FI - The olive Vans are in ok shape, but they are only one of 2 pairs of casual winter shoes I have (plus one gear boot), so maybe this is a good buy? Still on the fence...
As for comfort level, it depends on which model of Vans you are looking at, as different models come with different insoles. Only one model is comparable to an athletic sneaker, and that is the EXO (first find). It is lightweight with inner support and rivals what I consider to be a "gym shoe" - although, not a high-impact running shoe IMO, it's supportive enough for hiking, walking, strength training, and you can buy or custom build them with different levels of weather-resistance.
The more popular Vans are the Old Skool (with the side stripe) and the Era (more like a Keds, and similar to the one in your comment). You can buy (or build) them with different levels of support or materials (canvas, suede, leather; weatherproof, reinforced soles, etc)
I have the Old Skool Pro (green suede; #2 find) that comes with a supportive insole (ultracush insole, which is stronger/firmer than the comfycush, which is more squishy, but still semi-supportive) and reinforced soles and toes. They are designed for pro skateboarders and can take a major beating (which is what I wanted since I manage to wear holes through the soles of chucks in a year...). But, they are certainly not an athletic shoe. They are heavy, and rigid, and while I don't find them TOO heavy for lots of urban walking, my tolerance for heavy shoes is high.
There is the Vans "Era" (first photo) that looks like Keds, and similar to the one in your post. It has a padded COLLAR (so around the ankle), but not a padded insole. You can find the Era with a comfycush insole, or build one via the "vans customs" site, but colors tend to be more limited.
The MTE has an insole similar to the ultracush (it actually may be the ultracush), but a liner over it for warmth. It is rigid like the ultracush, but not as noticable, if that makes sense... you can get an Old Skool MTE (low top, looks like my green Pro) or a high-top MTE (like the brown in my post, or the olive in my last find).
ETA: there is also a slip-on (no laces) that you can get with a comfycush insole. Again, not an athletic shoe. I don't have any experience with the slip-on; I don't care for the style.
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