I took my first trip to Dublin in the middle of November, which everyone told me was a foolish thing to do, and honestly they were sort of right. It rained sideways. But I have never had more fun getting dressed in my life.
There is something about a gray, misty city that makes you want to layer up in wool and knits and just wander. My sister came with me, and she packed all the wrong things (a linen skirt, of all things, in November) and ended up borrowing half my suitcase by day two.
So I started keeping a running list of the looks that actually WORKED. The ones that kept me warm on the walk to the coffee shop and still looked put together in every photo my sister made me pose for.
My Go-To Cold Weather Combinations for a Northern City Trip
Oversized Wool Coat With Straight-Leg Jeans
This is the one I reach for first, every single time. An oversized wool coat in oatmeal or camel over straight-leg jeans is just foolproof, and it works for walking, for coffee, for pretending you know where you are going when you are actually lost.
The trick is letting the coat be big. Really big. You want it to feel like you could hide a small bag of groceries in there, because on a cold day, that roominess is your best friend.
Camel Coat With Cream Knit Dress
A camel coat over a cream knit dress is what I wore the day we went to Trinity College, and I felt so chic even though my feet were soaked.
The two neutral tones sitting next to each other look expensive without trying. And a knit dress is secretly the coziest thing you can wear because it is basically a sweater you can walk around in all day.
Chunky Knit Sweater With Wide-Leg Trousers
So here is the deal with chunky knits: they balance out wide-leg trousers PERFECTLY. When one piece is oversized and the other is flowy, the whole thing reads as intentional rather than sloppy.
I like a cream or dove gray sweater tucked loosely into the front of high-waisted trousers. Not fully tucked, just the front bit, which is a small thing but it changes everything.
Long Puffer Coat With Leggings And Boots
Some days you just need to be warm and you do not care about looking fancy. On those days, a long puffer coat with leggings and boots is the answer, and it is a good answer.
My husband makes fun of me for owning what he calls “the sleeping bag coat,” but I am the one who is comfortable when we are standing outside waiting for a bus in the drizzle. He is the one shivering in a thin jacket, so who is really winning here.
Gray Wool Blazer With Dark Wash Jeans
A gray wool blazer over dark wash jeans is my version of dressing up on a trip. It looks polished, but it is still just a blazer and jeans, which anyone can do.
I layer a thin turtleneck underneath for extra warmth. That way the blazer does the styling work and the turtleneck does the not-freezing work.
Cable Knit Sweater With Pleated Midi Skirt
This is such a pretty combination and it photographs beautifully against old stone buildings. A cable knit sweater tucked into a pleated midi skirt has this soft, romantic feeling, especially if the skirt swishes when you walk.
I wore this to a little museum and then to lunch afterward, and it carried me through both without a single wardrobe complaint. Add tights and ankle boots and you are done.
Trench Coat With Black Knit Set
A classic trench coat over a matching black knit set is the outfit I feel most like myself in. There is a reason the trench never goes out of style, and it is because it just works over everything.
The matching knit set underneath keeps it simple. Same color top and bottom, and then the trench does all the talking. Easy, clean, and it does not wrinkle in your bag.
Chocolate Brown Coat With Knit Dress
Brown is having a moment and I am fully on board. A chocolate brown coat over a knit dress in a warm cream or caramel tone feels rich and cozy at the same time.
I will not lie to you, I bought my brown coat specifically for this kind of trip and I have zero regrets. It goes with absolutely everything I own, which is the mark of a good coat.
Striped Sweater With Relaxed Denim
A striped sweater with relaxed denim is my low-effort day look. When I do not want to think about it, this is what I grab.
Stripes just make an outfit look considered even when it is not. Navy and cream stripes especially. Pair them with slouchy jeans and you look like you tried without actually trying, which is the whole goal really.
