Unlimited Options of Newsboy Hat Outfit and Tips for Winter Hats

Unlimited Options of Newsboy Hat Outfit and Tips for Winter Hats

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Casual outfit for women over fifty

Unlimited Options of Newsboy Hat Outfit and Tips for Winter Hats

Today it’s all about a newsboy hat outfit along with styling a beanie as the last in the series about winter hats. I thought it would be fun to showcase both a neutral and a colorful newsboy hat and beanie with this same outfit.

Quote of the day: “Be less curious about people and more curious about ideas.” Marie Curie

This quote caught my eye because I feel like I’m always trying to reason the idea of why an item of clothing works or doesn’t work. And trying to figure out tips and tricks to help you in those decisions.
Winter hats can be just as functional as summer hats. Sure, maybe you don’t need them to protect you from the sun as much, but there are other elements at play. Besides, they can help with a bad hair day (as Charlotte showed earlier this year with a totally different option too), and they can add style to a look.

Other winter hats we’ve discussed
Winter Hats– Shrewd Ways for Wearing a Fedora and a Cloche Hat
Styling a Beret: Ideas for Unique Winter Hats

Jeans: Second Yoga ~~Sweater: Hand knit by me ~~Boots: Naturalizer ~~ Purse: Kate Spade-thrifted

I kept my outfit for these hat outfits relatively muted and simple. A pair of jeans (that have a burgundy tint especially on the seams and back pockets) along with a knitted sweater (more about that below) and a brown pair of riding boots.

Since I am an avid shopper and avid hat wearer, I thought I’d also share some tips at the end of this post!! And I always love to hear your secrets too!

Newsboy Hat Outfit

The newsboy hat is one of those you see for men, older men no less at least here in my retirement community, LOL! Yet they work wonderfully for women too.
I think of them as a fancier version of the baseball cap. It’s close to the head in the back, and still has a brim.

Here I’m showing both a colorful plaid hat which was found thrifting. And a neutral plaid one that I “borrowed” from my husband. I wear his hats ALL the time and you can see this one with an entirely different outfit last fall.


Beanies are those winter hats that most of us think about only for outside. Yet even when I was still practicing dentistry, some of my younger, women employees would say they would wear them out on the weekends. Even when they went inside to shop and eat.
Of course, at that time I was much more limited in my style views and I thought that was silly.

However, now I get it. It’s a hat. Meaning just like with my newsboy hat outfit, it can stay on my head the entire day.
Again I wanted to show examples of a colorful variety and a more neutral one. BTW, the “neutral” one is light pinkish/purple, yet from far away seems more grey.

This orange/peach beanie is one that I knitted for a friend. When she passed away, her husband gave it back to me, so it’s a wonderful memory of her.
Right now, I adore the pom poms that are on many of the beanies. I didn’t knit the pink beanie, but I love how you can buy these pom poms and add them to any knit hat.

Insider tip: SO many colors/prints look different from a distance. Sometimes we get too hung up looking at colors/print right in front of our face. Try putting it on a table and back away to see how others really see it.

Tips for Winter Hats

Here’s a couple of tips and tricks for finding the right hats for you without always spending an arm and a leg.

1-Make sure to “shop” any of the men’s hats in your household. Out of the 6 styles we showcased this week, you could probably find 4 of them (I doubt the men would be wearing berets or cloches).
2-If you are new to hats and not sure what looks good on you, take a friend shopping with you. A truthful and unbiased friend. Most of the time if you don’t normally wear hats, you won’t think you look good in them. It’s truly a matter of getting used to the look as it is with all fashion styles.
3-Check out the thrift or consignment stores! This is wear you can find some of the best deals. AND again, check the men’s and even kid’s sections.
4– If you have a bigger head, then it’s absolutely smart to focus on the men’s hats. And if you have a smaller head, the kids ones may fit much better.
5-You can always “decorate” your hat to make it more unique. Tie a scarf on it or add a brooch.
6– There are sites that specialize in hats which can be helpful if you’re hard to fit. I’ve been gifted many hats from Tenth Street Hats in the past, and appreciate their page on sizing for hats and fit tips.
7- Many hats have an inner drawstring to make it smaller. Another option is the sizing tape that can be purchased.

See how we’ve decorated our hats in the past
Styling a Scarf with Ladies Summer Dress Hats
Different Accessories on which to Wear Your Brooches

The Rest of the Story

This is one of my hand knit sweaters that I love and wear often. One of the reasons I wear it is because I paid $80 for the free pattern. It’s a long story, but suffice it to say that I’ve learned to google the exchange rate before ordering overseas!!
If you caught the “free” part, that’s because the pattern for this sweater was supposed to be in this knitting magazine, yet when I finally got the magazine, they said it was a free online pattern!!!

Luckily it’s a good story and I made sure to knit up the sweater right away so I could get my money’s worth, haha!

Plaid newsboy hat outfit
Newsboy hat outfit

Photo credit: Rob Filogomo

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