I made another post like this back in the day in 2011. That dated post cannot be found anymore so, I’ll make a new one.
First I’d say you go and buy yourself plain toe boots. As we all know, shoes make a difference, they can promoto or degrade you, so investing a couple of hundred is worth it. Well actually it is the pathway to hell, because eventually you end up having multiple pairs of shoes anyway. So your first pair should be something that can be used with almost anything.
Red Wing Beckman 9016
Now that you got all purpose roaming shoes ready, you might want to get a lighter pair with them - a pair of sneakers. Choose any pair you like that goes with raw denim. Right now I’d go for New Balance 998s
Our next step is to update your lame low rise slim jean cabinet to the proper stuff. If you already have a descent pair of selvedge denim jeans, good, if you don’t… well. prepare to lose your money.
Luckily there are many descent jeanmakers so choosing your pair is pretty much up to you. For a fit, I’d suggest tapered or straight fit with at least medium front rise (<10”). LVC, RRL, Sugar Cane, The Flat Head, A.P.C., Carhartt, Raleigh Denim, Iron Hear, 3sixteen, Nudie, Real Japan Blues, Dry Bones, Buzz Rickson… and the list goes on forever.
Next you should acquire a couple of crew neck sweaters. The price range is pretty much from $20 to infinity, depending how much you are willing to pay for a one. Uniqlo offers a pretty goods choice and on crewnecks (as well as their jeans too).
Shirts. You prefer button downs or workshirts? Or maybe both? A chambray shirt would be a key piece of your wardrobe. A contemporary chambray shirt is cut to the length that you can keep it tucked or un-tucked. You should note that the collars on your shirt are proper, not too large nor too small. This one is from Post O’Alls
For the next shirt, I’d got with a basic clean white OCBD. Gitman Vintage hands down.
Next you need a jacket. A bomber? A parka? Jean jacket? All of them. If this would be your first, I’d suggest you keep it simple and buy some versatile piece that goes with pretty much everything, like all the rest of the stuff in this post. A clean mountain parka from Beams+
You pretty much got it now. Grab your basic T-shirts and socks from Uniqlo.
But… where’s the henley?
Good one. I don’t really know. There are quite of few henley shirts out there, but they all seem to be more or less crap. The collar and button placket should look like this:
While most of the henleys we see are just t-shirts fitted with too narrow placket and plastic buttons and the descent ones wee see cost +$100. That will make your crusade for the henley shirt pretty challenging. Unless you want to compromise, but take it as advice, compromise is hardly worth it..