Nike Air Force 1 '07 vs Red Wing Iron Ranger

“You cannot wear iron rangers. Based on the language your firm uses, they likely expect a navy blazer and wool odd trousers. since you just want to dress nicely for work I’ll spare you my rationale and cut to the point, but I’m happy to clarify. Navy jackets communicate business in a way that other odd jackets have trouble with and you won’t need as many of them in your rotation due to being inconspicuous. I recommend solid navy rather than a pattern for this reason. If you’re wearing a jacket every day (it sounds like you are) you should have 2-3. For trousers you should look into flannels and tropical wool ranging from light-medium grey or tan. Ensure these are high rise and sufficiently wide to drape cleanly over your shoe. Loafers and derbies/bluchers are all you should consider for this type of outfit. Black is fine and so is **dark** brown. The main takeaway is that your shoes should generally be darker than your trousers. For shirts I would get a bunch of classically cut OCBDs (read full cut ). These can be worn with a tie, open, and work with everything from jeans to suits (both in the real world and imo). Make sure your shirts are Cotton or linen, and not non-iron. For jackets and trousers I shop at O’Connells. Ben silver, J press, the Andover shop, the armoury, the anthology, Epaulet, and Samuelsohn are also all really good (good enough where you don’t need to worry about quality). Spier and Mackay is a good budget option but everything fits incredibly slim. You sound like a bigger guy so the whole Italian cut isnt going to work great with you. For shoes I’d recommend grant stone. Meermin is an okay budget option and Allen Edmonds is somewhere in the middle (on sale). For shirts I’d go with mercer, Kamakura, J press, O’Connells, and brooks brothers in that order. Final word of advice is to avoid Reddit, YouTube, and short-form content for advice on menswear. The vast majority will give you really bad advice. Forums are going to be a lot better for that kind of thing. I’ve attached a photo of what I like to wear to work (I work somewhere in between front and middle office in finance). It would look better with a tie but that’s not really the culture in my office. Weirdly enough ties seem to have evolved back into something you wear for self expression where a lack of tie signals conformity. https://preview.redd.it/1p5gk1acig4f1.jpeg?width=1170&format=pjpg&auto=webp&s=9cf838a216e4cdac1e3527ebfac5505d4eaa8c97”

“I tried AF1s on for shits and giggles and it felt like I was wearing a cardboard box on my foot.”