As I type this, the wind and rain is lashing hard against the window of my study. I think it’s pretty safe to say that summer is over kids and it’s not coming back! So, with this in mind, I thought I would compile a list of the top ten items that I’m looking to purchase for the coming colder months and that you may be interested in getting yourself.

As a general rule, the first five are what I consider to be more ‘basic’ pieces that are easy to incorporate into a winter wardrobe, while the remaining five are slightly more ‘fashion-forward’ (although I seriously hate that term).

So, here we go:

1. Real Man Boots – For Real Man Weather

This one really is a no-brainer. Although you could find me last year rocking a pretty heavy pair of brown military boots, it’s time for an upgrade and the reason is simple – the boots just weren’t cutting it. Sure, they were great for wearing with thick socks when temperature dropped but as soon as it started to pour with rain, or blizzard with snow, it was game over and I was on the floor.

This time around I’m looking for something with a big chunky lug sole for grip, better design to support my ankles and quality leather to keep the water out. I may even swap the laces for some bright red ones just to add a punch of character. This way, I can spend all my days jumping in puddles like I want to.

  • Pointer Calum Leather Hiking Boots
  • Tan Duck Boots
  • Nicholas Deakins Chocolate Vibram Forest Hiking Boots
  • H BY HUDSON Garrett Tan Boots
  • Yukon Boot
  • grenson Dougie boots
2. Invest in Some Tweed

This is both a practical and stylistic decision. First of all, by its very nature, tweed is a warm insulating material. Made in the highlands, it’s a rough unfinished wool that is durable and moisture-resistant and perfect for winter.

I’ve already got a grey tweed blazer laying around from last year so this time around I’m going for some suit trousers instead. They are perfect for wearing casually with a t-shirt and a cardigan but can be dressed up just as easily with a shirt and jacket. I’m probably going to be looking for one in a tobacco brown or rich navy.

  • Comune Kristof Tweed Trousers
  • Biscuit Herringbone Skinny Carrot Fit Trousers
  • SCOTCH AND SODA 80014 Grey Trousers
  • Fudge Donkey Herringbone Blazer
  • ASOS Slim Fit Tweed Hunting Blazer
  • PIOMBO Blazer
3. Horizontal Stripes

They are not just for summer you know. Although rather than having them on your t-shirts and in bold colours, why not try them with thick-knit jumpers and cardigans, in tonal colours like navy and teal or olive and mint green?

  • Red Zip Funnel Neck Jumper
  • Margaret Howell MHL Striped Wool Sweater
  • Navy Stripe Lambswool Crew Neck Jumper
  • Jack & Jones Intelligence Roll Shawl Neck Stripe Cardigan
  • marc jacobs Cashmere dual colour cardigan
  • A.P.C. Jacquard Knit Lambswool Sweater
4. Bring Some Colour In

This is a simple one really. For whatever reason, autumn/winter tends to make guys stick to black, grey and navy. Now there’s nothing wrong with monochromatic colours, they can be a great foundation for a look, but why not add a shot of warmth into it as well.

Sunburnt oranges, olives, rich browns and striking burgundy were all over the runways, so will soon be filtering down to the shops too. Get involved!

  • Burgundy cable crew jumper
  • Firetrap Submere Wool Crew Neck Knit
  • Kenzo Homme Velvet stand alone jacket
  • Washed Burgundy Skinny Chinos
  • Bottega Veneta Straight Crumpled Corduroy Trousers
  • Gant Rugger Classic V-Neck Sweater
5. A Shawl Neck Jacket

It can often feel, during these more depressing months, that when it comes to formal wear you are obliged to wear something traditional like a black notch lapel suit. Not so. In fact, a shawl neck collar on a suit jacket was favoured by nearly all the 50s and 60s Hollywood movie stars and can really smarten up any look.

I’m going to buy one in grey or burgundy with black lapels and trimmings to smarten up my jeans and polo shirts when I head out into town for the evening.

  • Navy Tape Shawl Skinny Jacket
  • ASOS Skinny Fit Blue Jacket With Shawl Collar
  • Maison Martin Margiela Wool Shawl Collar Blazer
  • Black Label Slim Grey Suit
  • AAA Charcoal Shawl Suit Jacket
  • McQ Cotton Tuxedo Jacket
6. Tangled Up In Plaid

More specifically, plaid wool ties. With everything else in your wardrobe getting more bulky, thick and durable, make sure your ties don’t get left behind!

A tweed or flannel suit combined with a silk or cotton tie just doesn’t translate. Invest in a wool tie in a colourful pattern like red and blue plaid – and wear the hell out of it.

  • POLO RALPH LAUREN Plaid Wool Tie
  • Alexander Olch The Penn Plaid Wool Tie
  • Alexander Olch The Walter Plaid Wool Tie
7. Double Monk Straps

They are having a huge resurgence across the pond and on the blogs – and for good reason. Think of them as the slightly older, more refined brother of the desert boot when it comes nailing that smart-casual look.

  • Jeffery West Muse Punched Monk Shoes
  • ALLEGRO Moccassins
  • Ralph Lauren Shoes & Accessories Leather Monk Strap Shoes
8. The Turtleneck

Check out Ben’s recent article on why you should at least think about investing in one. Enough said.

9. Pick a Pattern

You can have fun during the winter too. Whereas the summer was all about Breton stripes, floral flourishes and Hawaiian vibes, this autumn/winter can be all about folkloric, Peruvian and Norwegian touches.

I’m personally going to be looking for a crew neck jumper with a snowflake pattern on it for when the weather really kicks in.

  • Navy placed ikat pattern crew
  • Burgundy Reindeer Cable Crew Neck Jumper
  • Navy Snowflake Crew
  • GANT Fairisle Jumper
  • NIGEL CABOURN 1940’s Natural V Neck Knit
  • Eleven Paris Sloyd Graphic Cardigan
10. Leather Varsity Jacket

L ast year’s varsity jacket just graduated… with honours.

  • Uniforms For The Dedicated Varsity Blazer
  • JOFRÉ Leather outerwear
  • Barneys Originals Leather And Wool Baseball Jacket

So there you have it guys, my picks for this coming season. What do you think? What are yours?

Matt Allinson