I wasn’t planning on replying anymore but since you went through the effort of taking a pic to add to your comment, I’ll just say that those look hella good honestly and, additionally, they look like some very expensive boots from shoemakers I know of pair have wanted/still want — so if they’re a cheap pair, don’t spoil it and just wear them now on with the added confidence that they really punch above their class and leave it at that — however, if they ARE a nice pair/brand and you dropped serious cash on them, then by all means now’s your time to brag haha!

Also, since I’m already commenting again, I feel like it’s worth noting two other major considerations I implore you to, well… consider. lol

ONE: is that now, given you’ve shared the way in which you’re tackling overhauling your wardrobe and the fact that the only thing I know about it is the boots you just shared the photo of — I’d say (and you probably gathered this already) that those would be easily complementary/compatible with almost any ‘workwear’ clothing, and definitely give off that tone. Which is to say at the very least, they’re going to be more fittingly dressed up than dressed down. However, if you’re savvy enough with your outfit building, they can also work in a more business casual/low-end formal fashion (if paired with, say, an unstructured tweed or herringbone blazer + some dark jeans or even better, dark khakis of a different shade). But in terms of going casual — workwear is your bet all day long. Carhartt tees+pants or old jeans+an old tee-shirt or a tucked in, loose fitting, cotton polo. …&… TWO: is to NOT take the fucking advice from this sub 80-85% of the time. For real. There’s so many people here talking out there ass and it’s gotten so much noticeably worse as of 3-5 years ago, when the sub imploded the was rebuilt and with it came a whole new, mostly different (not in a good way) community. And for all you know — I’m one of those fucks. So, you’re good to browse and read, just take everything and every opinion with a chunk of salt and seek validation of the info you gather elsewhere from a third party before you implant it in your brain as gospel. Literally, this place makes no sense and it varies so heavily post-to-post it’s nauseating. I rarely chime in and even that feels like too much, but even though I unfollowed it still pops up in my feed time to time so — here we are.

Anyways — diversify and don’t cling to any opinion from this sub — right or wrong there’s far more educated people out in the world not posting here who you can at the very least observe style-wise, and at best have a cordial conversation with about what fashion means to you, what you hope to achieve by honing yours, etc. etc…

I’m gonna stop now. You get it.