Vintage Fashion: How to dress retro and stylish

In this article we will share some tips on how to pull off retro and look stylish. But to begin with, we have to first look at what dressing retro style actually means.

There are many ways to go about dressing in a vintage style – from absolute authenticity to a sprinkle of retro charm. Only you can decide what suits your style and budget. Above all though, however you do it, do it your way and enjoy it.

What is ‘dressing vintage’ anyway?

Vintage style clothing can mean a lot of different things to a lot of different people. Have you ever seen a guy dress head to toe in old-fashioned gear from a charity shop? That is certainly dressing retro, but if no consideration is given to it as an overall look it can simply look sloppy and ill-fitting.

True vintage clothing

Retro style can mean dressing in genuinely vintage clothing which means sourcing an actual item produced and worn in the era of interest.

Here’s a great photo of Debbie Reynolds in a 50s swing dress from 1953.

Debbie Reynolds in 1953 on the set of I Love Melvin wearing a classic 1950s swing dress

Gorgeous, isn’t it! Imagine owing a vintage frock like that to wear. Incidentally, did you know that Debbie Reynolds actually collected famous vintage outfits like Marilyn Monroe’s white dress from The Seven Year Itch?

For many people who choose to wear true vintage clothing, the hunt is half the fun. These kinds of shoppers used to scour flea-markets and charity shops and hope for an amazing find, ideally at a bargain price. Nowadays they can add scouring online trading sites like eBay to their list too.

The success of the hunt will depend on a few factors. First of all the era you want to dress. The further back you look the harder it will be to find a good quality and well preserved piece of vintage clothing.

You might buy head to toe authentic vintage. But this look can be difficult to maintain and it can also be tricky to wear. For example, unless you are exactly the right size to suit that era you’re going to find it tough to always find something you like, in your size and in good condition. Once you find it, you may also find that as those vintage items are more fragile due to their age, you may not be able to wear them all the time or just out and about every day. Just imagine how that gorgeous vintage swing dress you unearthed at a flea market on your last holiday would look after a while if you started wearing it to work regularly. True vintage clothes may also need much more delicate washing and maintenance which means that they aren’t likely to be the kind of clothes that you’d want to wear out dancing every Saturday night.

Reproduction retro style clothing

The other alternative is to buy modern reproduction clothes. It can be expensive and difficult to buy real vintage dresses, but buying modern reproduction or retro or vintage style (as they are often called) vintage dresses is far easier. These days, this is often the most accessible option for anyone wanting to dress in a vintage look or retro style. There are also different types of retro style clothes to suit a variety of tastes. Some replicate the original design, pattern and material as much as possible. Many may even use actual vintage dress patterns and materials to recreate the item and avoid using any materials such as stretch which were not available at the time.

Other retro style clothing simply replicates the outward style and cut of the item, such as those classic 50s swing and wiggle dresses, but in modern materials. These days, many brands and manufacturers make clothing inspired by practically every decade of the 20th century so whether you love flapper dresses, 1940s dresses or those classic 50s dresses you can buy them online in a bunch of modern materials.

Since the fabrics are not retro, you get the advantages (and disadvantages) of modern materials which can be much easier to wear and look after than many of the restrictive fabrics of the day.

So now that we have the what out of the way, we need the how. How do you put a retro look together where you still look stylish?

Once you’ve decided on true vintage vs vintage style (or a mix of both) for your clothes, you’ll have to work out what sort of look you’re after. There is the look which is extremely difficult to keep up and that is the ‘just stepped out of a 1950s movie’ glamour look. Think of the effort Dita von Teese goes to – everything here from head to toe is perfect. A glamourous pin up dress along with retro shoes and a retro hair style. Even the underwear has retro detailing and shaping with a corset and suspenders to ensure every detail is perfect. All this topped off with 50s style make up and manicure.

Here she is looking immaculate in a 1940s style frock.

Dita snapped in Paris in a 1940s dress

This is an amazing look but really hard to keep up beyond a one off special occasion. An easier version is a retro style dress paired with retro themed shoes along with a vintage or retro touch to the hair and make-up. Or better still for an easier everyday look if you don’t have time to do the hair or make up, try adding some true vintage or vintage style accessories like a hat, necklace or handbag. And voila, your retro look with a modern twist is complete! This mix of old and new is such a flattering look, not to mention so popular right now.

