Men’s Cold Weather Fashion: The A-to-Z Guide

Hey Ned,

Yeah, I usually lag a bit with creating weather/occasion specific style guides so this time decided to do it before it gets freezing to give some time to prepare :)

Also it's great to hear that you enjoyed my book!

Now as for your questions:

Not a fan of the first example as for the one you bought - as mentioned in the article I generally try to avoid puffy jackets (especially with large pockets) but if it gets that cold that you're considering adding another one underneath you should probably stick with it. Coats are great but not for extreme cold temperatures.

Here we get ~-20 C (sometimes goes as low as ~-25-30) during the coldest months in winter and I find that Coat with inner-warmer layer + knitwear + tee/shirt underneath + thick scarf is enough to keep me comfortably warm.

The down jacket you shared would look pretty good as the top layer but I would not recommend it as second/middle layer: with a puffy jacket it will really make your upper body wide compared to your legs and there would be a slight clash in styles with a pea coat.

Have you tried using thicker wool knitwear as a second layer for the epic Canadian Winters? Could be combined with a flannel shirt for extra warmth :) And then of course any coat if you were to go in this direction would need to have its own warm inner layer.

And the jacket (you mean the black one, right?) is a variation of a "wool jacket" or "wool car jacket"

Hope this helps!

Glad you enjoyed it!

The naming gets kinda fuzzy with these styles, but you could try "wool car jacket", "wool car coat" (will generally be slightly longer but not topcoat long) and "wool short coat".

Anon, also included good options to look for.

As for where to get it - I'm actually not sure regarding the specific brand used in this example, there are some similar options on Amazon and other stores but can't say about their quality.

Hey Metal,

Definitely stick with with shorter designs - anything that significantly covers your legs will make you legs appear disproportionately short and make you look shorter overall in turn.

Medium length is best for guys who are average or above average in height.

Hey Joe,

I think you mean brogue shoes and yeah, it's a good looking option if it doesn't get cold enough to the point where you need a warmer alternative.

You have two main options where to take it from there: a smart/sharp look or an elegant-edgy outfit.

If I understood you correctly, you have brown brogue shoes (similar color as in the example) so you can either go with black jeans for a more elegant-edgy combo or blue jeans for a more toned down version that's suitable for day time.

Color of the shirt - avoid red (doesn't look that great with brown) but other than that whatever you prefer, I really like white shirts when wearing brown shoes/accessories.

As a rule of thumb, you usually want to match shoes with belt, stick with a slick, clean design.

And yeah, brogue shoes are a perfectly good looking option (though of course this depends on the actual style/design).

Average height should be the cut-off line for longer coats. Shorter guys by default should avoid any designs (whether that's a coat or jacket) that cover a significant portion of their legs.

Hey Tennant,

Sounds like a cut/sizing issue - what cuts are you currently wearing? Slim?

As for fit itself, when you're wearing jeans they should firmly mold around the buttocks, thighs. As a rule of thumb, it should be a bit difficult to put a wallet/phone into your back pocket so it doesn't just slide in.

Also might want to experiment with lower rise jeans.

The experiment is a bit unfair - in first example the guy's tee includes a fake beer gut and the rest of the outfit sucks completely too. So yeah, if your alternative is looking like a weirdo - sure, go for a suit.

But take a properly cut tee with the same graphic, build a playful-edgy outfit around and it will perform at least as well as the suit during day time and likely even better in some of the night game venues (student bars and alike).

Also, just picking up a suit doesn't mean that you suddenly have a free "go out of jail" card where you don't need to worry about colors, cuts, accessories - pick an ill-fitting suit in goofy colors and butt-ugly shoes and instead of smart you'll look like Dwight from "The Office" - not exactly an improvement over the nerdy look

Now, about wearing a suit in general I'd say it's all about congruence - if you're wearing a suit to work and during your lunch break decide to run some day game then sure, wear it when meeting women but dressing up just to walk around town and run same game sounds a bit try-hard and I've actually seen it back-fire pretty bad (seen a few young college guys trying to pull it off in a club in crappy, ill-fitting suits - had some good laughs).

Think of it this way - okay, you make the right first impression, you get her number, now what? Do you like the idea of wearing suits every time you meet her or do you have an alternative? Do you like the image of a man who dresses in a full suit when he's going for walk to run some game? How do you think this will fall into the lover-provider spectrum when combined with your personality and does this take you in the right direction based on your goals with women?

These are just some of the questions to consider when thinking how what you wear affects your personal brand and how you're perceived.

That said yes, suits (and dressing smart in general) is one of the easiest ways to look good because there are relatively few moving parts that you can screw up. But instead I'd like to encourage you to go through my past articles especially those with specific examples ("5 outfits for...", "6 outfits for...") - and see if maybe some of those suit your personality better than dressing up in a full suit and don't worry, they will perform at least just as well (in most cases better).

But let's say you actually enjoy "suiting up" and that's the image you want to go for, then when it comes to winter you will generally want to stick with thicker fabrics, less flashy colors compared to summer. In terms of perception nothing really changes, you will still look like a dressed up professional first, potential lover second.

Hey Anon,

To be honest, Timberlands is one of my least favorite boots brands, they had a good run a few years ago but that's that. Simply put, they are just not very good looking.

I would recommend checking out Hudson boots https://www.hudsonshoes.com/au/h-mens/boots.html they have a lot of very good looking designs that would get complimented my women left and right.