How to dress in winter

Winter is upon us. After going through the first stage which is denial, you realise the shoulder season is over and your denim jacket and hoodie just won't cut it any more. You accept with resignation the fact that you have to layer up: it is a matter of survival. Ok, not literally. But if you do not layer up, your life will be miserable every time you step outside. So you might as well dress for the cold. And you know what? It can be fun! But it requires patience. It can be tempting to just grab a light jacket and head out. However you will regret it after a couple of minutes of walking around. Maybe you should take your time and go through every single item you need to be comfy and toasty.

Every single part down to the accessories plays a crucial part. And you do not want to neglect any of them.

OK, let's jump right in; we have a lot to cover.

Note: when I say "winter" I am talking 5 to -5 degrees celsius. It never gets any colder in Paris, where I live. I am afraid I will not be able to help if it gets colder where you live... I just do not have that kind of experience. But I guess this article will be a good starting point.

1. Outerwear

Like I have said before, you can either start an outfit with the outerwear or the shoes. I usually start with the shoes, but for this one, I will start with the jacket. For, this is the most important part of a winter outfit (even though every part is important as I have previously mentioned).

1.1 Down jackets

When it comes to insulation, it is hard to go through winter without a down jacket. The warmth-to-weight ratio is simply unmatched. It is the easiest way to protect from the cold without having to carry an armour, which is why it is a hiker's best friend. But don't get it twisted: down jackets ABSOLUTELY belong in the city. 

I would recommend going for a model that can transition seamlessly from the outdoors to the city and pull double duty. There is nothing like being able to use a garment in multiple scenarii. For me, the Patagonia Down sweater is the king of this category. The "urban outdoor" look is superb. I know it comes at a premium (around 280€ without the hood), but there are deals to be had. 

If you are on a budget, the best possible deal you can get is the Decathlon MT100. I bought mine on sale for around 55€, which is arguably the best purchase I have ever made. Check out reviews, it is THE best value for money you can get when it comes to down jackets. It is a bit more outdoorsy-looking, but feature-wise, it is up there with some of the best down jackets on the market. I know Uniqlo also has interesting ultra-light options.

Whatever model you go for, I would advise you to take the hoodless version for a cleaner look if you are going to use it mainly in the city. Hooded versions are better suited for outdoor pursuits.

Quick note on colour: if you know for a fact your down jacket will never leave the city, you can go for a neutral colour for a more polished and understated look. For both everyday and outdoor wear, I would recommend a more vibrant colour (vibrant blue, orange, yellow, fuschia, red, etc.) for safety reasons. Vibrant colours can easily be seen in the great outdoors, which can also come in handy in the city if you are cycling; or if you are after a New York streetwear look! A good middle ground between neutral and vibrant colours is pastel. Remember: if you go for a vibrant colour, make sure to tone down the rest of your outfit: think black/brown/army green pants; same for accessories and shoes.

Is the down jacket perfect? Absolutely not. And the reason? It just does not handle water well. A down jacket is for dry cold days only. A drizzle is fine. It is usually water repellent. But if the feathers and down get soaked, it will stop insulating, take ages to dry and you will get very, very cold.

Waterproof down jackets exist, but they are rare and very expensive: Bonding a waterproof membrane to a down jacket is rather intricate and not a lot of brands bother.

Down jackets can also leak feathers, which is a hassle.

At any rate, if you care for your down jacket properly, it will last you a lifetime, and that is exactly what we are looking for.

This Patagonia down sweater jacket is smart enough to work in different scenarii while keeping you toasty.

1.2 Insulated synthetic jackets and Parkas 

Synthetic jackets are usually seen as a great option for urban use since they handle moisture way better: they will keep insulating when wet, which is a real boon. The downsides? They are less durable and will start losing loft after a few years, especially if you compress them (which is less of a concern in the city). Moreover, the warmth-to-weight ratio is not as good as with down jackets. But they breathe better, and are usually cheaper, which is a plus.

However its real advantage lies in the way it manages moisture, like I said at the beginning. Some of them are actually waterproof, especially those in the form of parkas.

Parkas are usually longer than jackets, and they are perfect for urban use thanks to their extended coverage. They also have the advantage of offering a more polished look.

Even though down parkas exist, parkas are more often made of synthetic materials.

Let's be honest: being able to grab a piece of outerwear that is both insulated and waterproof which you can dress up or down is absolutely priceless -and if you were to buy ONE jacket for winter (this is for my minimalists out there), this should be it.

But in an ideal world, you would own both! Remember having more than one jacket brings variety to your outfits and the rotation helps them last longer.

Note: you know I had to get technical at some point. Although I referred to jackets made of 2 layers as being useless in my article on rain jackets, just know 2-layer waterproof insulated jackets/parkas are perfectly fine. They actually are the most common type you will come across. 3-layer waterproof synthetic jackets/parkas do exist but they are usually way too expensive and rarely worth it, in my humble opinion.

