I polled around a little a while back on /r/malefashionadvice/ to see if the sub would be receptive to a thread like this. The response was that yes, this is advice that a lot of men could do with, but there needs to be a couple of disclaimers first. Additionally, I'm more than happy for conversation, disagreement or additions to improve this guide. If the majority of MFA disagree on something I suggested then I'll amend.

What this thread is: If you're completely new to the intimidating world of fashion, perhaps because you've arrived on MFA for the first time (maybe your significant other has gently suggested that you could try a little more) - this thread is for you. Chances are you've been unconsciously mismatching things your entire life because up until now the only person who gave you feedback was your mother. With some of these basic principles you can avoid some of the more obvious pitfalls of a bad outfit. If you want to dress less badly but you currently don't have the first idea how, this thread is for you.

What this thread is not: This is not a list of absolutes. There's no "never" or "always" in style and fashion. This is a dumb and limiting way to think, and if it were true then the way people dress would never change. Truth be told, everything suggested here could be ignored, given the hands of a competent person who understands the why and how. If you're new to MFA then this probably isn't you, and if you have to ask then this definitely isn't you. This thread is also not intended to passive-aggressively insult the things you like, even if my tone gets a little biting at times. It's all tongue-in-cheek, I promise.

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So, here we go:

1. Square-toed dress shoes.

This seems to be the fallback of sys-admins or guys who have one pair of dress shoes for that yearly wedding. It's time to stop. These are bad. Feels bad man. Square-toed dress shoes are sort of a relic of an era when suits were much baggier and boxier, and so having a big boxy shoe to match kinda made sense. But clothes have come a long way since the late 90's. Opt for rounder toes, or if you're still really attached then get a subtle chisel toe. No, none of this means you need clown shoes.

This is what those look like: one and two

(Alternative shoe styles are more or less limitless. Square toed shoes just follow all the same styles of shoe as other dress shoe styles, except for the toe...which is square. Have a look for oxfords, brogues, derbys, monkstraps, chelsea boots, desert boots, penny loafers, etc. - just something that's not oddly capped off at the end as if cut with a dull knife.)

2. Loose fit, long cargo shorts.

Never has a single item of clothing been so defiantly defended by men who never cared about how they dress in the first place, and at the same time been met with total indifference-to-revulsion by women.

There are a couple of very specific examples where this might not be a problem. Maybe if you're camping and you need a place for your flashlight and swiss army knife and book and portable tent, or in the event that you somehow miraculously got the only well-fitted, non-bulky pair of cargo shorts on the market. Maybe you have 4 kids and you need somewhere to store all those toys and wet wipes. But generally you are not, and you did not, so stop. And stop making references to ball space requirement. You do not have elephant testicles, and wearing anything other than curtain-loose shorts is not a threat to your masculinity. Even for casual get-togethers there are better options that don't involve bulking up your legs with all those satchel-sized pockets (legs are generally attractive features, you should show them off a little more).

This is what those look like: one, two and three

(A simple alternative could be flat-fronted chinos. Just like cargo shorts, but without the frumpy pockets and with slightly less length.)

3. A vest/waistcoat with no jacket.

The orphaned vest is a goddamn mess. I know you were going for "classy, but fun", but what you actually got is "have you been served yet, ma'am?" Look, in very rare very well put together and extremely well-fitted outfits it can work, but if you have to ask then no, you did not make it work. Usually the jacket is too long, it gives the impression of narrow shoulders and fat square tummy, and the colour combination honestly makes people think you're there to serve the drinks. It's also kind of a nonsensical thing to wear most of the time, because you've thrown an item from a 3-piece suit (a very formal, almost archaic style) into a more casual outfit with jeans, and as a piece of clothing by itself it doesn't serve much function. Just hypothetically, imagine wearing a top hat with jeans and a shirt - it's not a lot different.

This is what that looks like: one, two and three

(as /u/HarryWang94 points out, you'd be better served with a cardigan instead of a vest, which fills the same function you're going for, but gives you a great piece of clothing that's applicable to so many levels of formality and different kinds of style. Here's an example of that.)

4. Gold jewelry if you're white and on the paler side.

This has nothing to do with race or culture. This is purely about contrast. If you're white and pale (like me), then gold will wash you out and look quite gaudy. You'd be better off wearing silver or gun-metal if at all.

It's almost impossible to find pics of what that looks like but nevertheless I always seem to meet pale ginger kids with gold rings and such: one

(As /u/pootlepower points out, this is actually not true if you know your cool shade/warm shade undertones. If you are fair you are more likely to have a cool (pink) undertone, which clashes horribly with gold jewelry. You can however be fair and have a neutral, warm (yellow) or even olive undertone that works well with gold. But I figure if you know that stuff then you don't need to follow this particular bit of advice.)

