Best Fashion for Classy Indoors

Question from Leon V.

What in your opinion is the best fashion for men who want look classy indoors in their leisure time? I mostly wear t-shirts and comfortable pants, but it’s really hard to not look like a lazy slob and not feel like one, especially when I have to study and be proactive. Where I live, the weather is pleasant, but the winter can be rough.

Pants and boots

I am 18 and I am 6 foot 1 and 175lbs of progressing muscle with a goal of 185 or more. I am what would be considered a country boy and kinda dress the part. Not like a wranglers western add or anything, more along the lines of casual like Luke Bryan just without the such tight fitting pants. I wear cowboy boots and Old Navy bootcut jeans, which in the seat of the pants tend to have excess material and look goofy. I gave wranglers a try but they make my legs look like thin tubes which really isn’t all that appealing. I find it hard to find a pair of pants that work. Should I maybe take mine to a tailor?

the big suit issue.

i am having some trouble finding the right pair of pants. you see my thighs are quite big which means i need quite large pants to fit me well. and for my legs not to look to big ill go with a pair of slim jens or pants but one or two sizes to big, whitch looks quite nice on me. the problem is my suit, the pants are straight and with my big thighs the pants are ( from what i think) way too big. and for the past 6 month i have lost some pounds whitch means they are too big around the waist (and i mean WAY too big). the suit was rather expensive (700$) and was somthing i had saved up for. i dont know if i should buy a new suit, get it tailored(and than get it tailored again after a while) or or just stick it out.

ps going to wear it on new years eve and some formal events in the weeks after.

thx

Monogram on Pants

What do you think of monogramming pants? I have never been of the shirt or sweater monogram type, but have been thinking of possibly having my chinos done. I would appreciate your thoughts, be sure!

Type of Shoe

What is a good pair of shoes to wear with brown khaki pants? I already have brown boat shoes, black dress shoes, and brown Dockers penny loafers but I am willing to buy a new pair if any of those wouldnt go well. I am traveling to Italy soon and I need some advice, thanks