The most beautiful hats for autumn and winter

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Rain, wind, and weather – while our summer hats are made to protect our head from the sun, hats for autumn and winter face completely different challenges. Of course, they should look pretty, and protect the hairstyle. Furthermore, it would be great if the are weatherproof, and protect our ears from freezing. The good news: There is a great variety of hats for autumn and winter available, so I’m sure everyone finds something suitable. In the following, I’m going to show you the in my opinion most beautiful hats for autumn and winter, and tell you when to wear and how to style them.

Hats for Atumn & Winter: What to keep in Mind & where to buy them

Before showing you the most beautiful summer hats, I want to give some advice on what to keep in mind when buying hats for spring and summer.

  • Felt hats are a classic for autumn and winter, that’s for sure. If they are made of high-quality felt, they are usually waterproof and therefore a perfect choice for the cold season.
  • Always make sure your hat fits you perfectly. Just a gust of wind and your hat may fall down to the street, if it is too big. So fix your hat with a ribbon or hatpin, if necessary. If your hat, on the other side, is too small, it feels very uncomfortable and can even lead to headaches.
  • Although most felt hats are not as sensitive as most straw hats are, they don’t like it when they get pleated or squished. So it is best to store them in a separate rack in your closet or a specific hat box.
  • I want my hats to be beauitful, unique, and last a lifetime. So I personally always recommend high-quality hats, which can’t be seen on every second head. I recommend to visit a millinery (in Munich, like Nicki Marquart, for example), or search in vintage stores for unique vintage hats. Platforms like Etsy or Ebay are good places to search online for vintage hats.
  • Here are some online hat shops I can recommend that have a great variety of especially vintage inspired hats:

Pretty Hats for Autumn & Winter: Fedora & Trilby

RetroCat mit einem lila Fedora im Herbst

Fedoras and trilbys are a wonderful choice for autumn and winter, as they look stylish, cool, and are able to add that certain something to every daytime outfit – no matter if your outfit looks very feminine or quite masculine.

Shop Fedoras & Trilbys:

Styling tip: I like to team fedoras with swing skirts and blouses – just like women in the 1940s did. But of course this hat also looks great in combination with trousers and even jeans and t-shirt.

Beautiful Hats for Autumn & Winter: Berets

RetroCat mit rotem Kleid und schwarzer Baskenmütze für den Herbst

Berets are super easy to combine, perfect to keep your head warm, and are even able to cover a bad hair day – a real must-have for autumn and winter!

Shop Berets:

Styling tip: Berets go well with a lot of different outfits. Depending on the style of the beret, they look great with elegant outfis as well as more casual ones. For a cheeky look, wear the beret near to your face at a tilt, if you want to cover your hair, simply tuck it in and wear the beret at the back of your head.

Beautiful Hats for Autumn & Winter: Turbans

RetroCat mit einem Turban im Vintage-Stil - perfekt für den Herbst und Winter

Turbans are an elegant and a bit more fancy alternative to berets. They keep you warm, look stylish, and can even be super glamorous if teamed with sparkly accessories like brooches.

Shop Turbans:

Styling tip: Turbans go very well with elegant, vintage inspired outfits and can be worn with both, daytime and evening attire.

Beautiful Hats for Autunn & Winter: Cool Hats with a Bill

RetroCat mit Blazer und 50er-Jahre-Hut mit Schild

Hats with a bill look cheeky and cool and are perfect to add that certain something to everyday outfits.

Shop cheeky Hats with a Bill:

Styling tip: These kind of hats make dresses look cooler, but also go very well with more casual outfits. I especially like to team them with swing trousers, blouses, and blazers.

Beautiful Hats for Autumn & Winter: Stylish vintage inspired Felt Hats

Hüte für Herbst und Winter: RetroCat mit einem stylishen Filzhut im Vintage-Stil

Felt hats are available in all different kind of shapes and colours. I especially like vintage inspired ones with cheeky details and a unique look. My beautiful felt hat, for example, is by “My wunderbarer Hutsalon” and inspired by the style of the 1930s.