5. Brown shoes with black suit pants, or brown belts with black shoes and vice versa (formal wear only).

You can break this one fine if we're talking jeans or chinos, but when it's suits it's better not to mess with it. Hell if we're being picky then yes you can break it with suits also, but if you knew how to do that you wouldn't need any advice. It's a really simple thing to match your belt to your shoe colour and gives you a nice feeling of symmetry and coherence, something that even someone who doesn't care a lot about fashion can appreciate.

This is what that looks like: one and two

(Here is a pretty safe guide to colour matching shoes/pants, but just don't take it as gospel. Nothing is gospel.)

6. Wearing hats with more character than yourself.

It's too easy to pick on the fedora because everyone gives that a bad rep already, but this is really a wider thing about hats in general. If you're using the hat to try and stand out and show your zany side, you're definitely doing it wrong. I actually support all hat types, even the fedora. But it seems that most people do a bad job of wearing them, and a lot are clearly trying to make a very contrived statement. It's also a problem because a lot of hat types are relics of much older fashion styles, and don't necessarily pair well with modern dress.

This is what that looks like: one and two

7. Polo shirts as a "catch-all" for all your formal and casual needs.

There's nothing inherently wrong with polo shirts, and I could find lots of examples of really nice, really well-worn polos, but it seems like a lot of guys just have wardrobes full of them because they never know if they should be wearing a t-shirt or a dress shirt. The result is kind of like a permanent "just been golfing" look. And it's always Ralph Lauren for some reason. How about you save your money and just get more button downs made with casual materials and nicer t-shirts?

This is what that looks like: one, two, three and four

8. Wearing a crewneck undershirt so that the crewneck is visible under your dress shirt.

This is one of those weird late 90s things that has oddly persisted. An undershirt is to stop your dress shirts from getting pit stains or to keep you warm. It's not generally a part of the outfit (and no, we're not talking about layering here). Especially don't pair a crew-neck shirt with a v-neck sweater. You'd be better of buying a v-neck undershirt which would be successfully hidden under a dress shirt.

This is what that looks like: one, two, three and four

(An alternative here is to use a V-neck undershirt, which serves exactly the same purpose but won't show any visible undershirt neckline. Example here.)

9. Black shirt and red tie.

Don't be black shirt and red tie guy, or red shirt and black tie guy. Understand that the issue isn't some intrinsic relationship between red and black that should be avoided. There are a lot of ways an outfit can use these colours to great effect. The issue is all those extremely saturated bold colours covering your entire body, it's eye-watering to behold. And often both the shirt and tie are high gloss or silk, which makes it even more distracting.

This is what that looks like: one and two

(If you were really deadset on being black shirt red tie guy or vice versa, you need to really think about the level of contrast here. You'd be better off with less bold, solid-colour patterns. Try not to wear things where you have two or more colours fighting for visual dominance. Here is how you might do that. See how it doesn't make you want to put on sunglasses like the other examples? Balance is important.)

10. Matching your tie to your pocket square exactly.

Maybe you don't like pocket squares altogether, but if you were wanting to wear one, here is what you don't do. When you go and buy a pocket square and tie, quite often they come in handy little packs where you get the tie and pocket square of the same pattern all bundled together. You'll even see helpful product photos showing the effect, like this Do. Not. Wear. Them. Together.

The issue here is that a pocket-square or tie is just supposed to be a little accent. It's a tasteful little flourish in what is otherwise a fairly colourless, pattern-less outfit (as most menswear tends to be ). When you match the tie and pocket-square exactly, the effect is very distracting. Anyone looking at you will just see that same pattern repeated on your outfit in more than one place, and it naturally draws the eye away from your face. So rather than adding something to your outfit (designed to flatter you), it's taking away from it by creating an intense visual distraction.

Here's what that looks like: one (on the right), two, and three

(You'd be better off wearing something that plays with the same colours of the shirt, or something that complements all the colours put together, like this.)

11. Thin rectangular frameless glasses.

This is a sensitive one. And you really don't need to agree. Maybe you find frames visually distracting and you'd rather just be able to see perfectly than feel impaired by a frame. And that's fine. Of all the things on the list, this is one I'd be prepared to compromise on. But if a frame doesn't actually bother you, then purely from an aesthetic point of view you can do so much better. Even without a frame, most face shapes would be flattered better by something other than envelope-thin rectangle. It's that IT + accountant look all wrapped up into one.

This is what that looks like: one, two and three

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I'll finish with this: there's a pattern to most of these points, and it's that bad clothing decisions usually come back to the misguided attempt to throw together what you're wearing without giving critical thought to how it all works together as one outfit. The less you start thinking about your items of clothing as if by themselves in a vacuum, and put more thought into the overall affect of all those pieces together as an outfit, the better off you will be. This means thinking about how the overall shape is going to look, how the colours work together, whether the formality of your shoes match the formality of your pants - and so on.