Ask the expert: Is it a fashion no-no to buy multiples of the same item?

Q: What is your opinion on the purchasing of more than one of the same item? I've always heard this was a big fashion no-no. However, as a very busy woman who doesn't have much time to shop, when I find something that works, I tend to grab two, sometimes three, of the same exact item.

A: Ahh, buying multiples. A shopping practice beloved by many, but also one with hidden pitfalls.

If you've worn something into the ground, buying multiples of its replacement makes sense. You know from experience that this item works for you and gets worn regularly. And since the first version got worn hard and long, replacing it with multiples will allow you to spread the wear and tear over several garments.

If you find a particular garment painfully hard to fit and stumble across a version that looks smashing on you, buying multiples makes sense. The obvious example here is jeans; we all love them, but finding the perfect pair can feel impossible. So when you do find that pair, go ahead and buy a few so you'll have ready reserves when the first pair bites the dust.

In almost all other cases? Buying multiples is a risky practice. Most people know what they like, but few can accurately predict which items will become wardrobe staples. Just because that top looks amazing on you doesn't mean you'll wear it every week and therefore need several versions in rotation.

Most multiples end up unworn, taking up valuable closet space. So unless you are certain that this brand new, untested item will become a pillar of your personal style, take one home and leave the rest.

Q: Can you recommend some fashionable yet practical commuter footwear?

If your work outfit is skirt- or dress-based, you've got several options. Quality ballet flats with support are a great choice for women of all ages, and look lovely with most skirts.

Don't cheap out and pick up a fast fashion pair; they'll tear up your feet and fall apart in a matter of weeks. Instead invest in Clarks, Børn, or another comfort brand. Flat Mary Janes will cut off the leg line a bit higher, but are a comfortable, walkable option for women who prefer the secure fit of a strappy shoe. And as the weather cools off, consider tall flat boots that hit an inch or two below your kneecap. I'm a big fan of cognac brown, which looks rich and expensive with everything from neutrals to jewel tones.

With pants, things get trickier. If your slacks are hemmed for heels, walking 10 blocks every day in ballet flats will gradually destroy them. You need a sturdy, comfortable shoe in a height that prevents your hem from sweeping the ground. A chunky heel or small wedge will offer more comfort and stability than a stiletto or platform. Chunky heeled Mary Janes from companies like Miz Mooz, Sofft, and Cobb Hill (a sister brand to New Balance) should work beautifully.

And in the snow? All bets are off. Invest in a good pair of waterproof boots and carry your office shoes in a separate bag. Anyone who looks askance at a woman with her suit pants tucked into her Sorels has never lived through a Minnesota winter.

Q: How do I deal with questions like: Why do you always wear black? People ask me that constantly.

Questions like this generally have more to do with the questioner than the questionee. The fact that you wear black all the time interests or annoys or confuses this person, so I'd start with, "Why do you ask?" This is a fabulous way to respond any time someone questions your dressing choices because it forces them to articulate their motivations. A less defensive version of "What's it to ya?"

The answer may help direct further conversation, but also consider creating a succinct response phrase. Something like, "I feel chic and elegant in black, and all of my clothing goes together," or "I find black to be flattering and versatile, and it makes me feel powerful to wear it head-to-toe." In most cases, this will do the trick and you can move on to other topics.

If your questioner insists on digging deeper, try to avoid losing your cool. Questions like this are frequently in the teasing/goat-getting realm, so don't take the bait or get defensive.