Tucking in your shirt is both practical and sociable. Practical in that your shirt will not billow around your torso when horse riding, and sociable in that it signals commitment to excellence.
Personally I’m in the untucked camp for two reasons. First because I’m a rebel and any rule (particularly one from school) is not going to apply to me. The second reason relates to functionality, as keeping shirts tucked in throughout the day is practically impossible for me, and I don’t have time to re-do a job ten times every day. The mushroom effect is also not a look many guys love, and so for practical reasons many gents wear their shirts untucked.
Although an untucked shirt is not necessarily a sin, it’s definitely a less formal look. Longer shirts that fit around the seat comfortably are definitely helpful as they wont billow as easily, and for the really committed gent here are two shirt stay options
These Y-Shaped Stays that attach to your socks are definitely the easiest to use, and I feel very confident in this type of clasp. Although they do damage your shirt a bit, any clasp will do that, and it’s a part of the shirt not generally visible.
You can get them off Amazon here
My main concern with this type of stay is that they’re sometimes visible, and although no-one would notice unless specifically looking for it, my own awareness of it is enough to drive me insane.
I did find this pair a bit short also, though I’m freakishly tall so…
Stays that connect with your thigh or calf are another option which are definitely less visible. Having more points of contact with the shirt also keeps the tuck neater, and is less damaging to the fabric.
These are less comfortable to wear, though you get used to them after a while. But visiting the throne in not the least stressful experience.
You can get them off Amazon here
Depending on your job type it’s worth the extra snaz that a tight tuck brings, or just for certain occasions depending on how dedicated you are to the look.
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The Green Tailor 