Those of you who have been reading my blog for awhile know I am a hat person. Hats are amongst my favorite accessories. I try to keep my face out of the sun as much as possible. I spent way to many years baking in the sun. We are so fortunate that there are so many options available. Let’s talk about how to embrace the season in style: five fabulous fall hats for women over 50.
Once I put my straw hats away and transition to my cold-weather options, my hat of choice is a version of the wool felt fedora. I love all hats. The beret, the newsboy hat, and the beanie are flattering on others. A brimmed hat is more flattering on me. I wear baseball caps, bucket hats, cloche hats and others. My favorites are what I will categorize as ranchers.
In this fall look, I am wearing the black london hat by Wyeth. It is made of Australian wool with a brown leather band and it has an adjustable interior band to perfect the fit. This hat has a stiffer wool brim than the Billie but has a similar look. The scarf is from IBU a few years ago, they have a similar one here.
Here I am wearing the Lysse Fringe Coat, their faux leather pants, and my gentle souls booties.
SHOP THE LONDON LOOKS
Another favorite in my fall wardrobe, is the Gigi Pip Rue hat. The round crown gives this hat a level of elegance that I like. Gigi Pip is having a pre-black friday sale with 15% off sitewide, 20% off 200, and 25% off 400. This hat has a stiffer wide brim which I like.
SHOP THE RUE LOOK
I have the wren hat from Gigi Pip in cream and brown. It also has a flat brim. I love the adjustable drawstring neck cord. If it gets too hot you can wear it on your back.You can also tuck it inside the hat like I have done here. The Artemis smoking shoes are on flash sale today here.
SHOP THE WREN LOOK
The Wyeth Harper is a great casual hat to wear with jeans or a jean skirt outfit. It also has an adjustable inside band for a perfect fit.
Here I am wearing it with a Ralph Lauren utility jacket, a jean skirt from Etsy and my comfy Gentle Souls boots.
SHOP THE HARPER LOOK
I love the unique gray color of the Wyeth Billie hat. This wool fedora , is a fall classic and one of their best sellers. It’s brim is less stiff than some of the others, so it is more flexible. It comes in many different colors and is flattering to many face shapes.
Unfortunately, the Anthro cashmere sweater I am wearing is sold out. The lily skirt from CP Shades is still available, and I also found one in a cinnamon color that I linked below on eBay if you can wear a medium.
SHOP THE BILLIE LOOK
These are my top picks for my best fall hats right now. I hope you enjoyed Embrace the Season in Style: Five Fabulous Fall Hats for Women Over 50. Do you enjoy a great hat? I would love to hear about your favorites.
If you struggle with what type of hat suits your particular face type,Hats.com has a great article here about choosing the right hat for your face shape. Wiki How also has another informative article Wiki How-How to Select the Best Hats for your Face Shape here. You might also enjoy my post Ten Chic Ways to Style Olive and Black for fall here.
Hi Cindy, I don’t think I have ever left a reply, but I really enjoy your posts. Your outfits are elegant and you put them together effortlessly. Amazing! I like to try to copy the looks on a budget.🥰 I love hats but it has to be the right one for me and that’s a bit difficult for me at age 72. You’re always looking great, Cindy! Bless you!
Hi Vivian
So glad you are replying now. We love hearing from you. It sounds like we need a hats on a budget post!!
Love your blog…I am a hat person too…Love Atwood NEVADA Spanish style flat brim, get so many compliments and everyone wants to try it on, which is the best compliment ever, right?
I’ll check out GiGi Pip next time we are in Paso Robles.
Hi Valletta
I am going to check out your hat of choice!
Hi Cindy
You wear everything so well! Always looking incredibly classy and stylish.
I wish my hair was thicker, I hate wearing a hat and getting the dreaded line across my head afterwards. But I do have a few that I wear regardless,, and it is important to keep our faces out of the sun ! What is your suggestion for storing your hats? That’s my nest problem to solve in my closet.
Enjoy these early days of November,
xo Heidi
Great hats & styling! I’d love for you to do a post on your closet and how you store/organize your hats and all your wonderful clothes & accessories.
I love hats too. I wear them when I will be outside for any length of time. They do add interest to an ensemble and provide great skin protection. My husband is a hat guy too. Thank you for sharing so many nice ones. You wear them beautifully.
Hi Cindy! This article on hats is so much fun! I can recommend a hat I ordered this season from J Crew Factory called the Bow Fedora in camel, which is a warmer, rich color.It’s on sale now for a terrific price and it also comes in dark claret and sand. Two sizes are available. I wear it outside as it has become cold and I still want to shield my face from the sun during walks.
Once again, LOVE your accessories and especially love the way you belt a long wrap over your clothes. Looks wonderful.
But to the hats! You’ve worn one in the past which I can best describe as a gaucho’s hat. Low crown, stiff brim – very Spanish looking. It’s probably my favourite of all, but not featured today.
Nevertheless, they all look wonderful and inspired me to go and buy a straw hat. We’re on the cusp of summer, here and I lost 1/3 of my right ear last year with invasive skin cancer. All the more reason to wear hats, despite dreaded ‘hat hair’.
I love your posts and might have to move! I live in Toronto Canada and love the southwest style! Some I embrace but all …. Gorgeous!
Am loving all the outfits and hats. Unfortunately, my head is too big for most women’s hats. Sometimes I can find the similar style in men’s sizes. I especially like the Gentle Souls boots. Have been trying to find a winter white/light taupe version of those boots. Can’t find them.
HAPPY FALL CINDY,
The “Fedora” is perfect for the shape of your beautiful face. The unique styling with your outfits is elegantly sophisticated,, playfully fashionable, and totally inspirational.
Grateful in this season of Thanksgiving,
Diney on Mercer Island
I love the poncho in the Gigi Pip Rue photo with the large button. Where did you get it?
You have such a great style Cindy! I love hats too! Thanks for giving us some options and places to find them. Happy November!
Hi Barbara
Thank you so much. Happy November to you! I cannot believe the holidays are upon us!!
Well, I was jumping up and down putting outfits together from this article. I love the handmade Levi jean skirt from Etsy. The hats look so good on you and what a fun topping – so-to-speak. Thank you,
Hi Lynne Anne
I am so glad you like the skirt. I thought it was really fun and reasonable. I know you may be in the minority ha ha!!
Love all of the looks that you’ve put together. I think I need a Wren hat! I found a good one that I feel acts to span seasons since it’s neither straw nor wool It’s cotton but done in a nice weave so has some texture and also has the inside drawstring. It’s made by Kooringal and has built-in 50+ spf. I found it at the Garden Gallery in Morro Bay and I think it was only about $50. Shall we both be mad hatters on Tuesday? 😉
Hi Wren
Let’s get Diane circled in as well!! I have a summer Kooringal hat too.
Wonderful hats, wonderfully worn!
Hi Marcie
Thank you so much! Happy November!
You look fantastic in all the hats! How do you avoid hat hair or do you not have an issue with it?
Hi Ann
I just fluff my hair back up when I take the hat off. I often wear hats on days that I don’t do my hair, so I don’t have to worry about it!
You wear them so well! 🙂
Hi Pam
Thank you so much! How are you and the fam?