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Anonymous asked: Hey man, Just wondering if you could share some wisdom, basically I have long hair and a beard and am normally a t shirt and jeans and desert boot kind of dude but I find when I try and keep it classy it feel pretty jaring wearing a dress shirt. and any thing but jeans. Should I just stick to t shirts? (obviously this isnt always cool for smart events!)

Hey - this is tricky question, as the heart of it is pretty personal. However, I will say that you can dress up a bit more past the jeans and t-shirt look (which is great, don’t get me wrong) without it being too off-putting for you. There is definitely a medium you can find and you will likely need to dress up a bit at some point, especially for those events you mentioned.

Why not go for some casual button downs and trousers? You could try some washed or patterned dress shirts for example - something slouchy, but a bit more dressed up than a t-shirt. Khakis are great too and come in so many different colors and styles these days that I’m sure you can find a few pairs to your liking. Try and look for clothes that fit according to what you’re used to - base the khaki fit on your jeans for example. Throw on a casual blazer and your desert boots, and rock that beard and hair proudly - I’m sure you’ll look sharp, without going beyond your comfort level and losing your personal style.

Basically what I’m trying to impart is that there are degrees of formality out there that you can embrace, should you have to, without ending up looking like someone you’re not.

  1. tailormadestyle said: Throw a decent blazer/jacket on over the t-shirt, if you don’t mind jackets. Simple, practical, and it will definitely step up the look.
  2. downeastandout posted this

"The time has come," the Walrus said, "To talk of many things: Of shoes, and ships, and sealing wax Of cabbages and kings And why the sea is boiling hot And whether pigs have wings" downeastandout(at)gmail(dot)com