Anticipatae Quaestiones

Not yet Frequently Asked Questions :

Brief :

In the Middle Ages, some laymen would wear their Rosaries on their belts. On the one hand, this provided easy access for the sacramental, but on the other hand it showed devotion and reminded others of Mary our Mother. The Middle Ages were bad times. There were constant wars and battles between different countries and even noble families. There were heretics spreading their errors, and there was the ever-present Muslim threat to the East and South.

But our times are far worse! Relatively speaking, few Catholics even go to Mass and receive the Sacraments, and only a few of those strive and hope for Sanctity like our Lord commanded. Even many Bishops and Priests preach little about fundamental doctrines and lead their flocks tepidly. Many follow the spirit of the age, seeking feelings from God rather than a living, mortifying, and Sanctifying Union with Him in the bond of dark and obscure Faith, expectant Hope, and transformative Charity.

Anticipated Questions :

Why should I wear a Rosary?

Why not?
To please our Lord.
To make the One, Holy, Catholic, and Apostolic Church more visible in secular society, in a world built on the ashes (cf. Enlightenment) of the ashes (cf. Protestant Revolution) of Holy Christendom.
Because it’s cool.

I’m afraid I’ll look weird, boring, or overzealous.

Be not afraid.
People wear some pretty dumb stuff nowadays, and it’s passed by as normal. In my experience, very few people will bother you about it, probably because they are more concerned about how people are looking at them. There is nothing to worry about. Just gird your loins and act naturally.

I can see Religious wearing Rosaries, but seculars / lay people?

This is not the same thing as wearing a habit. Our Lady begs us to wear the Miraculous Medal on the outside and also the Brown Scapular, which is mystically a Carmelite habit. We are already supposed to look Catholic and, mystically speaking, dress as Carmelites (albeit not outwardly).
The Religious Habit, not the Belt Rosary, distinguishes Religious from seculars ; most Benedictines, for example, do not wear Rosaries, but they are no less Religious than a Dominican.

What am I getting involved with?

Don't worry.
There is only one requirement: dress and act modestly (generally past the knees and elbows; tight clothing does not count). If we would visibly be a picture frame for the Faith, we should present ourselves well and not be sloppy. Modesty is a part of the virtue of temperance and combats vanity and sloppiness, helping us to be free from the subtle attachment to our own taste and/or sloth instead of God’s Will. Dressing modestly with a cheerful heart is a basic courtesy and respect for God and our neighbor and even helps with battling insecurity and anxiety, if you pour yourself into it.

I feel like it’s a bit proud or ostentatious.

Don’t scrupe.
Plenty of people wear Catholic t-shirts to express their Faith and encourage it in others. We might call this "holy ostentation" as long as it is done reasonably. Now, the shirt has more surface area and tends to have explicitly Catholic or Christian messages, whereas even a large Belt Rosary is more subtle.
Wearing the Rosary can be an occasion of pride, if you allow it to affect you that way, just like any other good thing can be an occasion of pride, BUT, you would have to actively consent to that pride for it to be a sin. Wearing the Rosary, however, does not cause pride, nor is it in itself an act of pride or vainglory. Pride is in one’s disposition, and so, if wearing the Rosary is done or even just attempted in a spirit of Faith, Hope, and Charity, our Lord will be pleased. Meditating on these virtues is important for anyone and would be especially helpful for this devotion.