Ask a Stylist: headbands and how to wear them

Can I wear an headband without looking like a child? And are they best avoided at the office?

The humble headband can be a pretty way to finish off an outfit. But they come loaded with connotations — Sloane being the main one. In the 1980s, Princess Diana, Sarah Ferguson and numerous well-bred young girls about town wore them for every and any occasion. Catherine, Princess of Wales, also wears them regularly and rather well, although some of them are more of a hybrid — half headband, half hat.

Schoolgirl is another inescapable association for the headband — which, for many of us, can stop us even attempting to wear one as an adult. I am not going to pretend that they are an easy accessory, but it can be done. Here’s how.

Those who have been reading my columns know by now that I begin all my musings on clothes with a look at body shape and how it should influence what we wear. Getting a headband right requires considering your head, frame size and face shape. I know it sounds complicated but, honestly, it’s not.

In general, headbands look best on small or medium-sized heads. If you have a larger head (in stylist lore you have a large head if your jaw measurement, which is from ear lobe to ear lobe tracking the jaw, is over 30.4cm), then you need to keep them flat to the head. You don’t want to make your head look bigger, as this makes you appear shorter and knocks you out of proportion. Aim to keep it all close (see more on ballet bands below).

You also need to bear in mind your frame size. This is your bone size essentially and it dictates what size your accessories should be. If you’re a large frame you need thicker, wider headbands around 2 inches at their widest point. At the top end, Alaïa does a fabulous cut-out wide band (£437, mytheresa.com). You can also find numerous thick bands on the high street.

For medium frames, look at approximately 1 inch at the widest point — I love this sophisticated, goes-with-anything tan headband from Jennifer Behr (£130, brownsfashion.com). For the small-framed among you, opt for slim bands, under 1 inch, like this pretty satin style from Roseings London (£30, roseingslondon.com).

Headbands particularly suit square and round faces, which both benefit from the added detail or depth at the top of the crown as it helps to lengthen the face. This sunny textured shape from Becksondergaard is perfect for spring (£22, anthropologie.com), and the company does a beaded one to boot (£46, anthropologie.com). You can also wear the twisted knot type, which gives a definite boost to the top of the head — take a look at the huge selection Lele Sadoughi offers (from £64, lelesadoughi.com).

Long, rectangular and heart-shaped faces are the ones most likely to be flummoxed by this accessory. I advise you to keep to the flattest headbands so they don’t elongate the head further and make you look like a creature from Area 51. Try a ballet hair band. This elegant chocolate brown elastic from Skims is rather nice — just remember to hide the logo under your hair if you don’t want to show it (£24, skims.com). You are going for elegant chic here. Easy to add to a casual weekend get-up like a jean, T-shirt, blazer and white trainer, for example.

In fact, if this suits you, make the ballet head band your entry point. You can then progress to something a bit more out there once you are comfortable hanging out in this version. Use kirby grips to keep it in place and check out images of Audrey Hepburn at the barre, dressed all in black with a thick white ballet band. Nothing chicer than that, in my opinion.

A word of caution: make sure you don’t wear it too far forward. If your forehead is shallow, it can truncate the face and make you look a bit squashed. These elastic styles easily translate for the office, but I would stick to neutral colours, choosing elevated, plain fabrics and keeping your hair neat and simple. See Carolyn Bessette-Kennedy as your role model here, always with the hair neat whether it was up or down.

I love wearing headbands in lieu of a hat to a wedding or smart party. I have a gorgeous pink tweed number covered in big, fat pearls — it’s a little Anne Boleyn, and I’m undecided if this is a good or a bad thing, but I wore it at Christmas, much to the amusement of my children.

This Alaïa metallic cut-out style is really expensive, but it covers all “going out” looks — imagine this with a simple black dress and silver sandals or a green suit and heels (£430, mytheresa.com). For a smaller, if not quieter, option I adore this pretty confection from Simone Rocha (£250, matchesfashion.com). Add a bit of classic sparkle for an evening do with this Swarovski crystal headband by Lelet NY (£220, net-a-porter.com)

To avoid looking childish I would swerve away from bows, too much embellishment (unless it’s a big party and the outfit is very plain) and loud prints. These are more likely to leave you feeling like a six-year-old at a party. As much fun as that would be, it’s not what we are going for here.