How to Wear a Hat

An oval face is slightly longer than it is wide, with a gently rounded hairline and a jaw a little narrower than the temples. Balanced, in other words.

Best hats for an oval face: almost anything, which is a real advantage rather than a cop-out. Fedoras, cloches, bucket hats, berets, wide brims and baseball caps all sit well on a balanced face. Spend your attention on scale and on what suits your wardrobe instead.

What to watch: scale more than shape. An oversized hat can tip a balanced face out of balance, which is the one thing an oval face has to lose.

Oval subtype · Diamond

If your face is diamond-shaped

Widest at the cheekbones, with a narrower forehead and a narrower jaw. The tell that separates it from a heart shape is the hairline: a diamond's is narrow, a heart's is broad. Most oval guidance applies, with two adjustments.

A little width at the forehead helps, since that is where you have least. Berets and newsboy caps do it naturally.

A lower crown tends to suit you better than a tall one, and anything that adds bulk at cheekbone level is adding width at your widest point.

Browse all hats →

A round face is roughly as wide as it is long, with soft curves throughout: full cheeks, a rounded chin, a curved hairline and no sharp angles anywhere.

Best hats for a round face: height and structure. A taller or more defined crown, clean lines, and asymmetry. Fedoras, newsboy caps and structured brimmed styles all do this. If a brim is straight, wearing it at a slant introduces the diagonal your face does not have.

What changes the effect: a rounded crown pulled straight down repeats the curve you already have, and fullness at the cheeks adds width where there is width.

Prefer a rounded hat anyway? Plenty of round faces look wonderful in a cloche, which is about as round as a hat gets. Lift the front a little, add a tilt, or push the fullness toward the back so the hat is not echoing the same curve in every direction.

Fedoras · Newsboy caps · Cloche hats

A heart-shaped face is widest at the forehead and cheekbones, narrowing to a small or pointed chin. The hairline is broad.

Best hats for a heart-shaped face: a medium brim, which really is the answer here rather than a hedge. Cloches, medium-brim fedoras, baseball caps and structured caps all sit well. Asymmetric brims are flattering.

What changes the effect: the two opposite extremes. A very small brim makes the forehead look wider, and a very wide or floppy one makes the chin look narrower by comparison. If you love a wide brim, wear it, and expect it to be dramatic rather than balancing.

Cloche hats · Baseball caps

A square face has a strong, defined jawline and a broad forehead, with roughly the same width across forehead, cheekbones and jaw. About as wide as it is long, but with angles where a round face has curves.

Best hats for a square face: curves. Rounded crowns, bucket hats, berets, bowlers and soft slouchy shapes all contrast nicely with a defined jaw. Wearing the brim at an angle helps, and a hat sitting a little higher on the forehead lengthens the lower half of the face.

What changes the effect: flat tops, tapered crowns and sharp geometric lines echo the jaw rather than balancing it. A structured hat can still look excellent on you, particularly with a curved brim or worn slightly off-center.

Square subtype · Pear

If your face is pear-shaped

Narrow at the forehead and widest at the jaw, usually with a rounded chin. The reverse of a heart. You are still softening a wider jaw, but you also want a little width at the top to meet it.

Width and interest above the eyes does the work. A full crown rather than a tapered one, a reasonably wide brim, or detail at the crown. Anything that draws the eye upward balances the jaw.

A tapered crown works against you, narrowing exactly where you want width and making the jaw look wider by contrast.

Bucket hats · Berets

An oblong face, sometimes called a long or rectangular face, is noticeably longer than it is wide, with a similar width at the forehead and cheekbones. Often a high forehead or a longer chin, and the sides run fairly straight rather than curving.

Best hats for an oblong face: width and a low crown. Wide flat brims, floppy brims and cloches worn low all shorten the face. Pulling the brim down toward your eyebrows shortens it further and is the single most effective adjustment on this shape.

What changes the effect: tall crowns and narrow brims both add length you already have. A high-profile cap is not off limits, but wear it lower and pair it with something that adds width rather than pointing straight up.

Wide brim and summer sun hats · Cloche hats

Long hair looks fabulous under a hat. Wearing a hat with long hair comes down to two questions, though, and the second is the one that gets forgotten: which hats suit it, and what to do with the length once the hat is on.

Which hats. Structure. A firm crown and a defined brim give the eye a clean line to read against all that movement. A soft, floppy hat tends to blend into long hair and lose its own outline, so hat and hair read as one shape and neither wins. Fedoras, structured wide brims, newsboy caps and cloches all hold their line. Soft styles are not out, but wear a beanie loosely rather than pulled down.

Where to put the length. This is the part people get wrong, and it changes the look more than the hat does.

