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What are tween and teen boys wearing right now?
Reader be warned, this is both a very niche and very exciting post1. I’ve received quite a few requests to write about shopping for teens and tweens and could never quite figure out when to dive into the subject, but as summer begins to wind down (don’t worry, I’m not diving into fall styling content just yet) and back to school campaigns run rampant, I thought there’s no time like the present. Because I have boys, who I’d argue are just as hard to shop for as tween girls for reasons I’ll get into, I’m starting with them.
I have, with surprising ease, convinced my nearly-thirteen-year-old son to share his thoughts on style and clothes, as well as pose for some pics2. A small miracle that I don’t take for granted. Peter is not a clothes horse, maybe in reaction to me or maybe because he’s still very much a kid who enjoys legos, playing video games with his bros, and mangas, but he does have pretty specific preferences.
He likes a cargo pant but hates jeans; he likes a graphic tee but prefers the artwork on the back of the shirt with a small icon or logo on the front; he’ll wear sweats but they must have a straight leg and wide opening; he wants his pants long, but doesn’t want to sag, he does not like hats, so please don’t suggest he wear one; he only wears gym shorts to workout3; he likes a hoodie not a crewneck; he only wears Jordans, Birkenstock Bostons, and maybe a slide if necessary, and always with socks (ankle or crew, natch); and as mentioned, he wants his shorts to be long.
He’s historically worn the things I’ve bought for him, unlike his younger brother who learned early how to say no with conviction and ease, and besides putting him in jeans as an infant4, I think I’ve done a pretty good job. Sticking to Hanna Andersson, Target, Crewcuts, Nike, and Crocs from preschool through elementary school, I started to mix in Uniqlo and Gap as he hit his first pre-adolescent growth spurt in 4th grade, and more recently Cotton On and Uniqlo’s younger brand, GU. I like to throw in some concert tees (Peter famously wore a Haim tee to his first day of 4th grade at a new school), merch, counterfeit (and real, come on now) jerseys from our travels, J.Crew for dressier pieces, and second hand gems from Poshmark. I try to slip in some cool brands here and there, but he generally sticks to what he knows and likes.
He hasn’t yet found a love for shopping, in fact he loves it just as much as he loves picking up dog poop, but I can do a lot very quickly at the mall if trips to the Nordstrom Cafe and GameStop are involved. And I know that soon I’ll be taking him to the thrift, negotiating clothing allowance, and approving Poshmark purchases like the other teen boys we know.
If you’re anything like me, you’re likely baffled by your tween on a daily basis. They’re both incredibly smart and tuned in yet also dumb as a box of rocks, they’re so so so messy, and man, can they be hard to please. But I’ve learned a lot in my thirteen years of parenting, and though I don’t claim to be a parenting expert, I am literally a professional when it comes to getting dressed. So buckle up, we’re headed to the mall, and yes, I’ll be having a glass of wine and a Diet Coke with lunch.
Let’s start with the tween essential, the graphic tee. Lucky for all of us, these have been an adolescent wardrobe essential for at least fifty years, so they’re always readily available no matter where you’re shopping. It’s an easy way for even the most self conscious child to add a little personality to their daily uniform. Uniqlo is my first choice - I love their museum collabs and they currently have a selection featuring Peter’s favorite manga series - followed by merch and concert tees, but there’s literally a graphic tee out there for everyone.
A quick note about sizes: Peter is tall and currently wears anywhere from an adult medium to an extra large, so I’m focusing on adult brands and sizes here today. If your child is wearing a L/XL/XXL or 12/14/16 in kids, they can easily wear an XS/S/M in adult, which opens up a lot more options for a picky tween. Peter was one of the first of his buds to wear Uniqlo tees, and naturally, it made him feel good when people asked where he got them. Yes, kids clothing is less expensive, but there is generally a huge jump in quality when you move into adult sizes, so it can be worth it.
Peter’s daily uniform consists of a graphic tee, cargo pants or wide leg sweats, and Jordans or Birks. He really doesn’t stray from this formula unless he’s swapping in a pair of shorts or adding a hoodie.
You may have noticed a lot of the tees out there are cropped, even for the boys, and if Role Model reportedly buying his tees at Brandy Melville is any indication, the youths seem to be dabbling in less oversized tops. I’ll admit the idea basically broke my brain when Peter and I went shopping last summer, but I often have to remind myself not be such an Old when it comes to adolescents, and really, if the girls are wearing a cropped, boxy top, why can’t the guys?
