How to make the ripped and holey trend seem natural instead of like a mistake

Q: How do I make the ripped up and holey trend look natural and not like a mistake? A dude was convinced my tee with a long tear down the front was an accident, but I totally bought it that way.

A: Accessorization and context will be key here. In order to make a distressed item look intentional, you need to surround it with other items that express extremes.

For instance, destroyed, hole-ridden boyfriend jeans look amazing with tailored blazers, blouses and heels. The juxtaposition makes it clear that the jeans are supposed to look that way and have been added for intentional contrast.

Not a fan of buttoned-up looks, or drawn to ripped clothes for their rock-star appeal? Make sure your entire outfit is edgy. Stick to a dark or neutral palette, add spiky or chunky jewelry, and opt for kickin' boots. In this visual context, a shredded sweater or distressed tee will make perfect sense.

Q: My hair is currently one length, mostly straight, and shoulder length. I'm 45, and it's been this way or longer for 26 years. I'm so tired of it, I've made an appointment to chop it off. My question is, do you have any advice for when I get up out of that salon chair and take my first few forays in the world with dramatically different hair? Any advice for walking into work that first day?

A: Since I chopped my shoulder-length curls into a pixie nearly four years ago, I have some experience in this department.

When someone makes drastic changes to her appearance, others become naturally curious. This means you will get questions and comments from your friends and co-workers, some of which may be less than diplomatic. I advise preparing confident, positive replies like, "Isn't it fun? I've been thinking of getting a pixie for ages and am delighted with how it turned out!" or "Getting a new hairstyle felt like the perfect way for me to mix things up."

Q: I work in a business-casual office and find myself needing to replace my wardrobe of trousers every year or so. And every year it is an ordeal. This past weekend I tried on 18 pairs of pants and left my final dressing room in tears. Do you have any tips on how to not end up emotionally hurt walking out of a dressing room?

A: First off, I'm so sorry to hear this! And I hope you know you're not alone. Most women find pants incredibly difficult to fit — myself included — because a ridiculously narrow range of trouser styles is offered for our wide variety of body shapes.

A few things that might help on future shopping excursions:

1. Do some research ahead of time. Before you hit the mall, poke around store websites and read customer reviews. Your fellow shoppers often are very detailed and offer input on rise, fit, quality and other factors that might help you eliminate some options and encourage you to investigate others.

2. Quit before it gets too bad. I know you need new trousers, but anyone who has tried on 18 of anything and left empty-handed will feel demoralized. I'd say limit yourself to five or six of a given item. If none work, leave the store or leave the mall altogether. Pants will still be available next week, when you can try again with fresh eyes and more energy.

4. Remember that clothes should fit you, you needn't fit them. There is nothing wrong with your body just because it won't fit perfectly into off-the-rack everything. It's not you, it's the clothes.