How to Wear a Pillbox Hat

Pillbox hats are a bit of an enigma, I reckon. They have gone through phases of being an insanely popular style, and they are relatively easy to make, which makes them an extremely easy-to-find vintage hat style. Today pillboxes are readily available in a multitude of colours and sizes, with all sorts of trims, in genuine vintage and in modern reproductions.

But, apparently, not many people wear them. When I published my first "how to wear" post, and asked what other styles should be featured, it was pillbox hats that were most requested. And when I went looking, it wasn't exactly easy to find great outfit photos featuring pillboxes. But I persisted, and in the end I've turned up gold! If you aren't inspired by these ladies to dust off your own pillbox, I'll eat mine.

(Each photo links to the full outfit post by the individual blogger, if you want to see more images of the outfits.)

When a pillbox shape first started to appear in the mainstream millinery fashion radar in the the 1930s, they were small, and worn tilted, but pillbox hats of any size can be worn angled and look fabulous.

Wearing your pillbox on the side gives a great opportunity for your hair to shine on the hatless side, with curls or victory rolls for example, or a swept-to-the-side fringe. I particularly love a tilted pillbox with a party frock.

Kristina, of Twee Valley High, is an absolute star of this look. Angled pillbox, full skirted silhouette, beyond-cute accessories. Summer or winter, she rocks a pillbox, and loves them so much she wrote an article about it

On the back of the head is the "quietest" way to wear a pillbox hat. This is the way that Jackie O, Audrey Hepburn, and more recently Kate Middleton chose, and it oozes class, and can also remain really subtle, if you are tentative about your first pillbox outing.

This option works perfectly with winter outfits, and also really suits a suit or a simple elegant dress. It is great for a lot of hairstyles, as long as you make sure your hair isn't going to get in the way at the back. It can show off a fringe or curls at the front beautifully.

Sara, of Ladylike Delicacy, lives up to her blog's name with these very ladylike outfits, featuring classic vintage separates, with a straight, structured silhouette and fabulous jackets, in flattering neural colours.

Kate mixes her pillbox with modern elements, shorter skirts/dresses and opaque tights and statement tops and jackets. (Kate's blog Schwurlie is not recently updated, but she has some great tutorials that are worth checking out, and her own excellent post on how she wears a range of hat styles) These outfits of Kate's really show how a black pillbox is not any scarier than a black beret, and is so versatile and wearable.

Wearing a pillbox straight is a very classic and true-to-vintage way, and for me it is an in-between option in terms of bravery. There's no hiding it away at the back, but it's a more modern-seeming and casual-suitable way. Of course, it's going to flatten your hair a bit, so you may want to keep that in mind. It will work really well with shorter hair, a bob, or plaits. Again, I love this with winter outfits and vintage-fusion looks with jeans.

Judith, of Style Crone, is a hat lover and great promoter of hat wearing through her Hat Attack link ups, and she can wear any hat, including pillboxes, with superb style. She also wears them with jeans, and I don't know about you, but any inspiration for stylish dressing that still involves jeans is good news to me.

The star of my title image is Amanda, of Styleynn, who I love extra for being a vegan style blogger. Her pillbox looks I'm sharing here are both amazing studies in all-black dressing, but show how she wears her pillbox to the side or to the back with equal ease and elegance. Heavenly.

If you are nervous about going out in a pillbox, or think "I'm not a hat wearer, I can't do this," then start easy! Don't stress yourself out. Stick to neutrals colours and wear your pillbox in the winter, when at least a lot of people are wearing hats (even if they aren't as classy as yours).

I really hope this provides you with style inspiration and I'd love to see your pillbox outfits if you take the leap. Leave a link in the comments below or tag me (@tanithrowan) on instagram or twitter.

I think it's time for my good old Jackie O hat to make another appearance in my wardrobe this winter.

This series will be continuing with more inspiration for more hat styles, and the fortnightly newsletter has regular hat-wearing inspiration. Go on...sign up!