This waterproof Krakatau synthetic parka is stylish enough to be worn to the office and protects me from the cold by up to -20° celsius!

1.3 Keeping it smart: wool coats

Let's be real: the beauty of winter is that you are not supposed to look fancy most of the time. The number 1 priority is not to be cold; you can totally do that in style, but no one expects you to look your best -and you can totally pull up at work or a restaurant in your favourite down jacket.

That being said, for my classy people out there, there are ways to dress up a little during the colder months. And I think the ultimate winter chic lies in the wool coat. Either get a vintage 100% wool one or a modern one made of a wool blend (the synthetics can make the coat sturdier; just be sure the proportion of wool is superior). Even though those coats are usually pricy, you can get very good deals on the second-hand market or at shops like Uniqlo and Gap for brand new models.

Warning: these coats are quite heavy and longer than their down / synthetic counterparts. Therefore, they will not be as practical. Besides, they will not be as warm, or as wind / water-resistant. But they will make up for it in style. A common winter hack consists in wearing a light puffer vest as a second midlayer for added warmth and wind-resistance.

Those coats are the epitome of relaxed elegance. The flowy silhouette is magnificent and the best part is, you can dress them up or down. Going out to a classy soirée? Wear it over a turtle-neck wool jumper with a scarf and put on some leather boots. Going for a more casual vibe but still want to dress to impress? Pair your wool coat with some nice high-top sneakers (and maybe use a hoodie as a midlayer for a Kith/Aimé Leon Dore/Fear of God-type vibe).

A good alternative to the wool coat is a Shearling coat, which is equally stylish. You can get one at any decent thrift store for a reasonable price.

A good example of how you can wear a wool coat in a relaxed way.

2. Midlayers

2.1 Fleece

So, let's say you have looked out the window, checked out the temperature and decided to either go with a down jacket if it is cold and dry or with a waterproof parka if it is cold and humid. Now you need to decide what to wear underneath. And that is where fleece comes in.

Fleece was invented by Patagonia and Polartec (the latter had a different name at the time), 2 household names in the outdoor industry. It was originally meant to be a substitute for wool which used to be the only winter go-to. Wool is a natural fabric made from sheep that is absolutely perfect for winter. But it is hard to care for, heavy, itchy, fragile and expensive. Fleece is usually cheaper than wool, it is light, easy to wash and more robust.

But it has one inconvenient that scares some people away: it is synthetics; polyester; plastic; the result of the petrochemical industry. 

This means it is less breathable than wool, will release microplastics when you wash it and stink after a couple of wears.

But if you only wear it for a few months (mainly winter), try not to wash it too often and you will appreciate its practicality; it is a true winter staple. The warmth-to-weight ratio is incredible, and it is the number 1 reason why a lot of people wear fleece when the temperature drops. Other reasons include its ability to wick moisture away, its cosiness and archetypal wintery look. Fleece tops scream "I know it is winter and I am prepared" like no other garment. And they are very, very comfortable; reassuringly so.

Now, there are 2 main types of fleece tops: full-zip and pull-over. I would recommend going for the full-zip version if you tend to sweat a lot. Pull-over fleeces can get very warm and are far less breathable than full-zip fleeces. Another way you can work around the lack of breathability of fleece is by getting a fleece top made of Polartec. This is not indispensable (at least in the city) and comes at a cost, but it is a nice-to-have. Polartec tries to mimic the breathability of wool, which works to a certain degree.

Last point: there are a lot of oversized fleece jackets or pull-overs out there which I really like the look of. But that means you have to go for an oversized parka or down jacket, since a regular-fitting jacket will probably not fit over a bulky fleece (or wool sweater). This is the golden rule of layering: the layer that goes underneath cannot be bigger than the one on top. Your 2nd and 3rd layers can both have a regular fit. but your 2nd layer can certainly not be oversized if your 3rd has a regular fit.

Therefore, if you were to only get 1 fleece, it should probably be a regular-fitting one for versatility.

In the realm of fleece, Patagonia reigns supreme. But "Patagucci" fleece tops can get a bit pricy (although they are way more breathable than most of the competition in the casual category, which is priceless). Make sure you go for a casual model like the Retro Pile jacket or the Synchilla (the originator!) for instance. A cheaper, versatile option with premium materials but a thinner build is the Helly Hansen daybreaker. But if it is roomy fit, advanced design and affordability you are after, Uniqlo's collabs with Japanese designers often come up with great pieces (rarely on the breathable side though). At the lower end of the spectrum, you can get very good, durable fleece tops for a ridiculously low price from Decathlon's hiking section. These tend to breathe pretty well for the price, too (make sure you size up though)!

