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With all of the Fashion Weeks over and done with, we’re happy to that they delivered fall/ winter 2019-2020 hat trends that we’re going to be happy to wear! The fall 2019 runway hats were crafted by expert milliners to be wearable yet beautiful, with some odd exceptions sprinkled in.


Fall/ Winter 2019-2020 Hat Trends


If you’re expecting an extra snowy winter in the coming year (and many of us are thanks to climate change), then you will likely appreciate the extra cozy beanies, fuzzy hats, and trappers that were so ubiquitous. The fall/ winter 2019-2020 hat trends gave a real new style to embrace: updated bucket hats or cloches will be the perfect choice for those wanting for something new and stylish to spice up their autumn look.

Casual old school hats like berets, newsboy caps, and Sou’westers were also notable fall 2019 headwear trends, and we’re even surprised that we didn’t mind the comeback of the fedora! Lastly, but certainly deserving of a mention, are those hats that were wacky and odd – the fall 2019 runway hats that everyone will talk about, but only the brave will actually wear.


#1. Cloches and Bucket Hats

The bucket hats last season were as lively and casual as can be, coming in bright colors and covered in prints. Sophisticated bucket hats may sound like an oxymoron, but these are exactly the kinds of hats we saw for the fall 2019 headwear trends. This season bucket hats came in a slightly more solid, mature form that also ended up blurring the lines between a cloche, a bell-shaped women’s hat from the ‘20s, and the more casual bucket.

The truest bucket hat shape was used on the Christian Dior runway, where models wore flexible bucket hats in leather or printed fabric to match their outfits, and looked as ladylike as possible.

At Emilio Pucci, bucket hats were a little wacky. One was white and the other was antique moss, and both were embellished with two layers of fringe that surrounded the crown. Adorable bucket hats at Vivetta were covered with floral prints, and came fit with straps that were tied around the neck like chokers.

Fall/ Winter 2019-2020 Hat Trends: Cloche & Bucket Hats


#2. Beanies and Toques

Popping on a beanie or a toque is usually the go-to choice for protecting the head and ears as the weather gets cold. These hats are suited for everyone, but it’s undeniable that they are as casual as can be, or at least they were until the fall 2019 headwear trends came along. The knitted cap was all dressed up this season, to become a high fashion item.

At Versace, for example, knitted caps made of fuzzy yarn were fancied up by the addition of large, bejeweled brooches. Knit beanies were given the Marc Jacobs treatment with all kinds of feathery decorations that matched the gowns they were paired with.

The knitted beanies at Missoni were totally gorgeous, as can be expected from a label that knows how to source the best yarn. The shimmery beanies sat tight against the hat, with the bottom rolled up chunkily. Urban brand Zadig + Voltaire as well as Coach 1941 also presented their takes on the toque, which were more casually styled.


Fall/ Winter 2019-2020 Hat Trends: Beanies & Toques

Fall/ Winter 2019-2020 Hat Trends: Beanies & Toques

#3. Caps

From tight swim caps to elegant caps to pair with an evening gown, this old-school piece of headgear is one of the more unique breakout fall/ winter 2019-2020 headwear trends.

Tight leather caps at Louis Vuitton had an oddly sporty effect, since they looked like the crown of a baseball cap, sans brim. The caps at Saint Laurent are the ones that reminded everyone of swim caps. They were made of velvet and sat extremely close against the head, but they were given a glamorous touch by the addition of crystal embellishments.


A draggy take on the 1920s was aided by the neon-colored jewel-studded caps that models wore at the Christian Cowan show. The effect of caps at Kate Spade also reminded us of the roaring ‘20s, but in a more restrained way. Made of silk, these caps were delicate and ladylike.

Fall/ Winter 2019-2020 Hat Trends: Caps

#4. Fedoras

Fedoras developed a pretty bad reputation in recent years, and perhaps unjustly – the true hat many scorned was actually the trilby, which has a narrower brim. However, in many instances the issue really was with fedoras, which were styled poorly with overly casual ensembles. The fall 2019 hat trends give you permission to rock a fedora again, as long as you get the styling right.

Take heed of the Chanel runway, where a tweed fedora was matched to a slouchy tweed suit and a long, timeless trench coat. At Saint Laurent, gorgeous silk fedoras in various colors were worn with dark party clothes that were both slightly masculine and also very sexy.

