- Dress to your body (not too tight or too loose). This also goes to things like stripes. If you're chubby, don't wear horizontal stripes. If you're short, wea

- Dress to your body (not too tight or too loose). This also goes to things like stripes. If you're chubby, don't wear horizontal stripes. If you're short, wear vertical stripes to elongate you. If you're short wear waist or butt length jackets not long trenches. If you're tall, don't wear things that would elongate your lines, like wearing the exact same color through your shoes and pants. Silhouette is the term you're going to want to looking for in discussions. - Honestly, just go to https://www.reddit.com/r/malefashionadvice/ https://www.reddit.com/r/malefashionadvice/ and go through the sidebar. +1 at MFA, but take it as a getting started guide on fits, and then once you get fits down, explore your own style. Check their WAYWT threads for lots of pictures of fits. You want to have a versatile wardrobe, not one with a ton of clothes that you can only wear with one or two things. I'm a huge fan of /r/streetwear personally with a touch of the flavoring of MFA (like collared shirts, polos, non perfecto leather jackets) and a bit of Americana like flannels and boots. Also SHOES! Shoes are super important. I'm a sneakerhead, but if you're into more officey/professional vibe, Allen Edmonds makes some terrific shoes. Broguing on a shoe is more informal than not, a good cap toe in black and brown will serve you for a very long time. For boots, the MFA recommended Wolverine 1000 Mile and Redwing Beckmans are fantastic and can be dressed up or down.