Another bad hair day? Wearing a perma-ponytail? With these 19 different types of hats – and style tips on how to wear them – you’re covered!
Athleisure, anyone? A favourite on the runways of the likes of Alexander Wang and Fenty, the baseball cap has recently become one of the hottest headgear to own. Simple, casual and easy to wear, baseball caps feature a medium sized bill that is usually curved and a little button on the top.
Work it: A baseball cap is so versatile, it looks good with almost any outfit, but we love it with a pair of skinny jeans, ankle boots and a leather jacket for that model off-duty look. If your look calls for a touch more glam, opt for a satin finish baseball cap instead.
NEXT: Beanie →
Right out of the 90’s, the beanie is a knitted cap that basically resembles a sock for your head. They can be tight fitting, or have a longer crown that slouches down the back of your head, with more feminine variants featuring a little pom-pom on the tip.
Work it: This style of hat is usually worn in colder climates as it helps to keep your head warm, and might be a touch too hot for Singapore’s weather! If you must rock it, we suggest choosing one made out of a thinner fabric. Pair it with a crop top and a pencil skirt in monochrome hues, and add some glam factor with a pair of heeled mesh booties.
NEXT: Beret →
Sometimes called a ‘flat hat’ a beret is a round, soft, flat hat with extra material around the edges, giving it that extra ‘pouf’. This style of hat is associated with elegance and style and of course typically associated with the French, inspiring many ‘mademoiselle-esque’ looks.
Work it: Think a chic French lady sipping her café au lait at a bistro in Paris. As the French do, keep it effortless and trés chic by pairing with a boat neck top (stripes optional) tucked into a pleated midi skirt, or high waist sailor jeans. Finish your look with a red lip and a sleek ponytail.
NEXT: Boater →
Also called a ‘skimmer’, the boater is traditionally made of straw, featuring a small to medium sized brim, a short crown and a flat top. From ribbons to even feathers, modern day boaters with all sorts of embellishments are easy to find.
Work it: This is a great hat for brunch under the sun, so think casual chic when styling. Pair it with a light sundress and strappy sandals, or with a kimono, t-shirt and shorts combo and don’t forget the oversized sunglasses! The chic boater also looks great with a sleeveless button-up shirt and tailored pants, if you plan on wearing it for a more serious occasion.
NEXT: Bowler →
This hard hat is usually made of felt, featuring a short brim that of about 2 inches and a high, rounded crown. If you think it looks familiar, you’ve probably seen a Charlie Chaplin flick.
Work it: It may be a hat that was popular in the early 1900’s, but bowlers are slowly making a comeback, favoured for its elegant, formal look. We say take a leaf out of Charlie Chaplin’s book and style it with a more masculine outfit: Think cigarette pants, a well fitted t-shirt and a sharp blazer.
NEXT: Bucket Hat →
Featuring a downturned brim made of a softer material, it is as it’s name suggests: an upturned bucket. While many are (understandably) apprehensive about this style, it’s been spotted making rounds at festivals and in the music scene, with major brands like Carhatt and Fred Perry releasing their own versions. Translation: it’s cool again.
Work it: Definitely opt for a streetwear-inspired look with this hat. Think joggers, cropped tops and a bomber jacket, finished off with a pair of strappy heels or stiletto ankle boots for a touch of glam. We recommend choosing a bucket hat with an interesting print or pattern to add a touch of fun to your outfit, but if you prefer a little subtlety, opt for one with a printed underside instead.
NEXT: Chullo →
Sometimes referred to as the Peruvian beanie, the chullo hat is easily recognized by its knitted fabric in Aztec patterns, a pom pom on the top and two tassels that hang off the bottom of the ear flaps on either side. There is hardly a need for this hat in our part of the world, but is a cute must-have if you’re visiting the northern hemisphere.
Work it: This hat is a little louder than most winter options (unless we’re talking a full on fur cap), so we suggest styling it with a more toned down outfit. Think elegant neutrals like camel or grey in clean lines, and materials like cashmere for an overall polished look.
NEXT: Cloche →
Shaped like a bell, the cloche (French for ‘bell’) is a close-fitting hat that is rounded at the top that gently flares at the bottom. It has become a popular style in recent years and is available in a wide variety of materials, from straw to wool.
Work it: Get inspired by this hat from the flapper era and style your cloche hat with a fringed dress, sheer leggings and flats. For a more modern (and office friendly) take, style it with a turtleneck top and a pencil skirt in neutral tones. If you are in a colder climate, the cloche looks amazing with a pea coat and gloves.
NEXT: Cowboy Hat →
This American icon is hard to miss, with its turned-up brims and pinched crown. They are typically made of felt, leather or straw, and feature a strap that you can secure under your chin (so it doesn’t blow off while you’re horseback riding).
Work it: While we don’t really recommend wearing this hat to work, cowboy hats can be a fun addition to a festival outfit, where anything goes. Pair it with a maxi kimono worn over high waist denim shorts, a bodysuit and knee-high cowboy boots, and keep your hair in loose curls or braids. If you are more daring, pair it with a chic, all denim outfit (skinny jeans and a well fitted denim shirt) and ankle boots for a modern take on the old, wild west.
NEXT: Deerstalker →
Basically, the hat that Sherlock Holmes is often depicted in. Usually made of wool in a plaid or houndstooth pattern, the hat features several panels with rounded sides, and a visor in the front and back.
Work it: Get inspired by the world’s most famous detective, and match your deerstalker to your trousers. Keep the rest of your look simple with a well-fitted tailored blouse and flats, and nude makeup.