• All down, parted in the middle, under a sun hat or wide brim. Straight lines balance a big brim rather than competing with it.
• Half up, the top gathered loosely and the rest left falling. Good under bucket hats and caps, and it keeps hair off your face without losing the length.
• A low ponytail through the back of a cap. Low is the easiest height under a closed crown, because anything higher competes with the hat for the same space. A high ponytail works fine with an open-back cap or a hat made for one.
• Two braids, parted down the middle. The best answer if your hair is thick, because it takes the bulk out from under the crown instead of packing it in.
• One side tucked behind the ear, under a cloche or a baseball cap. Softens a cloche, smartens a cap, and shows an earring.
• Wavy and loose under a fedora or a newsboy cap. The texture suits the attitude of those styles, and waves survive a hat far better than a smooth blow dry.

And two things worth doing before you go out. A lot of hair takes up room, so a deeper crown will sit better than a shallow one. And before the hat goes on, lift the hair at your crown with your fingers to leave a pocket of air underneath. That small gap is most of the difference between a dent and no dent.

Short hair and hats are smashing companions, and wearing a hat with short hair is easier than most people expect. With no length to hide behind, the hat becomes the feature. Its shape shows completely, which is why the right hat on short hair looks deliberate rather than merely fine.

It cuts both ways, mind. The fit shows just as clearly, because there is no volume to disguise a hat that is slightly too big. That is why short hair and a borrowed-looking hat turn up together so often.

Which hats, by cut.

• A pixie: beanies, especially slouchy ones, and baseball caps. A side-swept fringe showing under a beanie is one of the best combinations there is.
• A bob: berets and structured caps. A blunt or sleek bob under a beret is the classic, and it is classic because it works.
• Growing out, or an awkward in-between length: bucket hats. The crown sits lightly rather than pressing down, so it does not flatten your layers or your fringe.
• Any short cut: a wide brim. The width balances how close the cut sits to your head, which is why short hair and a big brim look so intentional together.
• Winter: short hair leaves your ears and neck far more exposed than you are used to, so warmth matters more than it did. Winter hats for short hair want depth and coverage rather than a shallow perch. A cuffed beanie pulled over the ears, a wool cloche, or a lined newsboy cap all suit ladies with short hair and keep the cold off. Many older women find a soft lined style the most comfortable of the lot.
• Use a little care with very tall crowns, such as a bowler. Without length to balance the height, they can tip into costume on a very short cut.

And what to do with it.

• Let some of it show. A fringe, side pieces, whatever you have at the front. A hat pulled down over everything reads severe.
• Wear it a little higher than you would with long hair, so the shape of the cut stays visible under it.
• Tuck one side behind your ear. Breaks the silhouette and shows an earring.
• A little texture at the roots first if your hair goes flat, since there is less of it to spring back on its own.
• Add a band or a scarf around the crown. It brings back texture that longer hair would otherwise provide.
• Wear earrings. A pixie cut, a brim and a pair of dangly earrings. Is there anything cooler?

Wearing a hat with curly hair takes a little negotiating, because the two things that ruin a curl pattern are compression and friction, and a hat delivers both.

• A smooth liner underneath is the single biggest fix. A soft, smooth liner reduces the rubbing against wool or acrylic that causes most of the frizz and breakage, without flattening the curl the way a hat's own lining can. Note that smooth reduces rubbing rather than adding hold. If your problem is the hat sliding rather than the frizz, you want a gripper band instead.
• Choose a deeper crown so your curls have somewhere to go instead of being compressed against your scalp.
• Wear it looser and further back than you would with straight hair, so the hat is resting rather than clamping.
• Let some length out at the front and sides. A few curls loose around the brim reads relaxed and deliberate, if that is the look you want. A fully covered style is equally polished, and plenty of women prefer it. What matters more either way is not crushing the curl in the first place.

Wearing a hat with fine or very smooth hair brings two problems, and they are opposites.

Hats slide off. Smooth hair gives a hat nothing to hold onto, so beanies in particular creep backward until they are hanging off the back of your head. This is a friction problem rather than a size problem, so sizing tape will not help. A thin headband worn underneath gives the hat something to grip, a scarf gripper does the same job and is made for it, and a little texture spray at the roots works too.

And the dent shows. Fine hair marks more easily and has less volume to hide it. Keep the hat as loose as it will sit without sliding, and lift at the roots rather than brushing when it comes off.

Wearing a hat with no hair, or with hair that is thinning, can feel stark at first, and the usual instinct is to blame the hat. In most cases the hat is fine. What is missing is the small amount of volume and edge that hair used to provide, and that is easy to put back.