There were plenty of fedoras at Dolce & Gabbana, which happened to be just slightly oversized. The fedoras, which were either solid or beautifully printed, were matched to the suits or trench coats the models wore, keeping the overall look tailored yet masculine.

Fall/ Winter 2019-2020 Hat Trends: Fedora Hats

Fall/ Winter 2019-2020 Hat Trends: Fedora Hats

#5. Newsboy Caps

Also known as a newsie or a Gatsby hat, this vintage style was once associated with working class boys. It adds a fun addition to a list of fall 2019 runway hats that were historically masculine, but only as long as we can avoid styling these hats like we did in the early 2000s.

Plaid Gatsby hats at Michael Kors were worn with matching suits in a way that contributed to the ‘70s vibe of the collection. Leather newsboy caps at Sally LaPointe were made of leather, and matched to soft, monochrome outfits, lending them a bit of edge, while a little black leather newsboy hat at Balmain gave off punk vibes, thanks to its material as well as a smattering of small metal spikes all over its crown.

Fall/ Winter 2019-2020 Hat Trends: Newsboy Caps

Fall/ Winter 2019-2020 Hat Trends: Newsboy Caps

#6. Berets

There is much more to berets than the French mime stereotype would lead you to believe – and why are mimes French anyway? I digress, the fact of the matter is that the fall 2019 hat trends are bringing back berets in interesting ways that break stereotypes.

In fact, the only berets to give us that cool French girl vibe were the leather ones that showed up on the runway of Australian label Zimmermann. For winter, we really loved the slouchy knitted berets at Michael Kors, which contributed a touch of coziness to the atmosphere of the runway.

The black berets at Simone Rocha were decorated with a shiny, beaded embroidery, which gave the hats a feminine touch. Instead of being worn traditionally, the berets were styled to sit high on the forehead and obscure the hairline.

Berets at Acne Studios and House of Holland sat high on the head and were low on bulk, so they ended up reminding us of military berets.

Fall/ Winter 2019-2020 Hat Trends: Berets

Fall/ Winter 2019-2020 Hat Trends: Berets

#7. Oddly Cute and Just Plain Odd

Every season it’s important to expect a few really weird creations, with some of the most exciting oddities being hats, of course! These are the strangest fall 2019 runway hats that we saw.

On the adorably odd side of things we have the animal ear caps at Loewe. So while the effect was perhaps not fully intentional, the result certainly reminds us of a mouse or a perhaps a long-eared dog with its ears perked up. This effect was achieved by attaching raised panels to the inner part of the cap, as well as another similar embellishment right at the top.

Who could imagine strange headgear at Gucci? Literally everyone! Alessandro Michele delivered some truly bizarre creations, including a bucket hat with a visor over the face, and a cap decorated with a bow from which a rhinestone fringe cascaded down over the face.

Sun hats at Vivetta seemed to be made for women truly afraid of exposure. The low-brimmed hats covered the face, but were fitted with two eye holes so as not to blind the wearer. Decorated with ribbons, these hats were cute but weird.

The hats at the Matty Bovan show were actually the result of a collaboration with Coach, so they combined the earth tones of the latter with the zaniness of the former. The result was a cap with fur-lined hoops extending out horizontally from it and a fur hat augmented with oddly placed (and ineffective) ear flaps, and decorated with massive tassels.

Fall/ Winter 2019-2020 Hat Trends: Odd Hats

Fall/ Winter 2019-2020 Hat Trends: Odd Hats

#8. Warm Fuzzy Hats

Furry coats, furry bags for fall 2019, furry boots, even furry fall 2019 hair accessories, and yes, also furry hats. This may not be the most animal friendly of the fall/ winter 2019 hat trends, although some of these furry hat options were made of cruelty-free faux fur.

Andreas Kronthaler for Vivienne Westwood delivered massive faux fur hats that were shaped like bowls, and in some instances even looked like wigs. At Fendi, horse racing helmets were given a cozy touch, covered as they were in black, white, or brown fur.

Hats adhered to a few of the fall/ winter 2019-2020 hat trends at Anna Sui, as they were elongated, covered in an animal print, and as fuzzy as can be. We never would have thought that a fuzzy hat could be dapper, but then we saw the hats at Tom Ford. Brimmed fuzzy fedoras were ultra-stylish, worn as they were on a devil-may-care angle.

Fall/ Winter 2019-2020 Hat Trends: Fur Hats

#9. Elongated Hats

One of the more dramatic fall/ winter 2019-2020 hat trends is the elongated crown. Crowns were elongated on a variety of hat styles, giving the sense that hats were either oversized or a little witchy.

