Timberlands? Too 90s?

[Thisismynewname123]

I need a pair of boots I can comfortably walk around a cold city for hours, with no rubbing. Mainly to be worn with jeans. I'm wary that they're very 90s, but I wouldn't get the yellow ones. Something like maybe these:
Timberland
or these:
Timberland Chelsea

Some questions:
Are they too much of a throwback to the 90s?
Can they be styled with anything other than skinny jeans? I'm trying to move away from skinnies, but I don't know if these could be worn with a wider leg.
How comfortable are they for someone late 40s, narrow feet but bunions make shoes difficult, narrow ankles often causing chafing.

Alternatively, because I need to move away from white trainers so looking for a compromise, are these awful? I can't decide.
Timberland 3

And final question, if not these, any alternative that are super comfortable and casual for walking for a few hours around a very cold city?

Pic didn’t attach! But I really like them, be great as it gets colder and wear with jeans on school run as well as woodland walks!

@StewPots, they could only be worn with skinny jeans or leggings, really, so doesn't help my quest for new boots :)

I've ordered 2 different pairs of timberlands now so I'll decide when they arrive.

Get Timberlands from Office. The styles they have are very modern.

First ones- love my yellow ones