• A hat with hair already attached. The simplest answer, and the one most people reach for when they want to stop thinking about it. See hats with hair →
• A halo, or attachable bangs. Both put a little hair back at the edges without the weight of a wig, and a halo can be swapped between every hat you own. How the three options compare →
• A padded headband or a volumizer worn underneath, which restores fullness and gives the hat a shape to sit on. See volumizers →
• A soft liner, which adds a little shape as well as stopping a hat feeling scratchy on a sensitive scalp. It also means you can wash the liner rather than the hat.
• Statement earrings, which do more work here than in any other situation. They pull attention back to your face and balance the whole look.

And if a hat still is not sitting comfortably with you, a pre-tied scarf is just as easy to put on and gives a different kind of fullness and framing. Plenty of people move between the two depending on the day. Our cancer hats guide goes further into coverage, fabric and staying cool.

Here is the thing that makes this much easier than it sounds. Under a hat, the only hair anyone can see is at the edges. The crown is covered. So you do not need a head of hair, you need edges, and edges are light, cool and inexpensive in a way a full wig is not.

Three ways to do it, and they suit different people.

• A hat with the hair already in it. Sewn in at the sides and nape, ready to put on, nothing to line up. The simplest of the three and the one most women pick when they want to stop thinking about it. The trade-off is that the hair belongs to that hat, so a second look means a second hat.
• A halo worn under any hat. A band with hair attached that sits around the circumference of your head, so hair falls at the sides and the back while the crown stays open. Halos and hats are natural partners, because a halo has nothing on top and a hat covers exactly that. One halo can work under a good many of your hats, as long as each has enough depth to hide the band, and the open crown makes it noticeably cooler than a wig.
• Attachable bangs. A fringe on its own, fixed inside the front edge of a hat, turban or pre-tied scarf. The lightest and least committal option. If what you miss is the framing at the front rather than length at the back, this is the one, and it is the cheapest way to change how a hat reads on you.

And they are not really three separate choices, which is the part worth knowing. Bangs attach to our Instant Hair headband as readily as to a hat. Hook-and-loop strips are sewn into the band, so a fringe presses on and pulls off in seconds, and it can sit at the front, at the back, or at both ends at once. One headband and one set of bangs gives you a fringe one day and length at the nape the next. Add a second set and you can wear both at once.

See hair halos and bangs · See hats with hair

A beanie is three different hats depending on how you wear it, which is why the same one can suit you on Tuesday and not on Wednesday.

• A single cuff, sitting just above the eyebrows. The classic. Covers the ears, frames the face, suits almost everyone. It also covers the most forehead of the three, which shortens the face. If you are only going to wear it one way, this is the way.
• Rolled up, sitting higher. Shorter and tidier, and it gives you back a band of forehead. That opens the face up rather than closing it in, which suits a rounder face, and it is worth trying if a single cuff feels like it is swallowing you.
• Slouchy, pushed back with the extra fabric behind. The height goes above the crown rather than around your face, which lengthens the whole silhouette. Good on a round or square face, less so on a long one. It needs something to grip, so on very smooth hair or a bare scalp wear a headband underneath or it will keep creeping backward.

One thing worth knowing: a beanie sitting high and tight on the crown, with no fold and nothing at the sides, is the shape that makes any face look longer and narrower than it is. If a beanie has never suited you, that is probably why. Pull it down, or add a cuff.

Slouchy beanies · Fitted beanies

Caps vary more than they look. The two things that decide whether one suits you are rarely on the label.

Profile is height. Structure is stiffness. They often come together but they are not the same thing. A low profile crown sits close to the head; a high profile one has more height above the brim. A structured crown holds its shape off your head; an unstructured one softens and follows your head.

Height is what changes your face. A high profile cap adds it, which helps a round or square face and can overwhelm a small or fine-boned one. If caps have always made your head look tall or boxy, high profile is why.

The brim can be curved. A flat brim draws a hard horizontal line across the face; a curved one wraps toward you and softens it. Which you want is taste rather than a rule, though a curve is the easier of the two to wear. If yours came flat and you want it curved, bend it gently with your hands over a few days rather than forcing it in one go.

Baseball caps

This is the fear that keeps most of us in baseball caps, and it is worth naming out loud: the worry that a proper hat looks like you are playing a part rather than getting dressed.

Three things separate a hat that reads as costume from one that reads as yours.

• Everything else stays ordinary. A wide brim with a plain sweater and jeans looks like a person who wears hats. The same hat with a matching outfit, statement boots and a scarf looks like a look. One interesting thing at a time.
• The angle is not straight on. A dramatic hat worn dead square is theatrical. Tilted, it relaxes immediately.
• It fits. A wide brim that is slightly too big is what actually reads as dress-up, because it sits low and swamps the face.

