I personally think that baker boy hats look best when paired with items that are a little bit more offbeat rather than super preppy or simple – like these cropped jeans and this cute sweater. Try two big fall trends at once to look like you just walked out of a magazine: a plaid blazer and a baker boy hat. These two really do work together well! There’s a fun contrast when wearing a baker boy hat with something futuristic, like metallic sunglasses in a funky shape. Again, I think baker boy hats look best when worn with more unique items! That’s probably why I love this combo of the cap with the yellow jacket. Add your baker boy hat to any basic fall outfit to give it a little more oomph. Pair your cap with a statement clothing piece to really stand out – like this velvet sweater. Make a basic outfit, like a white shirt and black pants, a little more interesting by adding a baker boy hat. A baker boy hat looks really cute with a fall skirt and sweater combo – add a trench and some ankle boots, and you’ve got a pretty stylish look. Go for an all-out early 2000s/late 90s vibe by wearing your newsboy cap with an oversized denim jacket. I don’t know why, but baker boy hats look especially good worn with round or smaller sunglasses. If you want to do something different, opt for a newsboy cap in a pattern instead of a solid color. Baker boy hats and leather jackets don’t seem like they would go together well, but they actually kind of do! Add a baker boy hat to an oversized sweater dress and over the knee boots for a super simple fall outfit. Adding boots, a newsboy cap, and a big scarf to any dress automatically makes it work in cooler weather. Opt for a suede baker boy hat for something a little different and perfectly suited for fall. A turtleneck, plaid skirt, and cute ankle boots are a perfect outfit with a newsboy cap and some round sunglasses. Add it to even a super casual outfit, like a t-shirt and jeans, to look more put together. Get super cozy for fall with a sweater, jeans, over the knee boots, and a cute baker boy hat. Add a newsboy cap to a dress and tights to make the look more casual. Make a summery floral dress work for fall with a baker boy hat and over the knee boots.