A Beginner’s Guide To Wearing Vintage Clothing

  • , by Alex Torres
  • 6 min reading time
A Beginner’s Guide To Wearing Vintage Clothing

When it comes to being fashionable, there is a huge emphasis placed on being cutting edge. We’re always looking for what is “in” and pick our clothing carefully, out of fear of wearing something that’s “so last year.”

But humans have been finding ways to make their clothing aesthetically pleasing since they started wearing clothes. That means there is an extremely long history of fashion looks that are still beautiful despite being “out of fashion.”

Because of that, a growing number of fashionable folks have been embracing vintage and retro-inspired looks. If you want to open your closet and find all of time at your disposal, we’ve crafted a beginner’s guide to wearing vintage clothing.

Identifying a Time Period

The history of fashion is divided into different eras, and each era has a distinct look. When you’re crafting a vintage-inspired outfit, you will want to stick with style elements of one particular time period. Otherwise, your outfit’s look may feel a little muddled.

While there are an untold number of fashion eras to choose from, here are a few of the most common eras we modern folks like to imitate and the elements that make the style distinct.

The Victorian and Edwardian Eras

The time periods in which Queen Victoria and then her son King Edward VII reigned spanned over 80 years. Over those decades, there were a wide variety of different looks and shapes, from hoop skirts to bustles, from morning coats to cummerbunds.

Naturally, unless you’re looking to get into the exciting world of period dress, you won’t be adding most of these items to your daily dress. However, a few elements you can add to call the time period to mind include:

  • High collars
  • Long skirts
  • Headwear
  • Structured bodices
  • Vests

Roaring Twenties

The roaring twenties, also known as the jazz age, was a huge shift in societal views and expectations. And as society changed, the fashion world changed with it, bringing a whole new world of style elements, such as:

  • Drop waist skirts that hit just below the knee
  • Fur wraps and collars
  • Art deco, geometric patterns
  • Long pearl necklaces

The Fearless Forties

A lot was happening in the forties that impacted fashion. World War II created a need for practical looks made with less fabric. At the same time, we were at the height of the golden age of Hollywood, creating a whole host of glamorous looks. A few ways to capture the styles of this era include:

  • Clean silhouettes
  • Clothing items that are simple and unadorned
  • Practical, close-fitting jackets, sweaters, and skirts
  • Clothes made of cotton or nylon
  • Zoot suits

The Fabulous Fifties

There are several faces to fifties-inspired fashion. There are the more elegant looks you might see on shows like The Marvelous Mrs. Mazel, or there’s the soda-shop, rockabilly style looks you might associate with Grease. There’s a whole host of style elements you might employ, such as:

  • Cinched waist, such as pencil skirts
  • Leather
  • Patterned clothes, especially gingham or polka dot
  • Cardigan sweaters
  • Letterman jackets

The Late 20st Century

Those of us who were around during the 80s and 90s remember it fondly. And the recent uptick in shows set during this time, like Stranger Things and Young Sheldon, have made this era one of the more popular to imitate for lovers of vintage fashion. A few style elements you can use from this time are:

  • Distressed denim
  • Shoulder pads
  • Bright, bold colors and patterns
  • Baggy clothing and athleisure wear

Blend Modern With Vintage

One of the most important beginner’s rules for wearing vintage fashion is this: wearing vintage-inspired clothing is different from wearing historical costuming. Your goal isn’t to look like you stepped out of an old-fashioned catalog. It’s to nod to the aesthetic of a time with your own modern twists. There are a few ways to go about this.

Capture the Shapes of the Time Period

Different time periods value different types of figures. For example, the 50s valued an hourglass figure while the 80s was all about big sleeves. The nice thing is you don’t have to wear a poodle skirt or genuine 80s power suits to achieve this look. All you need to do is find modern pieces that employ the same shapes.

Incorporate Hair

If you want to make a bigger vintage splash, you can try styling your hair to match your preferred time period. Here are a few retro-inspired hairstyles:

  • A Gibson girl bun
  • A close-cut bob
  • Slicked back combover
  • Finger waves
  • Victory curls
  • Pompadour
  • Quiff

Remember, you want to avoid looking like you’re wearing a costume. If you’re going to do a distinctly vintage hairstyle like victory curls or a greaser pompadour, you will want to keep your clothing a little more subtle.

Choose a Vintage Statement Piece

Sometimes the simplest way to give an entire outfit a vintage vibe is to bring one piece that is from your selected time period while the rest remains modern. Here are a few easy-to-add vintage statement pieces.


The right jacket, sweater, or cardigan can instantly add a vintage charm to any outfit. Longer jackets especially, like trench coats and double-breasted pea coats, tend to make people think of older times while easily fitting in with a modern fashion landscape.


Vintage accessories are perfect if you want your vintage nod to be a little more subtle. Jewelry, such as pearl necklaces or big earrings, will add a fun touch to your look. Another option is to use hair accessories like scarves, headbands, or flowers.


A hat was part of everyone’s everyday wardrobe in years gone by. Because of that, a hat is the quickest way to make even the most modern outfits seem a little more retro. If you’re looking for the right hats for your time period, here are a few classic hat choices for different time periods:

  • Flat and newsboy caps, as well as bowlers, work well for turn-of-the-century-inspired looks.
  • Cloches and boaters are quintessential 20s hats.
  • Wide-brimmed fedoras and berets work well for any look from the 20s through the 40s.
  • Fisherman hats and bucket hats are great for a 1990s look.

Acquiring Vintage Fashion

Wearing vintage fashion is one thing; acquiring it is another. There are plenty of ways to get your hands on vintage fashion, depending on how close to the time period you want to look. Thrift and even antique stores are often treasure troves for pieces that are of the time period you’re looking for.

However, as we said, you don’t have to wear genuine, old-time clothes to adopt a vintage-inspired fashion. Just as often, you can buy pieces that are reminiscent of a time period from retail outlets that will still give your outfit the old-fashioned charm you’re craving.

Whether you’re looking for a cloche or boater to complete your jazz-aged wardrobe or a classic fedora hat for your 1940s look, Fashionable Hats has the hats you need to cap off your vintage look!

A Beginner’s Guide To Wearing Vintage Clothing

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