A Week of Outfits: Kayla Sossin
This summer, my friend Kayla wore all denim to her birthday picnic. “It’s my go-to daytime look,” she told me. “I stole the shirt from my mom, and I wear these $40 sneakers to death.” Inspired, I asked if she’d be up for sharing a full week of outfits, and luckily she said yes…
Shirt: J.Crew, similar. Jeans: Rag & Bone. Shoes: Banana Republic Factory. Sunglasses: Ray-Ban.
“This boat painting is from First Dibs, and it’s my favorite thing I own. It’s five feet tall and was originally $1500. I couldn’t justify spending that much, so I went online and got it down to $800! I can’t negotiate in person because I get too nervous. I come from a long line of Jewish women who don’t pay full price for anything, and my mom and nana would have been like, ‘Come on!’”
Dress: Shona Joy, similar. Bag: Marshalls, similar. Heels: Jessica Simpson.
“This dress is my go-to date night outfit. My fiancé Jeremy and I usually go to dinner at Bar Bête in our neighborhood. I have small boobs and don’t always need a bra, but I can’t have my nipples all over the place. So, I wear these round pasties. ”
“I just got into Jones Road Beauty; I’m a huge fan of their Miracle Balm. For nails, I like pale pinks. I used to bite my nails so much. I was like, it’s an anxiety thing, I’m an adult, I hate it, and my friend was like, get gel polish so you can’t bite it. That was my strategy, and it worked.”
Shirt: Vince. Pants: Abercrombie & Fitch. Shoes: Banana Republic Factory. Roadrunner charm: Take Me With You. Sunglasses: “I stole them from my dad; they’re very old Armani.”
“I’ve been wearing hearing aids since I was eight. When there’s background noise, like at a party, it’s hard for me to hear – the words get garbled. I’d like to be more social in those situations, but it’s tough if I don’t understand what someone’s saying. You don’t want to be the person who is like ‘What?’ ‘Whattt?’” It takes more energy to be in those environments; it’s worth it, but it’s hard.”
“I didn’t tie my hair back until I was 24 because I didn’t want people to see my hearing aids. Now strangers sometimes stare at my ears. It’s fine — maybe they see the little tube and think, What is that, an earring? But it really bothered me when I was younger because I didn’t want people to know that part of me. It’s hard enough to grow up as a girl, a teenager, a young woman, without feeling different. For a long time, I felt like something was wrong with me, instead of just, this is how I am.”
Sweatshirt: similar. Jeans: Reformation; “they have the best jeans and they’re always on sale.” Shoes: Banana Republic Factory.
“Our dog, Lenny, is the best thing that ever happened to me, besides Jeremy. I told Jeremy I wanted something Lenny-themed for Valentines’ Day, like one of those mom necklaces with their kids’ initials. I wanted an ‘L’ one, and Jeremy was like, That’s insane. Then he discovered these custom pet sweatshirts. I wear mine all the time.”
“As a hobby, I run a bakeshop on Instagram called Shortcrust. I make custom birthday cakes and elaborate floral cupcakes, and I join pop-ups in farmers markets and craft fairs, like the Hester Street Fair and Brooklyn Pop-Up.”
Blazer: Banana Republic, similar OR similar. T-shirt: Reformation. Belt: vintage. Jeans: Reformation.
“I work for NYC’s emergency management agency, and I wear this outfit to the office when I need to look nice. The vintage belt is stolen from my mom — she got it ages ago in Florence, Italy. She’s going to see this blog post and be like, You need to return all my things.”
Shoes: Caron Callahan, sample sale.
“I work in a very male-dominated field, and when I first started, I lacked confidence. I would wait for direction from senior people, even when I already knew what to do. But then I realized, I got this job for a reason, and I work my ass off, and I can trust myself. I’ve had a lot of toxic bosses and absolutely bizarre experiences, but I’ve finally developed the confidence to know when I’m right and when to push, versus when to shut up. Surprisingly, the ability to recognize when I don’t know the answer also makes me good at my job. I work with a lot of subject matter experts, and I’m very comfortable listening to other people. You can’t have every single answer every single time, you have to rely on the team. Everyone contributes something.”
Thank you so much, Kayla!
P.S. More people share their week of outfits, including a stay-at-home mom who loves clowncore and a scientist with a new baby.
