Fiqh-us-Sunnah Volume 5, Hajj and ‘Umrah, Fiqh 5.065B.

One may enter Makkah without putting on a garb of ihram if one does not intend to make Hajj or ‘Umrah. One may be a frequent visitor to Makkah as a wood-cutter, a grass cutter, a water carrier, or a hunter, etc., or not a frequent visitor such as a merchant or a visitor. Regardless of whether one enters it in a state of security or fear, all such people may enter Makkah without ihram if they do not intend to perform Hajj or ‘Umrah. This is Ash-Shafi’i’s opinion which, of his two views, is the more accurate one, and is also supported by his companions.

Muslim reported that Allah’s Messenger (peace be upon him) entered Makkah wearing a black turban and without an ihram. It is said about Ibn ‘Umar that he returned after travelling part of the way and entered Makkah without ihram.

Both Ibn Shihab and Ibn Hazm hold entering Makkah without the ihram garb permissible. The Prophet (peace be upon him) set the markers (Mawaqit) around Makkah only for those who intended to perform Hajj or ‘Umrah.

Wearing ihram is not compulsory for those who pass these markers if they do not intend Hajj or ‘Umrah. Allah and His Prophet (peace be upon him) did not forbid entering Makkah without ihram. To insist on it is obligating people to which they are not obligated by Shari’ah.