The most beautiful headbands, styling tips & matching hairstyles

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I already mentioned it once, but I’m going to say it again: Headbands are one of the biggest accessory trends of 2019! While in the last few years, we saw headband, if at all, only on little school girls, or maybe some nostalgic vintage fans like me, they are the new it-piece for fashionistas, now. So I guess the wisdom “everything comes back into fashion one day” really is true. And what looked great on the ancient Romans, Greeks, the ladies of the Middle Ages, the 1920s flappers, and on Blair Waldorf, still looks amazing in 2019. 😉

The trigger of this latest headband hype most likely is Prada. They already dressed their models with headband when showing their spring/summer collection, and the trend isn’t over, yet. So in this blogpost, I’m going to introduce the most beautiful headband for different occasions, tell you how to wear them, and show matching hairstyles. I’m an absolute headband pro, by the way. Until I was about 14, I wore headband every single day. I had a huge collection and wore them with braids, ponytails, or just in a classy way. So you definitely can trust my headband-style-advice, that’s for sure. 😛

The most beautiful Headbands: Huge Headbands that add that certain Something

Huge handbands that migh even be padded and therefore resemble the French hood literally crown your outfit. Depending on what you like, you can either choose plain ones or decorated ones. For everyday life or work, you migh prefer a “flat” hairband.

What to wear with huge headbands: These kind of hadbands really can be worn with many different outfits. Here are just a few examples.

  • Flat, wide headbands look amazing when worn with 1960s inspired outfits and add that certain something to everyday looks.
  • Largely decorated headbands can either be worn as a breach of style with jeans and t-shirt, but also look great with elegant and even evening outfits.

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The most beautiful Headbands: Flower & Fruit Details

RetroCat trägt einen Haarreif mit Früchten aus den 50ern

Die schönsten Haarreifen: RetroCat trägt einen schwarzen Blumenkranz zum düsteren Outfit

Floral headbands are at least as beautiful as huge headbands and definitely look fresh and fun. If you like the dark look, you can also choose black roses like I did.

How to team floral hairbands:

  • Colourful ones look amazing in combination with a dirndl and are a perfect accessory for Oktoberfest.
  • Furthermore, they make every retro outfit look even more beautiful and are a wonderful accessory for summer and early autumn.
  • Dark headbands worn in combination with a black dress look very autumnal and even go well on Halloween.

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The most beautiful Headbands: Glamorous, thin Headbands

Thin, sparkly headbands always look super glamorous and make every outfit immediately look more elegant. Beside sparkly ones, I also like headbands with pearls, by the way.

What to team with sparkly headbands:

  • Thin, but glamorous headbands look amazing together with evening gowns or elegant dresses.
  • For an elfin look, team your thin, sparkly headband with a tulle dress.
  • Sparkly headbands can also be worn with a daytime outfit, and even look amazing together with a striped shirt.

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The most beautiful Headbands: Cat Ears & other fancy Headbands

Die schönsten Haarreifen: RetroCat trägt ein Modell mit Katzenohren

If you are brave enough, you can also wear cat ears or similar fancy headbands. These kind of accessories are definitely head-turners and always should be worn with a twinkle in ones eyes. 😉

What to wear with cat ears: If you don’t want to look like a child, you definitely should team such kind of headbands with grown-up outfits:

  • Cat ears look great in combination with the little black dress, for example. The outfit will still look elegant, but a bit more cheerful. 😉
  • Chic, elegant trousers, stylish tops, and pretty dresses might look great in combination with cat ears as well.
  • What you shouldn’t team with such headbands are very girly outfits/dresses. It is better to wear cat ears as a breach of style, together with a classy outfit and grown-up makeup.

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The most beautiful Headbands: Decorated Headbands or Fascinators

RetroCat trägt einen Haarreif/Fascinator zum blauen Kleid

Last but not least, decorated headbands are able to lift every outfit to the next level. Depending on how decorated headbands are, they might even be called fascinators. However, I really like these kind of headdress and therefore didn’t want to miss it in this blogpost. There are so many different options available, that I wrote a full blogpost only about fascinators, so have a look here for further information. 😉


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What Hairstyles to wear with Headbands:

In general, headbands look great with almost every hairstyle. There are hairstyles, though, that go especially well with this kind of headdress. So here are my best tips:

A (huge) Bun

RetroCat trägt einen Dutt zum schmalen, eleganten Haarreif

A Bun looks very elegant and goes so well with headdresses. Depending on your preferences, you can wear a low or high bun – both will look great. 😉

And this is how to master the bun: Start with a ponytail that is placed either low or high, depending on your preferences, on the back of your head. Afterwards, put a so called hair donut over your ponytail and place your hair around it. Pin everything and put on a hairnet around the donut to fix the hairstyle. Now, you only need to add your headband and your wow-look is finished.

By the way: hair donuts are available in a lot of different sizes and colours. The bigger the bun, the more exciting the hairstyle. Also, make sure to use a donut close to your haircolour.

What headbands to wear with a bun: This hairstyle is an all-rounder and looks great with every kind of headband.


The Gibson Roll

RetroCat trägt eine Gibson Roll zum Fascinator mit Feder von Faunauge

The Gibson Roll has its roots in the Edwardian era and came back into fashion in the early 1940s. Which acutally is no surprise, as the hairstyle is practical, looks beautiful, and keeps the hair out of the face – perfect for the working women during war time.

And this is how it works: As my hair is quite short, I love to use a little gadget that makes it look more voluminous: A hairband with a little roll*. So the only thing I have to do is rolling my hair around this hairband-roll and pin it with some hairpins. Now, add your headband and you are ready to go.

What headbands to wear with a Gibson Roll: The Gibson Roll looks great with vintage inspired headbands decorated with feathers, or together with a French hood like headband.


Wild Curls & pretty waves

Vintage-looking waves and curls always remind of the 1920s to 1950s look. Depending on the look I want to achieve, I choose the kind of rollers I use for the hairstyle. For wild curls, I use small foam rollers*, for soft curls or waves, I prefer soft sleep-in rollers*. No matter what kind of rollers you use, the next steps are the same. I usually put the rollers in my hair in the evening, after washing them, when my hair is still moist, but no longer wet. A huge silk scarf around your head will help to keep everything in place while you are sleeping. In the morning, I check if my hair is completely dry. If not, I use a hairdryer. If your hair is still wet when putting out the rollers, your curls most likely will hang out in no time.

After putting out the rollers, I brush* my hair. The longer you brush, the softer will be the curls. So just stop when your hair has the shape you desire. Afterwards, you can use some pomade to get those baby hairs under control. PS: handcream is a good alternative to pomade. 😉

What kind of headbands to wear with wild curls or soft waves: Wild curls often remind of the 1920s to 1930s and therefore go very well with thin, sparkly headbands. Softer curls or waves look amazing with every kind of headband.


A 1960s inspired Beehive

RetroCat trägt einen Haarreif mit Katzenohren zum Beehive im Stil der 60er-Jahre

A beehive simply looks amazing together with a headband. For this look, you have to backcomb the hair at the back of the head. Depending on how high your beehive should be, you have to backcomb more or less, and maybe even add a foam pad or artificial hair. Definitely make sure to use enough hairspray and pin the upper part of your hair at the back of your head. If you like, you can let some strands fall down to your face.

What kind of headband to wear with a beehive: This kind of hairstyle look great with all the different types of headbands, but for an authentic 1960s inspired look, I would choose a wide one.

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