How to wear a hat: tips and tricks from fashion experts

While the concept of how to wear a hat isn't difficult, choosing the right hat or mastering how to wear a fascinator for maximum sartorial style can be a tricky one. Instantly elevating your look, from weddings to the races and even summer vacations, the right headpiece can make or break an outfit. 

When it comes to what to wear to a wedding, or what to wear to the races, a hat should definitely be number one on your shopping list. With many dress codes for summer events including some form of hat or fascinator, deciphering which look works best for both your style and body type, as well as for your outfit will put a quick stop to any outfit meltdowns. Depending on the occasion, your hat needs will differ, but if you're looking for the right hat to complement the best mother of the bride outfits, or best mother of the groom dresses, or even as a guest, be guided by the type of day the couple are having as a starting point. And regardless of the event, make sure your final choice has a synergy with your outfit. 

“I usually suggest to my clients to start with the piece they love the most, and this could mean a hat, a dress or even a pair of shoes or a handbag. Use that as your starting point and work the rest of your outfit around it,” explains Lisa Tan Millinery. And don't be afraid of going bold.

“Don’t feel you have to perfectly match your millinery to your outfit either, as quite often a color clash or a contrasting tone can provide a more interesting element,” says Lisa.

Beverley Edmondson Millinery agrees, adding, “Matching everything completely can lead to a bland outfit where nothing ends up standing out. Choose your ’hero’ piece of the outfit and let everything else softly complement that.”

How to wear a hat - the best styles as chosen by a fashion editor

1. Fascinator

Fascinators can vary from the cute and quirky to the full-on ridiculous but they are the perfect choice if you want to inject some playfulness to your look. When working out how to wear a fascinator, there are no hard and fast rules, but they are usually worn at the side of the head, secured with a band or clip. They're less likely to blow off in an unexpected just of wind and are easy to slide on or off at the last minute. Often elaborate affairs, expect embellishment details such as feathers, or sculptural mesh styles for added impact.

If you decide to go bold, keep the rest of your outfit pared-back - a block-colored dress or suit - and let the headpiece take center stage. “Sometimes a simple outfit needs a stand-out hat that can really turn the dress/suit into something far more exciting otherwise if the dress is quite busy and patterned, selecting one of the colors from the pattern will create a look that allows the hat to frame all the interest in the outfit, and lift colors from the pattern but not compete with it,” says Beverley.

Fashion editor’s picks…

2. Wide brimmed hat

An elegant choice of hat, a wide-brimmed design is ideal for summer event season. Most recently showcased by Megan Markle at the Queen's Platinum Jubilee celebrations, this statement style is usually best suited to taller frames, as it can feel overwhelming on petites. If you're usually in the best petite dresses, you can make this style work by investing in some high-heeled shoes, as an elongated silhouette will carry this look off with ease - pair with a midi-length dress for maximum elegance. To add further instant inches, color match your hat to your outfit for a seamless look, and sweep your hair back into a sleek bun or pony for a sophisticated finish.

Fashion editor’s picks…

3. Halo Headband

Headbands are one of the top fashion trends 2022 and they’re a good way of easing yourself into headpieces and fascinators if you’re new to the hat game. You can always rely on the Duchess of Cambridge for inspiration when it comes to sartorial elegance and her headpiece styling is no exception. Stick to classic hues of black and cream for a more subtle approach or add a pop of color for a bolder look. An evening do might require something more glitzy so look for beaded embellishments and pretty prints for added glam, and make sure you swot up on how to wear headbands.

Fashion editor’s picks…

4. Pillbox Hat

Made popular by former First Lady Jackie Kennedy, a pillbox hat is an occasionwear classic. And if you want to learn how to dress like Carrie Bradshaw, the fictional style icon is a fan too. Chic and understated with a vintage twist, the small round hat has no brim and sits neatly on the head attached by elastic or pins. A stylish and flattering choice for petites, it's a go-to for what to wear to a christening or wedding and looks best paired with formal outfits such as a tailored dress or skirt suit and the best designer heels.

Fashion editor’s picks…

5. Straw Hat

Practical and stylish, a straw hat is a summer essential keeping you protected from the rays whilst looking effortlessly chic too. More casual than a pillbox or fascinator, this versatile hat design can be an everyday piece or dressed up for special occasions. Look to structured styles such as a boat or trilby to keep it on the smart side and team with the best dresses or sleek separates. The neutral hue is guaranteed to go with everything too from chic whites to pastel shades. 

More casual iterations of this trend make great vacation partners and to keep your hat safe in transit, you might want to add it to your 'what to wear on a plane' look. Pair with your best beach cover-ups and best beach bag - in a similar straw or rattan design for a chic poolside outfit. 

Fashion editor’s picks…

6. Trilby and Fedora Hats

Both year-round staples and another versatile choice of headgear, the trilby and fedora straddle the casual and smart arena. Similar in style, the main difference between the two is the brim size. A fedora has a slightly bigger brim, but both silhouettes are incredibly flattering on all face shapes. Available in many iterations from autumnal felt to summer straw, they can even be worn with your best jeans and best blazer to give a sharper finish on more casual days. Take note from Pippa Middleton (above) and go for a color-coordinating look for a stylish day out in the sun.

Fashion editor’s picks…

How to choose the right hat

Much like body type dressing, when selecting a hat or fascinator, you should consider your face shape and which styles will flatter you most. You will also want to consider investigating 'what color suits me', as the hat will sit close to your face.

"If you have a square-shaped face you want to go for a hat that has slightly softer curves as well as something that gives angle to your face. If you have a large forehead I would suggest a piece that would cut the forehead. If you are short do not go for hats that will overwhelm you like an extra-large or extra high (hat), if you are tall you can pull off large hats," says Merve Bayindir Millinery.

Weddings and race days can be long so comfort is also key when choosing your hat.

“When shopping for millinery, do make sure the piece you choose is comfortable to wear. You’ll be wearing it for at least a few hours – or several hours if it’s a race day – so choose a piece that feels right and sits well on your head,” says Lisa.

Merve Bayindir believes big race days such as Royal Ascot are the best events to go big with your hat, whereas at weddings you can go for something more subtle.

"I usually suggest stronger hats for races especially if they are one of the big ones, as I believe races are the best place to show off your hats. For weddings, unless it is a destination wedding, I insist that the mother of the bride wears a proper hat instead of a small fascinator. At least close members of the family, especially at a church or synagogue should keep in mind that it is not just the bride and the groom that are being presented but the entire close family members. So hats should show this off."

Of course, as long as you feel 100% confident in your hat, it doesn't matter what style you go for. 

Lisa adds, “Have fun with your millinery – how often do we get the chance to wear a hat? Embrace it! And if you’re worried your hat might be ‘too much’, I can almost guarantee that will never be the case on a race day, as there will always be someone with a bigger, louder hat!”