NEXT: Fascinator →
After Kate Middleton and Prince William’s wedding, suppliers couldn’t make these hats fast enough! Seen on many guests at the royal wedding, the fascinator is a quintessentially British headband style hat with embellishments attached to it that can range from understated to extremely ornate. They can be worn as a headband, or clipped to the hair.
Work it: Don’t we wish we constantly had occasions to wear the fascinator to! This style of hat works best at weddings, balls or any other event that requires fancy dress. We recommend an elegant black shift paired with a fascinator with netting detail for an Audrey Hepburn vibe, or a more ornate, flowery number with a fit-and-flare dress.
NEXT: Fedora →
One of the most easily recognizable hats, the fedora is a classic hat that features a short to medium sized brim that is upturned in the back. This style of hat suits most face shapes, and comes in many materials from straw to felt.
Work it: This style chameleon is suitable for a number of occasions. Think straw with flowing summer dresses in warmer climates, and wool in a dark hue with a leather jacket and skinny jeans in colder temperatures. A fedora instantly smartens any look, and is appropriate for the more casual offices.
NEXT: Flat Peak Cap →
AKA the snapback, a flat peak cap is similar to a baseball cap, except the crown tends to be stiffer and is designed to be fitted, available in gradual size increments. In some circles, some brands of flat peak cap are considered collectables, with some brands releasing limited edition versions yearly.
Work it: If you’re aiming for the ultimate off-duty look, then why not pair your snapback with a pair of well-fitting denim overalls and a cropped, sleeveless top under, and finish off the look with a pair of strappy sandals. You can also wear it with a t-shirt dress, ankle boots and a shirt tied around your waist.
NEXT: Floppy Hat →
The popular big brim or floppy hat features a floppy brim that can reach up to 10 inches, providing excellent shade from the sun while oozing beach chic. The straw variation of this hat is most frequently seen on the beaches of Bali, Australia and Thailand, while woolen or felt versions in colder climates.
Work it: Depending on your location, the floppy hat makes a great addition to any outfit! If you’re hitting the beach bars, pair your floppy hat with a sexy one-piece and gladiator sandals with a light robe and simple accessories. If you’re in a colder city, a felt version will help to keep your head warm while elevating a basic outfit of jeans, knee high boots and an oversized cardigan – keep everything in neutrals for a super polished look.
NEXT: Newsboy Cap →
Featuring a flat, large, rounded crown and a small brim in the front, a newsboy cap is typically finished with a button on top. This vintage cap is back in fashion, with Pinterest seeing a search increase of 327% over last year, thanks to It girls Bella Hadid and Kaia Gerber photographed rocking the style.
Work it: The fitted style of the newsboy cap works as the perfect balance to a chunkier sweater, while helping to keep your hair in place! As the newsboy cap leans towards a more masculine feel, we say run with it and pair it with jeans, a blazer and a t-shirt, and finish with a pair of sexy stiletto heels.
NEXT: Pillbox Hat →
A small hat featuring a flat crown and straight upright sides with no brim. Usually worn by women, the pillbox hat is a super elegant style of hat that was made super popular by style icon Jacqueline Kennedy, who was known for always being seen in them. It gets its name from the small, cylindrical cases that pills used to be sold in.
Work it: While this style of hat isn’t too common, there’s no reason why you shouldn’t rock it! Extremely feminine, we recommend pairing this hat with a short sleeved dress fitted at the waist, ideally at midi length for a super elegant ladies-at-tea vibe. If you prefer something a little more modern, style it with a sleeveless shift dress, oversized sunglasses and a red lip for a touch of old Hollywood glamour.
NEXT: Porkpie Hat →
Made popular (again) by hit TV series Breaking Bad, the porkpie hat is recognized for its flat-topped oval crown and a small to medium brim. Lending an edgy touch to any outfit, we love porkpies with a little embellishments on them, such as a small bow or even feathers.
Work it: This hat is so versatile, it can be worn with anything from dresses to shorts to a sleek jumpsuit. For a quirky-meets-elegant look, pair a bright porkpie hat with a plunge jumpsuit and finish off with sky-high heels for drinks out with the girls. If you prefer something a little edgier, style with a pair of leather-finish jeans, a ripped vest and high-top sneakers.
NEXT: Sun Hat →
Designed to protect the face and shoulders from the sun, the sun hat is similar to the floppy hat, except with a stiffer brim. Typically made of straw, the sun hat gives off major French Riveria vibes and is perfect for our tropical climate.
Work it: Style your sun hat with an off-shoulder top and wide legged pants for a bohemian look, and complete the look with long necklaces, chunky bracelets and strappy wedge heels. If you prefer a more laid back look, pair your sun hat with a cute little romper, sandals and sunglasses.
NEXT: Turban →
Slowly making a big splash in the fashion world, the turban is a wraparound headgear fashioned out of a scarf or long strip of cloth. While it has connotations with religious dressing, the turban was also a hit back in the 1920’s and 30’s, where old Hollywood glamour icons like Joan Crawford and Gloria Swanson looked incredibly sophisticated in them.
Work it: Whether you’re looking to hide a bad hair day or add an instant dose of chic to your outfit, the turban is an incredibly versatile headgear no matter what outfit you’re rocking. We recommend learning how to wrap one yourself, so you can purchase a large variety of scarves in various prints to keep things interesting! Juxtapose your turban with an athleisure-inspired outfit, structured coats and jackets or even a simple jeans-and-tshirt combo for the ultimate model off-duty vibe.
NEXT: Baseball Cap →
By Mona Teo, HerWorld, January 11, 2018
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