I have a Coach coin purse I’ve used since 1990. It’s almost black from sitting in the bottom of my purses all that time. I also have a Kate Spade wallet I’ve carried 15+ years. Both sit in my King Ranch purse that I have been carrying 10+ years. I don’t like changing bags or wallets very often.

I recently bought a small purse at the suggestion of my doctor from my doctor from an independent maker and I am in love. The quality is amazing. If the maker knows his craft and knows how to translate that into good photographs, it’s absolute gold. I prefer to support small businesses, especially artists and makers. I think that’s really important in this economy.

I have a Tory Burch one that is zippered and excellent.

Look for all parts to be heavy high quality leather and hardware. Avoid any little plastic windows for ID.

Banana Republic stretch khakis. I still have a pair from years ago and theyre super comfy. I fluctuate in weight also whether eating too much pizza with my kid or riding bike and putting off.

Duluth’s firehouse pants hold up really well.

My fossil wallet is still going strong after several years of near daily use. I love it.

Would mention you check out Mascot workwear pants. There are a number of online retailers in the USA for this Dutch brand. I have used them for many years as daily wear work pants.

I've had my Fossil wallet for over three years now and it still looks new.

Which isn't really a long time, but it's apparently way better than Target.

I can confirm Coach wallets last, I have a friend who has one that's still going and I believe she's had it for around ten years. Of course, idk if newer Coach wallets are just as good.

I got an REI branded backpack decades ago. After about 15 years, it was starting to show some wear. I happened to have the receipt still, and I took it in and since they didn’t carry the same model anymore the just refunded the full purchase price.

Idk what a backpack by REI goes for these days, but that impressed the shit out of me. (Note: they would have had fewer options if I hadn’t kept my receipt.)

Otherwise, I picked this up about 4 years ago and it’s still in like new condition, and I use it daily. I love it for the amount of space, and the laptop pocket opens from the back of the bag without having to open the main compartments. (This also means I feel safe keeping snacks in my bag bc the laptop pocket is completely separate and never gets crumbs in it, even if something spills in my bag.)

Obligatory Technology Connections video.

Kate Spade New York. I bought one six years ago that’s still in perfect condition, the only reason I replaced it is because it’s hot pink and it’s too bright for me now. The one I bought was similar quality, and the prices in the outlets mean it’s very worth it

For loafers (admittedly on the higher end of your price range) is Grant Stone's traveler loafer. I love mine and they have great support.

If the budget is a little tighter, I'd probably go with something cheaper with more foam in it (like Cole Haan, maybe florshiem, something you might see at DSW or Nordstrom Rack).

Take $1900, go on a trip to Italy. Enjoy the food, stay in a nice place, and spend $50-$100 on a hand-crafted, unique briefcase. Get some gelato with the remaining money.

It looks like OP posted an AMP link. These should load faster, but AMP is controversial because of concerns over privacy and the Open Web.

Maybe check out the canonical page instead: https://sackclothandashes.com/products/camp-forest

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I bought a Kate spade passport wallet. Have had it since 2012 doesn’t be even have a scratch, loose thread or tear. They are the literal best.

If you don't mind the price you can commission a wallet over at r/leatherclassifieds

There's plenty of people selling their premade ones too

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Kipling!

Thomas Burberry (not standard Burberry). My wife’s is in tip top shape years in. I’m also partial to Montblanc. Solid craftsmanship!

Thirded! They come in great colors too. I've bought their Almost Perfect line a few times, and haven't noticed any issues or imperfections.

Try Sakroots

Some women put money between their boobs. Should last a lifetime

Definitely Hobo! Sometimes you can find on sale at a Nordstrom rack too (if you have one near you).

Thanks for the mention!

Cuyana

The classic zip-around is what you’ll most likely want out of their product line.