Have you ever had one of those occasions where you want to wear jeans, but you need to look a little more sophisticated? Maybe it’s a business lunch, a meeting, or a nice event where your everyday jeans outfit just isn’t going to cut it.
This is one of my favorite formulas for making jeans look really classy. Start with a pair of dark-wash flares, add a beautiful tailored jacket, heels, and some elegant accessories, and wow—what a difference!

I wore this outfit several years ago, but I’d happily wear it again today. I love the long, lean silhouette, and those flares make my legs look like they go on forever.
Here are the five little things that make this look work.
1. Start with Dark-Wash Flare Jeans
If you want your flare jeans to look classy, start with a dark wash. Deep indigo denim looks richer and dressier than a faded or distressed wash, and it’s incredibly flattering too.

These Veronica Beard jeans are fitted through the hips and thighs and flare out from the knee. Add the dark wash and extra-long length, and you get that gorgeous, long-legged silhouette.

2. Add a Structured Jacket
A beautiful tailored jacket can take jeans from everyday casual to classy in a flash.
I paired my flares with this bright yellow double-breasted jacket, and I love the contrast with the dark denim. The strong shoulders and tailored shape give the outfit structure, while the shorter length lets you see the shape of the jeans.
A double-breasted jacket also has a little more presence than a simple one-button jacket, which works beautifully when you’re going for a more elegant jeans look.
Underneath, I kept things simple with a slim-fitting sweater. With the flare at the bottom and the structure of the jacket, you don’t need anything complicated underneath.

3. Wear Heels with Long Flare Jeans
The length of your flare jeans is a big part of what makes this look so fabulous.
Full-length flares should almost skim the ground, but they shouldn’t puddle around your feet or drag on the floor. These jeans are very long, so I definitely need heels with them.
That little bit of extra height lets the jeans fall properly and creates one long, uninterrupted line from your hip right down to the floor. Hello, legs!
If you need to have your flare jeans hemmed, decide which shoes you’ll be wearing with them first. Even an inch can change the way they hang.
4. Finish with Classy Accessories
This is where you can really have some fun.
Jeans may be casual, but add a beautiful bag, some fabulous jewelry, chic sunglasses, or a great pair of shoes, and suddenly the whole outfit feels much more special.

I carried my Dior bag and added some beautiful jewelry here, but your accessories certainly don’t have to be designer. It’s really about choosing pieces that feel elegant and intentional.
That mix of casual denim with more luxurious-looking accessories is what gives this outfit its classy feel.
5. Stand Tall!
And here’s one style tip that doesn’t cost a thing—good posture!
Flare jeans already create such a long, lean silhouette, so show it off. Stand straight, put your shoulders back, hold your head high, and don’t forget to smile.
You can be wearing the most fabulous outfit in the world, but how you carry yourself is what really brings it to life.

So there you have it: dark-wash flares, a structured jacket, heels, beautiful accessories, and great posture.

It’s a simple formula, but take another look at these photos. This outfit is several years old, and I’d still wear it today.
Some looks really do never get old.




I really like how all the pieces are paired together for the perfect, classy, and stylish look…but why are the prices of most of the items, not even affordable or practical for a regular working woman. How about fashion on a lower budget?
Love this look on you! Very fresh and classy. You look so tall and slim!
Great jeans! I bought a pair from Old Navy several years ago & still, wearing them. They were Diva bootcut or flared. Fit very similar & loved them. I paired mine with a short peplum striped top with a ruffle on the peplum part in navy & white striped. They were great to wear with boots in the winter since I had a lot of taller heels. With the almost sweeping the ground makes a tall look for Petites. You look amazing!
Looks great! I love the sunglasses – where did you get them?
Hi Becky, Glad you like them. They have been my go-to sunglasses for while now. I love the shape. I just included the link, so check the shop the post pictures again to do directly to the store to buy. Thanks!
What a great look! I think this type of jean is universally stylish on just about any shape.
Deborah you look gorgeous in these jeans. Many ladies look great in long flared jeans – thank you for posting.