I've modified/honed my list a bit to more specific purchases, now that F/W stuff is starting to pop up in shops.
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A substantial winter coat: I'm hopeful for what Mauro has in store with the pea coat.
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Epaulet Flannel: Purple all the way, baby.
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Apolis Thomson Jacket: This caught my eye because of its resemblance to the Context collab from last fall. I'd still prefer the collab to this because of its versatility, but beggars and choosers and all that.
I've realized buttondowns are generally the most flattering sort of shirt I can wear, so I'm ready to dedicate some funds to better quality BD's...
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MJK Houndstooth: Never owned a houndstooth, but the recently posted MJK version is sharp.
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Dunderdon Shirt (on the right): Like the brand's cuts and at the price, I want to give them a shot.
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Uniqlo OCBD: I'm starting to experiment a bit with a different look for myself to break the monotony of previous F/W. This means mixing in some neckties and pocket squares. Uniqlo seems to have some of the more reasonably priced OCBD for the cut. I know the brand gets some heat on here for not being that slimming, but their shirts have worked out great for my dimensions.
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Black/Grey Chambray: Still searching, but leaning toward Epaulet's grey chambray, though the absence of a pocket is a bit of a hang-up.
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J. Crew Poplin Utility Shirt: On the fence about this one. I'm sure there are comparable shirts out there with better quality and similar price tags.
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Gap Thermals/Sweaters: The two thermals I have are great, so no desire to break the bank on ones from higher end brands. I don't wear sweaters that often, so I'm not going all out for those, either.
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Boots: Still looking for that right black boot. Brown, too. The Dayton Service boots are great, but completely out of my price range unless a rich relative buys the proverbial farm. I'd love to get a black boot with contrast sole, but haven't seen many options.