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5 Winter Menswear Essentials that Never Go Out of Style

What items never go out of style? What does every guy NEED in their wardrobe in the winter? Worry not. We’re here to tell you.

1. Overcoat

Essential winter navy overcoat on grey background

Nothing ruins a good look like bad outerwear. You need an overcoat. 

Go with a lined wool option, because it will be warm enough for most winter days and it will last longer than synthetic blends. We like options that have either a large lapel or a zippered windfly that covers the chest and back of the neck for the extra cold days. 

Tip: Have your outerwear dry cleaned at the end of each season before putting it away for the summer. This will ensure that odours and stains don’t work themselves in. 

2. Lightweight Roll Neck Sweater

Essential orion green roll neck sweater against grey background

Roll neck sweaters are the epitome of cold-weather layering pieces. They’re timeless, they’re slick, and they’re functional. We suggest having at least a couple of colour options in your wardrobe so you can rotate. You will likely find yourself wanting to wear them multiple times per week, whether with your suit, under a cardigan, with a vest, etc. etc.

Choose a fine-gauge knit in a natural, breathable fabric like Merino wool. The lightweight nature of this kind of fabric makes it excellent for layering in all sorts of ways without being too bulky. Natural fibres are also more resistant to odours, so you can go longer without washing your knits, thereby improving their longevity. 

Tip: Always fold your knitwear, never hang it. Hanging it will stretch it out.

3. Lace-up boot

Essential winter lace up shearling boot

The beauty of a lace-up leather boot is that it is easy to dress up and down. It’s a timeless style that can work just as well with suits as it does with jeans. Go with brown leather, because black can look a little militant. 

Tip: If you plan to wear your boots outside in the winter, we highly recommend getting a pair of goloshes. Leather protectants will only go so far, especially if you’re in a climate that gets a lot of snow and ice (and thus, salt). Take good care of your boots, and you’ll be able to wear them year after year. 

4. A Flannel Shirt 

Winter essential red and navy flannel shirt

Flannel plays many roles in a man’s wardrobe in the winter. A nice solid colour flannel looks great with a relaxed sport jacket. A rugged check is great for a night out at the pub. A dark plaid looks great with jeans for family dinner on Sundays. Wear it under knitwear, on its own, with a vest, or as an overshirt with a tee. 

No matter how you wear it, one thing is always true: it’s cosy as heck, and you’re going to feel great in it. 

Tip: Flannel doesn’t always have to be bold. If a buffalo check isn’t your style, you can find plenty of flannel shirts in solid colours, too. 

5. Good leather gloves

Winter essential cork suede gloves

Bad gloves aren’t AS bad as bad outerwear, but it’s up there when it comes to ruining a look, and it’s something we find a lot of guys gloss over. If you’re still rocking your nylon Thinsulate ski mitts with every outfit, it’s time to upgrade. 

Leather gloves are a classic, and when cared for properly, they will last you years. We suggest having two pairs if you can so that they can breathe between wears. Black and brown are foolproof choices, but tan is a great neutral option as well. 

Tip: When you first try on leather gloves, they should feel a little tight, and when you bend your hand upwards slightly, you should see a slight fold at the knuckles. They will stretch and form to your hand as you wear them. We’ve got more tips for caring for your leather gloves here.


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