Here is a quick visual of all the different types of bags. Plenty of choices categorized by style, size, and utility potential. I personally prefer a messenger bag, suitcase, or a traditional backpack!
This is a Sunday brunch with the guys or family outfit! I feel like you don't have to wear dress pant to wear a blazer with a dress shirt. Just throw on some plain, simple jeans and add on that beige blazer with a neutral color dress shirt.
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Here is an example of a basic suit. It's simple yet classy. Do not forget the tie clip! A floppy tie is enough to bring your whole look down. Also, a fitted shirt is key. You don't want to look like you are swimming in your clothes.