I recently bought a barleycorn tweed flat cap and a herringbone tweed flat cap, both in medium, and they look great and fit really well. Here's a look at both patterns, general flat caps, and how to get the sizing right — with eBay UK links if you'd like one yourself.
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Barleycorn tweed gets its name from its small, flecked weave, which looks a bit like scattered grains of barley up close. It's a subtler pattern than a bold check or herringbone — from a short distance it reads as a plain, textured tweed in a muted colour, which makes it an easy one to wear with almost anything.
I picked up a barleycorn tweed flat cap in medium and it's been a great all-rounder — smart enough for a jacket and shirt, casual enough for a walk in the countryside. It's a good pick if you want the classic flat cap look without a pattern that shouts too loudly.
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See barleycorn tweed flat caps on eBay
Herringbone is probably the pattern most people picture when they think of a tweed flat cap — a broken zigzag weave that forms a series of V shapes, named after the bones of a herring fish. It has more visible texture and definition than barleycorn, giving the cap a slightly more traditional, "country gent" look.
My herringbone tweed flat cap, also in medium, fits just as well as the barleycorn one and has a slightly bolder feel to it. If you want a flat cap that clearly reads as tweed from across the room, herringbone is the one to go for.
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See herringbone tweed flat caps on eBay
Barleycorn and herringbone are both woven tweed patterns, but flat caps come in plenty of other fabrics and styles too — plain wool, moleskin, tartan and check, waterproof and wax finishes, and lighter cotton versions for summer. There are also related shapes like the baker boy or newsboy cap, which has a fuller, more rounded crown than a traditional flat cap.
Worth thinking about before you buy: what you'll wear it with (a flat cap suits tweed or wool jackets particularly well), the season (wool and tweed for autumn/winter, lighter cotton for summer), and whether you want a subtle colour or something with more pattern. If you're curious what else I get up to outside of flat caps, take a look at my homepage.
This link goes to eBay UK and may earn me a commission at no extra cost to you.
See men's flat caps on eBayFlat caps are usually sized by head circumference in centimetres or inches rather than S/M/L alone, so it's worth measuring your head (wrap a tape measure around the widest part, just above your ears) before you buy. As a rough UK guide:
Small — around 55–56cm (6⅞–7)
Medium — around 57–58cm (7⅛–7¼)
Large — around 59–60cm (7⅜–7½)
X-Large — around 61–62cm (7⅝–7¾)
I'm a medium in both the barleycorn and herringbone caps I bought — that's a 57–58cm head circumference — and they fit true to size, snug without being tight, with a bit of give from the usual elasticated panel at the back. Sizing can still vary a little between sellers and brands, so it's always worth checking the specific size chart on the listing before you order.