Let’s make sure we’re on the same page here. We are NOT doing this kind of riding boot from 2012 with a cardigan or tunic. No ma’am. We are applying ALL the rules to make this one work. An oversized blazer paired with a more modern boot. Think a really sleek low heel leather boot, the new western trend boot, or a chunky lug sole knee-high boot. There are a lot of really great ones out now.
Skinny Jeans Outfit Ideas For 2022
Button Down Tucked In With A Preppy Shoe or Boot
This look on the left from Brooklyn Blonde is so Parisian chic to me and a really classic outfit. Just avoid a really fitted button down. Those remind me so much of my first 9-5 wardrobe that was sourced entirely from Express. Keep it a touch flowy, or slightly relaxed. And on the right is a more edgy way to do this with your jeans tucked into a very on-trend knee-high boot (not a riding boot!).
Cropped Cardigan With Platform Sneakers
Whether you leave the cardigan open, or button it up and do a slight front tuck, this is a great option. Slightly oversized, a bit of a big balloon sleeve, good balance. And I truly think this look would feel off if the shoes were not platforms. Some sort of chunky shoe on the bottom (especially if it’s a sneaker) I think is key for skinny jeans being updated from 2012. You could do a cool loafer or a combat boot. But to me, a classic Converse would feel off here and feel very 2012. Would also be cute with a sleek kitten heel shoe.
Long Coats With Skinny Jeans
This combination is great for winter. Just add a long coat to your skinnies over your oversized sweater. You know what we’re not doing? Wearing really short coats with this. Unless it’s a super cool oversized short puffer, I think we’re sticking to long lines here.
Oversized Blazer With Skinny Jeans
My go to. This is how I’m getting the most use out of my skinny jeans. I feel a bit sloppy with an oversized blazer (especially the really big ones) with relaxed denim. It’s definitely in style, but it’s just not for my body type. As I always say, take what you need, leave what you don’t want when it comes to fashion trends. We don’t have to subscribe to them all. But when I want to wear a good oversized blazer, I always reach for my skinny jeans. Keep them in a dark wash too with no ripping.
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