Zara Barracuta Jacket: I just picked up this same jacket myself on a trip to SF and love it. The styling and details are traditionally masculine and rugged, but the fit is slim enough that it still looks modern and updated. While a blazer is more dressed up, this is a great layer for your casual game. $80
Levi’s Inky Blue 511’s: This image doesn’t have a link as you’re better of buying these in store. You should be able to find them for a great price at TJ Maxx, Marshall’s, or Macy’s during their sale weekends. If these are too skinny, then the next best choice is to go up to the 513’s. $35
Grey Converse All Star Low Tops: Black will look too angsty and white is too clean. Grey strikes the right balance while still being neutral enough to wear with everything. These can be worn with or without socks and should supplement your Clarks. $30
Target Mossimo Henleys: The fit of these is the best I’ve ever found in a henley. They’re slim without being constricting and the sleeve length is right where it should be. I’d do one in white, navy, and grey. $45 for all three
We’re going to go with three suits from Dragon Inside. The name sounds a bit silly, but I had them make a suit for my brother and it turned out great. The cloth is from one of the oldest Italian mills in the world and is a mill we use at my shop as well. I recommend starting with three fairly simple suits – a blue three-piece (that can be worn as a two-piece as well), a lighter grey, and a brown. All three are solid, but have some visual texture in their weave – making them interesting but not attention seeking. These will be your biggest investment at $1660 for all three.
We’ll stick with Dragon Inside for shirts as well. Most men (myself included) when first getting into the world of custom overly embrace the idea of bold patterns. They can be great, but doing too much too quickly is one of the biggest giveaways of a newbie. I honestly wear a white shirt more days than not, because I’ve come to appreciate the subtlety of letting my suit or some particular point besides the shirt do the talking. I recommend getting two of the white, two of the blue, and one each of the two patterns I’ve included. It’s more than enough to get you through a single week, and all of the shirts will pair great with each suit. $740 for all six.
Both shoes will be Johnston & Murphy (affiliate link). They’re a great bang for the buck and the shape of their last is slim without being too aggressive. I recommend the double monk in the brown and a cap toe in the black. You can wear the black with the grey and navy suits, and the brown with all three. The brown can also be worn with jeans. $320 for both
Back to Dragon Inside for these. The trick to a good tie is using a simple pattern that looks timeless. Too many ties belong at a thrift store because they look like something from a given decade. The more classic and/or subtle the pattern, the more mileage you’ll get out of them. $130
Nordstrom 12-pack cotton handkerchief: This is what I use for my white pocket squares. They’re minimal, fold up well, are washable, and just do the job. After you’ve gotten a bit more comfortable wearing all of this, we can start to expand into patterned squares, but white’s the ideal way to start off. $13
For socks, I recommend going to target and picking some out. I’d show you photos, but it’s always kind of hit-or-miss in each shop. Focus on grey and brown, but get a pair or two that are black, and then grab a pair or two that are loud as well. They usually run about $3 a pair.