The backstory: Approximately 2 months ago I made the decision to educate myself on style as my next life project, which I take pretty seriously (involving months of research, organized binders, commitment in time and money, etc.) I have definitely made some strong initial strides given how completely unaware I was previously, and concentrated most of my early efforts on altering/tailoring a lot of the clothing I already owned to actually fit me correctly, and researching without necessarily buying a lot of what I want my eventual “look” to be. About to hit my 30s, I have settled on a dressier look exemplified on the StyleForum WAYWRN thread – dressier shoes, blazers, shirts, pocket squares, etc. – obviously it will take years to get to this point, but I am willing to put in the effort.
The issue I am currently facing is given my budget on my wardrobe for the year and the significant upgrades that are basically required across the board, how to prioritize what to purchase. I am hoping some feedback here might help narrow my focus. I have a list of “wants” and tried to trim it down to what I would consider “needs” based on simply not having these items represented in my wardrobe:
* Pair of black dress shoes
* Pair of brown dress shoes
* 2 Dress shirts
* Pair of jeans
* 1 Suit
* 1 Blazer
* Pair of sneakers
* Pair of casual dress shoes
I am doing my due diligence with trying to be as economical as possible – regularly visit thrift stores, scour ebay/craigslist, and check the styleforum for sale sections, follow dappered.com for clearance items, hold out for the rare super-sale, etc. My budget for this year is ~$1,100. There are a couple reasons it is tough for me to prioritize these items.
I am trying to value quality that will last my years over quantity that I will need to replace in a year. A great example is the shoes – I was one of those guys that thought the bottom-barrel leather square toe slip on shoes from Marshall’s constituted legitimate dress shoes to pair with a suit. One of my first new purchases after starting this endeavor was to go out and get a pair of decent leather brown oxfords that matched most of my dress attire from DSW, but being my only pair of dressy shoes I feel comfortable with over these last couple months these things are not surprisingly starting to feel the wear of being worn almost every single day without rest day after day.
From talking with some shoe salesmen at higher-end stores and reading online, the more higher quality dress shoe absolutely makes a huge difference in terms of comfort and longevity, but even $500-600 shoes (that I can grab on ebay for about $250) can’t be worn every day – I need a minimum of 2 to alternate, ideally 4 at some point to truly keep them fresh.
A similar situation with my suits – in retrospect, part of me wants to wage war on MWH for putting no effort back when I bought all of my last round of suits into educating me on how to determine what I should wear – I have 2 suits, one that is very serviceable, one that is acceptable, and the rest of my closet is full of either super-padded shoulders, shoulders that are too big for me, pleated pants, etc. Again, with a suit quality definitely matters in terms of longevity – I don’t need to drop $1k on a suit, but there are plenty of suits around that price range going for $300-400 if you search long enough. My work will entail me being at conferences/trade shows that last 3-4 days in a row where + regular use for work and I am concerned of both repetitiveness and burn out of the two I currently own.
Between these 2 shoes and 1 suit alone, even being relatively frugal, that is basically half my budget right there. That doesn’t even address more casual wear – I currently have only 1 pair of jeans that actually fit me (formerly too big at the waist boot-cuts now collect dust in my closet), my previous casual shoe was a dreaded generic gray New Balance, and I am in pretty desperate need of dress shirts that fit properly and aren’t worn down.
To top it all off, much of the stuff I am looking at will also require tailoring (suits, blazer, dress shirts). I finally got off my ass last year and dropped around 20+ pounds off my frame – hence why basically all my clothes needed to be tailored, and forced some stuff that couldn’t be to become obsolete (jeans, some jackets, dress shirts). This will only further cut into my budget.
So all this being said, how should I look to prioritize my spending? I am not even including the accessories that I need to acquire at some point down the road, pocket squares, ties, coats, another watch, etc.
**TL;DR – between learning how to not dress like an idiot and losing 20 lbs., need to start overhauling both work and casual wardrobe with $1,100 budget for the year – need help prioritizing spending. **
