Fall and Winter Hats I’ll Be Wearing on Repeat

Hi, friends! If you’ve been following along for any amount of time you might have noticed one thing about my personal style, especially if you shop from my LIKEtoKNOW.it frequently. Any ideas? Hats! I am such a hat girl and love adding them to pretty much any look, especially fall outfits like this and this. I get asked quite a bit which ones are my favorite or how I like to style them so I thought it would be a fun blog post to put together for you ladies. After all, they are one of my favorite accessories!

I based my picks on my personal favorites and style for the Fall and Winter season. I linked lots of my go-to’s for y’all so if you’ve been on the lookout for a good Fall hat, you can find it here!

Beanies Without Poms

I think beanies without poms are potentially the most ‘on trend’ hat this season and probably the most versatile. I like to wear them with casual outfits that have more of an edge. For example, maybe with a shacket [arguably this season’s biggest trend], high waisted denim and combat boots or a Chelsea boot [SIDENOTE: I’ve really gotten into combat boots this year – lots of picks here]. Something like this beanie is a really great option to go with the outfit I just described – I snagged it in grey and crimson! I also love this one from J.Crew that I wore in Maine last year in white and went back and got it in the light grey color this year for when I don’t want to wear a label.

Beanies With Poms

My style tends to lean much more girly and feminine, which is why I think I love beanies with poms so much. I tend to throw one on with super casual and cozy looks like this, but also wear with jeans like I did here. This is honestly a look you see on repeat from me quite a bit! I tend to reach for this beanie a lot but also really love this light pink one and have recently been seeing some really great options including this one [if you want a faux fur pom], this one and this one [love the animal print here].

Here’s some outfit inspiration from years’ past of me styling knit beanies with pom’s [gosh, some of these are MAJOR throwbacks! Be sure to check old Instagram Roundup’s from November and December, my posts from Canada, and old holiday posts for outfit details on these]:

I could go on, but you get the idea! Ha! Be sure to check old Instagram Roundup’s from November and December, my posts from Canada, and old holiday posts for outfit details on those if you’re curious.

Fiddler Cap

Oh, the fiddler cap! I am completely aware this might not be everyone’s cup of tea, and that it’s potentially going ‘out of style’, but for me, a fiddler cap easily completes any fall look. Anytime I wear one I feel like it instantly elevates my outfit in a chic way. Big fan of the fiddler cap over here! 🙂 I have a few different ones I reach for consistently including this one and this one. Also really loving this olive green option – very seasonal!

outfit likely linked in one of my Vermont posts


These are from my time in Vermont in 2018.

I know a lot of people love wide-brim hats for fall, but personally, I don’t reach for mine as much as I did a couple of years ago. They are really cute and look great with cozy sweaters and leggings, I just tend to reach for a beanie or one of my fiddler caps more often. Since I know a lot of you love them, I still linked some favorites of mine for you below!

I’d love to see some of you girls wearing and styling your favorite fall hats too, so be sure to tag me on Instagram the next time you put a look together! Until next time! xo.


Editor's Notes



  1. JOE wrote:


    Published 11.16.20 · Reply
  2. Hi Alyson.

    Beanies with or without Poms looks quite incredible and the variations you have pointed there are worth to give a try.

    Published 2.20.22 · Reply