Written by Menswear Style in Essentials on the 13th December 2018

As the weather gets colder, it opens up avenues for expressing yourself with more experimental styles. As lookbooks become littered with densely-layered outfits, it can be difficult to know where to start building your winter wardrobe. Sticking with these five staples below can keep you relevant, forming a good foundation in which to bring out your own personal style this winter.

1. Chelsea Boots 

The Chelsea boot has been a menswear staple since the 1950s, with its versatility being paramount to its appeal. The boot balances formal and informal, blending itself to a variety of looks; the boot can be dressed-up or down, while ensuring it is suitable for work and play. Simply put, good quality Chelsea boots are classic for a reason, and are suitable to the earthy tones and layered silhouettes of the season. For example, these Chelsea Boots from Crew Clothing are a great investment and will last years. The boots' timelessness ensures that it will see you through many winters, not just this one.

2. Fleece-Lined Jacket 

In shocking news, winter can get cold. Therefore, it should be a priority to find a jacket that is versatile, warm and of course, fashionable. Generally, opting for a fleece-lined jacket is the way forward, as they offer warmth without being too bulky. Lined jackets can come in a variety of styles; Sherpa-lined denim jackets, parkas and borg jackets, plus even dressier styles such as pea coats and trench coats. The style is entirely up to you, but we recommend picking a jacket around whatever you’re going to use it for. For example, if it’s for work in an office, a trench or pea coat would work, whereas more outdoorsy uses should centre on Sherpa denim or borg coats.

3. Christmas Jumper 

You’ve got to own a Christmas jumper. I mean, it should be law by now, right? Even if you’re the second coming of Scrooge, a festive jumper is bound to put you in the Christmas mood. Not all of them have to be cheap one-offs, either. A lot of designs actually make for good jumpers generally, so don’t be afraid to treat yourself. No Christmas jumper equals instant placement on Santa’s naughty list, you heard it here first.

4. Flannel Shirt 

You can’t go wrong with a flannel shirt, especially a thick, winter-ready one. This versatile shirt from Crew Clothing can be dressed up or down, but most importantly it offers warmth and potential for layering, which is essential for the colder months. Flannel shirts can be used in both informal and formal functions; it’s probably the most adaptive item of clothing a man can own during the winter season. Channel your inner lumberjack; there’s a reason why they wear these shirts, y’know…

5. Reliable Beanie 

Finding the right beanie is a bit like finding “the one”: when you know, you know. However, a good place to start is opting for thicker, more neutral coloured beanies. Keeping your head and ears warm is important (plus, if you’re having a bad hair day, a beanie can be the perfect camouflage!) We recommend going for a black or navy beanie if you want something versatile, but going for bright autumnal tones of orange, burgundy or green can work too. There are a whole variety of styles around now, from fisherman’s hats, skateboarder-inspired cuff beanies or just the classic style. Experiment away, there’s a whole world of headwear out there for you!

We list Chelsea Boots, Fleece-Lined Jacket, Christmas Jumper, Flannel Shirt, and a Beanie Hat in this guide to 5 Men’s Must-Have Winter Wardrobe Essentials.