How to dress — and play — the leading lady

RECENT seasons have seen the return of a retro ladylike style aesthetic.  A real favourite of mine, the ladylike style trend means its time to embrace the woman within and express her femininity. She is seductive yet demure, confident yet controlled. Think peplum waists and modest hemlines.

Coco Chanel once said that “a woman should look classy and fabulous”. But according to legendary Spanish designer Cristobel Balenciaga, No woman can make herself chic if she is not chic herself”. However, being a lady is much more than the way you dress.

Yes, money will buy you lots of gorgeous things, but you don’t have to spend a fortune to look polished and stylish. And you don’t need to go to finishing school to act like a lady. Dressing like a lady is half the equation, the rest is up to you.

HERE’S HOW TO DRESS LIKE A LADY

DO … 

  • Keep nails short and paint them in a neutral colour 
  • Wear classic pumps or elegant slingback kitten heels
  • Wear a belt and show off your waist
  • Shop vintage — think elegant and glamorous ’40s and ’50s styles
  • Be inspired by ’50s icons such as Audrey Hepburn, Grace Kelly or Jackie O and modern muses such as Cate Blanchett, Helen Mirren and Scarlett Johansson
  • Keep your hair well groomed and manageable. If you like it long, wear in a classic low chignon or ponytail.
  • Make sure your skirt, dress or gathered full skirt falls just above or below the knees
  • Show off real jewellery or top-quality statement pieces
  • Wear classic straight-leg jeans
  • Opt for high-waisted pants — the higher the waist the longer the legs. And who doesn’t want longer legs!
  • Find a perfume and make it your signature fragrance. Have another one for evening
  • Wear a watch, preferably a classic tank or round face with Roman numerals, such as a vintage Rolex Sydney, to complement your style elegantly
  • Carry a structured top-handle handbag or buy the best quality leather bag you can afford
  • Handwrite invitations and invest in monogrammed stationery
  • We all love our smartphones, but a real lady carries a diary or notebook and a good quality pen
  • Subscribe to certain publications so you are well versed in global news and cultural affairs because a lady’s mind must also be attractive!
  • Be polite and respectful, and learn to listen. And remember, if you dont have anything nice to say, say nothing at all!

DON’T …

  • Paint nails in neon or glitter polish or unmanicured
  • Wear shoes with scuffed heels
  • Wear ill-fitting tops
  • Shop retro, grunge or bohemian
  • Be a girl behaving badly
  • Shag your hair or wear your bed hair as a badge of honour
  • Wear a skirt so short it leaves nothing to the imagination
  • Keep your good jewellery in the safe
  • Look like an old hippie or gypsy
  • Wear embellished, dip-dyed or distressed denim
  • Expose your bum cleavage or muffin top!
  • Smell unisex or au naturel
  • Wear a gimmicky or digital watch
  • Choose a backpack or bumbag, and don’t even think about carrying a small dog in your handbag!
  • Send mass emails
  • Carry your money, keys, phone, lipstick, bus tickets, credit cards etc in a plastic bag or in your pockets
  • Ignore news, local affairs and global events
  • Be rude and obnoxious, and talk too much.

Related: What every stylish woman knows


Are you also celebrating the return of ladylike style? How should a lady dress and behave? Like to add a few points of your own? Would love to hear from you. Ever stylishly yours …

* Picture: Pinterest

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10 Comments

  1. Anonymous
    February 24 / 6:02 am

    Love your blog! Can't wait for more posts. Very inspiring and has given me a much needed boost and many ideas for making over my look and my wardrobe. thanks!

  2. February 24 / 8:26 pm

    Hi Anonymous,
    Thank you for your feedback! Yes, I'll try and get more regular posts happening.
    Cheers,
    Anne-Maree

  3. Anonymous
    March 9 / 3:45 pm

    I read this in the Sunday Telegraph today and I have to say that it's one of the most ridiculous things I have read. Why should women have to meet these standards that you have categorised as "lady like"? Have you failed to recognise that not all women will dress in this way? This sets women back into the 50's. The idea that we have to dress a certain way,act a certain way,be a certain person. I find it saddening and more then anything annoying and outdated. Who's to say that a girl dressed in bohemian clothes isn't ladylike? Or someone with short hair isn't classy. If you are such a lady that you think you can tell other females what they can and can't wear,how they should act and what they should do,why don't you build up our girls and women of today and tell them that as long as they are kind people and confident in who they are then they can be anything they want to be regardless of wether or not they're wearing neon nail polish or a French manicure. Regards,Montana Belle.

  4. Anonymous
    March 27 / 5:56 am

    Hi Ann Maree,
    I hope you continue to post on your blog. I only discovered it two months ago and like your posts. You have a great eye and I can relate to your style. Please don't be put off by the comment rant that 'Montana belle' posted. She has her opinion but many of us get what you are about. I know you were not saying that ladylike means only one thing. It is a particular style and phrase that describes that style. Just as bohemian describes a style. lLooking forward to more posts in the near future. Cheers, kathy

    • no one
      July 1 / 9:57 pm

      Hi, I really liked your post! I am a business woman and my style should be classy like you said. Keep posting because it helps me so much! Oh, I would like you to write about colors and how to match them for a nice view.

      • Anne-Maree
        July 7 / 10:02 am

        Thank you, and thanks for dropping by!
        Anne-Maree

  5. PRECIOUS
    August 6 / 7:19 pm

    Love your blog, its educative

    • Anne-Maree
      August 11 / 12:00 pm

      Thanks Precious, I aim to please!

  6. August 22 / 10:30 pm

    This is just awesome. Thanks for putting them all in one place. Great effort.

    • Anne-Maree
      August 25 / 1:19 pm

      Thanks for dropping by Iris!