While being the mom of two teenagers is – honestly!! – tons of fun, there’s no doubt that teenagers can also be savage. And while my husband typically bears the brunt of my boys’ ridicule (they make fun of his clothes, his face, the way he eats, breathes, sleeps, talks – literally everything), I do get my fair share of teasing. So when I get an unexpected compliment, it tends to stay with me.
These Mom Outfits Are Actually Cool, According To My Teenage Son
Over the last year couple of years, Raines, my oldest, has suddenly started caring about his clothes. And with this newfound sense of style, he’s also started to notice mine. Not often, mind you – teenagers are typically more focused on themselves (totally normal) – but every once in a while I wear something cool enough to break through his teenage haze.
So. Here are the outfits I’ve worn over the last year or so, that caused Raines to actually pause and say, “Mom! Cool outfit!” (And did I immediately run upstairs to take a photo of that outfit? Yes. Yes I did.)
Outfit 1: Elevated Bike Shorts
top (s) | shorts (s) | slides | bag
I wore this to brunch at Cafe Lutecia last summer and garnered some surprised praise from Raines. Do I know why he liked it so much? No I do not. But he was literally like, “Whoa!! Mom, you look really cool in that!” so ok then.
One reason I think this outfit caught his eye? Because this shirt is freaking magic – I love how it’s cut away at the bottom, giving that nonchalant, slouchy vibe that is often only achieved while posing for photos. It makes all outfits look cooler, and I’m thrilled Favorite Daughter brought it back again this year (in red!!).
Outfit 2: Overalls + UGGS
overalls (xs) | tank (m) | similar tank | UGGs
I’ve worn this exact outfit a ton since this photo was taken, but in this instance, I was – again – headed to Cafe Lutecia for brunch with the fam. Raines saw it and was all, “awww, Mom, I really like this outfit!”
Sidenote: I hate to tell him, but overalls totally do it for his Dad, too. 😉
Outfit 3: Jorts
tank (4) | jorts (30) | sandals
Raines lost his mind over this one: “Yes, Mom YES! See how awesome jorts are???” Good grief. Truth be told, I had ordered two pairs of jorts for him (in different sizes), and the pair that was too small…I took for myself. In early summer/late spring (aka before tanned legs) I’ll admit that a longer short is pretty darn nice to have. I might bust them out this fall, too.
Outfit 4: Oversized Tee + Tiny Shorts
top (xs)| shorts (4) | sneaks | bag
This is an outfit I wore while running errands with Raines. It’s pretty basic, but he made a point of saying how cool I looked? IDK. Honestly, I think it’s because I’m dressed like most teenage girls: oversized tee, tiny shorts. It’s like he was surprised that I knew this combo, and I didn’t have the heart to tell him we invented this shit in 1992.
Outfit 5: Stripes
I think I’ve worn so many stripes over the years…and dressed both boys in so many stripes over the years…that it’s now a core memory. Raines took only look at this very comfy mom-outfit and was all, “Mom!! Love the stripes!”
HAHAHAHAHA.
Outfit 6: Leopard Print Pants, But Casual
tank (s) | pants (us 6/uk 10) | sandals | bag | hair tie/bracelets
Ok, so technically speaking, I don’t actually remember if Raines said anything specific about this outfit, all I know is that I’ve been getting a TON of compliments from teenage girls whenever I wear these pants: at the airport, walking around downtown, etc. And compliments from teen girls are DEEPLY exciting. Such high praise!!
Sooo…that’s it, Gang. Over the last year or so, these(??!!) are the handful of outfits that my 16-year-old has actually liked enough to say something about. Do with that what you will. 🙂
xo,
S
A thing for overalls. I died.
It’s those 90’s guys. 😂
Ha! What an endearing article. One of my faves and the kind that keeps me reading TME year after year
Wow – such a nice comment. Thank you!!
Wait, is Raines taller than you?!?!? I’ve been reading since he was a tiny munchkin at ANMJ!
Omg Raines is taller than his DAD!!
Love the outfits including Raines’s cargos! My son would love them…where are they from?
Suuuper old Topshop for men. I’ll see if I can find something similar.
The overalls linked don’t look the same. Would love to know the actual ones you have even if unavailable (possible thrift option!). Thanks!
They’re FP Rayna Carpenter overalls – same sort of barrel shape, but the back is different. https://shopstyle.it/l/ce4Oh
My daughters are 11 & 14yo and they are *very* stingy with the outfit compliments! I’ll have to start taking pics for my self-esteem (aka proof that they once approved)
“We invented this shit in 1992.” THANK YOU! 😂
I’m about to pull the trigger on the leopard print pants, but I see you’ve cuffed and rolled them, so I thought I’d ask you about the fit. They’re a little pricey for a cotton pant, but they are super cute. How’s the fit? Too high/stiff in the waist? How’s the fabric?
The waist is high and the pants are stiffer than I expected – but only in this era of super soft everything. The cotton just feels rugged, and they soften up great (but without losing that thickness that makes them feel durable). I mess with both the waistband and cuffs depending on the shoes I’m wearing. For my flattest shoes, I usually flip up the cuff once, and flip the waistband down once – it makes the pants the shortest they go. If I’m wearing low heels, then I only do one (cuffs or waistband). If I’m wearing high heels, I flip nothing. The high waistband is actually pretty cute and flattering, but they are DIFFERENT. When I first put them on I was like, NO WAY. But then I couldn’t stop wearing them. And now gahhh I love them so much.
What a fun and fascinating topic for an article—a great idea and wonderfully executed! Your strong relationship with both your sons is such a beautiful (and fun!) part of the TME landscape—so enjoyable to hear their hot takes!