How To Wear a Newsboy Hat Three Ways

February 4, 2018

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Did I ever think that I would be channeling my inner newsboy and wear a hat that every single news-slingin’ paperboy of yesteryear would be proud of? No, no I did not. Did I think that I would love said hat so much that I would end up wearing it three days in a row? Also, no. Did both things happen? Why yes, yes they did. 

I have ended up wearing this hat so frequently, that Zach has asked me if I own anything else. I mean, not mad about that, I guess. It ended up inspiring me to write this post, because before this little cap of wonders came into my life I was somewhat intimidated to take on this trend. Odds of looking like a train conductor are high, but who says train conductors can’t be stylish? NOT ME. That’s who. If you’re on the fence on this particular trend, just jump on board! On board. Get it, because you’ll be train-conductor chic! Anyway…

With all that aside, I put together three looks that you can easily replicate to start rockin’ the baker boy cap/train conductor/newsboy look of your dreams. Papers not included (though, you should go buy your local paper. Print forever. #LongLiveThePaper.) Okay, sorry. That’s just my journalistic roots being a proud supporter of the printed press. 


The Neutral Newsboy

9 days out of ten, I look something like this when I’m headed out of the house. Neutrals over everything. Always. And forever. I’m a sucker for anything cognac, striped and denim, and this cap was the perfect add on to my everyday go-to look. This is an easy way to ease into the newsboy game while still remaining comfortable and casual with the rest of your ‘fit. 

You can shop the whole look below, including this denim jacket, that’s by far one of my favorite purchases I’ve made within the last year. A great denim jacket will never go out of style, and the boyfriend fit of this one makes me want to wear it daily. Just enough distressing, and the perfect oversized but not TOO oversized look. Believe me, you won’t regret this one.

Just doing my best to be a super serious fashion blogger


The Casual Newsboy

PEOPLE. Overalls are back and I am HERE. FOR. IT. Why these things ever went out of style is beyond me, but if they decide to go out again, I’m keeping this pair in my closet forever anyway. Because they’re just THAT good. I got this pair last summer and let me tell ya, I’ve never looked back. 

Did I previously rock the one-shoulder overall look circa the 90’s IN the 90’s? You bet your cute little butt I did. I’ve opted to start utilizing both straps these days, but regardless of your strap choice, I highly suggest you add a pair of these dreamy denim overalls to your wardrobe ASAP. Pair it with your new newsboy cap, and a great striped tee (or bodysuit, like this one below) and it’ll be the easiest outfit you’ll ever put together. 

P.S. did I tell you yet I’m a fan of stripes and denim…? 


The 9-5 Newsboy

Newsboys gotta make a livin’ too, ya know? Just to continue this massive striped kick I’m currently on, for my last newsie-esque look I paired my go-to cap with another favorite trend I’m so on board with: culotte’s. Likely hated by men (whatever) but loved by women (because, comfort) I own quite a few pairs of these fun pants in my wardrobe. It’s a such an easy and simple way to add some sass to your everyday work wear. The pair I’m wearing below is sold out, but I’ve linked tons of similar options below. Asos and Zara always have the best options, in my humble opinion, and they’re always very reasonably priced!

This option is perfect for the gal on the go who wants to add something a little extra to her work wardrobe. Headed straight from the office to drinks with your gals? Add the hat to make your happy hour sips that much sweeter (and a little bit sassier now that you have your cute new hat on) Go you, you trendsetter. 

I paired the culottes below with the comfiest mules from Kristin Cavallari’s shoe line. Sidenote: I will always be #TeamLC, for so many reasons, and now more than ever due to the massive lifestyle empire she’s built for herself. BUT. My girl Kristin knows how to design a killer shoe. I seriously swoon over every single pair in her line. If you haven’t checked it it out, do yourself a favor and get there now.

What are some of your favorite trends this year? I’m always lookin’ to add new pieces to spice up my wardrobe. Share with me in the comments, or come hang out with me over on Instagram!

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