Timeless Charm: 20 Exquisite Vintage-Inspired Hairstyles

Vintage updos are a go-to for formal occasions or the days when you just want to spice up your casual hairstyles. Looking to the past for new ideas won’t leave you empty-handed. We’ve got twenty elegant updos for you to try out, all inspired by charming hairstyles of previous decades and beauties from the past.

Elegant Vintage Updos

We love vintage-inspired hairstyles for their extra charge of feminity. They still may be a bit messy as a modern upgrade of popular styles from the past. Perfect hair-to-hair buns, bouffants and glorious rolls are waiting for you!

1. Reverse Tuck

Imagine you’re Cinderella at the ball with a handsome prince on your arm! Okay, so he’s actually just your boyfriend and you don’t even own glass slippers, but you sure look the part. With an updo like this, you don’t even need a Fairy Godmother to make your wishes come true.

2. Elegant Vintage Beehive Updo

When you think beehives, do you imagine a secretary from the ‘60s clacking away on a typewriter with exceptionally long but well-manicured fingernails? Volume like this can be achieved for you too; all it takes is a bath loofa to get this look at home… intrigued?

3. Pin-Up Victory Rolls

This updo is simply perfect! If you decide to test out this style yourself, remember to compliment the retro vibes in your hair with a matching makeup. Swipe on bright red lipstick, carefully create a winged upper lid, and you’ll look like a beauty that has just stepped out of a time machine.

4. Elegant Braided Vintage Updo

If you’re looking for something a little more toned down, try out this style. To do it yourself, split your hair into three sections. French braid the right side down along your hairline and then do the same on your left. Braid those two braids together with the chunk of hair left in the middle and tuck that braid into a small bun.

5. Swirl and Twirl

Don’t be that girl at the prom that has the same variation of the updo everyone else is wearing. This style can be worn to stand out from the crowd on the prom night while still maintaining your flawless sense of style. Be sure to hairspray lest the hair will flatten from all that dancing.

6. Simple Faux Bob Vintage Updo

Next Halloween, go as Daisy Buchanan from The Great Gatsby. This costume will give you the opportunity to show off your literary knowledge and dress like a ‘20s fashionista. Try this hairstyle to complete your vintage ensemble and don’t forget an appropriate headband.

7. Vintage Ponytail

Don’t ever underestimate the power of a ponytail. It may be the simplest style of all time, but there are various ways to spice it up. Take this lovely style as an example. A retro twist on the classic ponytail leaves you with a chic hairstyle for any occasion.

8. My Fair Lady Inspired Vintage Updo

Eliza Doolittle, anyone? If you haven’t been feeling particularly feminine or beautiful lately, do what she did and dress to impress (just do it on your own terms, ladies!) This My Fair Lady inspired hairdo is the perfect thing to liven up your style slump.

9. Pin-Up Swirl Updo

This sleek swirl is easy to mimic from the comfort of your own home. Section off the front middle section of your hair, that’s all you’ll need for your swirl! Lightly curl the ends, use hairspray and backcomb to create volume. Then simply rearrange the hair into the swirl and pin it into place.

10. Vintage Updo For Natural Hair

Rocking natural hair is always a nice break from heat styling and stressing over the perfection of your locks. The next time you skip the blowdry, try out this elegant updo before hitting the town. With your hair pulled back, earrings will be doubly noticeable, so choose your favorite pair.

11. Gatsby-Inspired Updo

Start taking notes on that Daisy Buchanan costume. Here’s another option for your hair if you decide to be Gatsby’s love interest next Halloween. This updo is accomplished with a headband and softly curled hair, and it gives off the flapper-esque vibe needed to be Ms. Buchanan.

12. Back Roll Vintage Updo

All you need to recreate this gorgeous back roll at home is a pretty scarf. Begin by tying it over your hair so that it circles from the base of your head to just above your hairline. Pin it into place. Finish the style off by tucking the hair into the scarf for a picture-perfect roll.

13. Rolled Updo With A Flower

This look is all about finishing off your hairstyle with flare. Back in the day, it wasn’t uncommon for ladies to pin flowers into their elaborate updos for a more finished look. The next time you choose a retro style, be sure to try the old trend out yourself.

14. Twisted Vintage Updo On Natural Hair

Here’s another cute updo for black hair. This gorgeous style can be worn out and about or for a relaxing night in with your boo. In the summer, this is a great hairstyle to stay cool and keep the hair out of your face.

15. Rockabilly Roll Hairstyle

Check out this cute ‘do! The front roll is the perfect addition to a simple high ponytail to give your hair some individuality. To achieve this volume, spray pieces of the front section with hairspray and backcomb to your heart’s desire. There’s no such thing as too much volume. Be careful not to flatten the achieved roll when you are smoothing it out!

16. ‘20s Inspired Vintage Updo With Finger Waves

If you’ve ever watched an old timey black-and-white movie, then you know what real finger waves are. This style is all about getting your hair set correctly. Wet the front pieces you’ll be working with and clip them into the proper wavy spots, spritzing some hairspray to keep them in place. With finger curls, you’ll turn any old updo into a vintage masterpiece.

17. Flirty ‘50s Updo

Here’s an idea for future brides to consider. If you’re having a vintage themed wedding or even if you’re just incorporating classic styles into your big day, try this hairstyle on your maids of honor. Pair it with a retro inspired dress, preferably something above the knees. They’ll look positively adorable!

18. Fancy Rosettes Vintage Updo

So you’ve got a big night coming up. It could be anything you’re excited about—an art show, a first date, a recital. The point is you want to look especially put together and impressive. This vintage hairstyle will surely do the trick! Swipe on some cherry red lipstick to complete the look and you’re ready for anything!

19. Vintage Roll Hairstyle

Rolls and twists were very common in previous decades; that’s why so many of these styles boast big voluminous swirls of hair. It can be fun to fuss around in front of the mirror until you get it right, but sometimes you won’t have time for that. For a more low-key vintage hairstyle that won’t take all morning to style, try this effortless roll.

20. Crisscross Vintage Updo

This is a fun updo that creates the illusion of a complex style while it’s actually based on two braids and a jumble of hair pinned up into messy perfection. Be sure to find a bow to top off your look! Nothing quite says ‘styled and put together’ like a bow.

Options, options, options! Choose your favorite decade and take a trip back in time with one of these vintage updos.