For instance, the polka dot dress in all its many incarnations such as halter style, wiggle, swing or sweetheart is probably the most popular and classic vintage style dress. It is flattering to most women. It can be dressed up or down according to the occasion and since it’s a classic, its relatively easy to find in stores or online.

Here’s a photo of Cameron Diaz looking fantastic in a black and white polka dot dress.



Cameron Diaz in a Christian Dior black and white polka dot dress at Paris Couture Fashion Week in 2012. Photo credit Nicolas Briquet/ABACA/

You can see although the dress is a classic vintage style dress she has added a modern twist to her look with gladiator sandals. In this photo Taylor Swift is also going for the classic, this time in a red polka dot dress. But again, mixing it up with a modern hairdo and make up has given her a sophisticated look. It’s retro but not overly costume perfect. She just looks feminine and stylish.

taylor-swift-in red-and-white-polka-dot-dress-jfk-concert
Taylor Swift in a red and white polka dot dress at JFK’s Terminal 5 in Oct. 2010

The blended look of retro and modern suits some girls fabulously and is so much more flexible and easier to maintain. Some days you may not want to slap on any make up. Or you might want to mix it up and wear modern chain store sandals with your rockabilly dress. You could just have your hair out loose without bothering to do anything ‘retro’ to it. Still beautiful and stylish. You let you and the dress do all the talking.

A next level down in terms of effort is simply wearing one retro style item and mixing and matching with something modern. You can still do this as long as you try to maintain some overall aesthetic with your combinations. For example cute modern sneakers with a retro dress. Or a retro style pencil skirt paired with a cute modern T-shirt. It can work. Or a completely modern outfit dressed up with a true vintage or retro style accessory like a hat or a brooch. Perhaps a polka dot headband with jeans or capris, a fitted T-shirt and ballet flats. Think of a sort of modern Audrey Hepburn look. The possibilities are endless. You don’t always have to wear a vintage style dress to pull off vintage. The main rule to follow is that you feel happy and comfortable in your outfit. Nothing is as sexy on a woman as confidence.

Vintage inspiration

If you can’t afford to go all out vintage or even to buy reproduction vintage inspired dresses, you can take retro inspiration from the shapes and silhouettes of the 1940s and 1950s as well as the make up and hair of that time. For instance, cinched in waists, red lipstick, strong eyebrows, pale skin are ways to give your look a bit of vintage flair.

What retro style suits you?

Consider what types of clothes suit you. Whether its dresses, skirts, pants or tops. The vintage style doesn’t automatically suit every girl. And even within vintage styling, some girls may be more suited to pencil or wiggle dresses and skirts while others have a body shape that’s just made for swing skirts. There is the danger too of trying to be unique through the retro look while completely copying a specific look of a celebrity. There is no point in trying to dress like Audrey Hepburn if her style doesn’t suit you. Having said that, finding a model to base your look on can be great way to get ideas or even inspire you about what might look stylish on you.

For example, if you are a curvy hourglass you could look to women like Sophia Loren or Jayne Mansfield and their style. Think about your specific body shape and pick the retro silhouette that would really highlight your look.

You can also see how certain celebrities use clothes to flatter and create the shape and look they are after. For example, Dita von Teese is quite slim, however she knows how to cinch in her waist and wear clothing that creates the illusion of curves.

You can see this at work in this photo of Dita von Teese in a blue floral dress.


Photo credit:

How lovely does Dita look here in a vintage blue floral dress!

She is probably THE most famous modern day celebrity known for her vintage style. For inspiration on how to dress retro and stylish you can read more about her and other modern celebrities who wear vintage here.

At the end of the day though, use retro the way you want to. If you want to go crazy and pair a vintage floral dress with sneakers then why not. But do it because that is exactly the look you’re trying to work.

Vintage fashion for special occasions

And just finally, there are many people who don’t want to dress true vintage or vintage style every day. But who doesn’t like to dress up a little vintage from time to time for a special occasion like a wedding, prom or formal or a cocktail party. A vintage prom dress adds just the right kind of glamour for the occasion. Where else can you wear a vintage evening dress without feeling overdressed? The vintage look is just perfect for weddings too. A vintage wedding dress, vintage bridesmaid dress or retro style dress can look just lovely at a wedding without upstaging the bride. (unless of course you are one!)