Long Wool Coat With Tailored Trousers
If you want to feel a little more elegant, a long wool coat with tailored trousers is the way. The long line of the coat over the clean line of the trousers is so flattering, and it works whether you are five feet tall or six.
I like this one in charcoal or deep navy. Something dark and sleek that skims right past the knee. It is the kind of thing you throw on and suddenly you are the most dressed person in the coffee shop.
Cream Turtleneck With Leather Pants
A cream turtleneck tucked into leather pants is a little edgier than my usual, but it is so good for a cool city evening. The soft knit against the sleek pants is a lovely contrast.
My friend Dana wore this on our last night out and I made her tell me where every single piece was from. Turns out the pants were secondhand, which just proves you do not need to spend a fortune to look sharp.
Quilted Jacket With Straight Jeans
A quilted jacket with straight jeans has this countryside-meets-city vibe that I find myself reaching for constantly. It is warm, it is casual, and it feels appropriate for absolutely any daytime plan.
Go for a quilted jacket in olive or dark green if you can. It plays so nicely with denim and it does not show the inevitable coffee spill quite as much.
Oversized Scarf With Neutral Knit Set
The scarf IS the outfit here. A giant oversized scarf wrapped over a neutral knit set turns something plain into something people notice.
I keep a big wool scarf rolled up in my bag at all times when I travel somewhere cold. It doubles as a blanket on the plane, a pillow on the train, and the star of my outfit when I actually reach the city. That is three jobs from one scarf.
Black Turtleneck With Wool Mini Skirt
A black turtleneck with a wool mini skirt and thick tights is such a good cool-weather look. It is a little bit French, a little bit sensible, and completely warm if you wear the right tights.
I add tall boots and call it done. This is one of those outfits that looks like you thought about it for an hour but really took two minutes to put together.
Burgundy Knit Sweater With Wide-Leg Jeans
Burgundy is my favorite color to wear when the sky is gray, because it just glows against all that dullness. A burgundy knit sweater with wide-leg jeans is cozy and a little bit moody in the best way.
The deep red brings warmth to your face on the days when the weather is trying its hardest to make you look washed out. I swear by this trick.
Charcoal Coat With Monochrome Layers
Dressing all in one color family is the oldest styling trick in the book and it still works every time. A charcoal coat over monochrome gray layers looks sleek and considered, like you know something the rest of us do not.
These are the kind of dublin outfits I lean into when I want to blend in with the locals rather than look like a tourist snapping photos of every doorway. Which, to be fair, I was also doing.
Fair Isle Sweater With Relaxed Trousers
A Fair Isle sweater with relaxed trousers is peak cozy season, and I am not sorry about it. Those patterned knits have so much charm and they instantly make an outfit feel festive without being over the top.
Keep the trousers plain so the sweater can be the fun part. Cream or tan trousers work beautifully underneath all that pattern.
Wool Midi Coat With Chelsea Boots
A wool midi coat with Chelsea boots is my walking-all-day uniform. The coat hits at a length that keeps you warm, and Chelsea boots are the most comfortable thing you can put on your feet for hours of cobblestones.
And they are easy to slip on and off, which matters more than you think when you are getting in and out of taxis and cafes all day. No laces to fumble with.
Nordic Knit Sweater With White Jeans
Do not be afraid of white jeans in winter. A Nordic knit sweater with white jeans is crisp and bright and it is one of my favorite ways to feel a little cheerful when the days are short.
The same idea travels well for oslo outfits too if you find yourself somewhere even chillier, since a good Nordic knit was basically made for that climate. Pair the white denim with tan boots to keep it from feeling too stark.
Longline Coat With Cozy Knit Dress
And to close it all out, a longline coat over a cozy knit dress is the outfit I would wear every single day if I could. It is warm, it is soft, and it requires exactly one decision in the morning: which coat.
The knit dress does the work of a full outfit on its own, and the long coat over the top makes it look like you planned everything. Slip on some tall boots and you are ready for whatever the weather throws at you.
