There are many schools of thought for equipping a PC. The quick summary of those I've encountered are:
1) Spend all your gold on a wide and varied selection of things eventually you will find a use for that stuff.
2) Buy only those items you know you will need. Gold can be spent on items as you know you need them.
3) Buy a standard set of equipment the same list of items every time for every character.
I must admit I usually option for something between options 1 and 3. This time, however, given that the campaign will be city based and Tillam is a moderately well to do businessman I've decided to go with a foppish style of equipment mostly clothing and changes of it along with a few pieces any good thief would need.
Very little of my equipment needs explanation it is all the basic stuff from the PhB but here I present his equipment. All the while trying to stay acutely aware of my carrying capacty of 35 lbs. I also do try to keep track of what is on Tillam's person and where in the event a pickpocket attempt happens.
Item  |    Notes  |    Weight  |    Local.  |   
Belt  |    -  |    Worn  |   |
Cloak  |    Cloth  |    -  |    Worn  |   
Leather Armor  |    AC 8  |    15  |    Worn  |   
Dagger  |    2 on belt 2 in boots 1 on   chest  |    5  |    Worn  |   
Thieves Tools  |    Special Set  |    1  |    Belt  |   
Boots  |    Soft  |    0  |    Worn  |   
Surcoat  |    0  |    Worn  |   |
Tunic  |    0  |    Worn  |   |
Breeches  |    0  |    Worn  |   |
Hose  |    0  |    Worn  |   |
Gloves  |    0  |    Worn  |   |
Sack Large  |    .5  |    Pack  |   |
Sack Small  |    x2   |    .2  |    Pack  |   
Backpack  |    2  |    Worn  |   |
Pouch Small  |    x2  |    1  |    Belt  |   
Pouch Large  |    1  |    Belt  |   |
Flint & Steel  |    in S. Pouch 1  |    0  |    Worn  |   
Chalk  |    in S. Pouch 1  |    0  |    Worn  |   
Hooded Lantern  |    Backpack  |    2  |    Worn  |   
Lamp Oil  |    x2 in L Pouch   |    2  |    Worn  |   
Lamp Oil  |    2  |    Stored  |   |
Torch  |    Stored  |   ||
Sealing Wax  |    Stored  |   ||
Gloves  |    Stored  |   ||
Hose  |    3  |    Stored  |   |
Breeches  |    2  |    Stored  |   |
Tunic  |    2  |    Stored  |   |
Boots  |    Soft  |    Stored  |   |
Belt  |    Stored  |   ||
Total Weight  |    31.9  |    
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