Denim bomber jacket or "sportswear" jacket. You should be able to find something good in a thrift shop. Jackets are good to buy in a thrift shop because it's usually okay if they're a bit big or something, and they're easy to try on anyway.
for what occasions/places you need it ?
the most versatile is set of two jackets - sport one and coat/suit like one.
but maybe funny jacket if you are into fashion...
or flashy hey look at me jacket
there is also that thing when you wear jacket for first time you know it's good one. it feels great. so try as many as you can.
This one kinda goes with everything, and it looks great in a timeless sense:
This one looks great in a hipster-hobo sense, but upon closer inspection it doesn't look very windproof. Jackets without a windproof shell are silly if you live in a cold place.
Save money by wearing 3 or 4 t shirts and a couple of hoodies, if you need something waterproof then wear a single layer windproof raincoat. Layers provide insulation which is key. You can even stuff scrunched up newspaper under a jumper for extra warmth. Also wear a hat. The more head coverage the better.
tuck layers into each other to achieve optimum protection from errant draughts. then simply stuff your jacket pockets with kendal mint cake and you're basically set for the winter
I have one thiccc winter coat that looks ok (it's like 12 years so it's starting to wear) and is very warm.
It's actually my brother's ex gf's coat. She left it behind and never retrieved it. So one day I was at my mother's, where she left it, and my mother said I could take it as I needed a winter coat. I was like "but what if I run into her". And she was like, "the chances of that is super low". So I took the coat and a few days later I had a work course where I had to travel by plane to Oslo. Being winter, I put on this coat, packed and headed to the air port with my coworker.
Turns out, my brother's ex gf who was planning on becoming a car mechanic, actually worked at the air port, so naturally I ran into her. Though, the story ends there, as she never said anything about it and I'll never know if she didn't care about the coat enough to retrieve it or whether she wanted it back when she saw me
And I have one for spring and autumn. Long coat, looks classy. It's the appropriate amount of warm for those temps.
I also have a rain coat if I'm going hiking, jogging or something. But I never need it for everyday use, so I wouldn't need one now if I didn't already have one. But if you like walk to work everyday and it sometimes rains a lot, then obviously you'll need something for that
So general recommendation: something you think looks nice and that suits you + the appropriate amount of practical.
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