I bought my first proper wool hat on a freezing trip to Boston about six years ago, mostly out of desperation, and I have not stopped wearing hats since. Something about the way a hat finishes off a look. It just makes me feel put together even on days when I am absolutely not.
My sister thinks I own too many hats. She is probably right but she also borrows them constantly, so I do not want to hear it.
So here we are – I pulled together the looks I actually reach for when the temperature drops and I want to feel a little more myself.
20 Ways to Style a Hat This Season
Suede Jacket With Wool Beret
A soft suede jacket in a warm caramel tone next to a little wool beret is one of those combos I fall back on again and again. It reads French without trying too hard, and it works over almost anything, jeans, a slip dress, whatever you have on.
I tilt the beret slightly to one side because that is apparently the rule, and honestly it does look better that way.
Oversized Blazer And Yankees Cap
Here is where things get a little unexpected. Take a big, structured blazer, the kind that looks like you stole it from someone’s closet, and pair it with a baseball cap. This yankees hat outfit is my go-to for running errands when I still want to look like I have my life together.
The contrast is the entire point. Sharp shoulders, casual cap. My husband calls it “confusing” but I think that means it works.
Trench Coat With Baker Boy Hat
A classic trench and a baker boy hat feel like they were made to be worn together, don’t they? There is something a little vintage about it, a little like you are about to solve a mystery in an old film.
I wear this on gray drizzly days when I want to feel dramatic. And in fact I once wore this exact thing to a doctor’s appointment because I had nowhere else to be that day.
Leather Jacket And Camo Cap
So this one is for the days I want an edge. A worn leather jacket, plain tee underneath, and a printed cap on top. This camo cap outfit balances the tough jacket with something a little more playful and low-key.
It photographs really well too, if that matters to you. Which, let’s be honest, it sometimes does.
Cable Knit Sweater With Fur Hat
Big chunky cable knit. Cozy fluffy hat. This is the outfit I put on when I want to feel like I am on a cabin weekend even though I am just at home.
A fur hat outfit like this looks its best in cream or oatmeal tones, all soft and matched up. I keep the rest simple so nothing competes with the texture. My friend Dana wore this look last winter and got compliments the entire day, and she does not usually notice things like that, so it must have been good.
Long Wool Coat With Faux Hat
A long wool coat is such an investment piece and it deserves a hat that respects it. I pair mine with a simple faux fur pillbox style, nothing loud, just a little bit of polish on top.
This is my “meeting someone important for lunch” look. It says I tried, but not TOO hard, which is exactly the energy I am going for.
Striped Knit And Beret
A striped knit and a beret is possibly the most me combination on this entire list. Nautical, sweet, a little bit Paris, a little bit I-read-books-in-cafes.
I wear a black or red beret with navy stripes and I feel unstoppable. Of course, unstoppable to me just means walking to the bakery and back, but still.
Barn Jacket With Baseball Cap
This is the everyday one, the outfit I throw on without thinking. A sturdy barn jacket, the waxed kind, and a plain baseball cap for a look that is practical and just a bit preppy.
Perfect for weekend walks, the farmers market, standing around at my nephew’s soccer games in the cold. Comfortable and warm and easy.
Relaxed Denim Jacket And Yankees Hat
Denim jacket, soft tee, a cap, done. This is the outfit I would wear if someone woke me up and said we are leaving in ten minutes.
It is casual but not sloppy, which is a hard line to walk some mornings. The denim and the cap together feel very lived-in and easy, and I mean that in the best possible way.
Tailored Coat With Faux Fur Hat
A tailored coat, clean lines, buttoned up neat, and then a fuzzy hat on top for softness. I love the mix of structured and cozy. It is the kind of thing that looks expensive even when it isn’t.
I keep the colors in the same family, so a camel coat with a camel-ish hat. It just looks intentional, and intentional is half the battle honestly.
Chunky Knit And Baker Boy Cap
Layer a chunky oversized knit under a jacket and top it with a baker boy cap and you have got a look that is both slouchy and stylish. This baker boy hat outfit works because the cap adds a little bit of shape to an otherwise very relaxed silhouette.
I wear this one a lot in November. It is warm, it is easy, and it does not require me to think very hard, which in November is really all I ask.
Monochrome Outfit With Black Beret
All one color, head to toe, and then a black beret to punctuate it. This is my “I want to look chic and I have exactly no energy” outfit.
Monochrome does so much heavy lifting. You look like you thought about it for hours when in fact you just grabbed everything black you own and put a hat on. And nobody has to know.
Quilted Jacket And Camo Hat
A quilted puffy jacket paired with a printed cap is such a comfy, sporty combination. This is the look for cold mornings when warmth beats everything else on the priority list.
The camo hat outfit gives the whole thing a bit of personality so you do not just look like a walking sleeping bag. Which, in a quilted jacket, is a genuine risk.
Wide-Leg Jeans With Yankees Cap
Wide-leg jeans are my favorite thing to wear right now and they look great with a cap and a fitted top. This yankees cap outfit is easy and cool and it makes even the simplest pieces look a little more considered.
I roll the hems, tuck in the top, add the cap, and walk out the door feeling great. It is a very low-effort, high-reward situation.
Teddy Coat And Russian Faux Fur Hat
A big fluffy teddy coat with a tall fuzzy hat. This is peak coziness and I am not sorry about it one bit. This russian faux fur hat outfit is what I wear when it is genuinely freezing and I have given up on looking sleek in favor of not being cold.
Somehow it still looks good though. All that texture together just works. I wore this to pick up my sister from the airport once and she said I looked like a very warm bear, which I took as a compliment.
Leather Bomber With Baker Boy Hat
A cropped leather bomber and a baker boy cap is a slightly cooler, slightly edgier take on the newsboy look. It pulls the whole outfit in a more relaxed, streetwear direction.
I like this with straight jeans and boots. It feels a little tough but the hat keeps it from feeling too serious, and I appreciate that balance.
Cream Knit Set With Faux Fur Hat
A matching cream knit set is so soft and so pretty and it looks incredible with a fluffy hat in a similar tone. Everything creamy and matched and gentle looking.
This is a “cozy but I still made an effort” outfit. Perfect for a slow morning out, a bakery visit, that kind of thing. I feel very soft-spoken and elegant in it, which lasts right up until I trip over my own boots.
Utility Jacket And Camo Cap
A utility jacket with all its pockets and a printed cap makes for a look that is functional and effortlessly casual. I wear this when I have a lot to carry and want everything on my body rather than in a bag.
The green tones tie the jacket and cap together nicely. It is practical, it is easy, and it survives whatever the day throws at it.
Pleated Mini Skirt With Beret
Here is a slightly sweeter, more feminine one. A pleated mini skirt with tights, a knit on top, and a little beret. It has a schoolgirl-in-the-nicest-way charm to it.
I add ankle boots and a small bag and suddenly I feel about ten years younger. In a good way, I promise.
Oversized Scarf And Russian Hat
Last one, and it is the warmest. A huge oversized scarf wrapped around and around, with a tall fuzzy hat on top. This russian hat outfit is what I wear on the coldest day of the year, the day I question all my life choices about living somewhere this cold.
The scarf and the hat together mean only my eyes are really visible, and that is exactly how I like it in January. Warm beats everything.
