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You do not need special stuff for quality leather shoe care.

1. 2 Gallon size plastic ziploc bags (Sharpie one black and one other)
2. 2 horsehair buffing brushes
3. 2 horsehair daubers AKA polish application brushes
4. 1 container of edge dressing
5. 2 cans of polish (Kiwi Black and Kiwi Neutral)
6. A bunch of buffing cloths (honker pack of microfibers)

You can get all the above from eBay for crazy cheap. Make you a black shoe kit and a brown shoe kit. You can use neutral shoe polish on every flavor of brown shoe as there are 934,893 shades of brown shoes and 63,214 shade of brown shoe polish and they odds of you getting a match are near zero. You can even skip the daubers and use old tooth brushes or sacrificial cloths. Don't mix up the kits as you don't want to blacken up your brown shoes. You polish your shoes every 3-6 months and perhaps buff when you see them getting dull. Youtube has an infinity of videos on how to do it.

Cobblers are a thing. You can take your shoes there and say, "Make deez good". Return in 1-5 days and for $20 and zero effort, you have nicely cleaned and polished shoes.

Anything you apply to make your shoes waterproof is a lie. Shoes are natively waterproof based on construction/materials, not some goo you rub/spray on. If you want waterproof shoes, but them out the gate that way.

You can wear for days in a row. Allowing them to rest is smart and will increase the lifespan and split toe shoe trees will help keep the shape when not worn. Rest is best practice, not a requirement.

GYW shoes can last your literal lifetime. I have two pair from the 80s. The real sweet spot is around $300 pricepoint for men. Anything less is lower tier. There is no such thing as break even point as that talks to your desires and budget and we know neither.

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TLDR Its 100% worth it

I literally made this same transition in my footwear / clothing approach. r/goodyearwelt is your best friend

Did my research and I invested in a pair of Redwing Iron Rangers ~$350ish. An American classic that ages well and is considered well built and good quality. 2 years later of wearing them literally daily (90% of the days at least) , they continue to look good as new. My only complaint is my tread and traction is worn down after 2 years, so they are a bit slippery in the snow (more on that later)

For upkeep and maintenance, it sounds daunting but is really very simple. Rose Anvil has some good walkthroughs. Kiwi Saddle soap with a dauber (small) brush ~$15 total acts as your cleaner. Some leather conditioner (I use cobblers choice) with a bigger brush ~$40 is your treatment/waterproofing. Shoe polish or wax is really optional. I do my boots once every 6months. Step 1 - Knock off any loose mud/debris, Step 2 - Spray the boots with distilled water and Scrub them with the lathered up saddle soap, Step 3 - wipe them clean with a clean rag and let them dry for ~24hrs. Step 4 apply some conditioner to the boots, either with your fingers or put some on the big brush and start doing some passes (think of it like lotion on your skin, enough to moisturize but not too much where it becomes overloaded and oily) Step 5 let them rest and dry for another ~24 hrs, just so the conditioner soaks its way in evenly.

FYI The conditioner is your weather protection and healing lotion. It doesn't completely waterproof the boots, but it greatly helps shed water on normal levels (walking through puddles, rain, snow etc) The only way my feet will get wet is if I stand in a river for a full 30 seconds. To completely waterproof leather boots you need wax or snowseal, and neither of those are particularly good for the leather's longterm health

All that being said, I am never going back to daily cheap shoes. Once the boots break in and form to your foot, nothing is more comfortable or feels as natural. Technically yes you should give your boots a break to breathe and fully dry out with cedar shoe trees, but I think of that more as a rule for the Vibergs and bespoke builds of the leather world, where more emphasis is placed on the finer details. Like I said, daily wear and my boots are doing excellent. A big part of that is the leather type as well, do your research into vegtan vs cromexel vs roughout vs cordovan etc, and pick the one that has the qualities that fit your lifestyle (or looks the best lol).

My solution for my treads becoming a little slick in winter...I ordered a pair of Nicks boots to act as my "winter set" and my Redwings will be my lighter "summer" boots. This is where cost vs quality starts to play a role. Again Rose Anvil does deep dives into the boot construction and quality, and you will see why Redwing and Thursdays are ~$300 and Nicks and other PNW boots are ~$600. You can usually see a direct relationship in the amount of material and leather and build quality that goes into a boot vs the cost. Stick to reputable and pedigree brands, and you will absolutely get what you pay for.

Hit me up if you have any questions

There are different levels to Goodyear welt shoes, especially for women as it hasn’t taken off in quite the same way in women’s fashion circles. But in short, I would say yes, they are absolutely worth it. If you get the right pair, the leather will stack up to the construction, and you’ll have them for 15+ years. Some brands I recommend for women are:

RM Williams. The OG Chelsea boot, and still some of the best out there.

Crockett and Jones. Exceptional pedigree, and a number of classic and daring styles.

Meermin + Carmina. Owned by the same family, they make shoes at slightly different price points. Meermin has a really good MTO program. Carmina is known for their unique lasts and their general elegance in design and construction.

Redwing is a bit of a toss up in terms of quality; some pairs still rock, but there have been many recent horror stories about them in the last decade or so. But the styles are classic and very good.

St. Crispins, John Lobb, and Edward Green are some of the highest level shoemaking brands, for hardcore enthusiasts only. Beautiful, to be sure, but oh so expensive.

The maintenance part of my stitched footwear is really quite minimal. The time and effort put into shopping for new shoes every few months is probably greater than my maintenance "routine" (for lack of a better word.)

You don't really need to waterproof high quality leather shoes. They can handle being wet. Those cheap shoes we all buy? They fall apart when wet.

Do you have a style that you like to wear now? Maybe we can help you locate something similar.