A boot that looks right in a photograph and a boot that survives eight wet weeks are not always the same boot. Four things separate them.
The sole
Look at the tread, not the shape. A flat, smooth sole is fine indoors and treacherous on wet pavement. A shallow but defined tread grips without looking like hiking kit.
The seam line
Water gets in where the upper meets the sole. A boot with a clean, tight join at that line stays dry far longer than one with a visible gap, whatever it is made of.
The opening
Chelsea boots pull on in seconds, which matters more than it sounds when you are late. Zip boots let you set the fit around the calf. Lace-up boots hold the foot best on uneven ground and take the longest to put on.
The heel
A low stacked heel keeps the foot dry and stable. Anything above about two inches turns a wet kerb into a decision.
And one thing that is not about the boot
Give a pair a full day off between wears. Boots dry from the inside out, and a boot worn wet two days running wears out at the crease long before the sole gives up.