My beloved Patagonia Retro Pile Jacket. One of the best fleece midlayers out there. This Krakatau parka features built-in straps for when it gets too hot!

2.2 Wool jumpers

I don't think I have to talk too much about wool sweaters, since they are a well-known, universal piece of clothing that has nothing to prove anymore. Apart from its more stylish look which makes wool tops the better choice for smarter settings, its best quality probably lies in its ability to regulate your body temperature. This is an incredible asset which makes wool the superior choice compared to fleece when it comes to breathability.

But like I have mentioned before, wool also has drawbacks: it is quite hard to wash, it gets easily ripped and most of all, it is expensive. Never spend money on a wool jumper that costs less than 100 euros; unless you want to buy a garment made of very short fibers that will not last as long as a more expensive wool top and will start pilling very quickly (don't pay retail if the jumper is over 150-200 euros: buy it on sale or second-hand).

That being said, pilling is not always a sign of bad quality and solutions exist.

105-euro merino wool sweaters by Danish brand Colorful standard are probably the best value you can get. Make sure you buy them directly from the shop if you can though; the quality/fit of online orders is known to be inferior. Other than that, the second-hand market is your best friend, granted garments have been properly cared for and were not accidentally shrunk in the wash. ALWAYS ask for measurements before pulling the trigger, and be wary of descriptions saying "this is an XL but it fits like an S".

This cableknit Levi's wool sweater is one of my go-to midlayers in winter because of how versatile it is.

3.3 Wait... No cotton?

We have covered this topic before when talking about how to dress when it rains: moisture is cotton's worst enemy. Humid cold is its second worst enemy. Have you ever noticed how cold your favourite hoodie is when you pick it up from the shelf in winter? That is because cotton holds on to the moisture in the air. This is why I would advise against wearing cotton midlayers in winter. Keep it for the shoulder season, which is when cotton shines (as long as it is not raining).

You CAN get away with wearing cotton as a baselayer in certain situations, but I will develop this topic in the next chapter.

3. Baselayers

Wool has 1 more advantage we have not mentioned yet and it is its capacity to naturally wick moisture away. This is exactly what baselayers are for. That, and providing a bit of warmth too. Merino wool long-sleeve t-shirts are perfect for that because merino wool is very soft, which makes it your best next-to-skin companion.

You could go for a polyester baselayer too; this type of baselayer wicks moisture even better than wool and dries more quickly, but it is not natural, nowhere near as nice next to skin, not as warm, and most importantly, it will start smelling after a couple of wears. Merino wool is antibacterial and does not need to be washed often, which is a great plus. Besides, merino wool t-shirts are easier to wash than wool sweaters (but are still fragile).

This is probably where fit matters most: always go for a slim fit. It will trap heat more efficiently and will make layering easier.

To me, the best value is the Decathlon 45 euro long-sleeve t-shirt that often goes on sale (in which case it is a no-brainer). You can also buy from Diling, or Seagale, for premium options.

Do not go for a t-shirt that is made of less than 80% merino wool.

One thing to keep in mind: if you are going to wear a merino wool baselayer, make sure you will not have to completely take off your midlayer. Merino wool long sleeve tee-shirts worn on their own can look a bit funny and if you know you are going somewhere where the heating is crancked up to the max and looks matter, it can be a better idea to wear a polo shirt or a shirt underneath (or a cotton t-shirt). Unless you know you are going to get very active, you can get away with wearing cotton as a baselayer in the winter for urban use. The rule of thumb is the following: never sweat. If you do, immediately take off the layer that is on top (or change baselayers if you can). There is nothing more unpleasant than being damp when it is cold outside -especially when wearing cotton, which takes forever to dry.

The ultimate hack when wearing cotton as a a baselayer is to wear a tank top underneath.

This is a mild rainy winter day fit. What I want to showcase here is the layering principle: slim merino baselayer, fleece midlayer, and outer shell.

4.  Shoes

I will not go into detail for shoes because it is basically the same as the shoes you wear when it is rainy and cold which I have already covered. Check out this article for more info.

5. Socks

Remember when I said every single part of your outfit played a role in your winter outfit? I really meant it. Down to the socks. 

Come on, I know you just rock the good old tennis socks with the stripes on top, like you usually do during the shoulder season.

That's OK, we have all been there. But that is not the way to go.

2 words: merino wool. Or just regular wool. Once again, your best bet when it gets very cold (and damp). Remember: it does not matter if you are wearing the thickest of leather combat boots or hiking boots; if your socks are cotton, you will probably get cold feet. Cotton holds on to the humidity in the air. That is why wool socks are your best friend.

However, wool socks can be a pain. If they are thin, they will slide down; and holes will appear quickly. If they are thick, they will take up space in your shoe.

