How To Dress Up For Winter: A Layering Guide

Winter has reared its frosty head. The temperature’s gone down. Your surroundings start to look like that Frozen movie all the kids are so crazy about. Each year, men come out, burying themselves deep in their bulky coats, their frumpy scarves and their gigantic ski-gloves. They will do anything to keep themselves warm, style be damned.

Trust us, you don’t want to join them. You’ve been honing your style sense all year and the last thing you want is to go backwards, but you don’t want to freeze your cojones off either.

So you’re left wondering how to dress for winter. Do you protect yourself from the cold, or do you endure it to keep your personal  style up? Here’s how to dress up for winter!

How to Dress for Winter to Look Sharp and Stay Toasty

When you dress for winter, you want to ensure that you’re both comfortable and warm. When you’re uncomfortable and shivering from the cold, you’ll look awkward no matter what you’re wearing. You should never sacrifice comfort and warmth just to look your best.

But you don’t have to sacrifice style for comfort either. You just have to adapt your outfits to the colder weather.

You can remain comfortable and warm and still look stylish by…

  • Layering your clothes
  • Choosing winter-appropriate fabrics
  • Wearing some key winter accessories
  • Wearing the right winter coat
  • Wearing the right footwear

Layering: The Key to Looking Sharp While Staying Warm

You have a lot more outfit choices. That shirt you wore on its own in summer can now be worn in many different ways.

Wearing multiple light layers not only makes you look sharp, but actually keeps you warmer than just wearing thick clothes. And if you do get too hot, you can just remove a layer to stay comfortable.

So let’s assume a basic winter outfit will consist of at least three layers. We can divide them into three categories:

  1. Base layers (e.g. undershirts, T-shirts, shirts)
  2. Middle layers (e.g. shirts, sweaters, cardigans, vests, denim jacket)
  3. Top layers (e.g. jackets, coats)

The general rule to keep in mind when layering is that you work from thin on the inside to thick on the outside. That means you want the lightest fabrics closest to your body and get heavier with each layer.

Another rule is that you should never wear so many layers that you restrict movement. You should wear enough layers to keep you warm while keeping your full range of motion, especially in the arms. You need to find a balance. And naturally, your outfit should look put-together. You can’t just grab random clothes out of your wardrobe and layer them on top of each other. You need to coordinate them. So before you get dressed, lay out your layers on your bed to ensure that all the clothes match.

Lastly, never assume the layers closest to your body will never be seen. You want to be able to remove each layer and still look sharp. If you wouldn’t wear it on its own, don’t wear it in a layered outfit either. Like I said, you might remove some layers as the day goes on. You never know when the day has an upswing in temperature, or when you walk into a building that has the heat blaring at tropical temperatures. So don’t wear that billowy shirt, thinking your sweater will cover it up, because you might just take that sweater off at some point. And besides, you can’t hide an ill-fitting item under another layer anyway. It will bunch, which will show through the layers on top of it.

Layering for Formal Wear

So let’s say you’re dressing for the office in winter; what do you wear? Well, you can start with a basic white t-shirt or undershirt as your base layer. Then, you can wear a dress shirt on top of that as a second base layer. Then, you can wear a sweater, cardigan or vest. Whatever you choose, it should fit snugly over your other layers and tie, but should not look like it’s cutting off your circulation. If you go for a sweater or cardigan, make sure it’s light-weight, rather than a bulky knit.

Then at last, you can wear a jacket, and a coat for when you go outside.

So to sum up a basic formal winter outfit from bottom layer to top:

  1. T-shirt or undershirt (base layer)
  2. Dress shirt (base layer)
  3. Sweater, cardigan or vest (middle layer)
  4. Suit jacket (top layer)
  5. Coat (top layer)

Now depending on your climate, you may not need to wear all these layers all the time. You need to adapt to your own circumstances. So if you find yourself breaking out in sweat despite the cold temperature, you’re probably wearing a layer or two too many.




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