I am starting to think that maybe the low-level clothes that give menace should go on the list. Anyone else agree?

I still can't figure out if this list should be more for the high or low level players.

Don't buy an Extraordinary Hat, because the item currently has no uses, and all its functions are covered by other items which are either cheaper, or have actual uses.

• +8 Watchful can be found for only 20 echoes more on the Semiotic Monocle (trivial if you can afford to the initial 330 echoes already), which is incredibly valuable at Christmas-time for increasing Taste of Lacre.
• -1 Shadowy can be gotten from the Exceptional Hat, which is a third of the price and has several in-game uses.
• +2 Dangerous can be acquired from the Pirate Hat, which is very cheap, and useful long-term for increasing your Suspicion, either at Hallowmas, or to stay in prison for reasons such as finding the Repentant Forger as an Acquaintance. If you play Fate stories, you can also get the Blemmigan Hat for +2 Dangerous.

[This section optional.] You might consider buying the Extraordinary Hat if:

• Suspicion is a serious problem for you, and
• You don't have the Fate-locked Blemmigan Hat, and
  
• You really want +2 Dangerous in the Hat slot.

Can I recommend that you aim the list at lower levels? Let's say, pre-POSI as an obvious marker. I appreciate the thought - and some of the frustration behind it - as someone who, ahem, bought those boots

But a lot of the uses here are either 1) decreasing stats for higher players for skill profession or 2) decreasing limits to draw cards you've grown out of, which requires you to know what those cards are 3) unlocks for areas outside of the main four parts of the board or 4) are useful at particular times of year. And that's not information newer players need as much as when to save your money and wait a day to buy better gear (and don't worry about going barefooted for an hour!). Perhaps 5) costs less than 30 echoes or some amount would be helpful.

For example, a Rat of Glory should absolutely be used for the Scuttering Squad if your pre POSI. It's a great deal - and then you can avoid any less than 5+ companion (except for that one stat it doesn't cover). But on this forum, lots and lots of people used it for the Enigmas - and I wonder if anyone saw that and tried on their almost impossible chance to do it since it was the popular advice.

• The Reprehensible Lizard and Sulky Bat (0.40 echoes) from Nassos Zoologicals. Others in this thread have covered why already (their pet cards are very, very good, even in the late game).
• The 0.50 echo outfits from Gottery the Outfitter (choose from one of two options for each stat boost except the Glad Rags)
• The Emergency Blunderbuss from Carrow's Steel (0.50 echoes) -- unless you're already going to jail enough to get the Prison Shiv (free)
• The Araby Fighting-Weasel (3.20 echoes), also from Nassos Zoologicals.
• The cheap Mittens and Gloves from Dark & Savage (3.20 echoes)
• The Scarlet Stockings from Mercury (4 echoes)
• The three menace-granting hats from Maywell's Hattery (4 echoes and 6 echoes)

• The Tasselled Walking-Stick can be changed into a very valuable Bejewelled Cane later, if you can scrounge up the glim and jewels. (At +2 Persuasive, it's otherwise the same as the free Warm Amber -- see below -- so feel free to put it off.)
  

• There's no point getting something that's more expensive for the same benefit as a cheaper item that has negatives, and fits in the same slot (clothing, weapon, shoes, etc). You can just change your clothes when a challenge comes up that requires them -- and owning items with negatives may help you later in the game.
• For example, the Stained Red Velvet Gown (Persuasive +2, 12.80 echoes) is a bit of a waste of money when you can get the Bundle of Glad Rags (Persuasive +2, Shadowy & Dangerous -1, 0.50 echoes) for drastically cheaper.
• That is, unless you have a special use for that item (in this example, you can sell the Gown for a tidy profit in Wolfstack Docks later in the game, if you hang out there and draw the Ragman's Barge card).
  

• The Prison Shiv, +1 Shadowy, +1 Dangerous. Acquired by going to prison again. (Going to jail is dangerous: it ups your criminal record! If you go early-game, then it's recommended to use the Pirate Hat to keep your Suspicion permanently up long enough to both meet the Repentant Forger, and to get the Prison Shiv if you want it. And then don't go back!)
• Bundle of Fourth City Rags, Watchful +2. Acquired very cheaply from a card, will give you a ton of Nightmares (but only once). This can replace the 0.50 Watchful items from Gottery's.
• Advancing far enough in the Making Your Name storylines will give you a free +4 weapon for the appropriate stat (one for all four stats, if you play all four Making Your Name storylines enough). This is more mid-game, but some people like to power through content!
  
