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!
To me, the biggest barrier to wearing a pillbox hat was figuring out how to keep it on my head! I don't know if it's the shape of my head or what, but they tend to fall of pretty fast. Now that my hair is a bit longer, I find that the easiest way to keep them on is to create a nice little beehive and use a hat pin to pin it on.
ReplyDeleteLove all these styling ideas, I'm going to have to bust out one of my pillbox hats again soon.
Yes...this is a surprisingly tricky part of hat wearing. I've actually only worn one that fits my head and one that has little combs attached. Hat pins seem to be the fallback but I don't find them as easy as I'd like. Something for a future post, perhaps?
DeleteA string of elastic cord either clear or matching the hat threaded and tied at the inside band on each side and looped under the hair works pretty well for me.
DeleteFantastic, thorough, truly lovely post. Pillbox hats are not a style I own a great many of myself, because I find that they often don't look all that flattering on me. That said, sometimes I'll luck out and come across one that does and then I can't wear it enough, so - as with so many things in life - it's just a matter of trial error. I'll actually be sharing an outfit post in August that sees me wearing a pillbox hat for what may very well be the first time on my blog and I'm definitely excited about that.
ReplyDeleteAgain, stellar post! Your passion for this style is contagious! :)
Tons of hugs & happy weekend wishes,
♥ Jessica
Oooh I am very much looking forward to seeing you in a pillbox hat! I'll keep an eye out for that post.
DeleteThank you, thank you, thank you for doing this post! You already know all about my not-so-love of the pillbox, but in one fell swoop I think you just about changed my mind Tanith! You know what did it?
ReplyDeleteTilted pillboxes. I just adore the looks in the beginning of the post with the smaller pillboxes worn on the side of the head! Now I just need to get my hands on some *gasp* pillbox hats for myself! Or maybe make one?? I don't know, but I am DYING for some more hats in my wardrobe. :D Apparently hat love is contagious. ❤
xox,
bonita of Lavender & Twill
I am sooooo glad! I'm really pleased it was helpful to you, and I look forward to seeing your take on pillbox-wearing.
DeleteAWESOME! I just purchased a pillbox hat in Seattle in February and it's been sitting in my hat box at home doing nothing because I had no idea what to do with it. This post has inspired me to no end. Thanks Tanith!
ReplyDeleteLiz
Oh I'm so glad, Liz! I hoped it would be able to provide just this sort of inspiration. I hope to see you in your pillbox soon!
DeleteThis is so packed full of tips and inspiration. I love the look of pillboxes, now need to try wearing one!
ReplyDeleteI hope you do! Have fun :)
DeleteI want to wear a pillbox hat so that all my hair is inside, the pillbox is towards the back of my head with the first 3 inches of my hair showing up front by the hairline. This was common in the 60s but I cannot figure out how to keep it on my head. Any advice?
ReplyDeleteHi Talia! Because your hair is inside, this might be a perfect time to use a hat pin or two,since you can anchor it to your hair on the way through. This is a good blog post on using hat pins: http://www.vixen-vintage.com/2012/02/how-to-wear-hatpin.html
DeleteIt depends on whether the hat is easy to get a pin through or whether you are worried about damaging it as well. Another option could be to add small elastic loops and put combs or bobby pins through them to attach to your hair. I would probably do this at the sides, but you could experiment to see what works best.
I have short, textured hair. I stitched two of those hair clips that snap open and closed to the band inside the hat, one at the front and one at the back. I make a pin curl in my hair where I want to secure the hat then attach the clips to the pin curls. Invisible and secure! Love my pillbox hats and wear them often, mostly to church.
DeleteThanks for sharing that tip Christina!
DeleteThis is so inspiring. I have a handful of hats just itching to be warn. Its so windy here at times even a hatpin can't seem to keep my hat on.
ReplyDeleteThat's pretty windy! I suffered with a flying-off-hat recently and it ended up in the water, sadly! I still have some work to do on securing some styles.
DeleteHi Tanith, thanks for this useful article. I had been looking for any clues about how to wear pillbox hat and what kind of dress shall I match it with. I am Indonesian and in my country pillbox hat is not (yet) popular. However I plan wear one in my friend's wedding in Italy this September. I already have a long evening gown that I want to wear and I have ordered a pillbox hat with similar color, but then they don't really match. One question, are pillbox hats better off with shorter dresses?
ReplyDeleteHi! I'm glad you found it useful. I think that pillbox hats would often have been worn with shorter dresses, especially in the 1960s when they were the most popular. I don't, however, see any reason why a pillbox hat wouldn't look good with a long gown. If you like how it looks, go for it!
DeleteThis is great thank you! Just one question, my mum wants to wear a pillbox hat to my wedding but has quite short hair (middle of neck) and a full fringe so cannot really put it up and it just does not want to stay on her head! How can she secure it without having to put her hair up. If it makes a difference she wants the hat on the back of her head. Any help gratefully appreciated!
ReplyDeleteI bought some of those snap open/close hair clips and stitched two onto the inner hat band. You can stitch front/back or side/side. If I wear a pillbox back on my head, I use the front/back clips and make a pin curl to attach it to in the front. I have short hair as well. Hope this helps.
ReplyDeleteGreat article, lots of great tips. Thank you all!
ReplyDeleteI just got a vintage pillbox hat as a gift from a friend, and I wasn't quite sure how to use it. This was extremely helpful, and I like that you put in so many suggestions for wearing it!
ReplyDelete