1950s, feminine and fabulous! Fifties style dresses have been made hugely popular due to celebrities such as Taylor Swift rocking these for both causal and formal occasions. This style of dress is also one of my go to favs for summer or winter!

Cute in summer, styled with a cardigan and wedges; or in winter with a denim or leather jacket and boots. These dresses can have cap sleeves or are sleeveless. Both are very versatile but if you work in a professional company where you can’t show your shoulders, go for the cap sleeve or a good cardigan (or in winter wear a merino under your sleeveless option).

Here are my 5 fabulous tips for wearing a fifties style dresses to work.

Flare size

Be careful with the fullness of the flare. Keep the flare suitable especially if you are planning on wearing these during the work day and not just on casual Friday.

The fuller the skirt the shorter you will look.

Shorter gals go for a subtle flare – think a circle cut skirt instead of pleats. Also always wear your dress with heels or wedges. The extra height reduces the impact on the puff in the skirt.

Taller gals go for broke with as many pleats as you want. You can also team the dress with ballet flats for a casual look.


There are two main necklines for these dresses – boat neck or V-neck. I have dresses with both but I prefer the boat neck because it balances out my hips (as I’m a pear shape). I especially prefer this neckline in the winter months since it’s much warmer. :-)

  • V-neck is the ideal style for my apple shaped ladies! Be careful the ‘V’ isn’t too deep – this is more for a flirty night time date than a meeting at work. Also if you’re apple shaped I would avoid the boat neck because it has potential to produce the ‘monoboob’ look… Not ideal!
  • The whole idea with the necklines of these dresses is to balance out your shape. If you’re heavier on the bottom (pear shape) then the boat neckline broadens your shoulders – giving the perception that look more like an hourglass shape. If you are broader at the top (apple shape) the fuller skirt on the bottom does the opposite – also creating an hourglass. All in the meantime making your waist look nice and trim. Now don’t we all love that!


Now that we have the neckline sorted, there are two ways to add necklaces to your fit and flare dress. However the main idea with necklaces for this style of dress is to anchor the shape of the dress with a statement necklace – thus drawing the eye.

  • Short necklaces – this is a classic look, perfect for apple shaped gals wearing the boat neckline. I would channel classic 50’s glamour with a cluster of pearls at the neckline. This works with any pattern or colour on a dress and gives a very polished look. Another option would be to go for a coloured necklace which matches the pattern in the dress and brings people’s eyes to your face (this also looks fab with coloured shoes. :-) Now we are talking!).
  • Long necklaces – can be worn in a variety of colours or textures. I am a huge fan of wearing wooden beads with this style of dress as it gives it a more casual feel. The main idea of wearing long necklaces is that it draws the eye down the body – giving the appearance that you are taller. Great for any gals… let’s be honest, who doesn’t want to look taller! When wearing long coloured necklaces the same rules apply. Make sure the colour is prominent in your pattern (this is why I personally like florals0), but if you don’t have a colour in your dress that’s fine. Add the colour in by matching your bag, shoes, cardigan and necklace for a polished look – this looks great over your classic patterns such as spots or stripes.


Spots, florals, strips or even a retro print!

  • Pick a pattern which contains colours you like wearing (but remember colour packages!). If you have a lot of one colour in your wardrobe, chose a pattern which contains that colour. This makes it easier when matching cardigans or jackets, shoes, bags and necklaces.
  • My personal favourite is either floral prints or spots. Floral prints are great as they give you many options for styling. I love spots as they are sooo classically 1950’s – whether navy and white, or beige and cream. They are so much fun to wear.

Summer or Winter

Fifties style dresses are very versatile and can be styled for summer or winter. In order to achieve this you need to make sure your pattern is able to be adapted for winter boots. In winter you wear ankle boots for a more casual look (cute with a denim jacket) or with knee high boots and tights. If you are shorter I would suggest wearing knee high boots as they make the leg look longer.

These dresses can always be worn with court shoes – summer or winter – with nude tights.

Versatile and back in fashion – do you wear fifties style dresses to work? Let me know in the comments.