Nothing is too personal. I offer relationship advice, as well as the answers to the questions you’ve always had about guys in wing-tip shoes.
I’ve always had a thing for wingtips – so I’ll start with the obvious question. How you doin’?
Oh, I’m feeling a little ‘blah’ actually. I think it’s just work though.
Next?
What color is your suit? Cause brown wing-tips may not go with your suit. I’m just curious.
Do you know why the little perforations are in wingtips?
And what color is your belt? They have to match, dontchaknow.
Good question. I’m not wearing a suit, though. I’m wearing a pair of very nice khakis, and a brown and tan striped shirt.
The wing-tips themselves are a casual set, brownish-red in hue. More brown than red.
My dad always wore wingtips with his suits when I was a girl. Nothing says dress shoes like wing tips. I picture them as a conservative, traditional shoe. Do you see yourself as a tradtional person? Or do you choose them as a tongue in cheek reference to the fact that you are not traditional?
Are you in the habit of tapping your wing-tips in public bathroom stalls? If so, what kind of responses do you get? 
You sound absolutely “spiffy”!! 
Cause they look awesome!
A perfectly-matched brownish-red. More brown than red.
I would say nine days out of ten, I dress like a nerd; or, I dress in casual office attire, with leanings toward “conservative.” However, I am not a “conservative” person; just a bit nerdy. Not a “hipster,” however.
No, but I’ve had to wrangle in my “wide stance” in light of recent events.
You got that right!
It was a trick question.
The holes were originally in wingtips (and other brogues) to let water out (the shoes were originally worn for work in wet and marshy areas). The peforations are a holdover from the design.
Plnnr (who is wearing black wingtips as we speak).
Why thank you for the info! I guess today I can consider you my Ghillie Bro.
What socks go well with khakis and brownish red, more red than brown, wingtips? And if you don’t know, well, what are you wearing with them, at least?
Do you believe you were born wearing wing-tip shoes, or is wearing wing-tip shoes the result of a conscious choice you made?
Tan socks. Or brown. I’m wearing black.
Yeah - nature or nurture?
I really love mens’ shoes. (Please no Freudian jokes.) I even considered being a shoe designer for a few years.
Can you describe what shade of brown they are? Medium brown like milk chocolate or dark brown like dark chocolate or really dark brown that are almost black?
What size shoe do you wear? How wide is your foot? Do you think that wingtips only look good on guys with medium or narrow feet or on all types?
What color pants usually go well with brown wingtips? Could you wear them with black, navy blue, dark gray, tan, or olive green pants?
Do you also have a pair of black wingtips? I love wingtips, and the black ones are my favorite. I’m slightly bummed out that I can’t find wingtips for women. I don’t even know if they exist. I often wear mens’ shoes though I’m a woman, and some people think I’m weird or a lesbian or both, but I’m not. Once on the subway I saw this guy wearing black wingtips with blue jeans and a white t-shirt (this was in the 90’s), and I couldn’t help but stare and stare at how great they looked. I once dated a guy that wore wingtips, and I thought they were great though I didn’t comment on it because I thought it might sound weird. Okay, maybe I am a little weird for liking mens’ shoes so much.
What other types of shoes do you own?
Do other people comment on your shoes? How do these shoes affect your love life? Do you find most women like them? Do men ever notice your shoes or comment on them?
How old are you? Are wingtips more popular with an older crowd or do younger guys wear them too?
I was born wearing them; yes, I’m a Calvinist.