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Last Minute Advice Needed – Chestnut Shoes with Gray Pants

Tominator

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Greetings, Style Forum! I have been reading the forums here for months now but this is my first post. So first of all I wanted to send out a sincere “thank you” for helping a 28-year-old learn a thing or two about style for the first time in his life!

I will be attending my company’s Christmas party this evening and have decided on wearing a navy blazer in the absence of a proper fitting suit. For some background information; this isn’t an extremely formal event. Last year some of the men wore button-up shirts with slacks, some wore sport coats with no tie, and some wore suits. A majority of the suits were black and/or poorly fitting; probably their only wedding/funeral/interview suit (think engineers that normally wear polo shirts and khakis). And that’s not meant to sound condescending; I fall into the same category.

That being said, I feel confident that I will look fairly sharp regardless, but I know that SF members can help me kick things up a notch. I like the look of a navy blazer with gray pants, as long as I can avoid the dreaded “security guard” look. I love the way brown shoes add a bit of character to this type of outfit versus the conservative choice of black shoes. I’m thinking about wearing the combination shown in the pictures below; kind of medium gray pants with my Chestnut AE Cliftons. But I’m afraid I may have a number of factors working against me pulling this off (I’m partially colorblind and don’t trust my eyes just yet, these pants aren’t exactly light gray, these shoes aren’t exactly dark brown, this is an evening event, etc.).

So my primary questions are:
  1. Do the chestnut shoes work with this shade or gray?
  2. If so, would the combo only work during the day, or is it evening appropriate as well?
  3. Is the white PS with a TV fold a good idea?
  4. Tie bar too much, or look good with the silver/metallic buttons on the blazer?
  5. Thoughts on the narrower tie vs. the wider striped one?
  6. Any other comment or suggestions? Alternate shirt (light blue?) or tie suggestions?

I know there are minor imperfections with the fit (I would like the pants to be a little slimmer with less break, the blazer could stand to be brought in on the sides, etc), but do you have any other comments or suggestions? Thanks in advance for the help!


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