I didn't come from a family that took an interest in fashion/style, so I had to learn a few things by trial and error.
I'm about 40 now, and on my way to here I've bought some weird stuff because I got hypnotised by a brand, didn't understand the terrain, or got confused about what actually mattered. I've worked in office environments in a few countries, been in a lot of shops, and have been able to learn off people as I went.
In case it's of any use to anyone on here (whether you're a young person trying to make sense of stuff, a parent trying to help their son along, or just a person hoping to learn something new) I thought I'd write down a few things that I've just found to be proven performers that will work well for almost anyone. And will help you avoid the pitfalls of overpaying for nerd stuff that you're unlikely to even appreciate.
Of course, everyone's sense of style is different. The things I'm listing here are designed to be classic, standard, good quality gear you're unlikely to get sick of. Add your own flourishes for sure.
Shoes:
For casual shoes, getting along to a Converse factory outlet store and picking yourself up a $60 pair of low top or high top canvas Chuck Taylor All-Stars is how to do it. They suit almost everyone's personality, they have cred, and they don't go out of style. Air Jordan 1 (the original model) in leather is a bit more expensive (often achievable for $100 on Foot Locker website) but is also a fad-proof workhorse. For running shoes, pay $70-100 on sale unless you're training for actual races. Clarks suede desert boots in light brown are the step up in formality and they can be got on Amazon for well under $100 on sale. Try them on in a shop, note down your size, then wait. They can do you for casual Friday at an office job, random family events, and stuff like dinners on holiday. They look great with jeans and either a plain t-shirt or some sort of flannel/cheque button-up.
For work shoes, I've found that Clarks leather shoes when they're on Amazon sale are good value. Buy rubber-soled shoes unless you're working in a fancy place, the leather-soled ones are much more expensive, arguably less comfortable, and require a maintenance budget. Think hard before paying the $600 price of admission to the RM Williams lads club: that money is a return flight to about 15 different countries, and you'll be then expected to have opinions about crypto.
Jeans:
Forget about which brand is on the label. Jeans that fit your particular shape look good, jeans that don't fit right look shit. Start your search by going into a reasonably fancy store that has knowledgeable staff that can give you advice and feedback on what's fitting you. Sponge up that knowledge and start marching around cheaper shops looking for something that fits the same. You might have to try on 10 or more pairs of jeans before you discover the one, and that's ok. The other week I picked up some slim jeans at Big W for $25 and they fit really well. Who cares if they don't last quite as long, I paid a tenth the price of a fancy label. If you find a pair you're thrilled with after a couple of months of ownership, pick up two more pairs next time they're on sale and put them in your cupboard. You'll be sorted for years. If you do want a brand, Levi is a socially good company with a lot of different fits that can be got for under $100 on sale.
Tshirts:
Same deal as with jeans. Find advice on fit and then go apply what you learn. I've found that the slim fit plain tees at H&M fit me great and cost $15. Some of them I've worn hundreds of times and they're still going. Uniqlo has an interesting range of art and pop culture tees for $25, but again make sure they fit.
Watches:
With a smartphone in everyone's pocket, watches are semi-decorative at this point. But it's almost the only piece of decorative shiny stuff that a lot of blokes wear, so it's a nice chance to just have something pretty for the hell of it. There are two main types of analogue watches: quartz and automatic. Quartz is 1970s tech that has a replaceable battery and is more accurate. Automatic/mechanical watches use older tech that is more artsy and less accurate (and the watch stops if you don't wear it for a couple of days), but the watch nerds enjoy the whole artform of it. It's possible to get carried away and start building a collection of watches, but if you're a regular person who just wants to look good I suggest just two: a quartz Tissot (T1504101105100) for the office/events, which is often available at Mazzucchelli's for $450-ish, and a digital Casio G-Shock (DW5600UE-1D) for outdoors and exercise, which is often available online for about $150. Both watches are high quality and not cheesy, and the nerds will realise that you kinda know what you're doing without forking out the big dollars to get caught in their $5000 arms race. And keep away from fashion brands (Armani, Calvin Klein etc), they charge $300 for a $100 watch.
Suits:
Fit is what matters. Go to a menswear store, try some stuff on, get advice, and note down the measurements of what fits. Then go to ASOS or something and buy for less. If you only need to wear a suit sometimes, a wool-poly blend will be fine (rather than pure wool). Dark blue and charcoal are the two most versatile colours, it's weird to wear a black suit to work. Avoid pinstripes and stuff unless you really understand what you're doing. On the fit, allocate $60 or so in your budget for tailoring to ensure that the cuffs and hems sit right. That makes a huge huge difference and it's money well spent.
Formal shirts:
Same drill. Go get your measurements (chest, waist, neck, sleeve length) and advice, and wait for a sale at Charles Tyrwhitt. Should be able to get 3 shirts for about $120. The important things are avoiding a large amount of baggy fabric around your waist, not going so tight through the chest that the gaps between the buttons open up like you're a busty woman, getting the cuff to sit below the wrist bone, and avoiding the "collar too tight" Donald Trump turkey neck. You want the shirt cuff a centimetre or so longer than the jacket cuff. Subtle fine stripes are ok for shirts, especially if you're not planning to wear a tie and just need a bit of texture in the outfit. White and light blue are the most versatile colours.
Ties:
Don't be a gimmick with wacky designs or loud patterns. Skinny and wide ties swing in and out of fashion, if you're buying $15 polyester ties on ASOS you can afford to play along, otherwise chart the middle course with a couple of classic silk ties.
Socks:
For workwear, don't wear black socks with brown shoes, don't wear brown socks with black shoes. A safe method is wearing socks that are a darker tone of whatever colour your pants are. Places like TK Maxx sell 5 and 10 packs of brand-name socks at great prices.
Fragrance:
A bit subjective, but don't try to overpower the room. If you want a fresh clean scent for $20, Voyage by Nautica is often on sale at Chemist Warehouse and Amazon. The scent won't last for 8 hours or anything, but it's good for dinners and trips to the pub, and you could consider giving yourself a couple of top-up spritzes at lunchtime at work.
Belts:
Match the belt colour with the shoe colour whenever possible. Black shoes and brown belt isn't the way unless you're a risk-taking expert. Wear a belt even if you don't need one… it just looks right.
Coats:
If you're in a climate where coats are on the menu for a few months per year, it can be worth spending some real coin on a pure wool short trench coat from a good brand (in charcoal colour). It's the most prominent piece of clothing when you're wearing it, you can wear it day after day, and you'll get years out of it. Again, fit matters. Don't buy something online that you haven't tried on: you want the coat to come inwards where you do, outwards where you do, and be the right length at the cuff. There's a notion in interior design that you can get away with a few IKEA/cheap things in a room if you've got a really nice interesting item in the room that catches the eye and makes everything look swish. Same idea can apply to outfits… if your jeans fit you and you're wearing a nice coat, people will just assume that your H&M t-shirt is top notch too.
If there's a common theme here, it's to take the time to learn what a good fit is (YouTube can also help), don't get dazzled by designer labels, and for your core items go with things with a classic vibe that you won't cringe at in 12 months time. You don't need to make this your hobby or become an expert, you can get to a good level by just digesting the key points then shopping around for an affordable item that fits. I'm also not advocating being a dull human. Some of the most interesting and amusing people I've met are low-key dressers and it arguably boosts the impact. You don't see many stand-up comics wearing clown suits, the outfits tend to be neutral so people's attention is focused on what the person is actually doing and saying.
I've probably missed some stuff, but that'll do. Cheers!
What other time/money-saving tips have people picked up along the way?
Thanks for the advise