4 Challenges of Dressing a Teen – and What to Do


Parenting a teenager or tween is challenging enough. Trying to go shopping with one? You might as well buy stock in Clairol right now! It’s enough to turn you grey–or make you pull your hair out.


Today I’m outlining some of the biggest challenges I’ve faced both as a mom and as a stylist when it comes to finding the right clothes for these tough-to-shop-for ages, and letting you know what you can do to keep your sanity!


Awkward Body Composition

Teens and tweens are still growing and filling out their bodies, but in the process they may look a bit awkward and feel less than confident when shopping for styles that fit properly. Not only that, but many designers don’t take into account the fact that many teenagers fall between the children’s and adult’s sizes and style preferences–making it even more difficult to find the right fit and look.

What to do:

Stick to stores and labels that cater directly to the teen market. Places like American Eagle, Rue21, Hollister, Forever 21 and H&M are perfect for this age. And many of these stores are also in your budget, with clothes that won’t break the bank.


Unsure of Their Style

Kids are notorious for changing their minds quickly. It’s part of what makes teenagers so much fun to be around, right? (Or not!) Most teens and tweens look to the media to find their style, and change their preferences as quickly as the Kardashians change beaus.


What to do:

Give a little when it comes to shopping with your teen. Sure, you can’t afford to replace their wardrobe every time they want to try something new. But you can allow a few risks and experiments. Set a budget for really trendy pieces and encourage your teen to find pieces that fit within that budget. This is a great time to have them use some of their allowance as well.


Rough on Clothes

Tweens and young teens are particularly rough on clothes, as they outgrow the “play” stage and find themselves in more mature settings. With this being the case, you’re likely not ready to splurge on adult-priced clothing, even if your teen’s size dictates adult clothes. And don’t even get me started on the shoes. Prices seem to go up exponentially with every new pair.


What to do:

Many retailers, like Ross, TJ Maxx, Marshalls, Nordstrom Rack and boutique consignment shops, offer name-brand clothes for a fraction of the price you’ll find at larger department stores. Plus, there’s typically a much wider variety of styles at these types of stores. Until your tween or teen learns to really take care of their garments, save a little cash by shopping these stores.


Your Expectations

It’s common for parents to push their expectations on their children, especially when it comes to clothing. But there’s a difference between what Mom and Dad think their teen should be wearing and what he or she actually wants to (or will) wear. Have you noticed how much more stressful it is to shop with your teen than it was just a few years ago?

What to do:

It’s important to give your tween and teen some autonomy when it comes to clothes, with some guidelines. If there’s a certain style that you’re not okay with (low necklines, exposed shoulders or ripped pants, for example), talk about it before you go shopping. Then allow your teen to find styles she likes that stick to your moral compass.


Trying to dress your teen or tween can be a challenge, but you don’t need to throw in the towel. Invite her friends along and take them out to lunch as a little incentive. If that doesn’t work, bring along a close adult friend or hire a stylist (shameless plug for my profession!). Turn to online browsing or Pinterest to understand what your tween or teen wishes to adopt as her style.  

The point is, it doesn’t have to be stressful or cause a fight to shop with your teen if you approach the process with ideas in mind and help on your side. Find the right stores, invite the right “helpers” and you just may start to enjoy shopping with your teen!