Shop chic vintage inspired Felt Hats:

Styling tip: Such hats simply look amazing in combination with vintage (inspired) outfits, no matter if this consists of a dress, skirt and blouse, or wide trousers.

Beautiful Hats for Autumn & Winter: Giant Hats

Hüte für Herbst und Winter: RetroCat mit einem riesigen Hut im Stil von Audrey Hepburn

Giant hats inspired by Audrey Hepburn alias Holly Golightly in “Breakfast at Tiffany’s” are real head-turners and definitely only for brave vintage girls. Mine, by the way, also is by “Mein wunderbarer Hutsalon*”. To be honest, this kind of hat isn’t really made for everyday life. It looks amazing on special occasion, though, or if you simply want to be an eyecatcher.

Shop giant Hats a la Audrey Hepburn:

Styling tip: I recommend to team such giant hats with a chic but simple little black dress. This looks stylish, and doesn’t steal the show from the hat.

Beautiful Hats for Autumn & Winter: Hats without a Brim (Cloche)

RetroCat mit Vintage-Hut ohne Krempe im Winter

Hats withoug a brim, also called Cloche, appeared in the 1920s and were very fashionable back then. I especially love them as they look super stylish and chic, but are also suitable for everyday life.

Shop Cloches:

Styling tip: This kind of hat looks great in combination with elegant coats, chic dresses, as well as cool blouses. They are quite easy to combine and, of course, go very well with outfits inspired by the 1920s to 40s.

Beautiful Hats for Autumn & Winter: Pillbox Hats

Hüte für Herbst und Winter: RetroCat mit einem Pillbox-Hut von Miranda's Choice

If the weather is not too bad, I love to wear a pretty pillbox hat and team it with elegant outifts. Subtle pillbox hats look great with daytime looks, while more fancy ones can also be worn for evening occasions.

Shop Pillbox Hats:

Styling tip: You will find a lot more information about the pillbox, and stylings tips for this hat here.

Beautiful Hats for Autumn & Winter: Crazy Fascinators with Feathers & Co.

Hüte für Herbst und Winter: RetroCat mit einem Fascinator mit Feder von Faunauge

If you leave the house with a fascinator on top of your head, you have to be brave, as this kind of headdress usually gets all the attention. Nevertheless, I really like them. In autumn, I especially love warm-coloured ones with fancy details like feathers, for example. Fascinators are perfect for special occasions, but of course you can also wear them in everyday life, this is completely up to you. 😉

Shop fancy Fascinators:

Styling tip: Depending on which kind of fascinator you are wearing, you can either team them with very elegant outfits, or, just like I did here, with a more rustic-style look.

Beautiful Hats for Autumn & Winter: Small Cocktail Hats

Small cocktail hats are perfect for evening occasions and of course are a perfect companion for festive season. Depending on my mood and the occasion, I either choose a subtle, plain one, or a fancy one with veils, sequins, and lots of frills.

Shop elegant Cocktail Hats:

Styling tip: While more subtle cocktail hats can even look great in combination with daytime outfits, sparkly and more fancy ones are perfect for evening occasions. I love to wear the latter together with elegant evening gowns and classy accessories.

How to pimp your Hat

Hüte für Herbst und Winter: RetroCat mit einer verzierten Baskenmütze im Winter

Hats already look amazing and really can lift your outfit to the next level. With some simple and easy tips, though, you can even pimp the most beautiful hat:

  • I like to wear my hats at a tilt low on the face, just like the ladies of the 1930s used to. This makes the look cheekier and more stylish.
  • hairflower (from SophisticatedFlowers*, for example) clipped to the hatband makes your hat immediately look more extravagant. In autumn and winter, I usually choose flowers like roses or some autumnal leaves.
  • For a more glamorous look, I like to decorate my hats and turbans with a sparkly brooch. You will be surprised what a difference such a small piece of jewellery can make!
  • If you wear your hair in a snood underneath your hat, your look will immediately look more “vintage”.
  • If you are a DIY queen, you can also decorate your hat with netsveils, and accessories like velvet bows.

What about you? Do you like hats? And which kind of hat do you like most?

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