Honestly I think that mocking patterns falls into two basic camps. The "what is that and why did you need to do that?" and then there's the one where it's a mocking of the Aesthetic of a different era. I hope never to be a fan of fun-fur in garments.
Now I'm all for picking on modern patterns I often have issues with picking on older ones. Particularly those older ones that were of utilitarian bent. I think some of that comes from being a biker chick. Yes I am a pillion on a motorbike all too often, and this has taught me a few lessons.
Tuck it in. Oh yes, if it's loose it will provide an access point for the biting wind to nip you in places you never knew breezes could get into.
Wear Layers - multiple layers are a godsend. Layers up front, particularly around the neck and front seams, layers near your back... oh yes. I now truly understand dickeys, I need to knit some!
Buy the jacket that's a little too big - those layers need to go somewhere!
Low waist trousers may be cute but you will freeze. My trousers aren't low-waist, I still get cold above them. I couldn't believe it when my kevlar trousers were offered in low-rise...
So I do understand why many men depicted in early 20th Century pictures are shown wearing tight-fitting jumpers that tucked in. If I was in an army with a fairly strict dress code I'd want a jumper that could be worn as a relatively invisible layer. Colourwork also adds layers particularly Fair-isle (inartasia not so much) as you're using both yarns at the same time. Also if I worked in a place with a pretty strict dress code that was very cold I'd be inclined to have a jumper on under my formal jacket. Fashion and perceived right or wrong of a look has a lot to do with what we're told looks right rather than what actually makes sense for the person on the street. Who hasn't mocked the young girls who seem to keep warm in winter only from the looks they get? Only last night Mac and I went around to the shops and saw a guy walk past us quickly only in a shirt on his upper half while I shivered because I forgot my gloves. Oh boy did we mock him!
Looking at modern men's fashions I'm actually sometimes surprised at the snark about tight-fitting mens jumpers that is from only a few years ago. Yes I look at men's jumpers, I'm broad-shouldered and they look better on me than some of the alternatives!
I mean I mocked the knitted sleeves and leg-warmers, there are days I fantasise about having some! You still will never see me (unless for a very good charitable cause) in some of the designs I've seen on Yarn Yuck (though some of the snark is more about the models than the garments)