(Photos by Julia Robbs for Cup of Jo.)
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Comments
119 commentsThank you for talking about wearing hearing aids! My 10 year old son has worn hearing aids since he was 2-1/2 and got a cochlear implant when he was 3-1/2. I’m always on alert to read about adults with hearing loss and hearing devices.
In that last photo she looks just like Mini Driver with straight hair! Love the outfits too <3
Wonderful post! Thank you so much for sharing!
I don’t wear a hearing aid (yet), but I am deaf in one ear; it means so much to read about Kayla’s experience. The next time I’m in a loud restaurant taking many nervous sips of my drink because I can’t hear the conversation at the table, I won’t feel so alone. Thank you for sharing, Kayla! <333
My niece, Kayla, has been an amazing person since she was a toddler. At 2, she’d ask me if I wanted to dance to Mozart. I love the sensitive, smart and worldly person she has grown into.
Yes!! So thrilled to see New York City government employee!!! There are so many interesting people who work in government, I don’t think the average person realizes this!
Yes! I was just thinking I miss the CoJ days when the week of outfits was just a really interesting human in cool clothes rather than someone with a book coming out or wildly successful substack. I love seeing those people on here too, but nothing jazzes me more than a regular awesome person talking with pride about their life and their outfits. heart eyes forever.
Kayla, your cakes are just beautiful! Can’t believe no one is talking about the cakes lol.
“The ability to recognize when I don’t know the answer also makes me good at my job” — people, ESPECIALLY managers, who can’t do this are the worst to work with!! Discernment and humility and top-tier skills.
Loved what she said about trusting herself after lacking the confidence in the workplace and having had toxic bosses. I experienced that myself and still have had to psyche myself up before important work meetings, interviews, etc. It is true that not being the loudest, most confident person in the room can also be a superpower; it makes you more empathetic and ready to learn, and I think if you find the right workplace, those traits are highly valued and supported (I finally feel like I’ve landed in a place like that after many, many years). I’m also glad she is okay with people noticing her hearing aids now — we are all different and even if people notice this difference, a lot of times it is only curiosity, and many people are cheering you on!
For what it’s worth, as an Etsy site is linked – Etsy is currently supporting the sale of a lot of alligator alcatraz merch. It is pretty terrible and as of now they have not addressed it despite a lot of people reaching out and asking for it to stop.
Jumping in to appreciate the representation. My 11 year old has been wearing hearing aids for about a year. He’s not self conscious of them at all, but he does wish he didn’t have to deal with them (swimming, charging them at sleepovers, etc). Tearing up to see all these other mamas resonate, too. It can feel very isolating <3 And tell Kayla she is a beauty inside and out!
I typically gravitate towards timeless clothing, like I’d describe most of what you’re wearing, Kayla. The way I beamed when I saw your Lenny sweatshirt, though!! (Hi, Lenny!) It makes a strong case for both sentimental and statement pieces. Most of all, I appreciate the words about your hearing aide. While my own medical history looks different – a visible spinal condition that has dictated how I operate – my heart swells when others choose to disclose their experience with working around health challenges. I never felt like I fully belonged to either the disabled or able-bodied communities, personally, so I appreciate your helping me build my self-perception of carrying a body around with slightly unconventional specs.
I love the sweatshirt but I’m sad her fiancé didn’t get her the necklace. My husband gifted me a gold necklace about 5 years ago with my horse’s name and birthstone on it and I’ve never taken it off except to clean it. It’s not weird. It’s love.
I love all the week of outfit posts however this one was phenomenal! I am all for people wearing what makes them happy but I don’t personally wear bright colors or patterns. It was nice to see all the neutrals! And I love that she works in local government. I am an attorney for a county in the state where we reside. Yes to more of these profiles. Local municipal employee series?!?!
Yes! And federal workers too! Sending love to all the federal workers out there.
Yes, Cara! My husband is a federal employee. They are so undervalued!
This was just lovely. So moved to read about her experiences with hearing aids and gaining confidence at work. Great post! Was curious what Jones Day shades you go for Kayla? I want to take the plunge but not sure what would be most flattering, am kinda pale.
If you send Jones Road a photo of yourself in the sun with no makeup, they will write back with tons of recommendations.
Kayla – you are so bad ass in so many ways.
