A handbag is not a separate item - that's the first lesson. You need to choose a bag with as much consideration as the rest of your clothes. So that takes us back to your body shape. Try shopping for bags that are the opposite shape to your body, and are in proportion to your size. If you are tall and thin, you will look silly with a tiny messenger bag. Likewise if you are short and petite, you will look odd with a big satchel.
Here are some ideas on the type of bag you might choose to suit your body shape.
If you watch a woman buying a handbag, you'll see that she always tries it on - she'll put it over her shoulder, over her arm, hold it down at arm's length. A bag should 'fit' just like a dress.
It also needs to be practical as well as pretty. Save the clutch bag for the evening out. Think about how much you need to carry. You should opt for a bag that comfortably holds what you need. If you like a big bag for effect, make sure it's not uncomfortably heavy, and beware of filling it up just because you can. Empty your bag out regularly and don't keep items in there that you do not need. You won't walk well with one shoulder weighted down.
By the way, rucksacks are for walking in the countryside or for school books - leave them for that.
Types of bag
Terminology can trip up the best of us, so here's a useful glossary of handbag styles.
Baguette: Long, slender and rounded shoulder bag that looks a bit like a baguette.
Cigar box: Small, hard box-shaped bag.
Clutch: A bag with no handle, usually fairly flat, that is held in the hand if it's small, or tucked under the arm if it is larger.
Duffle: Tall shoulder bag, usually with a wider opening at the top.
Field bag: A flap-top shoulder bag with a buckle or Velcro closure.
Hobo bag: Crescent-shaped shoulder bag.
Kelly bag: Classic large, Hermès-style structured bag with distinctive closures named after the film star, Grace Kelly.
Messenger bag: Large, soft shoulder bag with long straps that can be worn across the body.
Pouch: A small, soft bag.
Satchel: A large bag with a fold-over top like an old-fashioned school bag.
Tote: Open bag with short handles, like a shopping bag.
Walking with a handbag
While you are out women-watching, pay attention to how women behave with their handbags. Some like the freedom of a messenger bag so that their hands are free to touch things and express themselves when communicating. Others like a traditional shoulder bag with one hand resting lightly on the top. Long-handled handbags can be carried or hooked over the shoulder.
Practise with your handbag until you look comfortable and at ease. Don't grasp it too tightly as though for moral support! Wearing your training skirt, practise walking with different types of bag, including a messenger bag to see how you feel without the comfort of holding on to something. This will be a great test of your confidence when dressed as a woman.