In early modern England, the worker in the city represented the middle and lower class of the city. These tradesmen were of professions to the left (and many, many more) and most belonged to guilds for their specific trades. Like Simon Eyre and Mr. Yellowhammer, tradesmen in the city had their shops in their homes. The wives of the tradesmen were not as integrally involved in the physical labor of the trade as were the women in the countryside.As Madgy, Simon Eyre's wife, the wives of tradesmen were responsible for keeping the home in order and feeding the workers in the shop. The wealthiest of the tradesmen owned their own shops in their homes, hired other men of their craft and taught apprentices. To enter a trade in the city an apprenticeship was required. The Statue of Artificers of 1563, made it illegal to practice any craft without having served an apprenticeship of seven years 25. An apprentice was bound by personal and legal document to his master, usually with a premium being paid to the master by the child's parents. There was normally no official cash remuneration for the apprentice- bed and board were all that could be hoped for- while the master enjoyed near parental rights over the apprentice 28. In addition to apprentices, tradesmen with large shops, such as Simon Eyre, may chose to employ more workers already out of the apprenticeship, such as Firk and Hodge in Simon Eyre's shoe shop.

Like the county, the tradesmen of the city that worked for a tradesmaster may receive food and drink to augment their money wages. Also, the city workers could have had perquisites as well. For example workers in the city dockyards might keep the was pieces of wood with which they worked 28.

After establishment as a successful tradesmen, some laborers who acquired enough wealth were able to ascend to "Lord Mayor of London". Just like Simon Eyre, as Lord Mayor, a guildsman was responsible for entertaining gentry, aristocracy, and other guildsmen. It was not common for those tradesmen lower on the trade ladder (shoemakers, masons for example) to rise to a position such as this. Yet many of the tradesmen did gain titles that provided them increased representation in England since tradesmen were not same privileged class as land owners and the gentry. These laborers, along with the laborers of the countryside, "had neither voice nor authority in the commonwealth, but are to be ruled and not to rule other; yet they are not altogether neglected, for in cities and corporate towns, for default of yeoman, they are fain to make up their inquests of such manner of people. And in villages are commonly made churchwardens, sidemen, aleconners, now and then constables, and many times enjoy the name of headboroughs" 13. Thus the laboring people throughout England, while comprising the most populated class had the least amount of representation in the commonwealth, and yet were not completely neglected.

• Tailor- maker of the outer garments of men, also sometimes those of women
• Shoemaker- One whose trade it is to make shoes
• Carpenter- one who does the heavier and stronger work in wood, as the framework of houses, ships
• Brickmaker- One who makes bricks as his trade
• Mason- builder and worker in stone; a person skilled in dressing and laying stone in buildings
• Goldsmith- A worker in gold; one who fashions gold into jewels, ornaments, articles of plate
• Clothier- A maker of woollen cloth; One who performs the operations subsequent to the weaving
• Grocer-One who buys and sells in the gross, i.e. in large quantities, a wholesale dealer or merchant

• Churchwarden-A lay honorary officer of a parish or district church, elected to assist the incumbent in the discharge of his administrative duties
• Sideman-One of the persons elected as assistants to the churchwardens or municipal or civil officer
• Aleconner-An examiner or inspector of ale
• Constable-The chief officer of the household, court, administration, or military forces of a ruler
• Headborough- parish officer identical in functions with the petty constable

As witnessed in Simon Eyre's treatment of his employees, not all tradesmasters were considerate all the time. The interactions between Simon Eyre and Firk demonstrate the subordination tradesmen may feel when not owning their own shop.

Not all was grim in the relationships between employer and employee. For example, Simon Eyre and Jack of Newbury provide their employees with a celebration. Simon Eyre holds true to his promise of providing his guildsmen with a celebration if he attend Lord Mayor. The conclusion of The Shoemaker's Holiday illustrates a festivity which all of Eyre trade are to enjoy. Simon Eyre's final lines, "Yet add more honour to the Gentle Trade:/ Taste of Eyre's banquet, Simon's happy made" (Scene 21, ll. 186-187) showcase the party which he has thrown. While these parties and songs that are present in The Shoemaker's Holiday and Jack of Newbury do not erase the hardships the workers suffer, they do support that not all times in the life of a worker in the city were consumed with physical activity and unhappy relationships with their trademasters.

The industrial revolution would forever change England in the coming century and in the Renaissance in towns and cities, as in Jack of Newbury, small factories were creating the sense that a change in the city was lurking. Just as the countryside was being revamped by the enclosures and thus agricultural production was increased. In the Renaissance there were subtle signs of the major change in production within the city that were destined to increase production in the city too.