I have also recently gotten into Jones Road miracle balms, I love them! Twice a year they offer minis so you can try a bunch of colors. Though be sure to tap it on, not rub it in!
Sorry to rant here, COJ lovelies. I love JR miracle balm and REALLY wish they would just sell the minis as singles!! The full size tubs are so big, I think they’ll go rancid before I could ever use up more than one, and they certainly don’t fit in my makeup bag or purse. I found the shade I like, and as a perimenopausal woman who is fed up with this type of gatekeeping, I feel so frustrated that in order to get the mini I’d like I have to purchase other shades that may not work for me. Am I alone in this annoyance?! I’ve been using Bobbi Brown’s (JR’s creator) makeup line for 30+ years, and I just feel so peeved by this. Obviously I am more concerned with real injustice and this is a minuscule thing, but had to let it out here. Thanks for reading, haha!
Alia, I’ve had the same tub of miracle balm since 2021 and it’s not rancid and is as good as new!
Alia I totally agree with you!! Minis should be offered all the time and available for single purchase. I don’t own a full size one, minis are big enough for me.
I know every person’s hearing accommodations are different, but my mom (who has had hearing aids for about a decade) recently visited me for a few days with this little microphone, and it made a HUGE difference in her ability to enjoy conversations in restaurants and spaces with a lot of background noise. The mic can be put on a table or clipped to the user’s bag or clothes; settings can be adjusted from the user’s phone. It was amazing, just in case anyone else could benefit. https://www.phonak.com/en-us/hearing-devices/microphones
Thanks for sharing, Julie!
Yesssss we use this everyday for my son at preschool! He’d be lost without it.
Thank you for sharing! I’m going to pass this onto my dad. His hearing aids are great but it’s so hard for him to participate in conversations during social gatherings and in loud restaurants. He uses a transcribing app which helps a bit but this sounds like a better option.
What??? I’m hearing impaired and am always looking for accommodations and have never heard of this!! Thank you. I loved hearing Kayla’s story. Hearing impairment is more a struggle than most people realize.
Beautiful! I loved every outfit. Kayla’s story about her hearing aids really touched me. I’ve had hearing issues my whole life, and finally, in my 40s, I got tested and received hearing aids—the best thing ever. I do wish they offered hearing aids for adults in colors other than ones meant to disguise them. I want people to see them. Even with hearing aids, my hearing isn’t fully restored. They help a lot, but I still have to position myself to hear better, I often read lips without realizing it, and I sometimes rely on context from partial conversations. It’s even more challenging because I’m doing all this in a language that’s not my first. I appreciate it when people know I wear hearing aids and adjust how they communicate—it helps me so much more than constantly having to play catch-up. I’ve learned that even when I tell people I wear hearing aids, they tend to forget. Since I function “normally,” they assume I don’t need any accommodations. Honestly, a hot pink hearing aid might be a perfect reminder that I do!
Here for the pink hearing aids!!!!
I got my first pair of hearing aids at 29 (45 now, somehow!) and they were lime green. I’ve never been able to find colorful ones for adults after that first pair, though there are lots of companies that make fun stickers and other covers for them. I want them to be as fun as my glasses! I’m not ashamed to need hearing aids and am also here for the hot pink.
My daughter is 22 and has worn hearing aids since she was 4. Now she insists on bright hot pink ear molds (the ones that fully fill the ear) so that people can see that she has a hearing impairment. It’s sometimes a struggle to get the provider to do that, so it helps if they work with pediatric patients too (who often use that time of mold).
This is my favorite week of outfits post ever. I love her style, it’s just so “normal” and approachable. It doesn’t make me feel bad, it inspires me to emulate her.
i agree — i love all of the week of outfits posts, but 99% of them are things i personally wouldn’t wear because they’re super loud or very pattern heavy. i love the look on others, just not on me. so this week’s was very refreshing because it’s very normal and “quiet” and looks like things i would wear!
Agree 100%!!! Loved this one!
I’m a very budget-conscious person and usually never splurge on jeans (because jeans are, by definition, casual, right?!) but I have a similar pair of Rag & Bone jeans and they are THE BEST. They literally feel like sweatpants and are light as air and very flattering. I have worn them so many times, it’s totally been worth the money spent.
