In preparation for National Hat Day, we have come up with some inspiring fashion tips on how to wear your favourite hats with glasses. Hats are highly fashionable accessories and have plenty of practical uses. They protect your face from the sun and keep you warm in cold weather. Some people wear them to make a style statement while others simply rely on a hat for practical reasons. How you choose to wear your hat with glasses (or sunglasses) and what designs you go for is completely down to your unique style and taste.
Hats with glasses can be an excellent fashion duo if you know how to combine them in just the right way. Style them incorrectly, however, and they will hide your best facial features. Also, the wrong hat and eyewear combination will clash with your outfit — which you’ll probably spend ages putting together beforehand. Knowing how to avoid a fashion disaster is key and that’s why we’re here to help.
What hats look good with glasses?
Your winter wardrobe is probably at the top of your priorities list at this time of year. Hats are must-have accessories and perfect for when you’re trying to keep warm. We have listed a variety of hats and glasses or sunglasses that go well together. Stay snug and look fashionable at the same time. Find something to suit your individual style and face shape.
Look trendy in a beanie hat with oversized sunglasses
Arguably one of the most iconic looks for winter 2024, wearing a beanie hat with glasses or sunglasses will give you a trendy look. Cosy and casual, these fun and informal hats were once seen as a stylish choice for talented hip-hop singers and skateboarders. Since then, they’ve evolved. Beanies make a stylish addition to your wardrobe and create a classic hipster look. They tend to be made from stretchy cotton or wool that covers your ears but is loose-fitting and therefore doesn’t cause your glasses to dig into your head at the sides.
Beanies come in many varieties from loose pear shapes to fitted and folded-over designs. Bobble hats are a stylish alternative and look adorable with a big winter coat. Vintage docker hats are also very on-trend. They resemble the beanie but are slightly smaller and cover the top of your head like an old-fashioned fisherman’s hat. They are ideal for any modern, style-conscious gentlemen.
We recommend pairing your beanie or knitwear with versatile acetate frames. You can create a geek-chic look, by choosing an extra-large pair. Keep the aesthetic the same and pair dark or light-coloured glasses with hats that are similar in style. If you choose a hat with a bold print, like stripes or polka dots, then try simple transparent frames which will frame your eyes perfectly whilst not distracting the focus away from your hat. Finally, if you go for a chunky knitted hat or a classic docker-style cap, match it with a simple pair of metal glasses for a retro-inspired look.
Our stylish model to the left is wearing a pair of Gucci sunglasses. Ideal for this time of year, sunglasses will keep you protected from winter sun.
Take your style to new heights with an aviator hat and glasses
If you’re always avoiding the cold, an aviator hat, also referred to as a trapper hat, is the perfect solution for you. The flaps at the side and chin straps will make sure you’re kept nice and warm. Most aviator hats are made of leather or wool and they have a well-insulated faux fur lining. Sometimes they are even waterproof which is essential for maximum protection from icy and cold temperatures.
You can easily create a cool retro look with classic Aviator glasses that will naturally suit this style of traditional headwear. An aviator hat also goes well with Wayfarer glasses, especially a very sleek pair. If your hat covers your forehead, we recommend you try an understated option, such as rectangular glasses or designs with a subtle metal frame. You’ll want to choose a shape that fits securely and isn’t too big for your face. Otherwise, your glasses will come into contact with your hat and move around a lot. This could cause discomfort and irritation throughout the day.
The model shot to the right reveals how well Aviator glasses suit this traditional hat. Create a retro look and stay warm this winter.
Try a fedora or a classic trilby hat with glasses
Trilby and fedora hats have an eye-catching and timeless design. The only downside to wearing these kinds of hats in winter is that when the temperature drops outside, your ears will be exposed to the cold air so you might feel a bit of a chill. Despite this, trilby and fedora hats are very trendy and you can always wrap up in a big coat or use a chunky scarf to cover your neck and the bottom of your face.
Trilby and fedora hats make a confident style statement and will help you achieve a sophisticated look. Ideally, you’ll want to choose a minimal frame design to allow your hat to grab attention and avoid cluttering your face with too many bold accessories. Sleek round metal glasses are ideal if you want to create a tidy and classic look. Alternatively, you can grab attention with a bold tortoiseshell frame which will stand out nicely.
