This is arguably the most important tip: too small and they won’t fit, too big and you’re in serious trouble. A common problem is over- or underestimating the top and bottom. Luckily, there’s an easy fix you might not have thought of. Take a look in her underwear drawer when she’s out and she can’t catch you at it. Check her knicker size, and the chest and cup size of her bras. Just don’t get caught trying them on – it’s probably a tricky one to explain away.


It’s time for another sojourn to the underwear drawer – this time for what styles, looks and colours she prefers. While buying men’s underwear is pretty easy, women’s underwear has to match different outfits and create different effects. Pretty, feminine styles tend to be a favourite – think beautiful lace, soft satin, rich colours and intricate detailing. It helps if it’s got a high-quality, expensive look. And if you suffer a crisis of confidence at the counter, just ask for a gift receipt when you buy and she can exchange it if needs be.


We’ve tried to simplify the process, but there’s no question that buying lingerie can still throw up unexpected problems. If you want to account for everything, pick her up a gift voucher. Some people might think of this option as something to fall back if you’re out of gift ideas at Christmas, but it’s actually very worthwhile. Think about it: you either get an exciting surprise in the following days, or you can partake in one of the more engaging shopping trips you’ll accompany her on. Our good friends at Rigby & Peller offer vouchers along with a 45-minute fitting from a qualified lingerie stylists to ensure a perfect fit. We wonder if they’re hiring…

Square Mile readers get a 25% discount of the tickets with Code SQFOHG. Full details are available on the Perfect Gentleman.