classy tweed jacket outfit

How to Find Your Own Classy and Elegant Style

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Oh, the perfect classy woman. We all have our own ideas about what this woman is like. Perhaps in your head, she is so swan-like and elegant. Gliding gracefully down the street, her clothes just seem perfect on her. She’s natural and unbothered. We’ve all got an idea of who that elegant goddess is, but guess what? That woman exists in all of us, just in our own unique way. You can be classy and elegant in every outfit and every day by following the basic principles of classy and elegant style!

What Do Classy Women Have in Common?

Naturalness- Instead of squeezing their body into something that looks 2 sizes too small, the clothes always look like the right fit for them.

Effortlessness- A classy woman dresses in clothes that don’t come across as overpowering or trying too hard. No dressing to show off or dressing for other’s approval either. They dress for themselves.

Timelessness- They don’t look like they’re chasing the latest trends. Classic style comes from quality, basic pieces, and a perfect fit.

So, how do you achieve these 3 pillars of class? First, be confident and unique in your own personal style. If you know your own style, your outfits will flow together easily. With that comes confidence. And confidence breeds class and elegance.

Where Can Classy Personal Style Come From?

Now let’s talk about where your classy style can come from. Having references from “way back when” can be a strong foundation on which you can build an outfit. And it makes getting dressed every day so much fun!

For example, maybe one morning you want to dress like Audrey Hepburn from Sabrina in her “comeback” scene. Or maybe you want to emulate the vintage European style of Grace Kelly in How to Catch a Thief.

The key is to identify fashions that you really love (i.e. Old Hollywood glamour, the women from Little House on the Prairie, etc.). Then incorporate stereotypical pieces (i.e. satin slip dress, a peasant blouse) into your own style.

Pick one stand-alone or statement piece and style everything else around it, in a neutral way. It’s not about trying to imitate someone else. You’re selecting items that resonate with you and wearing them in your everyday.

The movie references are just one example. Here are a few other places to go looking for your own unique references:

Related: 7 Foolproof Ways on How to Look Elegant

1. Personal

Looking at old photographs of family members is always a fun walk down memory lane, not to mention an exciting exercise. Everyone seemed to dress with so much dignity back then. Maybe it’s a specific way that your grandmother tied a scarf around her neck? It can be anything.

Both Yves Saint Laurent and Karl Lagerfeld were influenced by their mother’s way of dressing. In fact, one of the reasons why Karl wore his signature black fingerless gloves is because of his mother. It wasn’t exactly a positive reason, but still…

Is there a particular scent your mother wore that you remember fondly? In the wise words of the pioneer of classy and elegant style, Coco Chanel said, “No elegance is possible without perfume.”

2. Favorite Designers

Ok, so maybe we all can’t afford runway clothes. But do we max out our credit cards and blow our budgets anyway? Most definitely not! We recreate the basic concepts from the runway into our own wardrobes.

For example, wear a cropped tweed jacket with a simple t-shirt, jeans, and ballet flats. Every Chanel lover can pull off that look and look effortlessly chic while doing so. And I can guarantee you can get that look for hundreds of dollars, not thousands.

3. Movies

When real life gets too dull…we go to the movies. There are so many iconic fashion moments to choose from. This book, “Fashion on Film”, would be fun to flip through for ideas. Especially if you are a movie buff and love fashion history.

Related: How to Have a Modern-Day Grace Kelly Style

4. Music

Take a look at your favorite most stylish musicians and pay attention to their style. It’s as simple as that! The fashion of musicians is very dependent on attitude. And having the right attitude is half the battle when trying to dress classy and elegant.

Here, Jane Birkin, the 60s icon, transforms a simple trench coat with an upturned high collar.

classy and elegant style

Take inspiration from the photo below. Simple details! A collared shirt + knit = elegance.

classy and elegant style

What Wardrobe Staples To Have for a Classy Wardrobe?

These are always classy and elegant and can be customized in various ways, depending on your own personal style. Here are a few to get you started.

1. Monochromatic Pantsuit

classy and elegant style

Some version of a pantsuit has been worn by most every classy and elegant woman in history. The foundations are solid. And the possibilities are endless! Make sure to buy it in a good quality fabric. Wool in winter. Linen/cotton for summer. Easily customize to your own style:

  • Make it classier with pleated trousers
  • Opt for high waist flared pants for more 70s style
  • Wide-leg pants can be flattering on any body shape
  • Dress it down with a t-shirt
  • Add old-world glam with a scarf
  • For a casual look, choose an oversized blazer and pants in lightweight fabric

2. Midi Dress

So versatile, it may become one of the most worn items in your wardrobe. If you have a midi dress then pretty much all of your wardrobe is sorted out. I’d recommend a relaxed silhouette because it suits everyone and allows you to wear it on more occasions. Cinched waist & a-line is a classic shape. Customize:

  • Choose long sleeves and a warmer fabric for winter
  • Go sleeveless for summer (front button-down always looks chic)
  • Pair with espadrilles or strappy flat sandals in summer
  • Boots or can even do sneakers in winter

3. Quality Button-Down Shirt

Preferably in silk or high-quality cotton. Linen for summer, of course. Customize:

  • Wear tucked into mid to high-rise jeans
  • Style it like a blazer, unbuttoned, by simply adding jeans, a tucked-in fitted t-shirt, and a statement designer belt or a quality leather pick
  • For a classy look, finish off the look with ballet flats

How To Add Your Own Twist to Classy Pieces

For everyday life, you want elegance to look easy. You want to appear undone and like you didn’t try too hard. A simple way to do this is by styling formal and informal pieces together in the same outfit, such as wearing a silky dress with a wool cardigan.

You could take the midi dress we talked about and pair it with combat boots. Or take the pantsuit and wear it with sneakers.

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Hopefully, by now you can see that achieving your goal of being a woman that is effortless, classy, and elegant is not as hard as you think! It comes down to attitude and the right pieces/outfits with some simple styling tweaks.

And if you’re after some practical classy outfit ideas, you know I’ve got you covered too. Get inspired in this post- 7 Casual Elegant Outfits for Every Day

classy and elegant style


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.