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I wear leggings and a T-shirt most of the time, and use my Smart Carry even with these. I wear it on the right side at 3 o'clock. Sometimes I wear a cover shirt or vest, but if I am out doing yardwork I don't bother. I have started wearing an undershirt to protect against the velcro, but now that the weather is cooler, I even find that a plus.

I frequently wear my cell phone on a lanyard around my neck, under my T-shirt (to keep it from catching on things while working) It makes such a nice lump right in the middle that it really detracts from any other "lumps" I might have. Maybe not a fashion statement but it works for me.

SmartCarry under a dress or purse carry work for more formal wear.

So I guess my answer is yes, IWB!