A first hat that "goes with everything" usually goes with nothing. Decide the job: rain, sun, smart-casual or winter warmth. Then buy one silhouette and wear it for a season before buying a second.

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Eight starting points by job (UK)

One felt silhouette you will actually wear — not a costume.
One felt silhouette you will actually wear — not a costume.

Each link below is an Amazon UK search for that type of hat, not a single model: we haven't compared specific makers, and hats come in so many sizes and colours that one listing rarely suits everyone. Use the search to see what's available, then read the size chart and returns policy before you order.

JobStart hereWho it suits, and who should skip it
City, autumnFelt fedoraSuits coats and smart-casual jackets from October to March. Wool felt is the affordable starting point; fur felt is finer and dearer. A felt fedora search filtered by your size saves returns. Skip it if you mostly wear sportswear. Crushable felt fedoras survive a bag better than stiff ones
Everyday cityWool flat capThe easiest first hat in Britain: low, warm and hard to get wrong. Tweed hides wear well. A wool flat cap in a mid-grey or brown works with most coats
Summer dressPanama / toquillaA true Panama is woven in Ecuador from toquilla straw. Look for "toquilla" or "Ecuador" in the listing: Panama hat. Skip paper-straw copies if you want more than one summer from it
Casual summerCotton bucketCheap, packable and washable; good for festivals and children. Cotton bucket hat
RainWaxed cottonSheds British drizzle and dries fast; re-wax once a year. Waxed cotton hat
Rain, heritageBarbour-style waxedIf you already own a waxed jacket, a matching hat from the same maker keeps the colour consistent. Barbour waxed hat
Sun / travelWide brim, real UPFFor holidays and gardening. Look for a stated UPF 50+ rating and a brim wide enough to shade your face, ears and neck; Cancer Council Australia suggests at least 7.5 cm for adults. UPF sun hat
Outdoors, packableTilley-style travel hatCrushable cotton or nylon with a chin cord, for walking and boat trips. Tilley hat

Keep, clean and stretch gear lives on hat storage and hat tools, not in this first-buy table.

Check the returns policy before you steam or reshape anything, because a hat that's been altered usually can't go back. Skip a 10 cm brim you'll take off on the train. Skip cheap "straw" that splits in a week. Skip a bowler "for the look" unless you have an occasion that calls for one.

Fit before fashion

If it perches, it's too small. If it sits on your ears, it's too big. Brim and crown do the styling; the sweatband does the wearing. Measure your head with a soft tape about 1 cm above your ears and eyebrows, where the hat will sit, and compare the number in centimetres with the maker's chart: UK sizes, US sizes and S/M/L labels don't line up neatly between brands. If you fall between two sizes, buy the larger and add a thin foam sizing strip behind the sweatband. See face shapes once the hat actually stays on.

Then: measure, check material, read care. Outdoors detail: utility hats.

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