How to Style Your Hair When Wearing a Hat

As part of the “Hats Heard Round the World” Project, today we are getting some advice from experts on how to style your hair when wearing a hat! And as a quick aside, I would like to thank all the brilliant milliners who have sent their gorgeous hats so far…..including Maria Curcic and Trish Hirschkorn of Canada; Hania Bulczyńska of Poland; Denis Gulyaev of Russia; Yael Cohen of Israel; Steven’s Hats of Italy; Chris Van de Velde and Naomi Wuyts of Belgium; Majella Lennon of Ireland; and Ana Pribylova and Wendy Scully of Australia. You’ll be reading more about these gifted artists soon on BSSTW, so stay tuned!

The big question when wearing a hat is how to style one’s hair. This can make or break your look, but oddly, the solution can be very simple. Remember that the hat is taking center stage, so a low bun or chic chignon, with little or no visible hair showing, is almost always a correct option. However, with the headwear craze in full force, I want to examine some other, more creative alternatives for you today.

When donning a hat, remember that you should always show the line of your face, according to Michigan’s Gena Conti of Gena Conti Millinery. “The hat should enhance you, blend with you, become an extension of you,” she says, “as a flattering hairstyle does.”

Just look at this striking hat custom designed by Gena for her favorite client and muse, co-owner of Hair Lab Detroit, Lauren Moser, below, pictured here with her fiancé Rodrick Samuels.

First of all, this is simply an exquisite hat. Furthermore, the structure of the face is clearly visible, enhancing Lauren’s killer cheekbones, and although Lauren is an award-winning hairstylist herself, and can enviably do most anything with the hair that you can imagine, she has opted with her coif for a simple updo. Pure elegance. You cannot go wrong. This is utter perfection.

Remember: simplicity is the key to brilliance. And for a low-down on how to create this look with utmost simplicity, we turn to stellar stylist Edward Tricomi of the perpetually-chic Warren Tricomi Salons.

Please note that you do not have to be an accomplished hairstylist like Lauren or Edward to create this effect. “Pull the hair back into a low ponytail with an elastic rubberband. Braid, twist into a bun and pin with discretion” so that your pins are not visible, Edward advises. Be sure to check the back of your coif in the mirror by holding a hand mirror to head level, while facing away from your full-length mirror. Use your hands to feel that there are no stray bobby pins. Smooth strands gently with a bit of hairspray misted onto your palm. Spraying directly onto the bun may result in an unattractive, lacquered effect.

The Short End of It

If you have short hair, a bun or chignon is not always possible. In these cases, sleek and simple always works. Remember, the hat is the focus. Neatly slick the hair back off the face for a tidy couture look.

For a medium bob, pull hair back behind the ears if it’s attractive on you, in order to see the line of your jaw and your face, Gena recommends. A short Sassoon cut, like the one below, naturally enhances the bone structure and works fab with a hat, but the bangs can seem problematic until you play with them.

“Sometimes the client loves her bangs and must show them,” Gena states. In this case the hat should be either perched a bit back on the head as seen above, or pulled down low allowing the fringe to circle the face, she says. You can also wear the bangs sideswept, as seen below.

It’s a Long Story

If you want to wear your hair loose and long, it all depends on the texture and your desired outcome. Curls and waves are more feminine and romantic; straight hair equals severe drama or it can look perfectly casual, and there’s even room for frizz, if done correctly. Let’s take a look.

Curly Cues

Curls or waves can add a distinctly coquettish slant to millinery, especially a summer sundress worn with a floppy semi-translucent hat or a feminine, oversized, floral-embellished straw creation on Easter, for example.

Above however, the model is sporting soft curls with a masculine fedora, which is a great dichotomy and really works in this case. Very stylish. I love this classic look. It’s sexy as hell. Upon closer inspection it is clear that the model’s hair has been set for these rounded, barrel-style waves.

