Timeless but cool shoe recommendations

[sleeplessinwestsussex]

I need some shoe recommendations, ideally flat or small heel. I work in IT so often wear jeans. I like trainers, loafers, boots.
Please give me some recommendations of cool, funky, but timeless shoes that will refresh my style.

Grenson

Yep Grenson. I was thinking Vagabond but actually think Grenson are cooler.

For trainers, Veja are stylish and grown up, expensive looking but not designer. Work well with tailored trousers, midi skirts and dresses and jeans.

Funky but timeless is a bit of a paradox... I like Massimo Dutti/Uterque for funky flat shoes or boots that don't cost the earth but are good quality.

Dr martens all the way, they do boots with a heel too

I've just bought some Kickers. I love them.

Tracey Neuls. Not cheap but worth it.

Rogue Matilda or Grenson. The En Brogue blog is well worth a follow if you love shoes but don’t do heels.

Grensons are ridiculously expensive. I think the huge marketing on Istagram has made them so uncool. They are the equivalent of having an obligatory gallery wall!

Rogue Matilda’s are bordering on grumpy.

Docs will never lose their coolness but are t exactly spring/summer.

Massimo Dutti have great shoes but they are as good quality as Zara for three times the price and the last thing Zara is known for is quality.

*frumpy not grumpy!

I’d wait for Grenson in the sale or their sample sale. But the quality of their shoes is great - I’ve had a pair for 5 years and they look new (admittedly I don’t wear them regularly).

I don't think you can do cool and timeless. I would say brogues went close because they slipped under the radar for so long but as soon as they became fashionable, the clock started ticking. (I've always been a fan so this has made me cross.) Doctor Martens fell out of favour for quite a long time - which is partly why mine have lasted 35 years.