How tight should boots fit at first? It should not pinch across the ball of the foot or the toes, but should be comfortably snug in the instep area of your foot. Just like a good handshake. A new boot may slip some when new, but if it is snug in the instep, that slip will come out, after it is flexed from wearing.
Do boots feel tight at first? Your boots should not feel tight. They should feel snug on the forefoot, they should have plenty of room in the toe box, and the heel should not slip more than a quarter of an inch.
Will tight boots stretch? Leather boots are essential for colder weather months, but sometimes that snug fit is a bit too tight. Is it possible to stretch leather boots to make the fit more comfortable? Actually, yes.
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Do boots get looser? When wearing socks, boots should feel snug but never tight. However, new boots will need to be broken in, especially if they’re made of real leather. You can expect them to be a little extra snug at first and relax after several wears.