IMO the slightly cropped tees and camp collar shirts look best with oversized pants or long shorts, so that the play on proportion feels intentional rather than reading as too small.
Team gear is another easy way for tweens to show their interests and personalities without stepping too far out of their comfort zone. Remember, middle school is both about pushing boundaries at home and fitting in at school, whether we like to admit it or not.
Peter is built like an athlete, but is really just growing into his athleticism, that being said, he’s always loved team merch and a good jersey. Just like his mom, he’s down to watch any game if there’s good snacks and the off chance he might get a new hoodie out of it. He won’t go as far to wear is baseball jersey to school, and definitely won’t wear his football jersey on game day - an aversion he’ll have to get over if he plays on the high school team as planned - but he enjoys wearing his team hoodies and sporting professional and semi-pro team gear, counterfeit or otherwise, with his cargos and Birkenstocks.
We’re a Cowboys family (hush), of course the Blazers and Winterhawks are high on our list, we like the Spanish soccer teams because we love Spain, and now it seems we’re a Haaland family too.
Once boys hit middle school, sweatpants are no longer the only trouser of choice. After ten years of soft pants only, suddenly kids are wearing jeans and belts! Well not my kid, but kids are. My kid is wearing cargo pants, wide leg sweats, and maybe a twill pant if I can convince him they’re not actually denim.
It’s taken a lot of convincing to get Peter to wear his chinos, cords, and twill - NOT denim - pants to school. He’s long equated the fabrics to “dressy” clothes (see below), but my rule is as long as it wasn’t bought for a specific occasion, or that occasion has passed, all clothes can be school clothes. I’d rather my kids love and wear something to death than have it sit in their closet any day. So, I’ve finally got him grabbing them to wear with a t-shirt and sneakers, and on a very good day, with a short sleeve button up worn on top.
Peter’s height and aversion to jeans means inseam can be an issue. Uniqlo offers a few of their non-denim styles in Tall, as does Gap, but we tend to size up when more length is needed.
I’ve already shared Peter’s preference for long shorts, but I’ll give you a quick refresher. He wants them to be baggy, but not so baggy that they sag; he wants a soft waistband, no buttons; and wants them to be long, hitting at or below his knees. I think the parameters are easier for parents of children who aren’t in the 90th percentile, but I’ve managed to find a few styles from a handful brands. I’ve learned the hard way to just snag something when I see it. If it’s the off season, I’ll go one size up to ensure it fits when summer rolls around.
He wears his long shorts with graphic tees (duh) and Birks, maybe a sneaker during the school year. Does he look a little like Travis Birkenstock??? Yeah, he does. Clueless was basically my style awakening, the third prong in my fashion epiphany, so as long as he’s not hanging with the loadies on the grassy knoll, I’m okay with it.
With middle school and adolescence comes more reasons to dress up. Khakis and a button up are no longer limited to holiday brunches as the club or Thanksgiving dinner. There are dances, bar and bat mitzvahs, athletic awards ceremonies, and mock trials. Luckily (I think??) middle schoolers care as much about how they look as how they feel in the clothes, and they will tell you all about it.
When replenishing Peter’s dressy-ish clothes, I like to start with pants, because there’s nothing worse than a pair of khakis that are suddenly three inches too short after a sneaky growth spurt. Peter prefers a chino that has a wide or slightly barrel leg, he doesn’t mind a pleat or two, and he wants a good break above his shoes; he’s after volume and ease, even when he’s dressing up.
Next we think about what he’s wearing on top. He usually has one or two Good Button Ups - we both like the JW Anderson x Uniqlo styles - a crispy white tee with a wide, flat crew neck, and a sweater in his closet
If I’m really out to make him look nice but feel miserable, I’ll make him layer the button up under the sweater, but he usually sticks with the middle school semi-formal uniform of a button up worn untucked with the sleeves rolled up and sneakers. Just like the boys in my middle school, he needs help getting the sleeves rolled just right, it’s nice to know some things never change.
When we’re headed to a holiday brunch at the club or a family event, Peter will wear his khakis, a sweater with the crispy white tee underneath, and his “dressy” sneakers. I usually snag him a cashmere sweater from Uniqlo before the holidays, but this year I upgraded to a monogrammed style from J.Crew during their annual cashmere sale. I’m mindful of how much I spend on is clothes, especially because he’s still learning how to care for them, but some things, like monogrammed sweaters that can be carefully preserved or handed down, are worth investing in.
