Step 1: From sneaker to chukka
Put away your old sneakers and get yourself a nice pair of chukka boots. They are still casual enough to be paired with jeans, but they will be the first step towards your new look.
Desert Boots
Desert boots are the most casual version of the chukka. The last ten years or so, they have become pretty popular again, so nobody will notice them as too dressy. Clarks would be the first brand to think of, but you might find them from many other manufacturers as well. Traditionally, they come with a crepe sole.
Chukkas with leather sole, brown
If you want to go already a bit more dressy, you might consider chukkas with a leather sole. A not too dark brown will work with most of your outfits, but a lighter tan or sand is very nice, too, but will be harder to pair with dark trousers or suits.
Chukkas with leather sole, sand
Step 2: From jeans to chino
You spend some weeks sporting your new pair of chukka boots, that means: you are ready for step 2! Get yourself a chino!
You spend some weeks sporting your new pair of chukka boots, that means: you are ready for step 2! Get yourself a chino!
chinos (left to right: Levi's, Charles Trywhitt, Dockers)
There are some very casual chinos, like the Alpha Khakis from Dockers or certain Levi's stlyles. They will work with a t-shirt or even a hoody, so Danny will stay undercover.
If you are already becoming bolder, you could try a Charles Tyrwhitt weekend chino in slim fit. They feature a higher rise, so this is a serious step away from your average jeans. Still, if it's covered by a sweater, nobody will see it that easy.
Colors to be considered would be lighter shades of grey, brown or blue.
Step 3: From t-shirt to d-shirt
OMG, you are slowly but surely entering the WOM (World Of Menswear)! The next step will be the hardest one so far, as for normal, a dress shirt will be noticed by most people. But there might be a trick to get away with it a bit easier, it's called ocbd.
ocbd shirt
The light blue oxford cloth button down shirt, or simply an ocbd, is the solution to all problems in the WOM. It's casual enough to be worn with a jeans (it actually has a kind of denim feeling to it) but you can also pair it with a tie.
The "must-iron" and made in the USA version from Brooks Brothers is the original, but you'll find them almost everywhere. Just make sure the collar is not too tiny. I think I gonna talk more about this menswear staple later, it deserves it's own post.
Step 4: From whateva jacket to sports jacket
OK, you mean biz. I see. So, you should now say bye to the world as we know it and... get yourself a nice sports jacket! The prophets and keepers of the WOM agree to one law: the first sports jacket to have is a blue one. Not too light, not too dark. Patch pockets, a length that at least covers your butt and a cloth that has some kind of structure to it (like hopsack) are kinda standart. A sports jacket should not have the appereance of an orphaned suit jacket. And you always want to make sure that there is enough contrast to your pants, so, in case of a blue jacket, most lighter shades like grey or beige will be no-brainers. But there are many other colors that might work, just avoid the same color and shade, cause in this case, you could just have bought a suit. I personally like the Havana style from Suit Supply, but there are a lot of other brands.
sports jacket with patch pockets, hopsack fabric
with a tan chino
Step 5: From blowrag to pocket square
This is, after Step 4, a relatively easy one. Nobody will care too much and some won't notice it at all. But don't underestimate that step in concerns of "style". There are one million rules in the WOM about how a pocket square (from now on: ps) should match with the rest of your clothing. Also worth it's own post. But for the beginning, you might wanna go for white linen or cotton with a blue contrast border. These work great with a tv fold. A dark, multi-colored paisley silk ps can also be very versatile. Here you wanna go with a so called puff fold. Some products feature a nice front AND back side (like this Shibumi ps, currently unavailable):
pocket square (silk, paisley pattern), front side
back side
puff fold
Hand-rolled edges are considered to be a must or, at least, are very welcome.
Step 6: From, well, ahem... no-tie-guy to tie-guy
'Aight, buddy, you should stop right here. The rest is walking through minefields. How dare you wearing a tie! Nobody who doesn't have to has to!
Well, if you're into it, go for it. Start with a knit tie. Or a repp tie. Some consider a burgundy grenadine silk tie to be the "one-matches-everything"-tie. Well, if you take that step, you'll enter a whole new world anyway. You never will be satisfied with the amount of ties you already have. Just make sure, they are not made of or blended with synthetics. Really, doesn't make sense to write more, since this is defintely worth at least ten new posts... Ah, ok, one thing - shantung, bro! That's the word! If you wanna rock ish hot, rock a shantung tie! (Yes, there are also trends in the WOM ;) )
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Step ahead: tbc
Well, baby, this game doesn't stop anywhere. Find your own style by spending days and nights watching other guys on the internet or in the streets ;) Trial and error. Sprezzatura and tradition. Knowing and breaking rules. Good luck!