Our fashionable model looks suave and sophisticated in classic tortoiseshell glasses paired with a trilby hat and a smart black winter coat.
What is the difference between a trilby and a fedora hat?
Though slightly different in style, they are both recognised for their classic look. A trilby has a narrow brim that turns downwards at the front and subtly curves upwards at the back. A thin band is carefully trimmed around the shape of the hat. It is also very subtly pinched in at the front. The trilby has a taller crown than the fedora which for both hats is most often shaped like a teardrop. Trilby hats normally have brims that are no wider than two inches. They are most commonly made of straw, felt and tweed.
Meanwhile, a fedora hat is nipped in much more strikingly at the top and therefore has a very narrow dip in the crown. The bands of fedora hats are often made of ribbon and sometimes even adorned with colourful feathers. Fedora hats are recognised for their wide circular rim which is really good at shading you from the sun. Fedora hats are normally made of cotton, felt or wool.
Achieve a classic look in a baker boy or flat cap with glasses
Perhaps most famously worn in the television series Peaky Blinders, baker boy hats are very in vogue at the moment. They normally feature a visor at the front and consist of several panels which are neatly sewn together with a button top. These hats are most often made of materials like cotton, tweed and wool. A timeless classic, they make a stylish addition to your wardrobe whatever the season. The only downside is that your ears might be exposed to the cold when the temperatures really drop.
Similar in style, flat caps, or farmer hats as they are also referred to as, are often mistaken for baker boy hats because they have a visor at the front and are also commonly made of tweed and cotton. However, the similarities end there. Flat caps are much simpler in design and tend to be made of less fabric. Often modern versions of this hat are made of leather and other materials.
As is clear in the image to the right, Clubmaster glasses naturally suit baker boy and flat caps, especially if your wardrobe is retro-inspired. Popular amongst celebrities, this combination looks particularly eye-catching if you have tattoos on your chest and neck. Round acetate or oval metal glasses also create an exceptional look when worn with this type of hat.
Look elegant in a beret hat with glasses
The French beret is classy and refined. This style of hat can easily add a playful edge to your look whether you wear it tilted to one side or place it casually on the back of your head. Recognised as a classic military hat and also a favourite amongst fashionistas, the beret is very versatile.
Deciding which glasses to wear with a beret depends on the finishing look you wish to achieve. For a simple and refined finish, choose a pair of metal glasses and go for a geometric frame for a subtle touch of contemporary style. Check out this stunning image of our model to the left for an idea of what this combination looks like. If you’re looking for something a little more striking, try matching the colour of your beret hat with your glasses or go for a pair of statement-making black acetate frames. Meanwhile, a pair of cat-eye or chunky square glasses will create the perfect vintage vibe. Glasses with decorative details work really well with a beret which naturally sits neatly on the top of your head and doesn’t distract attention away from these intricate design details.
Look cool and casual in a baseball cap and sunglasses
Wearing a baseball cap with glasses is ideal if you’re always on the go. They are normally made of wool or cotton. The visor at the front of the cap keeps you protected from bright sunlight and the adjustable strap at the back is ideal if you want a more bespoke fit. They come in various styles from caps designed for ponytails to taller styles used for practical uses. For those of you who feel more comfortable in a baseball cap and know it complements your sporty sense of style, then we have some great suggestions for you.
A baseball cap will suit a pair of sports sunglasses, especially top brands like Oakley. We would also recommend a classic pilot-style frame or any similar modern alternative.
Meanwhile, if you want to contrast the sporty look completely, then a pair of classic Premium Designer frames will give you a chic and modern look. Give yourself an air of mystery whilst protecting yourself from the sun. We think our model to the right looks very glamorous in her baseball cap and designer sunglasses. Accomplish a real Hollywood-chic look.
Look chic in a winter headband
Tuck your ears away from the cold and make sure your hair stays in place with a stylish winter headband. Often used in the summer months to sweep your hair off your face, headbands are a highly fashionable accessory for women and ideal for casual wear during the winter months.
