Fall and Winter Men’s Apparel Essentials

Alright gentlemen, or ladies shopping for gentlemen, I (Geoff) have put together a list of some cold weather essentials for the traveller. If you’re planning a Fall or Winter trip, your luggage is going to get pretty full pretty quick. Fall and winter clothing is bulky, so you’ll want items that are multi-functional, like a pullover sweater that will look just as good with jeans as it does with dressier pants (trousers for my UK friends). You’ll also want to think in layers, thermal, base and outer depending on where you’re going and how long you’ll be outside for. If the sun comes out, you can take a layer off and still be protected and warm enough. Here is a curated list to help you find the right apparel to take with you.

For the Head

The North Face Men's Salty Dog

Geoff’s Pick – I bought this Salty Dog winter hat from the NorthFace store in Vancouver right before a winter trip that took us from Milan to Amsterdam and it was perfect. Looks great, feels very comfortable and it’s very warm!

Helly Hansen Men's Business Beanie

Also: Charcoal

All business baby! This men’s winter hat is perfect for those looking for a low-key, classic but functional hat this winter.  Stylish with a double layer wool/polyester blend from a trusted brand that specializes in battling the cold.

180s Urban Ear Warmer Earmuffs for Men

One Size

Keep those ears warm, and your hair in place with these ear muffs for men! Collapsable, one-size, fleece. Perfect for business travellers or those who just don’t like wearing hats.

The North Face Antlers Beanie

I love this winter hat.  A fun, vintage design, extra fleece around the ears makes this hat VERY warm.  Whether you’re a the ski lodge or on an urban adventure, you will absolutely love having this along with you.

Yamimi Men's Oversize Cuff Cable Knit Beanie

You can’t go wrong with a classic wool hat for winter.  A hat like this should be a staple in every man’s closet. Cheap, functional and always in style! Available in Black, Grey, Navy or Red. A heavy duty knit to help keep those ears warm.

Veniroc Men's Winter Cashmere Scarf

Wrap up your neck and keep your throat warm on your travels this winter.  Thick, soft and multiple designs to choose from.

Runtlly Plush Plaid Classic Men's Winter Scarf

The ultra classic winter men’s scarf. Bamboo fibre, multiple patterns to choose from.

Helly Hansen Men's Bearfur Hat


Go Scandinavian this winter and stay extra warm. Not actual bear fur but it will keep both your head and your ears warm during those long days exploring.

For the Body

Columbia Cascades Explorer Midweight Fleece

Size: S  M  L  XL

Anti-pilling micro fleece full zip base layer to keep toasty warm.  Also great on its own if it’s not too cold. Looks great, super comfy, zippered pockets, and machine washable. Multiple colour choices available.

ZeroXposur Men's Block Quilted Puffer Vest

Size: S M L XL

A perfect solution for those crisp late fall days. Keep those arms free! Light weight, machine washable and a great value.

Columbia Men's Frost Fighter Jacket

Size: S M L XL

Geoff’s Pick – I love how this jacket fits nice and snug, no extra loose material. Zippered pockets, it has a special material around the chin to eliminate that nasty chaffing guys get.  Water resistant, faux-down, awesome!

Dockers Men's Soft Acrylic Zip Mock

Size: S M L XL

Look great and be comfortable on your fall/winter trips. A great staple to have in our luggage as it looks great with jeans or khakis.

Helly Hansen Men's Seven J Jacket

Size: S M L XL

Stay completely dry in the wet weather. Water repellant and windproof, very comfortable and also has some nice material around the chin to prevent chaffing. Comes with a hood and storm flap.

Duofold Men's Mid Weight Varitherm Thermal Pant

Size: S M L XL

You are not going to go on a winter trip without thermal underwear. Long days out exploring the city, or hitting the slopes these are a must have!

ColdPruf Men's Crew Neck Base Layer

Size: S M L XL

Thermal underwear shouldn’t be limited to the legs. Stay completely warm with a base layer to help you stay out exploring longer!

HANES ComfortSoft Lounge Pants

Size: S M L XL

After a long day you won’t be able to resist sliding these on. Fall and winter are all about coziness and these are perfect for lounging around. Soft waistband, soft cotton, start relaxing!

For the Hands and Feet

3m Thinsulate Thermal Lined Winter Gloves

Size: S/M M/L

Keep those digits toasty warm on you trip this winter. Handsome, snug, knitted with thermal lining on the inside.  I had these for a winer in Prague and they were wonderful.

Columbia Men's M Thermarator Gloves

Size: S M L

Geoff’s Pick – These are my choice because I am always looking at maps or opening information apps on my phone when we’re travelling. The last thing I want to do when it’s cold and windy is take off my gloves so I can find where I’m going!

Dickies 2 Pack Acrylic Thermal Boot Socks

Shoe Size: 6-12

Geoff’s Pick – Warm and soft but not too thick. Wear them with shoes or boots, great quality.  Very comfortable, they come up just over mid-calf.

Spikerking Winter Thermal Hiker Socks

Shoe Size 6-12

Now if you need warmth and style, these are a great choice. Multiple colours, warm, stretchy and they have an elastic band to help hold them up.