I recently tried on a very similar pair of Rag and Bone and can confirm that they were so soft, so light, so comfortable–like buttah. I didn’t take the plunge but I think about those jeans daily, so I just might go for it.
Sounds like the elusive jean dream! It’s the featherweight style?
Love her style! That date dress is beautiful.
My husband has been hearing impaired since he was a kid. Like Kayla, he lives with the difficulty of being in an environment with a lot of background noise, and straining to hear conversations. The amount of effort that it takes for someone with hearing problems to get through that scenario is huge. It can be stressful and exhausting. Earlier this year, after more than a year of research and consideration, he got a cochlear implant, which has been life changing. The day after his procedure he heard birds for the first time in over 40 years. I am so pleased to read Kayla’s profile, and her description of her journey. People with hearing challenges are everywhere, and increased understanding and consideration benefits all of us. And she is lovely and looks fabulous. Love the dress, the blazer, and her excellent shoe game.
Claire, do the cochlear implants help him with background noise? They may be in my future and I’m curious, if you’d be willing to share. Thank you.
The part about her mom wanting her clothes back 😊 I have three sisters and we all live all over the country but we still pass clothes around. It’s fun bc I’ll see something on my San Diego sister that I gave to my Florida sister. My UT sister was getting rid of a pair of pj pants that I wore post babies that my little sister gave to me. I snagged it back and she was like “Oh good I didn’t want them but I’m glad they’re still in the family bc I still like them.” Hahaha it’s fun
Same on being deaf and feeling self conscious about hearing aides! Also same on small boobs but I just let the nips do their thing. I don’t think anyone is paying any attention, at the end of the day.
100% on my way to get myself a sweater featuring my idiot orange cat Maurice !!!!!
Loved reading about hearing aids and loving all the outfits, especially the Lenny custom sweatshirt, so sweet! Also, everything on the Shortcrust IG page looks delicious :)
Omg! I love your style and my 4 year old has worn hearing aids since he was a leeeeeetle baby! They totally are just a part of who he is! He looks naked to me without them lol. Did you get fun molds as a kid? He’s very into rainbow molds right now which is precious.
So happy to see a fellow Jew in a similarly creatively mediated, consensus-building job! Kayla, please tell me your dog is named after Lenny Bruce… Lenny Kravitz? Lenny Henry?
As someone with a rose tattoo on her bum to commemorate the love of her life (my 10.5-year-old rescued Olde English Bulldogge, Rosie), I would like to vouch for any and all purchases related to loving the hell out of our pets!! Get that necklace, girl!!!
Ok just found a Christmas gift for my husband- that dog sweatshirt made me laugh out loud and I know one made with our dog will make him laugh too. Thanks for this!
You can see her intelligence and warmth come through in her eyes. What a beautiful way to reflect your life and experience.
Thanks for talking about your hearing aids!! You seem like a really cool person.
I LOVE Kayla’s style!! So classic but fun, accessible and stylish. Thank you for sharing this!
She is so cool! Love this week of outfits!
My daughter is on the line for requiring hearing aides. I didn’t realize how much I was resisting the concept based on the fear she’d be bullied for it. This gives me so much hope, and I so appreciate this being covered!
I wear a hearing aid as an adult, and I work with differently-baled and differently-anatomies kids many of whom wear hearing aids. Nothing is better than feeling at ease in an environment. Get the hearing aid, and your kid can decide how little or how much to wear it.
If hearing aids allow your daughter to exist more fully in the world, to have better access to what’s going on around her, to not have to work so hard to follow (or mask), what’s to resist? Her world will only open up with greater access to it. Hearing aids are a tool, different, but also not unlike glasses. The technology is not perfect, but it’s pretty amazing — they work better than ever before and they come in cute colors. This is just how her body works and there isn’t one thing wrong with that. Good luck to you both! xo
That engagement ring! Elevates every outfit! Stunning!
I love her style! Not sure if those jeans will ship to Canada, but I’ll be checking!
enjoyed this in general but really did appreciate the last paragraph on finding her place/voice in her work. i wrestle with all the usual anxiety, imposter syndrome stuff (adulting!). it does help to hear from someone who has worked through this enough to both have the confidence to move forward and also recognize when it is GOOD to ask for input. go go go kayla!!
Kayla is gorgeous and her style is chic and minimal. I love the denim on denim and her blazer. I used to work in local government too—one of the best jobs I had.