A good alternative is socks made of synthetics like polyester and nylon (Decathlon have the best value synthetic socks in the hiking section).

But never cotton.

6. Pants

6.1 Taking it easy

Now, dandies reading this article will probably leave the chat after seeing what comes next, but I will say it anyway: if I am working from home, going out for a quick errand, picking up the kids from school, etc. I really do not mind wearing fleece trousers. They are extremely comfortable and will keep your legs nice and toasty like no other type of pants. Think joggers, but warmer! Do not start getting very active in them though, unless you want to feel the sweat trickling down your legs.

For a decent-looking, affordable pick, check out Uniqlo's collaborations with high-end brands. They usually make a comeback every year and are a great option.

6.2 Smarter look

OK, OK, you want to look your best when going out to a bar / restaurant or going to work. And as always, I've got your back.

If you want to keep wearing jeans (preferably in dry conditions), just go for thicker jeans (14 oz) like selvedge models. These do NOT come cheap. But they will last. Especially if you only wear them when it's cold. In my opinion, Edwin is the way to go.

Corduroy trousers are also a must, especially those from Carhartt, especially on sale. Even though corduroy is cotton, it is thicker and more winter-friendly than most other types of cotton.

Dickies 874 are also an interesting pick, mind you, probably the cheapest here.

But what if I told you there is a hack that allows you to wear ANY type of pants in winter, provided they have a bit of room to manoeuvre?

Decathlon sells fleece tights for about 12€ last time I checked; Best investment I have ever made. Wearing these under any pair of pants will keep you nice and warm all day long for a very reasonnable price. They are not very thick, therefore they are fairly breathable. Think baselayer, but for the legs.

These are the Carhartt corduroy pants I was referring to, in a nice dark winter hue.

7. Accessories

We are almost done, but not quite. Like I have repeated many times, every detail counts in winter.

7.1 Protect your neck

The Wu-Tang Clan have a song called that, for a reason. Even if you layer up properly, not wearing anything to block cold air around your throat will weaken your system in no time and probably cause you to catch some sort of virus.

Wool/cashmere scarves are a must if you are wearing a nice coat. Plenty of dirt cheap options on the second-hand market.

However, keep in mind one thing: scarves are not practical at all. For them to serve a purpose, they have to be wide and long (not too thick, otherwise you will quickly suffocate). And it can be tricky to put it around your neck every time you are heading out, or to put it away when you are inside.

This is why, whenever I can, i.e., whenever I am dressing casually, I go for a neck-gaiter. You can stuff it in your pocket when you do not need it (never put them on your lap when seated in a car for example, otherwise you will lose it in no time) and put it on quickly when going out. The best part is, you can put it over your ears and nose when it gets really cold (urban techwear ninja look guaranteed), and it fits under a helmet.

Bonus point: they are dirt cheap. You can buy one from any outdoor brand, or do as I do and get them from a military surplus shop for that rugged urban look.

7.2 Hats

I do not have much to say about hats or beanies; you already know it is a winter staple; every brand has one or more and most will do the job. Wool blends are nice, but they can get itchy around the head. A lot of times, Acrylic will do just fine. The Carhartt watch hat is an absolute classic made famous by 90's hip hop videos (although it is a bit too long for my taste). I also like those from French brand Picture Organic for a more outdoorsy look.

7.3 Gloves

Have you ever seen those videos on Youtube whose title is: "why you are always cold"?

I will sum them up for you: they say that no matter how much you layer up for winter from head to toe, you will ALWAYS feel cold if you do not protect your extremities. Hands and feet that is. If you are not wearing the right socks or gloves, you will suffer. We have already mentioned the type of socks you should be wearing. Let's briefly talk about gloves now.

If you are just walking around, I would recommend second-hand, lined leather gloves for a dressy look; and cheap fleece gloves for casual outfits.

What I do is I buy several cheap pairs of fleece gloves from Decathlon and stuff them in all of my winter jackets' pockets: one less thing to think about! 

There you have it! Finally a comprehensive guide on how to not be cold and desperate in winter.

What matters most is the layering principle, which is always mentioned as an outdoor practice but belongs in the city too: 

wool baselayer + fleece or wool midlayer + outer layer such as down / synthetic insulated jacket or wool coat.

As I have already explained, getting ready for going out in winter can be long and tedious. It requires patience; but the reward will be huge. Once you realise you can do anything when properly dressed in winter, new doors will open. Seriously. How many people have you seen give up on what they were doing because they were not wearing the appropriate gear?

The average Joe will just hold their breath and pray for winter to come to an end instead of dressing accordingly. But that is not us. Getting prepared and "accepting what is" as Eckhart Tolle has it, will help you be in the moment instead of waiting for a better time to come.