Suppose I better chip in as I've been mentioned by name!
Hi GadgetGran!!!
I do/did have made-to-measure leathers, I am a VERY odd shape, hourglass really doesn't quite cut it! I am a size 22-24 with a 36K chest (yes, that was a K and not a typo!) and my waist is quite a it smaller than my hips, most jeans have about 4 inches to spare at the waist when I get them to fit the hips so getting off the peg stuff that fits/matches/has the arms in the right place etc was always a challenge!
Leathers were made to measure by a chap in Nottingham, I love the jacket, it is such a novelty to have a jacket which fits, has all the limbs in the right places and less back than boob but the trews he did were terrible! Too wide at the ankle to wear inside boots, no elastic panels, heavy hard leather - they fit but a bit too perfectly to be moving around on a bike.
All resolved now though by getting leather trousers that were too big from JTS (as previously mentioned - and they are definitely worth the trip, I think for me the round trip is more than 200 miles as I'm in York) and then having them altered by a local leather alteration lady. The leather is incredibly soft and comfortable, fits perfectly and has been shortened to exactly the right length to go inside my boots and not sit awkwardly on the ankle.
If you are planning on riding all year round then at least consider textiles too and especially if you think you will tour on your bike. If you have just leathers then you will need to pretty much always carry waterproofs with you too and these are bulky and take up space, they also make moving around on the bike a little more cumbersome but a decent fitting set of textiles has waterproofing set in and are warmer than leathers.
What to wear underneath? With leathers I always wear thermal leggings and a thermal long sleeve top - even on the hottest days. This means when you sweat, and you will sweat... lots, the leather won't stick to your skin and will generally be more comfortable but they also keep you warmer on cooler days. I've also just bought a HUGE hoodie that will fit over my jacket for those days when you've been out for ages and are coming home as it starts to cool down. Under textiles I usually wear the same sort of thing but have space for an extra layer and there is room to put a work suit on underneath if the bike is coming to work too. (Dim and distant past now
)
Boots wise - have a look at Sidi Vertigo (Ladies style are called Lei) boots, the sports boots have a fully adjustable calf and the black rain calves are actually a reasonable size, I can get them both on no problem and I struggle with normal wellies for example. Sidi Vertigos are NOT waterproof but this can work in your favour, if you soak them completely, warm water in the bath for example then wander round in them then they bed to exactly the right shape. The other thing to consider with boots is whether it is your calf that is the issue or the ankle itself? I have a friend who I ride with who is quite a bit smaller than me and she struggles with boots because her ankle is a bit thicker than mine whereas her calf is about the same size so it is getting the zip over the ankle that causes her problems - incidentally she uses Sidi Black Rains and finds these fine. If it is your ankle, and unlike madam you have a size 6ish foot or above then consider mens boots as they seem to be a little wider in the ankle than the ladies ones.
Enjoy riding, hope the lessons are going well for you and if you come south in to Yorkshire then let me know and I'm sure we can arrange to meet in Whitby or something?