At first thought: Are hats dressy or casual? Historically, fedoras were dressy and worn year round. As times and style has evolved over the centuries we now know this: You can dress up or dress down any and all hats.
One of the best parts about wearing hats is that it becomes a part of your full outfit, just how your shoes, belt, and bag are all a part of it. Once you start incorporating hats into your wardrobe it does become that easy to style them.
What I've personally really enjoyed seeing in fashion is pairing stereotypical "casual" wear with wide brim and typically "dressy" hats. As well as pairing dressy clothing with casual hats and shoes. This dichotomy of fashion is so refreshing and breaks boundaries that we've always been told to do and not do. The best part is that it shows intention. You thought this through, used creativity, and went for it - and people will see this in you and it will turn heads.
My go-to move is to pair a blazer with a ball-cap or a flat sandal. Those two elements will dress down the blazer and make it feel less stiff and office-like. I also love pairing silk or linen with a ball-cap to break molds. Another favorite is to wear wide brim hats with sneakers. Typically wide brims look great with boots or heels - by pairing them with sneakers the wide brim hats becomes approachable and just another part of the full outfit. Pairing typically dressy fabrics and silhouettes with typically casual styles really steps up the game - I promise its so refreshing.
Outfit 1: linen blazer, tank, silk trousers, flat sandals and a camp ball cap // Outfit 2: ribbed cotton dress, silk hair scarf, sneakers, and a flat wide brim hat. // Outfit 3: silk maxi dress, flat and funky sandals, and a wide brim straw hat.
So next time you're putting on your suit, try a casual hat. Sweatshirt and sneakers? Try a wide brim. Be Bold. You Are Ready