How To Dress Like The Leading Lady

In recent seasons, there has been a huge comeback of the ladylike style, that sort of retro leading lady aesthetic. Back in the day, it was, of course, all the rave. And it was quite a welcome shock to see this particular style and image come back into fashion in this modern era, but I am certainly happy that it has! 

Dressing like the leading lady is all about embracing the power of womanhood, and about being unafraid to show and express that through femininity and softness. It’s about being seductive through elegance, confident while being poised and controlled, and about modesty paired with drawing the eye. 

I believe it was Coco Chanel that once said “a woman should look classy and fabulous”. And it’s not just about looks, the clothing accentuates the style, but ultimately, being the leading lady comes from oneself! 

But anyway, as this style and look have come back into fashion, I come across many people wondering how to dress in this way, and how to embody the ideals of a lady without making any fashion mistakes along the way. As this is certainly something I know about, I decided to put together a small guide on how to dress like the leading lady successfully! 

So..if that’s something you’re interested in, then I invite you to keep on reading! 

How To Dress Like The Leading Lady

What does it mean to dress like the leading lady?

Whenever I talk about this subject I always get people that ask me: but what is a leading lady? So I thought I would start by clarifying what it means to dress like the leading lady. 

So, the leading lady is essentially an informal term that is used to refer to an actress that plays the supporting role, or who is the secondary lead. Usually, she is also the love interest, and therefore supports the journey of the main lead character.

However, it can also apply to an actress that is the main character and protagonist! So basically, it applies to the most important actress in a movie. 

The thing is, being a leading lady doesn’t stop at being the actress in a film, it carries out into everyday life. So a lot of leading ladies were traditionally actresses of renown popularity, such as Lynn Fontanne and Helen Hayes.

Think of all the Hollywood female icons, and that is pretty much what we mean by the leading lady. 

The traditional and iconic golden era of Hollywood is what defined the ideals and image of the leading lady, and it is how all of these popular actresses portrayed themselves, and how they dressed and behaved. As well as the way in which they were typecast to be love interests embodying the ideal of elegance and desirability. 

As I mentioned in the introduction, being the leading lady is more than just the clothing, it is the whole demeanor and the way in which you carry yourself. It is embracing and expressing femininity, but taking power from it at the same time.

So it is being aware that we are desirable and cherished by men, but also be aware that this gives us power, and that we can choose to wield it in our own way. 

It is all about being elegant and poised, modest in that we are not vulgar or showy, but confident in our image and style so that we can use it to become desirable and wanted. It is about glamour in a subtle and refined way and all about the Hollywood dream. 

(As you might be able to tell, I’m quite passionate about this style, and it brings me great levels of nostalgia!)

How to dress like the leading lady:

Becoming the leading lady takes more than wearing the right clothing attire, as it is also about how you carry and express yourself, and about how you behave. However, the clothing is one of the most visible and important parts, and it plays a great role in the overall aesthetic. 

But how do you dress like the leading lady?

Well, I will start by saying that there is no need to spend large amounts of money or to go after expensive brands, in order to become a leading lady. You can dress like one in a very affordable way, and it is all about knowing what to wear and not what to wear, paired with carrying it all as best you can. 

If you’re not familiar with the leading lady style, then it can be quite challenging to properly determine what is right and what is wrong in leading lady fashion rules. And that is where I come in to help! 

Here are my top dos and don’ts when dressing like the leading lady!

Leading Lady Do:

  • Keep your nails short, and have them painted in neutral colors or with a French manicure
  • Wear classic pumps, or slingback kitten heels
  • Show off your waist, you can accentuate it through the use of a belt
  • Shop around for vintage 40s and 50s clothing, the more elegant and glamorous the better
  • Take inspiration from the 50s female icons of Hollywood, such as Audrey Hepburn, Grace Kelly, or Jackie O
  • For a modern take on the style, take inspiration from modern icons such as Cate Blanchett, Helen Mirren, or Scarlett Johansson 
  • Keep your hair well-groomed. If long, an up-do or ponytail is preferred
  • Your skirts and dresses should fall just above or below the knees
  • Use real jewelry and spend your money on accessories
  • If wearing jeans, make sure they are the classic straight-leg
  • High-waisted pants are best, to accentuate long legs
  • Experiment until you find a favorite perfume, and then make it your signature fragrance!
  • It is classy to wear a watch
  • Use high-quality handbags 
  • Carry a diary or notebook around with you for when taking notes, it is far more elegant than using your smartphone

Leading Lady Do not: 

  • Do not paint your nails in bright colors or with glittery nail polish
  • Wear shoes with scuffed heels or visible stains
  • Wear ill-fitting tops. It is important to show off your feminine figure
  • Do not look for retro, grunge, or bohemian clothing attire. This does not fit the style whatsoever
  • Do not leave the house with messy hair, or with wild hair left loose. You should appear to be well-groomed at all times, in a way that makes glamor look effortless
  • Do not wear short skirts
  • Do not wear cheap jewelry. In the leading lady style accessories are everything, make sure they are good
  • Do not expose your cleavage too much! Remember, elegance is key, and you want to avoid coming across as vulgar 
  • Do not use cheap perfume. The fragrance is an important part of Hollywood glamour
  • Do not wear a backpack or similar. You need a stylish small handbag. And no, you can’t carry a dog in it, this makes you look tacky. If walking a dog, it should walk beside you on a lead!
  • Do not carry items in your pockets, use the handbag

Other tips on how to embody the leading lady style:

Once you’ve learned how to dress like a leading lady, you need to behave like one, or else the clothing will be in vain. 

Here are some of my top tips to embody the iconic leading ladies of the Hollywood past:

  • Treat people in a personalized manner. This means no mass emails or generic messages. Focus on the individual so that they feel seen by you. 
  • Use pen and paper, and leave notes instead of sending a message over the phone. 
  • Practice your penmanship. Leading ladies had excellent writing skills.
  • Always be polite and respectful, no matter the situation. You should remain in control with poise even when faced with rudeness from others.
  • Learn how to compliment people with sincerity, and never speak ill of others 
  • Read up on global news and important events. Leading ladies are regarded as intelligent and knowledgeable, and you should show interest for the world around you