Bring a little night time glam to the daylight hours. Instead of being ultra casual, try jeans with strappy gold heels or a tee shirt with a sequin blazer. Maybe a pile of pearls with your henley. Don't forget lipstick! In the first set below, I uses sequins and patent heels to dress up jeans and a corduroy blazer. In the second set, I paired a velvet skirt and embellished flats with a chambray shirt.
Work in the colors. For decades, fine hats were part of a matching outfit. Your hat would have been the same shade and maybe the same material as your skirt and jacket. For one of the looks below, I went all out with a matching purse, skirt, manicure, and lip gloss. For the second look, I kept things more low key with just a matching bag.
Be retro. Many of these hats are vintage items. So think of how people from that period would have done casual. Stop thinking of tailored dresses and think jersey sportswear, capri pants, denim jackets, cotton skirts.
For this 1940s hat, I looked to Katharine Hepburn, particularly her love of wide-legged pants and loafers. I dressed it down with a loose sweater and kept things fun with a leopard print scarf.
For an early twentieth century hat with feathers, I thought about the women of Downton Abbey in their down time. (Note: I have not seen the third season. Spoil it for me and you will develop a karmatic allergy to peanut butter and puppies.) I used a comfy cotton maxi dress and booties. The leather jacket toughens things up a bit, but it's still a very feminine cut.
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