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I think it's hilarious that I'm getting monkey poo for this one. BUT the proof-is-in-the-pudding, no one else has stepped up with a suggestion. Boots simply don't belong in the office; this is finance, not a fucking rodeo.

 

Who said I’m IB? Check my profile.

It’s an office, not a fucking rodeo. Leave the boots at home, son.

 
Managerette:
I hope you mean "on casual Friday" if those are your plan.

Must they have laces? Chelsea boots are a much better option as they look dressy enough with a suit and good with slim jeans.

I think boots like these are fine even on regular days. (Sorry, don’t know how to insert pictures) https://www.allenedmonds.com/shoes/mens-shoes/boots/liverpool-chelsea-d…

https://www.allenedmonds.com/shoes/mens-shoes/dress-shoes/dalton-wingti…

 

If anything, Saint Laurent Black Leather Jodhpur's. I have those for "dress" and the tan suede for anything else. They're f'g awesome

 

Why don't you just go full retard and wear Wellingtons to the office?

And where are they letting you out early enough to worry how your shoes may look at the bar?

In any case, if you can afford it, check these out:

https://www.jeffery-west.us/collections/black-1

NOTE: Most of these are not acceptable at the office, but you might be able to pull of some of the more demure styles. Definitely go to the NY store before buying, though, as the sizes are different that you'd imagine.

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