• Playing "The Protégé of a Mysterious Benefactor" story will grant you a single +2 item of some sort, extremely early on.
• (If you care, the "best" option for the Benefactor is the shoes, which give Watchful +2; there's only one other item in the game that gives you Watchful shoes, only available at Christmas. However, all the options are good because they give you card-based unlimited second chances in one stat for the entire life of your character.)
• Meeting some Rubbery Men at the Carnival, then accepting a gift on their card, will give you Warm Amber, a +2 Persuasive weapon.
• Playing through the card-based Affluent Photographer storyline will give you clothing with +3 Shadowy, +1 Dangerous, and +1 Dreaded. (The Dreaded is important for later.)
• If you hang out in Ladybones Road, Spite, and/or Veilgarden early in the game, you have a small chance of drawing a Rare card that will give you a neat companion (a pet). Ladybones has an adorable weasel, Veilgarden has an adorable dog, and Spite has a weirdly adorable musical instrument. You can only acquire one. Keep in mind the musical instrument is less useful in the early game stat-wise, but it's the most unique! Even though the cards that give you these are Rare, they're (much) easier to get early in the game, because of how the card deck works (early in the game = less cards overall = Rare cards come up more).
  

• The Valentine's Day celebration, the Feast of the Exceptional Rose, offers a truly staggering array of companions if you participate enough in the festivities. Many are remarkably good stat-wise. All of them are very cool.
• The Fruits of the Zee Festival in August gives a larger number of remarkably good weapons if you do enough finishing.

• Chatting up the Loquacious Vicar in Ladybones Road and spending a whole lot of Fate will grant you one or two super-powerful Devil companions (Watchful +8/+9 & Shadowy +6)
• The Blemmigan storyline can give you a pretty great hat (Watchful +5, Dangerous +2)
• Soul Trade will give you a Shadowy +2 weapon
• Long-Lost Daughter can give you a Shadowy +5, Persuasive +2 companion (who is very powerful for high-level characters too, due to a high-level card)
  
• If it's Christmas, paying a small amount of Fate to help the Duchess gives a super-powerful Dangerous weapon (+12)
  

• Any 28.80 echo hat, weapon, pair of gloves, or shoes, is probably a good deal, especially if it's +5 instead of +4. Several of them are the best of their kind in the game. An exception: the Tasselled Sword-Cane (only a +2 boost in two stats, cheaper to just get two separate +2 weapons).
• As for 28.80 Companions (Redemptions), the Devious Henchman is a good deal, the Grubby Urchin is a bad deal. As for outfits, the Morning Suit and Formidable Gown are not great at this game stage, since you can get the Academic Gown.
• The Irresistible Drum (51.50 echoes) from Carrow's Steel is the best non-Profession Persuasive weapon, and cheap for that. (Conversely, don't get the Amber-Topped Walking-Stick, the second walking stick to be a terrible deal.)
• Every POSI character is going to want the Pair of Lenguals (Dark & Savage), the Pair of Kingscale Boots (Mercury), and one of the 400 echo hats (Maywell's Hattery) as soon as feasible, for Notability purposes -- they give +1 Bizarre or Dreaded. They're also very powerful. (For the hat, the Persuasive hats are recommended -- the Watchful ones overlap the Semiotic Monocle, which people participating in Christmas shenanigans will want, but the Persuasive hats are the only way to get Persuasive +10 as a hat.)
• Price tag starts mattering less for maximizing stats with gear. For example, the Pair of Masterwork Dancing Slippers and the Ratskin Suit may seem overpriced, but are the maximum possible in their slots. (On the other hand, the Insatiable Gloves are under-priced while also being max Watchful for gloves. Also, the most expensive items are not necessarily the best items for their stats.)

• If your stats are above 70, now's the time to get a profession, and its associated item.
• The Academic Gown is Watchful +5, and gives you +1 BDR (in the form of Respectable) if you don't have it yet in clothing. Get to the University via Making Your Name: Watchful to get this.
• There's no need to shell out for a Bizarre/Dreaded/Respectable main article of clothing, weapon, or companion -- you can get free items in these slots at this stage in the game. (Affluent Photographer quest or Academic Gown for clothing, Bejewelled Cane, Consonant Violin, Dilmun Club Badge for weapon, Connected Pets & more for companion.)

Am I the only person who wants to have at least one of everything, just because you can?

All the things should be bought (it's not like you have to wear 'em) once you have goats & spare cash. And scrolling through 2 yards of inventory to get to the booze is fun!

Am I the only person who wants to have at least one of everything, just because you can?

All the things should be bought (it's not like you have to wear 'em) once you have goats & spare cash. And scrolling through 2 yards of inventory to get to the booze is fun!