20 Style Tips On How To Wear Baker Boy Hats This Fall

I don’t know why this is happening, but it is: newsboy caps are back in style. Except right now they’re usually called “baker boy hats,” as if the new-ish term will make you forget how awful these once were and continue to be. I’m kidding (kind of). If you like these newsboy caps, wear them all you want! You don’t need my permission! And maybe I’m only being bitter because girls who are far more chic than I am make baker boy hats actually look cool and trendy instead of like something you wore as part of an early 2000s costume. I don’t know!

I mainly blame Bella Hadid for making these hats a trend again, although I am sure it’s not her fault. I also blame Gurl editor Sara Hendricks, because she predicted this would happen a few months ago and we all ignored her. ANYWAY. Baker boy hats are here, and it doesn’t matter who brought them back. It’s hard to escape them on Instagram, as style bloggers really, really seem to love them. Maybe you love them too, in which case, you probably want some ideas on how to wear them. They actually can be quite cute when styled the right way, so go for it, girl. Here are a few style tips on how to wear baker boy (newsboy) hats this fall: 

1. 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. 


Source: Instagram/@chiarasatelier


2. 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! 


Source: Instagram/@somekindoffashion_


3. There’s a fun contrast when wearing a baker boy hat with something futuristic, like metallic sunglasses in a funky shape.


Source: Instagram/@krystin_lee


4. 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. 


Source: Instagram/@siopaedit


5. Add your baker boy hat to any basic fall outfit to give it a little more oomph. 


Source: Instagram/@allthingssyd


6. Pair your cap with a statement clothing piece to really stand out – like this velvet sweater.


Source: Instagram/@eslilyfalconi


7. Make a basic outfit, like a white shirt and black pants, a little more interesting by adding a baker boy hat. 


Source: Instagram/@egmstyle


8. 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.


Source: Instagram/@sopharsosnaps


9. Go for an all-out early 2000s/late 90s vibe by wearing your newsboy cap with an oversized denim jacket. 


Source: Instagram/@daisysfashiongarden


10. I don’t know why, but baker boy hats look especially good worn with round or smaller sunglasses. 


Source: Instagram/@gracesurguy


11. If you want to do something different, opt for a newsboy cap in a pattern instead of a solid color.


Source: Instagram/@excessoriesexpert


12. Baker boy hats and leather jackets don’t seem like they would go together well, but they actually kind of do! 


Source: Instagram/@lucyrosefitz


13. Add a baker boy hat to an oversized sweater dress and over the knee boots for a super simple fall outfit.


Source: Instagram/@victoriafolkins


14. Adding boots, a newsboy cap, and a big scarf to any dress automatically makes it work in cooler weather.


Source: Instagram/@rhoxette


15. Opt for a suede baker boy hat for something a little different and perfectly suited for fall. 


Source: Instagram/@peplumpetite


16. A turtleneck, plaid skirt, and cute ankle boots are a perfect outfit with a newsboy cap and some round sunglasses. 


Source: Instagram/@natymichele


17. Add it to even a super casual outfit, like a t-shirt and jeans, to look more put together.


Source: Instagram/@abovetheplumtree


18. Get super cozy for fall with a sweater, jeans, over the knee boots, and a cute baker boy hat.


Source: Instagram/@jewelryandjeans


19. Add a newsboy cap to a dress and tights to make the look more casual. 


Source: Instagram/@velvet_milk


20. Make a summery floral dress work for fall with a baker boy hat and over the knee boots.


Source: Instagram/@modaapropos



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