Ask Jeanne

THE KIT Handbag dilemma

Dear Jeanne,

I work in banking but can’t be bothered to change my handbag to go with my outfit. If I buy one handbag, what should it be?



Dear Christine—

As much as I’d love to make your life—and your accessory options—easy for you, I simply can’t advocate buying one bag and one bag only to go with every office look and every business outing. It’s also kind of ironic that you work in banking, which is essentially focused on the business of where to put your money. Since purses are largely about that function too… well… I would think you’d really want to celebrate that particular accessory! That being said, there’s no way you should feel compelled to have a huge number of different bags to go with different outfits. But a healthy handful, say 4 or 5, in a variety of sizes, styles, and neutral colours (perhaps one that really pops), would be a good wardrobe investment.


Of course, we working women tend to haul our lives around in our handbags. And, unless they’re generous-sized totes, these bags can look pretty stuffed and rather déclassé very quickly. On those days when you must haul around a ton of stuff, a simple, chic tote, perhaps in leather or even faux leather, is a good investment. I have a sensational, very lightweight Tiffany’s tote bag that’s actually reversible: suede on one side, metallic leather on the other. It’s almost like having two bags. (Jennifer Anniston has often been seen sporting this Tiffany’s tote.) But this classic, hot bag is rather pricey. Still there are countless, very affordable stylish totes on the market and every workingwoman should have one, whether she carries it as her primary bag, or a secondary bag for schlepping stuff around in. Michael Kors makes great totes that are much more accessible, as does the great Canadian label Roots. I often pop a small evening bag or clutch into my big tote, when I’m going out directly after work. My favourite shape of bag for everyday “work” wear is a zippered satchel. The simple one from Azzedine Alaia, called a “trapeze bag” is a personal favourite, although rather expensive. But there are many styles of this nature readily available though at much more affordable prices. If your handbag stash is going to be a limited one, I urge you to consider well-designed bags that don’t have a lot of hardware on them (like buckles, studs, grommets, etc.), and that don’t look overly trendy. You’ll never tire of classic, simple, elegant lines, and since you’re not keen on changing up your bags too often, you might not want them to be that “memorable” to others.


Part of your problem in not wanting to keep changing your bag is that it truly is a hassle to keep moving our essentials from one bag to another. You might want to try a ‘purse organizer’. These clever items, made by a variety of different companies, come in various sizes and simply fit into your bag, acting as a liner, complete with pockets and compartments. That way, instead of dumping out your entire bag each time you change it, you simply lift out the purse organizer and drop it into the new bag you want to use, with all your essentials intact. ( is one site offering these organizers).


While I’m not advocating a whole slew of bags in umpteen different colours and styles to go with all your outfits, you really should have a bit of a handbag collection to see you through—especially when it comes to the different seasons. The bulky black bag that seemed so right and solid in the winter could look quite clunky in the summer, when you might want to go with something a little lighter and more streamlined. Just as you’d never consider only wearing one particular pair of shoes to work everyday (unless of course they’re part of your uniform), so you should try to mix up your bags just a bit. Accessories are such a great form of personal expression— kind of a punctuation mark to our outfits, really— and the fact that they’re so functional is really a great bonus. Just find the sizes and shapes that work best for you, or invest in one great classic tote that becomes a kind of carryall, and carry smaller bags with you for outside business meetings or after-work activities.