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?

If you do like the originals I’d go for them. My hair dresser, likely born in 1999, wears yellow timberlands and looks great. Wears them with skinny or slim leg jeans or tights and a skirt.

All the other options you provide looks nice too, I don’t think people would immediately recognise them as timberlands either so the brand isn’t relevant.

Yes, the third option are indeed awful.

The original is still the best, they're classics IMO, like DMs.

I've got these, similar type of thing. I walk a lot and they're very comfy.

www.julesb.co.uk/sorel-lennox-lace-boots-p834306#attribute%5B2%5D=11364

I like the first ones and I have some similar boots to those. I don’t think they’re too 90s. There are lots of boots like that around at the moment.
I wear mine with wide leg jeans.

I just bought these Timberland chelsea boots and I'm thrilled with them, so comfortable too.
I'm 51 and wear them with 80's style rolled up baggy jeans and striped or bright socks, look good with skinnies too.
www.timberland.com/shop/womens-ankle-boots/womens-greenstride-ray-city-chelsea-boots-black-a2jrq015

What about a pair of Doc Martens?

Love the first 2. Hate the 3rd. Seen lots of similar boots around this year but nothing as nice as your links yet.

Timberland are becoming quite trendy I think, they have some lovely ones on schuh and office. They sometimes have them on tkmaxx at half the price

They’re definitely 90s but the 90s are in! The 3rd pair are indeed hideous though. I do quite fancy a pair of yellow ones myself but I’m a 90s kid and thoroughly enjoying reliving my childhood.

Love the first pair, going to buy those myself

A friend has the chelsea boots and I thought they were gorgeous!

I do have to say that my 20 year old uber cool DS asked for some of the traditional lace up ones in black for Christmas last year and has worn them A LOT!

My son has a pair of yellow ones that he’s outgrown after warring about twice - they fit me so I am going to wear them. Do like the black ones though. I have a pair of knee high timberlands and they are very comfortable

@backtolifebacktoreality I wore DMs throughout my later teenage years and they just make me think school sixth form.

The general consensus is the third are awful, so I'll stick with normal boots. I just want something comfortable for walking that still looks good.

@Mifacagare I definitely couldn't carry off bright socks! I don't want to have to roll jeans up if it's freezing, so may have to just stick with the skinny jeans for now.

I still can't make up my mind so now considering just getting both and seeing which is more comfortable.

I've been considering a pair to wear with my slouchy jeans too, but I was worried I'd look like a middle aged TLC reject.
They should last me quite a long time though so I might go for it.

@megletthesecond haha I have similar to the 3rd pair and I wear with baggy 90s style joggers and this is exactly what I thought. But I did love that baggy look that TLC and Aaliya used to wear.

Timberlands are classics imo, very popular in my experience

I’ve just been looking at these and other similar ones. I also want to move away from skinnies but I’m not sure how these work with straight leg or mom jeans? I tried my baggier jeans with my flat ankle boots and they looked awful.
Also, I was worried that timberlands were a little bit, erm, hun….

The chelsea boots are lovely, but the laceups might be more comfortable.

I'd go for the 1990s original yellow ones but in brown

I'm wearing black lace up boots similar to your first pic (but cheap New Look ones). I love them and they go with all but the dresses outfits. Skinny and wide leg jeans, leggings, long and short dresses are all fine with them.

Dressiest*

Just get yourself a pair of red wing iron rangers.

Expensive but youll still be wearing them in 10 years if you look after them.

The best boots youll ever buy. I have a pair I got in 2015, they have been around the world with me, walked thousands of miles and are as comfy as slippers.

@Hyperion100 I didn't know what they were but just googled. That's really over what I'd want to spend.

I think the problem I'm having is that I've spent too long in trainers. I have some M&S biker boots from a couple of years ago, similar to these: M&S but I'm finding when I wear them that the top of the tongue is rubbing and blistering the front of my leg above my ankle. I don't know if I just need to harden up again! But they're too painful to wear for walking now. I don't want to find the same happens with a new pair of boots.

@WildStallyn, do you have any pictures of how they look with wider leg jeans? I've tried googling, but I'm just seeing images of similar boots with skinny jeans

I have 3 pairs of timberlands and love them! The ones that you've selected aren't to my taste, but I have a small frame and don't like boots that are too chunky.

I normally go for the slim premium style. I have two regular pairs of boots and a pair of Nellie Chukkas. Bought a few years ago and they currently don't have the same colours (unfortunately current colour selection isn't as good and they seem to have blinged them up a bit) but to give an idea:

www.office.co.uk/view/product/office_catalog/2,10/2328385527?referer=carousel

Because they aren't too chunky you can wear them with dresses and skirts etc

@MidnightMeltdown, thanks. I'm taller so ok with chunky boots. I'm just wondering how to wear them with wider leg jeans.

I'd prefer black because I have 2 grey jackets so want to keep it neutral.

Was inspired by this thread to have a look for some Timberlands on sale as I really like them. However they were still out of my price range so I went onto the Rocketdog site and found a really nice pair on there, 50% off!