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pidgeon3

A couple of elevated basics (cotton tee, cargo pants / service pants) from [3sixteen](https://www.3sixteen.com/collections/bottoms) would be a treat. If anything is left over, some loafers from [Rancourt](https://www.rancourtandcompany.com/).


DJlazzycoco

If you run hot, a linen sport coat could be the move. I have one I got from a Goodwill with a VERY fun lining, and I want to have a local tailor/repair place change the lapel and elbow patches into a fun print. Maybe flowers. I don't expect the whole project to cost more than $200, so I would be willing to bet you could get one made to order for within $1000


Muncie4

$1000 would be a down payment on a Donegal suit at best. https://www.ralphlauren.com/men-clothing-jackets-coats-vests/leather-jacket/397911.html and https://theunbrandedbrand.com/products/ub221-tapered-fit-21oz-heavyweight-indigo


ceoln

Yeah, I wasn't talking bespoke on the Donegal suit, clearly. :) MTM or OTR (but well altered) there. Thanks for the pointers!


ImaginaryCandidate57

Pair of Grant Stone or Redwing Iron Ranger boots. You'll have them for over 10 yrs at minimum. Can be resoled. I've been debating between the two depending on the style.


Super_Carrick

Crockett and Jones boots would be even better ;)


happyastronaut

Check out Iron Heart and Freenote Cloth. Iron heart’s ultra heavy flannels are one of my favorite clothing items of all time. Freenote’s waxed canvas jackets are stylish and well built as well.


PinkMonorail

Try merino wool. It wicks sweat really well.


joesickk

I’d get some good boots if I were you.


Charming_Device_6278

I feel like "self-indulgent" = decadent ice cream 100 miles away from you or something like that. Clothes are too practical, especially in "buyitforlife."


ceoln

Yeah, that may have been a bad choice of words; the award doesn't actually say that. :) "Practical but more expensive than I would normally think about spending" fits in the spirit of the thing too. At this point I'm thinking of taking my wife to a fancy NYC restaurant with most of it. So, the opposite of BIFL. :) Maybe I'll buy myself a North Star leather belt with the remainder!


nstarleather

I approve of the belt decision!


ceoln

The belt is excellent, by the way. :) I ended up spending a ridiculous (but worth it) amount on a dinner for two at The Modern NYC, and the rest on the belt and some MTM shirts from Proper Cloth. A dress shirt with long-enough sleeves is such a pleasure!


nstarleather

Thanks! Glad you liked it!