Silly little hats take over the catwalk and the high street

The baseball cap finally has competition. Hats with brims, crowns and a sense of humour are back, moving from the catwalk to the high street, The Guardian reported on 2 October 2026. The Guardian

The paper calls them “silly little hats”. Its feature, “Brimful of personality: the rise of fashion’s ‘silly little hats’”, runs from pillboxes and boaters to bicornes and buckets.

The strongest signal came from Loro Piana, the Italian luxury house known for cashmere and quiet tailoring. Almost every model in its seasonal collection wore a hat. The house showed its Spring 2027 ready-to-wear collection, clothes made in standard sizes for shops, at Milan Fashion Week. WWD

Thom Browne, the American designer label, went further. It showed straw boaters shrouded in colourful mesh in Milan. A boater is the flat-topped straw hat with a straight brim. The opening looks paired them with beekeeping veils wrapped around the crown. GQ

That Spring 2027 collection took inspiration from ‘A Bug’s Life’. Models carried watering cans cut from seersucker fabric, the puckered cotton cloth. Caterpillar and butterfly motifs ran through the clothes.

Chloé, the French fashion house, offered a lighter touch. It presented see-through hats and white sailor hats, worn with all-white outfits. Burberry, the British luxury house, sent out big bucket hats. A bucket is the soft hat with a downward-sloping brim.

The street has noticed. Pillbox hats were a common sight during Copenhagen fashion week. A pillbox is the small round hat with straight sides and a flat top. No strap. No brim. Just shape.

The high street has followed. Asos, the British online retailer, and H&M, the Swedish high-street retailer, were selling wool and pillbox versions. The collaboration between designer John Galliano and Zara, the high-street chain owned by Spain’s Inditex, includes Napoleonic-style bicorne hats. A bicorne is the two-pointed hat worn fore to aft.

This did not start this season. Vogue argued in July 2025 that hats were already back, and named Ukrainian milliner Ruslan Baginskiy as a big reason why. Vogue His “Formation” hat is an exaggerated boater made in gold, silver and metallic red.

What makes this stand out is the range. One season has delivered veiled boaters, sailor whites, soft buckets and historic bicornes. The common thread is personality. The hat is doing the talking.