Models wore elongated bowler hats at the Ann Demeulemeester show, which came mostly in black but also in red and white, and sort of reminded us of top hats but with a rounded crown.

The Valentino runway was opened with models wearing elongated cloches. These hats, which were sprinkled throughout the rest of the show as well, had brims so long that they obscured the faces of many of the models. They came in a variety of solid colors and prints.

Elongated cloches were also the headwear of choice at Nina Ricci, although these ones were extra-wide to boot. Both the brim and the crown on fedoras at Hellessy were quite long, so these hats also obscured the face in some instances. Made of suede, they contributed an old West feel to the Americana theme.

Fall/ Winter 2019-2020 Hat Trends: Elongated Hats

Fall/ Winter 2019-2020 Hat Trends: Elongated Hats

#10. Sou’wester Hats

The Sou’wester is a fisherman’s hat from the UK that has an elongated brim in the back. It is intended to protect the wearer from damp south-western winds. No one can take a fisherman’s hat and make it fashion than the continental fashion houses.

Sou’wester hats at Lanvin came in suede or silk, and were even paired in some instances with fishing-related garments. At Emilio Pucci, these fisher hats were made of sleek leather or satin and paired with glamorous outfits, showing that they really could be an elevated headwear option.

Fall/ Winter 2019-2020 Hat Trends: Sou'wester Hats

#11. Baseball Caps

Make no mistake, it’s not your dad’s baseball cap collection that’s coming back in style. The baseball hats that are part of the fall/ winter 2019-2020 hat trends are well-thought out and beautifully constructed, in order to fit with a variety of personal styles that go beyond the sporty or urban.

Brimmed caps were the hats of choice at Off-White. These hats sparkled with silver sequins, and were worn with both professional and casual wear.

The grown-up leather baseball caps at Sportmax are going to be a minimalist urban hit, since they pair very well with all the leather items this season was filled with.

Lastly, we gotta talk about hat headbands at J.W. Anderson. These structural baseball caps were attached to the head via a strap, so they ended up suspended over the cap-like hair of the models.

Fall/ Winter 2019-2020 Hat Trends: Baseball Caps

#12. Trapper Hats

Trapper hats, sometimes known as aviator caps or if they’re particularly furry as ushankas, are caps with large ear flaps and sometimes a strap to go around the chin. They’re excellent for cold climates, since they protect the ears well, and are particularly warm when lined with fur.

If you’re a true fashion slave, then one of the croc-embossed trapper hats at Versace will surely win your heart. They came in either the black or brown, with faux-fur lined flaps.

Leopard print trapper hats at R13 had an urban, ‘90s winter in New York vibe, and coming in both fur and puffy polyester they seemed as warm and insulating.

Fall/ Winter 2019-2020 Hat Trends: Trapper Hats

#13. Veils

Veils were surprisingly plentiful for spring, and the trend carried over slightly into the fall 2019 headwear trends. At Dior, for example, a length of fishnet veil was loosely wrapped around the brim of the ubiquitous bucket hats, adding to their sophistication.

In addition to the masculine fedoras at Dolce & Gabbana there were also some feminine caps with a black net veil applied over the front to cover the face. Seeing models in slinky dresses and veils followed by models in suits and fedoras definitely brought to mind film noir tropes of black widows and hardboiled detectives.

The effect of face-covering netted veils at Erdem was also sombre, with the veil gathered slightly above the head to add texture, and falling over the face, and in some instances all the way down to the floor.

Fall/ Winter 2019-2020 Hat Trends: Veiled Hats

#14. Shimmery Hats

Shimmer and shine are a great way to spark joy. A touch of sparkle made it on to some of the fall 2019 runway hats, albeit in a few different ways.

The shimmery hats at Rodarte were made to sparkle thanks to delicate beaded embroidery, although one sunhat was simply made of a shiny silver material.

Dolce & Gabbana, kings of bling, actually offered hats that were a little subtler than usual (they more than made up for it with their opulent fascinators, though), so the sparkle on their hats, including berets and fedoras, came from a shimmery golden thread used to embroider them in a brocade technique.

We’ve already mentioned the ultra-sparkly silver baseball caps from Off-White, but they were fabulous enough to merit a second mention.

Fall/ Winter 2019-2020 Hat Trends: Shimmery Bejeweled Hats

Photos via Vogue, Livingly