The curls above appear to be natural. Millinery, in my opinion, looks better with a light setting. Natural curls often benefit from heat curling, if you have the time and inclination. It might seem odd, redundant and counter-intuitive to curl curly hair, but the outcome is often quite glorious and worth the bother. Your curl pattern and bounce are going to look different than freshly-washed natural curls. They’ll be more polished than a natural curl, which can appear sometimes straggly or fuzzy when topped with a hat, something you might not notice when you’re wearing more casual attire. A hat is usually going to elevate an outfit into a more couture moment. At that point, you will abruptly see that casual curls–aka your normal “street hair”–no longer seems quite appropriate, unless you are wearing a knit cap, baseball hat, or other similarly sporty creation.

Making Waves

Use a bit of heat to set the curl, then let the standing curls cool, after which you gently brush them out section by section with a boar bristle Mason Pearson for incredible shine and a polished look. And always remember, the smaller the set, the tighter the curl obviously.

Setting the hair in standing pincurls with a setting lotion or lightweight gel mixed with water, spritzed onto the hair for hold, will create picture-perfect waves that look slightly more sophisticated than an untamed mane of feral curls.

Frizz Factor

Sometimes feral works for you, but I must admit this is a hit-or-miss, Grace Coddington-kind of moment that often looks better in a fashion editorial than it does in real life.

If you’re going to put the forté on the frizz, be sure you style your ensemble appropriately and adjust your makeup so that it looks deliberate, and not like you ran out of product and got caught in a windstorm on the way to the party. It can be tricky to pull off this look, even with a mane like Nicole Kidman’s, below.

Let’s Get Things Perfectly Straight

When opting for long and straight, it’s important that the hair is perfectly smooth and sleek, not flyaway or straggly or uneven at the ends.

If your ends are not blunt enough with a sufficient weightline, ie.–if they tend to look a little bit ‘see-through,’ this can be an unattractive menace and you might want to compensate with a synthetic ponytail or 3/4 wig beneath the hat for extra weight and volume, which can result in a truly spectacular, perfect look. There’s plenty of fake hair out there to go around so consult your local wig shop.

The Power of The Pony

Personally, I adore a chic, low pony, wrapped in its own hair, as seen below with this uber-cool seamless sculpted cap by milliner Yael Cohen. You’ll be seeing more from Yael in our “Hats Heard Round the World” Project by the way, so stay tuned for more about her.

I happen to have this very cap, a cherished gift sent to me from Yael, owner and chief designer at Justine Hats in Tel Aviv, Israel. I wear this constantly–very similar to the model above–with a low pony.

A high, more perky ponytail is also another style to consider but only if the hat rides high on the back of the head. So be sure to experiment, consult your milliner if necessary and ask his or her opinion. Research great-looking shots of chic headwear in the magazines and online. Examine the hairstyles selected for the looks and practice them on yourself. You may even want to take a few selfies to perfect your look when wearing a complicated piece, in particular if you are going to be photographed or it’s a special occasion. In fact, I highly recommend this process, for realistic self-evaluation.

It’s a No-Show

Sometimes the best solution to a hair issue is to ignore it completely. Yes, slick it back or pile it up under the hat for a “No-Show.” You can almost never go wrong.

Note these examples, where no news is good news, and the hair quietly takes second seat to the hat that adorns it.

Above, the hair is tucked into the belly of the hat for a dramatic effect. And below, sleek and smooth, the hair again is practically a non-entity with this spotted topper.

Pass the Accessories, Please…

Finally, you may want to combine accessories when wearing a hat. Use discretion. Below, all the hair is a “No-Show” concealed beneath a stylish scarf worn under that hat.

And a rakish top hat takes on a dramatic yet feminine appearance when the model’s hair is slicked back and packed inside a snood at Dior. So timeless, so femme fatale!

No matter your hair length or texture, there’s always a chic solution for every hat you may encounter, and now you know the industry secrets on how to style your hair when wearing a hat. Hats off to you!