Depends on your budget and how much you truly care about being fly (looking at fashion tips and blogs is work tbh, just buy and try what you like and works for you). For relatively cheaper and quicker options, I'd check out ASOS because they pretty much hook you up with whole outfit ideas (They have a "buy the look" section under each item) and they have every department
Men's jackets & coats | Men's trench coats, leather jackets | ASOS
Jean jackets (Levi's is king for that one), light/cotton bombers, quilted vests, trench coats, any of those would work for your desired look
Get you some boots (I'd recommend some winter boots if you're trying for an urban mature look. Aldo's has some dope selections as well. Or you could just rock with timbs), a nice everyday watch, and some joggers, cargos, and jeans. That's all you really need, plus some layer options (basic T's, dress shirts, hoodies, crewnecks, scarves, gloves) Tight fit is the wave nowadays so also make sure there's not too much bag in whatever you wear (unless you want the Kanye hobo look). You do have to update your wardrobe every year btw if you wanna keep up, what was a hot look last year sometimes can get easily played out the next (And sometimes things can stay around for a long time/remain timeless)
For the summertime you'd have to either get more creative or just go with dress shirt + chinos + dress shoes everyday.