If you have an adolescent boy, or simply a boy of any age, you’ll know the struggle that is outerwear. No matter how emphatically you ask or how many times you show them the weather app, they refuse to wear anything that will actually protect them from the elements. Peter will willingly grab a hoodie, he will less willingly grab a puffer or vest, he will not grab a rain jacket. He’d rather freeze at the bus stop than sweat on the bus, which actually make sense even if it makes me crazy.
Hoodies and outerwear are an area where brands and logos have more influence. If it’s not concert, sport, or vacation merch, it must be Stussy, Nike, Fear of God5, or totally without logos. I don’t make the rules. Fleece is preferred to French Terry, hoodies preferred, and that hood better have a drawstring.
As for puffers, Peter actually prefers a lightweight style like this one from Uniqlo6 that he owns and wears occasionally, or this vest that I’ll probably grab for him while it’s on sale, just in case he starts wearing vests again. But for the sake of fashion, trends, and Millennial nostalgia, I had to talk about what the other kids are wearing. The youths are all about a big, chunky puffer that’s just a little more cropped than the versions we wore in 2003, North Face logo preferred but no longer required.
Ahhh shoes. I tried my best to turn my kids into shoe people, but instead of collectors, they’re minimalists. Peter long ago decided he wanted one pair of sneakers a season that he’d wear until destroyed or outgrown, whichever came first. He’s since expanded his shoe collection to include Birkenstocks, rubber slides (he outgrew his Crocs era as he entered 6th grade), a pair of “dressy” sneakers to wear with the outfits above, and most recently, Ugg slides. Quite frankly, five pairs of shoes feels like way more than enough when your growth plates are wide open (the doctor’s words, not mine).
Peter doesn’t know this, but I’m getting him a pair of Dr. Martens for his birthday in two weeks. They’ve been back for a while, and I’d argue like to Sambas they never actually went out of style, but with the return of the 90’s and early aughts styles, Docs7 were bound to make it back into the rotation. Bonus points that the shoes are essentially indestructible, fare very well in the rain, and basically cost the same as they did twenty years ago. There’s a solid chance he won’t wear them, but it’s my hope that they’ll at least replace his “dressy” sneakers when the occasion calls for it.
And that, dear readers, parents, guardians, trusted adults, fun aunts, and child free but youth culture curious, is what the tweens are wearing. What are your tween boys wearing? Should I do this all over again for the girls? Let me know in the comments.
I hope you save this to reference when you brave the mall for back-to-school shopping. I know I’m going to refer back to it when Peter’s making me insane so I can remember how much fun we had. It was a real joy to spend the week talking to him, photographing him, asking his opinions, and laughing with him. Seventh grade was a complete shit show and he worked really hard to dig his way out of a difficult time, and it makes me so happy to see him happy. I know it can get worse again, but this moment right now, is pretty awesome. I’m constantly being reminded how kind, thoughtful, frustratingly smart, and hilarious he is, and as we head into Leo Season, I feel lucky that this one is mine.
Because I’m surrounded by so many Leos - there are three birthdays within seven days in my family, it’s a lot - it felt like a great time for a sale. I’m offering a 20% lifetime discount on all new paid subscriptions, through the end of August. Paid subscriptions are totally optional, but they support the many hours of work I put into this newsletter.
Moving forward my Window Shopping and OIW8 series’ will be behind the paywall, which means paid subs will now get two exclusive emails a month, plus access to the archive, the full chat, and my Google Maps.
I’m thrilled that last week’s newsletter was such a hit. I know that cleaning out our closets can be overwhelming and anxiety inducing, and I wanted to relieve some of that for you. I really do hope you bookmark the post, save the list to your phone, and refer back to it when you need a little cheat sheet. If you’re still needing support after the clean out, let’s chat. And if you’re LA based, I’m booking in-person appointments September 21st, 22nd, and 25th. DM me for more info, I’d love to work with you.
Thank you for reading, liking, and subscribing. I’m so happy you’re here!
Talk soon,
xx FANNY
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If it’s too niche for you, consider sending it to a friend with tween adjacent kiddos, or simply skip this week.
Peter was a willing and enthusiastic participant and gave consent to have his thoughts and photos shared here.
Something I’m very happy about.
Was I experiencing psychosis???
Don’t even get me started on the name of this brand.
Come on Uniqlo, sponsor us! We’ll be here when you’re ready.
Do any of my Portland readers remember the outlet store in the 90’s? I’m convinced it’s the only reason my mom agreed to buy me a pair in middle school, and damn, were they legendary.
Loved this! Please do one for girls
Omg he’s so cool. But of course he is, he’s Fanny’s son!