8 Rules for Shopping with Teenagers

teenager poses next to a statue of stacked macarons“Shopping was fun today, mom. Much better than times before.”

I could have done a jig when she said those words! Before was bad. Before had us both in tears. Before, angry words were spewed. Before, a hurt teenager and a rejected mama walked out of the store with empty hands and broken hearts. Before, her insecurities shadowed my insecurities, and my lack emptied her confidence.

I have made an effort to enjoy the teenage season. In fact, it may just be my favorite season of parenting. We celebrate them big. We tease each other and laugh a lot. And there is nothing better than getting to re-watch Gilmore Girls with my girls and experience the ups and downs of life in Stars Hollow.

But shopping. Shopping has been a tender spot in these growing up years. I always imagined how fun it would be to shop with my girls when they got older. To enjoy the hunt for the perfect outfit with the perfect shoes and the perfect jewelry. We were going to have a great time.

Oh reality, why are you so cruel to me? 

Something happens to girls around 13. It’s a myriad of hormones and attitude, extra feelings, extra curves, and ridiculous clothing trends that you regret as an adult. You wonder who in the fashion industry is out to get you, because now it’s here to take your precious daughters down!

Maybe your idea of fashion and hers just clash. Maybe you desperately want your daughter to feel beautiful and confident…but you also would like her to be fully clothed and not at risk of showing her butt if she sneezes. Or maybe you have serious fears about denim on denim, remembering the Spears/Timberlake catastrophe that was. And the idea of wide-leg jeans and tiny midriff-bearing tops is just too much.

How do we shop with our teens and keep from killing each other? How do we shop with our teens and enjoy them? How do we shop with our teens and make the experience build their confidence, self-worth, and our relationship?

Rules for Shopping with Teenagers

1. Feed them First.

Hangry is a real thing. And honestly, the key to the heart of your teenagers is food. Take that for everything it is worth. When they are moody, make them cookies. Offer them peace offerings of cereal. Always have popsicles in your fridge. Before you go shopping with teenagers, stop at Starbucks or CFA and feed the happy places in their tummies.

teenager holds a Starbucks drink

2. Bite your Tongue and Keep your eyes from rolling.

Seriously, ya’ll. When shopping with teenagers, don’t make snide comments. Don’t reminisce about the clothes you use to wear. Don’t roll your eyes when they choose something that you don’t like. Instead, walk with them and smile. When they ask, “What do you think?” Your mantra is, “Cute. Try it on.”

3. Don’t suggest anything!

Trust me. There is a time and place for suggestions to be made. At the beginning of the browsing, follow rule #2. Why? Because you are going to suggest something that you know will look good on them. But, since they are hormone overloaded and know-it-alls, they will reject you. Feelings will be hurt. Eyes will roll. Ungratefulness will bubble, while your generosity will deplete. Keep the peace. Relax. Don’t suggest anything.

4. Let them Lead.

When shopping with teenagers, let them lead; let them choose. Remember, IF they ask your opinion, what’s our mantra? “Cute. Try it on.” Hopefully what they will figure out is that the outfit is in fact not cute, does nothing to their figure, is too much or not enough, or it’s just blah. And it will all work out without you having insulted their nouveau style. Leave it all in their hands to lead, choose, and let go.

5. Suggest as they try on.

While they are trying on the 500 articles of clothing they have chosen, this is the ideal time to suggest. Never suggest by asking, “What do you think about this,” or “Do you like this?” That will ensure the teenage eyerolls and will lead to all the feelings (see rule #3).

Instead, after they are a little dizzy from trying on half the clothes, and slightly blinded by the overhead lighting, offer to find other sizes and colors. Then come back with your suggested items. “I found a few other things that may work, but you never know because things never look the same till you try them on.” It works. Promise.

6. Set the Rules and Stick to them.

teenager browses clothing on rackThis rule for shopping with teenagers is tough because you have to decide what works for your family as far as what you believe is appropriate. We do not allow fashion to dictate these rules. We do not allow friends to dictate these rules. My husband and I dictate the rules. My husband is a part of these discussions because he keeps us level-headed (both on budget and modesty).

Your teens will push the envelope. That is their job, and it’s ok. It’s your job to set the rules and stick to them. This is not the time to let them win, let them manipulate, or let them rebel. Decide beforehand what you will give into and where the line is.

Have lots of conversations about what is appropriate for their age and occasions. For example, my daughter tried on a rather short, flouncy shirt. She looked great, but if she sneezed…I bought her some dance shorts to wear underneath, and everyone was happy. She then tried on a dress that hugged in all the right places and plunged a little lower than necessary. She looked great. I reminded her she was barely 13 and we would talk about dresses like that when she was closer to 17. She understood and agreed by saying, “I’m gonna look amazing when I am 17.” Jesus, come soon.

7. Ask them the 3D questions.

Decisions are hard. Choosing a few items from a pile of stuff can be overwhelming and can aggravate all the teenage feelings. Ask the 3D questions:

Does it make you feel CONFIDENT?

Does it make you feel BEAUTIFUL?

Do you LOVE it?

If yes to all 3, then that’s a win!

8. Finally, be NOTHING but Encouraging.

Tell your teenager how amazing they look. Tell them how their eyes shine. Laugh when they laugh and think it looks ridiculous. If things aren’t fitting well, if it’s hugging in places it never hugged before, or certain body parts make them feel insecure or unsure, compliment them. Encourage them in something else. Don’t emphasize any of their uncertainties; instead, echo their confidence.

If she says, “I don’t like the way my stomach looks in this.” You say, “I love the color though, and sometimes dresses cut in the wrong places. Maybe try this instead.” Let’s be real, they would probably look great in a paper sack. If you could know then what you know now, and have that butt, you would trade with them every day!

We can do this mamas! We can make shopping with teenagers fun and life-giving. Stick to the rules, bite your tongue, drink your coffee, hug them and love them well, envy their youth a little, remember, hug them tighter and breathe. Happy shopping!


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Andrea is a true Houston native! Other than her college years at Baylor and a few summers with family in Guatemala, she has lived around the Houston area forever and cannot imagine living anywhere else. Especially because of family nearby as built in babysitters, so many friendships built throughout the years, and the great people of this city, Houston is so dear to her heart. In junior high her family moved to the Sugar Land area, but she attended a high school in town and spent as much time as possible at the Galleria in the 90s! After graduating from Baylor University with a degree in Secondary Education, she married her high school sweetheart, Orlando, and they moved to the Richmond area where they have been ever since and where she homeschools their son and 2 daughters, ages 15, 12 & 9. Andrea is very active in Women’s ministry at her church and in her community. She began writing for more therapeutic reasons when the kids were small and soon began writing publicly, remembering her love for writing and realizing the gift and calling that it was in her life. She published her first book, Breathless: Prayers from a Mother Learning to Exhale in 2018, a devotional last year and is currently working on a few new projects. In her down time, Andrea loves alone time, especially because she’s an enneagram 4! She also loves coffee, hanging out with her family and friends, traveling, New York City, musicals, especially Hamilton, fair trade jewelry, and charcuterie boards! You can find her writing at www.andreaportilla.com or follow her on Instagram @dreaportilla and on Facebook.


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