A winter headband is subtle in style so you can either contrast it with a pair of bright multi-coloured glasses or achieve a classy look with a pair of black frames. It is important to be aware that headbands can create pressure around your head when worn with the wrong type of glasses. Just make sure you choose a pair with spring hinges for added flexibility. This will protect you from any irritation or discomfort around your ears. Persol glasses are an excellent choice because they are designed with Meflecto temples which reduce pressure points around your head. Some sports glasses are designed with rubber panels on the inside which is great for a little extra cushioning. Equally, if you go for a headband that can be tied up or adjusted, you don’t have to limit yourself to specific designs.
Our model is wearing a sparkly black headband with a vibrant red frame from our exclusive collection which matches her bright lipstick.
Which hats suit me and my face shape?
When it comes to finding the perfect hat, it’s important that you consider what shapes and designs best suit your face shape and complement your features well. Below we have outlined the best hat styles to go for based on what shape your face is.
Oblong
If you have a very long face, try wearing a fedora or trilby hat with a wide brim and a low crown. This will make your face appear broader and slightly more well-balanced. A slanted hat like a beret or a circular baker boy cap will also add width to your narrower features. Aviator hats that are slightly fitted will disguise elongated features very well.
Diamond
Diamond faces are characterised by their wide cheekbones, narrow forehead and narrow chin. Draw attention away from the narrowness of the top of your head with a flat cap or baker boy cap which will add some much-needed width. If you wear a beanie, make sure it sits further back on your head to soften your broad cheekbones. We also suggest you try trilby and fedora hats with short brims and pinched crowns. Stay clear of hats with wide brims as this will only serve to exaggerate your prominent cheekbones. If you wear a headband, make sure it has a knot or distinctive feature and swivel it to one side of your head. This will help to soften any harsher lines.
Round
People with fuller, rounder features can create the perfect contrast with angular-shaped hat styles. The aim should be to add length to your face. Try your best to avoid hats with round crowns or very wide brims. A fedora or trilby with a high, square crown will really suit you. If you wear a beanie and have a round face, you should go for a fitted style and pull it lower over your forehead. This will help to elongate your face. A woolly hat with a bobble is another great style to help add length to your face. Baker boy and flat caps will suit round faces so long as they have fairly high tops and sharp angles. If you wear a headband, make sure it has a knot or prominent detail in the middle. This will naturally draw the eye upwards and give your face more definition.
Square
If you have a square face with a very prominent jawline, go for softer and more circular hat shapes. Stay away from taller hats with high crowns. You should also avoid hats with small brims, no brims or very square outlines. A fedora with a round crown or any hat with a wide circular brim is ideal. Baker boy hats are also perfect because they are very round in shape. If you want to smooth out your harsher features, try a baseball cap or aviator hat. A thick headband with lots of padding will suit you best. This will add volume to the top of your head and balance out your strong jawline.
Heart-shaped
Individuals with a heart-shaped face are recognised for their wide forehead, broad cheekbones and pointed chin. Ideally, you will want to choose hats that balance the width of the top half of your face. Try a subtle beret or beanie hat. Trilby and fedora hats with medium brims will suit you best. Just make sure that if you go for a hat with a brim, you tilt it to one side. This will slim your face down and draw attention to your eyes. A headband will look great if you sweep your hair to one side which will help to balance your features.
Triangular
If you have a triangle-shaped face, your forehead will be broad, you’ll have wide cheekbones and a narrow chin. Thankfully, this face shape is versatile and you have lots of different choices when it comes to suitable hats. Just make sure you avoid headwear with crowns that are narrower than your broad cheekbones. If you wear a headband rather than a hat, make sure it is not too chunky otherwise it will draw attention to your narrow chin. Go for trilby and fedora hats with moderate brims so as not exaggerate your prominent cheekbones. Any hat that is round will contrast your more angular features well. A baker boy hat or beret is ideal for this.
Oval
Just like triangular faces, people with an oval face shape are very fortunate because they have well-balanced features that will suit most hat styles. An oval face can be compared to an upside-down egg. People with this face shape have subtly rounded features and are characterised as having prominent cheekbones and a wider forehead than the jawline. A fedora or trilby is a great choice if you want to add a little bit of natural width to your longer face. Any hat that doesn’t have too much height to it and has a fairly wide outer shape or brim is ideal because it will not elongate your facial features too much. Berets, baker boy hats and flat caps will also suit you.
