Vintage-Inspired Look For Crossdressers

Trends come and go, but some fashion styles never seem to get old. There are styles one can wear year after year, decade after decade. But vintage fashion is a style that seems never to go away and is worn with pride.

It’s a style inspired by the 1950s and 1960s, even down to the 1920s, which is an era considered to be one of the best in fashion.

The vintage look isn’t just one look but a range of different looks that are sure to suit anyone who wears them.

Moreover, these styles are timeless, can fit in with any location, and are ideal for any social function.

There are so many reasons why the vintage look is so great.

A vintage look takes forethought & planning. Before diving in, research first to find the right theme for you.

There are hundreds of renowned styles from movies like Grease or Breakfast at Tiffany’s, or perhaps from stars like Audrey Hepburn or Marilyn Monroe themselves.

One can style from the 1940s sweetheart rounded neck dress to a 1960s baby doll mini dress.

Once we find the era we’re going for, we should stick to it and add everything else to match, such as vintage-inspired hairstyles, makeup, and accessories.

For example, if going for a pinup look or otherwise styling your hair in any way that’s associated specifically with the 1930s, ’40s, and ’50s, you might want to purchase vintage wigs in up-do, half-up, victory rolls, bangs, and pinup hairstyles.

Since anyone would really have had such big hair during those decades, it makes for a great accessory on its own!

To complete the vintage look, one can go with oxford shoes with white socks for a preppy vintage vibe or accentuate with a printed headscarf.

Opt for red pumps or mules to complete your vintage-inspired look for something chicier.

The vintage look is a popular one that many crossdressers enjoy.

Whether you want to sport a 1950s full skirt look or a 1970s retro style, look no further.

This list will help you with your vintage-inspired get-up.

This article is filled to the brim with vintage inspirations for all your cross-dressing needs and wants.

1. Different vintage-inspired looks for crossdressers

In the 1910s, empire waist, high collar, and floor-length dresses were the staples of fashion.

The trend continued through the 1920s when sheath dresses were known.

Shorter dresses were introduced with a sweetheart neckline during the 1930s, and by the 1940s, A-line bias cuts became popular.

The advent of 1950’s fashion brought about full skirts, off-the-shoulder, and strapless mid-calf dresses.

During the 1960s, baby doll mini dresses, as well as boho chic, were popular.

Along came the 70s, when the trademarks of fashion were puffy shoulders, wide legs, and pantsuits.

Throughout the years, the timeline of fashion has become cyclical, and the trends from before, more often than not, make a comeback in today’s era.

There are several different vintage-inspired looks you can find in modern clothing.

First, let’s start with the 50s. This is a simpler era, and this is one of my favorites.

Think poodle skirts and greasers. Second, there are the 70s.

This era is more of a whimsical throwback. Full of bright colors, fun patterns, and happy music.

Finally, the 80s. This era is the one I’m most used to. It’s based on music, movies, and the neon colors of the 80s.

Vintage-inspired outfits are great and look classy and cute. You can match different items and put them together to create your look.

There are many different types and mixes of vintage look that you can choose from.

2. What type of vintage look are you looking for?

First, determine the type of vintage look you’re going for.

Are you going for something classic, like the looks from the ’20s and ’30s, or are you more interested in something more hippie, like from the ’80s or ’70s?

From a crossdresser standpoint, we are aware that vintage fashions are not just clothes but also shoes, accessories, and hairstyles.

A lot of us don’t like the style of older hairstyles, so this might be a factor in your decision.

It’s also important to remember that fashions tend to change over time, so it’s best to go with a style that you like instead of what’s in, which could change as quickly as overnight!

For example, you can go for the grungy look that is popular among anti-fashion girls.

These outfits consist of baby doll dresses, loose-fitting jeans, and boots.

You can go for a more hippie-like look and wear a peasant top over a pair of ripped jeans and some sandals.

The vintage-inspired look that is popular among youngsters is the preppy look.

This outfit consists of a light-colored top and a plaid shirt with shorts. You can accessorize it with a pair of loafers.

Although one may not be versed in the era of the 1920s, it’s still possible to take pieces of the fashion from that time and create your unique style.

You can get vintage pieces, or you can create your own look.

Do this by simply wearing the right jewelry, accessories, and shoes!

You can find accessories or jewelry in vintage shops or even online.

You can also get them in new stores and simply give them a more vintage look.

3. Vintage hairstyles just for crossdressers

Hair is a big part of that vintage look.

We have to admit that if you have an impeccable 1950s ensemble but flowing wavy hippie-style locks, you won’t have nailed the look.

Again, you have to do your research and find an updo that matches the decade you’re going for.

A lot of retro hairdos could be quite complicated, so you will want to practice often and get a hold of some old-school accessories.

And, of course, our lifesavers are our wigs.

The shape and size of your face dictate which kinds of wigs will look best on you.

Short or medium-length wigs that are styled in fun ways like half-up or up-dos naturally soften the appearance of your face by covering more of your forehead and by lifting your chin.

Wearing vintage-inspired hairstyles (those from the ’20s, ’40s, and ’60s) along with wigs modeled after these styles are also great at making one appear more feminine!

Make sure you pick a hairstyle that fits your hair and personality.

Wigs in up-do, half-up, victory rolls, bangs, and pinup hairstyles are sought-after in a vintage get-up.

I think that the best hairstyle is the 50s hairstyle!

They are elegant and stylish, and this hairstyle is applicable for any age and any face shape!

4. Makeup for a vintage-inspired look

If you want to achieve a vintage look, you must avoid lipstick with a shiny finish.

Also, avoid heavy liquid eyeliners and mascara. Instead, look for powders, mineral makeup, and matte eye shadows.

You’ll also want to find lip colors that are either matte or close to it.

By following these steps, you’ll be able to achieve a glamorous vintage look that will have you feeling like an old Hollywood movie star.

The best makeup types to achieve a vintage look are large fluffy brushes, liquid eyeshadows, and black eyeliner. Start with a white base.

This will give your face an even and smooth surface.

Then, you can use a large fluffy brush to apply some black eyeshadow to the outer corner of your eye.

This will give it a smoldering look.

Then, use a liquid eyeliner to draw a line that starts thick and ends thin to mimic the look of the old liquid liner.

To finish, you can use the same brush to apply a little black eyeshadow on your lower eyelids to make your eyes pop!

5. Finish off with vintage accessories and heels

A clutch or a handbag can make your outfit pop, just like the right pair of glasses or sunglasses.

Paying attention to detail is also key and includes things like shoes and tights.

For example, accessories are important if you want your retro look to be authentic, whether the era calls for heels or flats.

Earrings, necklaces, and bracelets all work great.

Other wonderful vintage style accessories that can be added to your list include, among others, gorgeous vintage sunglasses, an hourglass belt, a veiled fascinator, and simply stunning pearls that won’t fail to take your breath away!

If flowers are your thing, then why not try adding some of those as a stylish hair clip or headband or perhaps even in the form of some beautiful lace gloves?

These are just some of the ideas to get you started!

Another vintage accessory to be added to the list is printed silk scarves tied in several ways around the hair, neck, shoulders, or any other part of your body.

Take inspiration from the ’70s – silk scarves were trendy when that decade was known as the era during which they ruled!

There’s just something about vintage fashion.

The clothes of days gone by and the way it’s cut to create lovely and tantalizing silhouettes are enough for us crossdressers to get excited!

We want to look our best every time we do this, as well as feminine and as classy as we can look.

That’s why we love classic clothing from decades ago; it fits who we are so perfectly!