In March 2015, during my university exchange days, my mum and I flew from Edinburgh to Reykjavík for a trip around Iceland.

I was wearing an Esprit down jacket. Mum was in a Uniqlo down puffer. We were, technically, dressed for winter.

We were also freezing our asses off.

I remember getting out of the car at scenic stops, lasting maybe ten minutes outside, then running back to the car. We'd warm up, drive somewhere else and repeat.

At the time, I didn't think much about what I was wearing. Iceland was cold. We were from Singapore. Of course we were freezing.

Except the same thing kept happening on other winter trips.

How I pack for winter now

I used to pack for winter by layering up, bringing the same winter jacket every time, and relying on heat packs when I was still cold.

Now, I start by understanding the trip: what the weather will be like, what I’ll be doing, and which layers and coat make sense for those conditions.

Why can you still feel cold in multiple layers?

I was wearing more clothes, but I wasn't really thinking about whether they made sense for the conditions.

My solution to being cold was usually another layer. If that wasn't enough, there were always heat packs.

So when I was still cold, I landed on a pretty convenient explanation: apparently, I'm just not built for winter.

For years, I thought being freezing was simply part of going somewhere cold.

The problem with having one winter jacket

I had the winter jacket.

Trip somewhere cold? Bring that one.

Different destination. Same jacket.
Different year. Same jacket.
Different weather. Same jacket.

It also meant every winter holiday photo was starting to look suspiciously familiar.

Years apart. Different countries. Same jacket.

What finally made me change how I packed for winter?

Packing for the Netherlands in December 2023 was the turning point.

I hadn't even left Singapore yet. Looking at my winter options, I was tired of packing so many layers and still feeling cold. And honestly, I didn't want another holiday where every photo featured the same jacket I'd worn for years.

So I sat down and started researching cold-weather dressing properly.

There was quite a lot I hadn't understood.

What should you check before packing for winter?

I stopped starting with what I owned and started with where I was going.

1. What will the weather actually be like?

I check the forecast and feels-like temperature for the destination, and whether I'm likely to be dealing with wind, rain or snow.

I've learnt that even a 5°C difference can change how I want to dress. It really can get that specific.

Previously, my planning was much closer to:

Winter = cold. Pack winter clothes.

2. What will you actually be doing?

I look at how much of the day I'll spend outside and how active I'll be. A day of outdoor walking or hiking is different from one spent moving between heated cafés, shops, museums and restaurants.

That's also why I sometimes bring two coats on the same trip. I choose between them depending on what I'm doing that day.

3. What layers make sense for those conditions?

My winter layering system is broadly:

Base layer → wool mid-layer → outerwear suited to the conditions.

I've become a convert to wool sweaters as my mid-layer after thermals. I'm also much more conscious of what my clothes are actually made of.

Most importantly, I no longer automatically reach for the same winter jacket. I choose the outerwear for the trip I'm actually taking.

Did changing how I packed make winter travel more enjoyable?

Completely. I don't dread going somewhere in winter anymore.

In Iceland in 2015, Mum and I would last roughly ten minutes at a scenic stop before running back to the car.

Years later, I've been able to sit outside on a patio in Mongolia at around -30°C.

That's my experience, of course. Not a temperature I'd expect everyone to find comfortable.

Winter is actually fun now that I've figured out how to dress for it.

Questions we hear about dressing for winter

Q: Will this coat be warm enough for my destination or the temperature I'm expecting?

It depends on the coat, the conditions you're travelling into, what you'll wear with it and what you'll actually be doing.

That's why, at A Lil Thyme, “I'm going to Japan from 3–15 December” doesn't tell us quite enough to recommend winter outerwear.

Q: How many layers do I need?

I always advocate for three: base layer → mid-layer → outerwear.

The layers themselves can change depending on the conditions, but having three gives you the flexibility to remove a layer when you move indoors and still be comfortable.

Q: Isn't it better to be too warm than too cold?

I hear this a lot, but I don't think warmer is automatically better. Being overdressed can be uncomfortable too, particularly when you're moving between outdoors and heated indoor spaces.

The goal isn't to wear the warmest thing you can find. It's to dress appropriately for the trip and have layers you can adjust.

Do you need to own a different winter coat for every trip?

No. Different winter trips can call for different outerwear, but that doesn't mean you need to buy a wardrobe full of winter coats.

For years, I kept trying to make the winter jacket I owned work for every trip.

At A Lil Thyme, you can rent winter outerwear for the trip you're actually taking, rather than buying one coat and expecting it to work for every winter afterwards.

It also means your holiday photos don't have to feature the same jacket for the next eight years.

Which, speaking from experience, is quite nice.