How to Use This Guide

Here’s a whole lot of content about the foundations of dressing. It’s a reference post rather than something comprehensive.

If I were you I’d use this guide in the following way:

  • Read through everything that’s already here – I added it for a reason and feel it’s important.
  • The handful of articles I provided aren’t the end-all be-all of the subject. Think of them as starting points.
  • Note down any questions you have that the resources below don’t address and ask them to me. I will probably be able to answer most of them. I can add my answers to this post, or to follow-up posts so we’ll have the information to refer back to lat.
  • There are several different dimensions on which you should think about dressing: Contrast, Color, Formality, Fit. Each of those is its own section below.

Start Here

This blog ‘Put This On’ is probably my favorite: it’s accessible, it has a ton of great content, it doesn’t assume you know too much, and it’s sensitive to the fact that people don’t have unlimited $ to spend on clothes.

They have a pretty comprehensive ‘Start Here’ section. It’s a LOT of content. So maybe read the first few in order and keep going if you like, or come back to here. https://putthison.com/start-here/

That will be good reference material whenever you are looking for more to read beyond this post I made. It’s probably the first place I’d head afterward.

Types of Styles

From the same Put This On blog, here are explanations several different distinct ’styles’ (i.e. preppy, workwear, ‘fashion-y’). It would probably be a good idea to look here and see what appeals to you the most.

Part 1 – https://putthison.com/five-starting-places-for-building-a-casual-wardrobe/

Part 2 – https://putthison.com/five-starting-places-for-building-a-casual-wardrobe-part-two

Fit

This is important in looking good.

I don’t think we really need to cover it much since from what I’ve seen you already wear clothes that fit well. Everything doesn’t have to be super slim, but given your body type, slim fit stuff will probably look good. You should be able to move comfortably and fairly unrestrictedly. There is definitely such a thing as too slim.

Try to find cuts that work for you – some brands just won’t have the right cut no matter what size you try on. You will generally probably have a fairly easy time of finding stuff that works for you though.

Contrast

Contrast explains why stuff that might look good on Jerome may not look as good on Chris – your hair and eye color influences this.

  • The ‘foundational goal’ of classic mens’ clothing is to frame the face, so the focus is on ‘you’ and not on your clothes.
    • The examples they give are suit and tie specific but you can think of it for more casual clothes as well (i.e. high contrast = black sweater with white t-shirt underneath, or low contrast = light gray sweater with white shirt underneath). Once you read this, start looking for it in some of the style pictures you see.
  • Contrast in a general outfit: https://putthison.com/a-basic-guide-to-sport-coat-trouser-combinations/
    • Again, this advice is for sportcoats and dress pants, but it applies to casual clothes as well.
    • This is different than contrast / framing the face and has more to do with the visual interest of an outfit. Outside of suits, it will look a little off if your pants, shirt, jacket all look the same color. You look kind of like a blob. This is why a navy sportcoat looks much better with khakis or medium gray wool pants rather than navy pants of a different shade.

Color

Formality

Some photos of people who I think dress well.

Look at the photos and figure out what they’re wearing and how it works on the different dimensions we talked about above: contrast, formality, color, and fit.

There are plenty of people to follow on Instagram too, I don’t really use IG but I do follow a few people and can recommend them if you want… but I know you don’t use it either.

When you come across photos you like (from the links above or elsewhere) – save them to pinterest or download them to your desktop and keep them in a Dropbox or something. There’s probably common themes/patterns among what you like in the photos, which is something I can probably help you work out if you need.

These are all things I like personally; you may prefer something different so feel free to look for your own. A great archive to look at is: https://putthison.com/tag/real-people/

Buying Clothes

Try to go shopping with Sol (or buy things from places that are returnable, and try it on at home to see what she thinks).

If your goal is to dress well, you (rather than she) should be the one picking things out based on what you like and have learned. If there’s something you like, try it on and see what she thinks. If she likes it too, it’s probably a keeper.

# This is why I don't write technical blogposts

def buy?(garment)
  if jerome.likes?(garment)
    (sol.likes?(garment) || jerome.reallllllly_likes?(garment)) && jerome.comfortable_in?(garment)
  end
end

If she doesn’t like the item, you can still get it, but try to understand what she doesn’t like about it so you’re making an informed decision. It might be her personal taste differing from yours, in which case you can still buy it… or it might just look bad, or too weird.