Lovely! Strong jeans game. (And, as a former employee, it’s 1stdibs (not First Dibs! :))
This was so relatable, I felt like I was reading a blog post about myself! Thank you for sharing Kayla!
This is a really special week of outfits, I feel like the focus is more and more on how the person feels in their clothes, their evolution of style, and little peeks into their special occasion wear. Really feeling warm waves coming off the page – you have some fabulous friends! I wish I could share my “reader week of outfits” about how I feel in my clothes!
We need like a fb group or something to do this? Wouldn’t it be fun? We could share meal ideas, home tours, week of outfits, 4 fun things from our lives, books…..I love this community and think it could be such a positive place, that is CoJ fan generated and curated with the same warm and loving vibes found here
My 5 year old daughter was just prescribed hearing aids. I loved learning about Kayla’s experience! My daughter will love to see how she rocked these looks – especially with her hair back!
My 4 year old rocks hearing aids! Did she pick some fun colors??
Excellent week of outfits! I literally clapped when I saw this today. Love her style and attitude. Also as always such great photography x
Keep it up with the inclusive articles! 25% of the US population has or will have a disability at some point in their lives!
Kayla! Thank you x1000 for mentioning your hearing aids. I just got some from Costco and was reluctant initially. I do like hearing better but accidentally put them in the washing machine (got a new pair from costco for free!) and got bad at wearing them. But I have a Phillips pair and there’s a Bluetooth feature on the hearing aid app if you’re at a party, you can press the feature I think called speech in sound and it’ll only focus on the person in front of you. I also think they should rebrand all the hearing aid brochures to include young people. It drove me crazy when I was getting a hearing aid to only see older people with white hair on the cover. I am sick so stopped wearing them but I will try to wear them again. I dont love how they feel but the more I wear them the more normal I feel and grateful to hear sounds like specific birds and rainfall and my husband’s voice. Thank you!!
Yesssss! Agree more young people in the hearing aid ads please!!!!!!
Totally agree about the young people! I have some anatomical differences in my middle ear that require annual exams and a hearing test. Last month the audiologist who did the exam was struggling to situate the headphones exactly right and she said, “Usually my patients are older and have way less hair than you!” I know she was trying to be nice, but it made me feel awful! As though I was the only young person in the world with hearing issues, which of course couldn’t be further from the truth. More representation is key!
As the mom of a 29-year-old daughter who got her first pair of hearing aids at age three, I could relate to Kayla’s comments about not wanting to tie her hair back and how it’s hard enough growing up without feeling different. Thanks for featuring Kayla, and thanks, Kayla, for your honesty.
Love this one! Her style is so chic but accessible. I also love that she has a “regular” job–I was surprised by how surprised I was by it! Love the loafers-and-blazer ensemble the most!
You.Are.Adorable.Kayla! 🌼
Love the custom dog shirt! So fun & funky!
As a mom with adult kids, I had to laugh at how many items she has “borrowed” from her parents. :-)
My oldest daughter, 37, has two of my full length coats. One I really loved the color of and the other was neutral and went with everything. I miss those coats, but they look great on her and I admit I am sort of flattered. And, well, she is my kid so that’s fine. My middle child steals my jewelry and when I ask for some back, they say, “Would you be happier if I just didn’t wear the ring when I am around you?” Being a mom never ends even when they grow up. I kinda love that.
As an adult with several pieces of my mother’s clothes and jewelery, it was never about the item itself, though sure, I like whatever I pick out; it is about having a small piece of her with me, giving me confidence and support through the wearing of it.
Ilia, that is so true! Never thought about it that way, but I treasure my mom’s purses/jackets, etc. not because I necessarily like the style on its own but because they remind me of her, and she looked so badass in them (but mainly because I look up to her and think she is so beautiful). They are cool because they are my mom’s. :)
That’s so beautiful Ilia.
My daughter (7) has worn hearing aids since she was 5 due to genetic hearing loss. She hasn’t yet become too self conscious of them, but I know that day is coming. I just showed her your photos and she said “wowww she’s so pretty.” Thanks for your honesty and for the representation. The next generation is watching!
oh my gosh I love this, Katy!
My 8 year old daughter wears hearing aids and when she sees someone with ear buds in she always yells, “I LIKE YOUR HEARING AIDS!”.
