Teen Boys: 5 Things They Want To Wear


This post is sponsored by Urban Outfitters.

“Ohhhh Raines,” I called, in a singsong voice. “Urban Outfitters just reached out…”

He was by my side in a flash. “Yaaas,” he says, immediately getting out his phone. “Mom, can Ekash do this one with me? We’ve been looking…”

Ekash is one of Raines’ BFFs, and happens to be Linzi’s son, so he understands this whole blogging thing. Fun fact: At career day in school (many years ago), I talked their class through a scenario with earnings from affiliate sales. “If 10 people buy these shoes for $100, and you make 10% of each sale…” Ekash was the first kid to understand. “SHANA AUNTY – WHAT IF 100 PEOPLE BUY THEM? ONE THOUSAND PEOPLE?? ONE MILLION??????” He thinks I’m a genius for “inventing” affiliate sales, and I’ve been riding that high ever since.

Ekash: button-up (m) | jeans (m) || Raines: hat | tee (m) | jeans (34)

Until 4/27, take 10% off with code MOMEDIT10 (it’s stackable with other promos, too)

But it was the whole, “we’ve been looking” thing that kills me, and I suppress a snort. These two have been looking at, what, exactly? UO online? Browsing in store? These two boys who used to cry over ‘hard pants’ and even the threat of shopping are now well-versed in Urban Outfitter’s latest spring looks? It boggles the mind.

As does this picture. Um.

hat | tee (m) | jeans (34) | shoes

Who is this MAN? Gahhhh what is happening??

But anyway, putting my They Grow So Fast Feelings aside, these posts are tons of fun. While the boys get deeply excited about a UO gift card, I get deeply excited just…watching them. I just sit back and listen and just, I don’t know – marvel – at how old they suddenly seem. These man-babies with opinions and thoughts and jokes (good grief – they are so witty) and it’s just freaking wild.

Two Teen Boys Walk Into Urban Outfitters…Here’s What They Pick

While Raines asked for my opinion once he was done choosing his pieces (“looks good!”), the choice of all items was 100% the boys. Which basically means: don’t blame me for the super-baggy jeans. 😉

Also, if interested, take 10% off your purchase with code MOMEDIT10, now through 4/27. It’s stackable with other promos, too.

1. The Oversized Moto Jeans They Both Loved

tee (m) | jeans (34) | sneakers

First things first, both boys independently picked these moto jeans. Like, their top choice, both of them. And then groaned when they realized. But it’s ok! I just told them to do what Linzi and I have started doing: text to make sure you don’t show up in matching outfits, haha.

shirt (m) | jeans (36) | sneakers

The important thing to know is that these moto jeans already come oversized, so sizing up isn’t necessary!! Raines is wearing his usual size 34, yet they still look…big. Ekash, who is basically the same size as Raines, originally wanted the 38 (eyeroll), but after trying on size 36, he’s happy.

Raines: tee (m) | jeans (34) | sneakers || Ekash: shirt (m) | jeans (36) | sneakers

Baggy & oversized is the thing right now. But your kiddo doesn’t really need to size up in these jeans – the fit is exactly what they want, right out of the box.

2. The Softest, Cloud Cotton Button-Down

shirt (m) | jeans (36) | sneakers

Ekash’s shirt is made from that same sort of cloud-cotton stuff that Linzi and I both love. Think: 100% cotton, ridiculously soft (like cotton candy, clouds, dreams) and comes in a ton of colors.

shirt (m) | jeans (36)

This top feels like a tee (softer, actually), but looks a little more formal. It’s such a good piece for summer, I might have to get one for Raines, too. (But not black, E – I promise!) Honestly, the peach or yellow are calling my name (or Raines’ name, I mean). This shirt runs a little big.

3. The Best Tee For Teen Guys

Raines’ favorite tee is – still – the Heavyweight Tee by Standard Cloth. He discovered it over a year ago, and now owns several colors. It has that oversized fit he loves, but doesn’t shrink in the wash. I’ve actually stopped buying other t-shirt brands for him, simply because I either have to go up so many sizes that they start getting oddly long and dress-like, or they shrink when washed (especially the sleeves). This one, however, is pretty forgiving with sizing (Raines owns both medium and large sizes), and washes & dries like a champ. Highly recommend.

4. Anything From Dickies

button-up (m)

Do you guys remember the brand, Dickies? I couldn’t believe it when both boys picked a piece from Dickies – ohhhhh the nostalgia. Actually, Dickies’ whole 2024 line is pretty fun, especially the graphic tees (the boys especially liked this one or this one).

tee (m) | jeans (34)

Like the Baggy Moto Jeans from their first outfits, Raines’ Dickies Jeans also have a baggy fit (which means that R is wearing his usual size, 34). Ekash’s shirt is a size medium, which means that Dickies’ shirts fit pretty TTS…but TTS in a way that is slightly oversized, the way they like them to fit.

Ekash: button-up (m) | jeans (m) || Raines: hat | tee (m) | jeans (34)

Both of these Dickies pieces are nice and lightweight, and, I think, will be great for summer, too. I’m crushing pretty hard on that specific shade of lightwash denim.

Ekash: button-up (m) | jeans (m) || Raines: hat | tee (m) | jeans (34)

5. Cool Accessories

hat | tee (m)

For Raines, it was this baseball hat with the upside down ‘THRILLS’ that caught his eye (seems appropriate for a kid who does backflips on skis), and also comes in a really pretty lavender color, too. And for Ekash? It was this belt:

belt (L) | button-up (m) | jeans (m)

I think E was more excited about this belt (that buckle!!) than anything else, haha. Full disclosure: we argued over it a bit. The belt is actually from the women’s section, and I was convinced it was going to be too small. Anyway, I ordered him the large and…it was way too big. We actually just added a few holes with a drill, though, so it’ll work (and grow with him).

Raines has also been loving these denim Vans, and I think they’re going to be perfect shoe at the shore this summer. My husband now wants a pair, too.

jeans (34) | shoes

Next up? Raines tells me they need new shorts. Specifically…these or these. And please send help because they are giant jorts, you guys. GIANT. JORTS.



A huge thank-you to Urban Outfitters for sponsoring this post! You continue to make all of Raines’ (and now Ekash’s) sartorial hopes & dreams come true. As always, all product choices were the boys’ and all thoughts, opinions, and jort aversions are my own. And readers, thank you for your continued support. It doesn’t go unnoticed and is very much appreciated!


  1. I love this! Being a long time reader, whose babies have also grown into teens, it’s so fun to read (and see how old they look!) and it helps this mom stay current on trends 🙂

  2. Funny, I have 2 boys, one year older and younger than Raines, also in Philly area – they do NOT wear the baggy look, at all. I can’t imagine my boys with this much fabric around them. LOL.

  3. It’s so funny how fashion recycles… these are the clothes my guy friends were wearing when I was in high school. My daughter (15) dresses so much like I did way back when (though I am SO glad I kept my flares and wide-leg pants from like 20 years ago). And who knew that UO was still cool?

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