Warmest Vest
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Without knowing the answer, and understanding that this may mar the aesthetic you're going for, it's likely warmest to wear the insulated vest beneath your leather jacket. Good luck, the forum has your answer.
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I'll parrot Giles' answer, and then add to that the IHV-09.
I haven't owned the IHV-09 myself, but I've owned the IHW-08 made from the same material, and it was a FURNACE… Few things are warmer than a close fitting THICK wool layer.
Either way, I'm fairly sure you're talking about something currently in stock... Eliminating the "fur lined" ones (IHSB-C3's, IHV-22's and IHV-31's), the only thing that would be considered remotely "warm" would be the new IHV-32's.
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I'll weigh in again. As stated on the product thread, the IHV-31's are going to be the warmest of those available if the IHSB-C3's are not an option. The combination of wool/alpaca lining and whipcord means they have excellent wind resistance while keeping warmth in.
I'll say this as well, it was about 25F/-4C this morning and I did the school run in a UHF with an undershirt, my IHSB-C3-Crew and hat and gloves. I was toasty.
Another thing, @mclaincausey and @UnTucked are right, a solid vest under the jacket is the best way to combine the two garments on a purely practical level. The IHV-09 is brilliant for this.
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LMAO!
Side Note: I would absolutely wear an IH gorilla torso vest, lol!
Funny I’m the opposite. I wear IH to cover up a gorilla torso. Different strokes…