@KML, same with my 4 year old!!!! He’s always checking people’s ears for hearing devices to compliment them on. He’s been aided since birth pretty much!
Loved every outfit. Chic and comfy.
Those loafers! And the green blazer!
This post featuring Kayla made my day as someone who is also Jewish and deaf! I’ve worn hearing aids since I was three and have had a few friends over the years with similar hearing differences (including one of my besties who I helped walk through the process of getting her first set of hearing aids), knowing others within your age range who have the same disability is really empowering and reassuring. Even now when I see an article or piece of media with Deaf/hard of hearing people featured I still get butterflies of excitement – and I’ve been deaf for 30+ years! It never gets old. And Kayla is very stylish and charming to boot! Her Canadian tuxedo looks very chic.
Yes! As mom to a hard of hearing kid, as soon as I saw the hearing aids mentioned I thought YESSSSSS! Omg this amazing style that reminds me of myself AND she has aids!? Love it.
I love this week of outfits! Very classic and similar to my own.
In the top photo, I thought she looks just like Meghan Markle! Just me?
Just came here to see if anyone else had said the same thing!
No, I thought the same!
Totally thought the same, Yelena!
Yes! I def see it!
Nope. Had exactly the same thought.
Oh myyyy. I had the same thought!
same!!! i love her beauty mark
YES!
Same thing! She’s gorgeous.
BOOKMARKING THE CUSTOM PET SWEATSHIRT SO FAST. My husband would flip if I got him one with our dog! Thanks for the genius tip!
hahahaha can’t wait to see dog sweatshirts popping up around town
I’d get one with our beloved, yet deceased cockatiel on it (obvs photos from when he was alive!). I’d wear it with pride!
I used to have that exact J Crew chambray shirt in the top photo. I’d recognize it anywhere. I wore it for maybe ten years. The fabric beneath the under arms began to shred and I finally got rid of it. RIP. I always imagine that when my kids are grown they will recall me in their minds wearing that shirt. (In reality they will probably just remember me nagging at them to pick up their socks and hang up their towels, but in my ideal/romanticized mind that’s how they will remember me one day.)
When I picture my mom young, I absolutely picture her with her hair in her signature velvet scrunchie… and her telling me to stop pushing my brothers’ buttons. It’s a both/and, I’m sure.
Look on Poshmark! My fave thing on Poshmark is old Madewell and J Crew button downs.
I love seeing someone featured whose job doesn’t involve them owning their own company or being CEO for a fashion brand. Not that there’s anything wrong with those jobs, this just feels a lot more relatable to my life!
I thought the same thing! I had a moment of trepidation when I opened the post, and was pleasantly surprised that the opening line didn’t have a link to their insta.
Agreed! What a refreshing read. It feels rare to come across a profile here that isn’t trying to sell a lifestyle, a product or an online persona. I appreciated that this story focused on someone who isn’t on Instagram, isn’t angling to become an influencer and isn’t operating with an endless fashion budget. She’s just a real person—with a relatable job, a minor disability, and great personal style — that feels both authentic and inspiring. More of this, please!!
we would love to do more of this type of relatable profile! thanks so much for the feedback. xo here are a bunch more week of outfits, too, if you’d like to read: https://cupofjo.com/category/style/week-of-outfits/
agreed! I am a city government worker too and it made me smile to see that Kayla’s among our ranks :)
@Jo – I revisit Week of Outfits posts (and house tours) alllll the time! Definitely some of my favorite content. We’re hoping to buy a house this year and I keep thinking about decorating it with “would it be worthy of a CoJ house tour??” in mind!
This was already shaping up to be my favorite week of outfits and then I learned she works at NYCEM! I work for NYS in health emergency preparedness and resonate with that last paragraph so much. The EP world is changing to meet the needs of our current moment and an injection of women leaders is helping to spur those changes (in my opinion ;)
I love that, Rachel!!!! Big thanks to you and Kayla for being leaders in this way!
Very interesting I lov it
I have a similar green blazer and it’s one of my favorite pieces to wear with jeans.Will absolutely be stealing the idea to pair it with some loafers – these are gorgeous! Love the orange dress too!
Going to find myself this exact outfit! So chic!
Beautiful taste and style!❤️
How cute is she! So stylish.