Hey Brian – it is probably a mixture of competition and optimism that makes me say that about "everyman." You're right. And while I know we don't always shout this part from the rooftops – mostly out of fear of sounding like Crazy Eddie - VALUE is the one thing I am really keen on passing along.
We talk a lot about "economy of time, mind and money." You need all three, but often in different amounts at different times in your life. Your career has progressed (congratulations on that by the way) and so, for you, time is probably worth more than money right now. When I was young and scrappy, I could spend lots of time searching for the perfect thing at a price I could afford. I actually loved doing that – I guess it was that competitive side of me as well – but now, like you and a lot of men my age, time is the most valuable resource I have. Now, I can't afford to spend a full day on something to save $30 (although it sounds fun.)
And economy of mind is more important than ever before – for all of us. There's enough going on in the world to worry about (are we still supposed to be sanitizing groceries?) without having to add clothes to the list. When you can be appropriately dressed and avoid the rabbit hole of insecurity or oh man, I should have worn X without spending a lot of energy thinking about it... THAT is freedom.
So investing in fewer, better things (in all parts of your life) is one of the smartest decisions you can make. And I can say with confidence it's one you won't regret. This applies not just to you, but every guy! My advice always has been to think about how often you are going to wear something, and factor that into the price. Nothing earth-shattering there, but it's better to have a few great things and wear 'em often than have a closet full of stuff and only wear 30% of it.We once made a "utility index" for a customer who led a consulting firm. He needed help with his wardrobe because he was high-profile, traveled a ton, and frankly, couldn't afford to spend a lot of time or mindspace on it himself. We set him up with a matrix of super-simplified options (think Mashburn meets Garanimals) but the one thing that got him over the finish line for us to dress him? That dang utility graph. It showed that when you amortize your items over how often you wear them... it is scary how few things you really need. And if you are using words like fiscally responsible – my bet is that you could make a graph of your own. But anyway, back to your question. What to invest in?
I put my money in shoes – I always have. There is nothing that kills a look more than cheap shoes. As you mentioned, we sell and love Edward Green shoes, which may seem like a splurge (they are,) but cost-averaging over the lifetime of the wear kinda puts things in perspective. Take the price of a pair of those, add in the eventual resole job, and you're looking at seventeen hundred dollars - which is a lot! But okay, let's say you're wearing them even just once a week (it'll probably be more) and that's 1300 wears over the next 25 years. That's cost per wear of $1.31, which is pretty great – and that's on the conservative side. Waiting to buy those shoes until you're 60 doesn't give you as much time to recoup your investment! (I bought mine when I was 45 – they haven't hit the 25 year mark yet but I've definitely gotten my money's worth.) I may suggest our own line as well, many of which are made in England just down the road from the EG factory, and – we think – are an incredible deal. Our cap-toe balmorals are $650, which kicks your CPW down even more... as in fifty cents per wear.
So shoes are big, but I'd also say a navy wool suit that can take you anywhere you need to go – from the most casual dates, interviews, parties, board meetings, weddings, funerals, to the dressiest dates. As an attorney, you probably have your fair share of tailored clothing, but a go-to, do-it-all suit that you feel good in even outside of the office? Worth its weight in gold. It acts like kind of a 2-for-1 with all the pockets for keys, phone, pen, notebook, Airpods, passport... no tote bag required. And remember that in a pinch, you can use the top half as your navy blazer. Just don't overplay that move.
Last thing I'd throw out there. A cashmere sweater gives back like crazy. I know that not everyone is dying to drop $400 on a sweater, but man, other than moths, you should be able to wear that thing for the rest of your life. And it doesn't have to be your typical "neutral," either - this is a grrrrrreat place to add some color. You can see from my closet that I love a green and a bright blue... and that new heathered purple's awesome. You'll be surprised at the CPW you can get, even on purple. Don't forget to get a sweater comb for maintenance. And when it does get a few holes – hey, now it's a sweatshirt. Look up a Youtube tutorial on darning if it's going to bug you, but I wouldn't sweat it. I have cashmere sweaters I have been wearing for 30 years.
I think the key to deciding whether (and when) to purchase is understanding the value it'll bring. Think of how much you'll enjoy wearing it, how you'll feel in it, how long you'll have to enjoy it, and any stuff you'll have to do down the line to keep it in good shape. Resoling, combing, conditioning, whatever. And then do the math on that cost per wear. If it comes out to whatever you spent on lunch today, you're probably safe to pull the trigger. So whether that means an alligator belt (a great purchase no matter what season of life you're in – just figure out the most ubiquitous footwear color in your closet, match to that, wear all the time), a great cotton shirt (for sure,) a tie you love (it's hard to wear out a tie)... the cost per wear is what to focus on, not the upfront price tag. Sounds like you've earned it.