A beret looks most relaxed pushed back off the forehead and pulled to one side. Worn centered and pulled down flat, it reads a great deal more severe. That one adjustment is most of the difference.

Berets · Wide brim hats

Losing a wide brim to a gust is a particular kind of embarrassment, and it is worth a minute of prevention.

• Get the fit right first. A loose fit makes wind far worse, and a hat that lifts easily is often slightly too big, so the fix is usually back in the fit section rather than out here.
• A headband underneath adds grip, which matters most if you have no hair, since there is nothing for the hat to hold onto.
• Wear it further back and tilted on a windy day. A brim angled into the wind acts like a sail.
• Hairpins through the band work if you have hair to pin to. Some sun hats have a hidden chin cord, which is worth looking for if you are somewhere properly blustery.

Modern etiquette depends far more on the kind of hat than on who is wearing it. Casual caps and beanies follow the old remove-indoors convention. Dressier hats worn as part of an outfit get much more latitude.

Off: at the dinner table, in a private home, during the national anthem or a moment of respect, at religious services unless head covering is part of the practice, and in a theater or cinema where a brim blocks the view behind you.

Fine to keep on: outdoors, and in the in-between indoor spaces people pass through rather than settle in, such as lobbies, corridors, elevators and shops.

Are hats business casual? A structured hat, a beret or a neat turban reads as part of an outfit and passes in most business casual settings, particularly on the way in and out. A baseball cap or a beanie does not. In an office, at a meeting or across a desk, the safe move is to take a casual hat off and leave a dressier one on only if it is clearly deliberate.

When you are unsure, read the room. If the setting feels formal or quiet, taking it off is the safer move. And if a venue posts a rule, follow it.

Crown down, never brim down, and never on the table. Resting a hat on its brim is what flattens and warps it over time, so this is as much about the hat as about manners.

A hat rack if there is one, otherwise an empty chair beside you. And hold it so the inside faces you rather than the room.

Sometimes. It depends on the room and the occasion. A fedora at a casual party, clearly part of what you are wearing, is fine. At a sit-down dinner or a formal professional event it is less so.

If you have a formal event and would feel self-conscious taking your hat off, an elegant turban or a pre-tied scarf solves the problem completely. Both read as deliberate dressing rather than as head covering, and neither needs removing.

Almost always a size problem rather than a hat problem, and the fit section has the fix in full: sizing tape inside the band, or a thin headband underneath, which also adds grip.

One exception worth knowing. If the hat is the right size and still slides, that is friction rather than fit, and it happens on very smooth hair or a bare scalp because there is nothing for the hat to hold onto. Tape will not help with that. A headband or a liner will, and a scarf gripper is made for exactly this, worn underneath to give the hat or scarf something to hold.

Yes, provided the hat and the outfit are speaking the same language. A structured brim or a good turban works beautifully with something dressy. A knit beanie or a baseball cap will fight it.

The one thing worth checking at an event is whether your brim is going to block the person behind you. If it might, choose something closer to the head.

Nine times out of ten it is one of three things, in this order of likelihood.

The fit. Too big is the most common, and it makes any hat look borrowed. Check that a brimmed hat sits clear of your ears.

The angle. Straight on is rarely the most flattering position. Tilt it and look again.

The shape. If a hat repeats what your face already does, it will feel off even when you cannot say why. That is when the contrast rule earns its keep.

If you have worked through all three and still are not happy, it may simply not be your hat, and that is fine. It took most of us a few tries.

A comfortably fitted hat is unlikely to cause hair loss. The evidence on this is not as clear-cut as either side of the argument suggests, but an ordinary hat worn normally is not the thing to worry about.

What can put strain on hair is a hat worn very tight, very hot or against a rough lining day after day, and more often the hairstyle underneath it. A tight ponytail or tight braids pulled back under a cap put far more tension on the roots than the hat does.

The rule of thumb is the same as everywhere else on this page. A hat should not pinch, pull, or leave a mark that is still there ten minutes after you take it off.

For women's hats, usually yes. Soft styles give, so one size covers a wide range of women comfortably, and that is why we do not ask you to measure for most of what we make.

The hats that really do need a size are the structured ones. A formal brimmed hat with a fixed band, the sort worn to weddings and race meetings, is built more like a men's hat and has no stretch at all. Those are worth measuring for. Everyday women's hats are far more forgiving.

Some women feel pressure around the head more than others. If that is you, you already know it, and it is a preference rather than a problem. Choose softer styles, and size up when you are between.

No, and trying to match exactly is usually what makes an outfit look overworked. Aim for the same tone family and the same general level of formality, then let the hat be its own thing. A neutral hat with a bit of texture will go with far more than a hat bought to match one dress.