How to Take a Teenage Boy Shopping for Clothes

February 11, 2011

There comes a time in the life of every teenage boy’s mother when she comes to the following realization: my child looks like a ragamuffin/street urchin/orphan and I need to take him shopping for clothes. This realization will send dread deep into her heart, as she realizes she will have to 1) find a time when both mother and son are available for shopping, 2) find a store that stocks affordable clothing for the impossibly tall and thin young man her son has become and 3) convince said young man that shopping for clothes is a necessary and required activity.

If you find yourself in this position, here are seven tips to help you survive your next shopping trip with your teenage son (these tips can also be applied to husbands):

Choose a time when nothing more interesting is going on. This will be nearly impossible since clothes shopping ranks with household chores in level of interest. You may have to ground him just so you can pull him away from his friends/the Xbox/Runescape.

Promise him lunch at his favorite restaurant. You’re just going to have to put up with the fact that his favorite restaurant is one you hate. You will either have to eat beforehand or find someplace acceptable nearby where you can buy take out.

Let him drive.

Once at the store, don’t express an opinion about the clothes on the racks until he does. Be noncommittal: “Here’s a blue shirt. What do you think?” Heaven forbid he try on something his mother says she likes. Even after he’s chosen something, be judicious with your praise. If you like it too much, suddenly he won’t. (The reverse is also true: if you hate it, don’t express that opinion, either, unless you want it to become the one thing he absolutely cannot live without.)

Fortify yourself with Starbucks (or other favorite treat).

Don’t try to shop for yourself, too. Never mind that you see an adorable top just your size…

Confine your trip to one or two stores to avoid shopping overload for both of you.

Clothes shopping with a teenage boy is not for the faint of heart, but it can be done successfully. And remember, it could be worse. He could be a girl.

What was your everyday adventure today?

You Might Also Like


  1. Hahaha! Two words...Old Navy! It's relatively painless there.

  2. You survived!! Hooray!

    Ummmm, did said young man?

  3. Kelly--I've heard that--but we don't have one close by! I'll have to petition the company!

  4. Laure--Yes, I survived! It wasn't too bad this time :)

  5. Glad it wasn't too bad Kathy. I would have liked your tips about 15 years ago - my son is now 29 (aack!).

  6. Cheryl--29?! How does that happen? It seems just yesterday that mine was 3 years old.

  7. My 10 year old doesn't even care if the underwear he's wearing is several days old, much to my chagrin. Thanks for the shopping tips - I have a feeling they'll come in handy when my son is a teenager. You're right though - it could be worse - he could be a girl. I've heard too many girl drama horror stories.

  8. Krista--Gone are the days when I could just buy what I liked and give it to him! He's picky about clothes, but at least he's not concerned with labels or what his friends are wearing, and I've never had him sent home from school for wearing something that doesn't meet the dress code, as at least one of my friend's with a daughter has had happen!