A Week of Outfits: Samantha Elise
Samantha Elise began Instagramming her outfit photos just for fun while in high school in Missouri. People took notice, and she’s now working as a stylist in Chicago. “I’m finally getting to a place where I can celebrate who I am and what I do,” she says. “It feels liberating.” Here, Samantha shares five looks she wore in a week and talks about ballet, growing up adopted, and where to find perfect blazers…
Shirt: Everlane. Sweater: ASOS. Jeans: Madewell. Glasses: Jimmy Fairly. Watch: “hand-me-down from my mom.” Purse: vintage.
“I call this my ‘no-fuss uniform.’ The jeans are loose, so I can eat happily. It’s layered, so I can wear it in lots of spaces, like a museum where the AC is blasting or with the sweater thrown over my shoulders outside if it’s warmer.”
Vest: Madewell. Pants: Naked Wardrobe. Glasses: Jimmy Fairly.
“You can wear a vest by itself or over a T-shirt or turtleneck. Just play around and embrace the trial-and-error of figuring out what feels good. I don’t know anybody who comes up with their favorite outfits the first time they put something together.”
“My sister drew this window tattoo. It shows my apartment in Boston, where I lived for six years while dancing for the Boston Ballet School. I danced ballet from age three to 19. I loved it for a long time, but the transition from doing it locally to dancing for a company was surreal. It’s similar to how the media portrays it — very intense and competitive. The whole atmosphere felt like Black Swan.”
“I wore a leotard eight hours a day, six days a week. The only time I put on real clothes was Sundays, my day off. I’d put together outfits and go people watch. Boston has a ton of colleges, so I’d see cool, inspiring streetwear. I also saw people walking around in refined office wear, like amazing suits and dresses. It felt so different from St. Louis, where the clothes leaned towards comfort, like sweatpants and Uggs.”
Tank: Madewell. Skirt: Madewell.
“I’m adopted, and as a kid, I thought a lot about my identity. My whole family is white, except for my other adopted sister who’s Black and Puerto Rican. And ballet is a predominantly white space — I was the only Black girl during my time at the Boston Ballet School. For the longest time, I was really quiet because I couldn’t figure out where I belonged. But I always expressed myself through clothes.”
“You know that TikTok video of horses running free on the beach? That’s how I felt the moment I stopped dancing. About two weeks after leaving the program, I chopped my hair off. To meet the company uniform standards, I’d had to heat train my hair, which left it damaged. I also started getting tattoos and committed to dressing myself every single day. Back then my #1 thing was resisting anything skin tight. It felt too similar to a leotard, and I wanted nothing to do with that.”
Blazer: thrifted. Shorts: Dissh. Poplin shirt: Gap Factory. Loafers: Dole.
“I love a good blazer — they instantly make me feel confident. The best place to get them is a thrift store. I’ve found vintage Ralph Lauren blazers for $5! And always search the men’s section. Men’s blazers are the best because the shoulders are huge; they add drama and feel so chic.”
“As a kid, I shopped for clothes at Goodwill with my mom. It felt like a big treasure chest, and everything was affordable. In middle school, I’d find patterned blouses with massive shoulder pads and pair them with my Jordans. My #1 thrifting rule is to never skip an aisle. These days, I like to walk in with a playlist that’s at least an hour long. Then I’ll listen to it as I comb through every single piece of clothing. It feels therapeutic.”
Shirt: Target. Jeans: Madewell, similar.
“When you understand denim washes, you can make denim-on-denim look effortless. I wore this outfit 50 times this summer. People think it’s a set, but the jeans are Madewell and the top is from an old Target collab that I found on Poshmark for $10. Still, because they’re both a medium wash, they work together.”
“I’m an intuitive dresser. Before choosing my clothes, I check-in with myself. If I’m not confident, I’m going to put on something that helps me feel confident. And those pieces change over time. For a while, I loved bolder pieces, like fire-truck red pants. But today I like to wear neutral colors with loose silhouettes. They just feel like me.”
Thank you so much, Samantha! You are wonderful.
P.S. More people share their week of outfits, including an architecture professor with a pink power suit and antique dealer with the best button-downs.
(Photos by Kendra Lynece for Cup of Jo.)
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95 commentsThis is one of my favorite week of outfits posts ever. I have always struggled with wearing oversized silhouettes, I’m petite and it seemed like I could never get the proportions right. But the oversized denim shirt she wears in this really stuck with me and I just bought one to wear with things like miniskirts so the effect isn’t too 2010s
amazing week of outfits! would you mind sharing where your nesting rings are from? i have been looking for something like those for ages…
OMG my favorite Week in Outfits ever! Thank you for sharing!
I feel like people always hate on Boston for being so unstylish so loved that take!
She’s a stunner and each outfit was fire.
I really enjoyed this week of outfits post and reading about Samantha’s experiences. Samantha, your outfits are terrific. I like thrifting too. I have an old cashmere camel-colored men’s long coat that I love. I also found an old women’s red cashmere coat with great big buttons. I really enjoy wearing these coats. I love the vest and pants combo. I haven’t found a vest that looks good on me, but your version inspires me.
As a former professional dancer, all of her words hit deeply. I know there is more depth and trauma under the words. Ballet/dance/gymnastics/figure skating is magic, but at the highest levels, it is mostly harmful. I don’t know a single dancer from my former company who didn’t require extensive therapy. Reintegrating into the “normal” world after reaching that level is so disorienting. I also don’t think everyone would appreciate how radical it can feel for a former ballerina to wear clothes that make the body bigger (shoulder pads, baggy pants, even a simple thing as layers). That act alone is liberation from the culture of ballet. Kudos to Samantha – you are on your way, love.
Hi Mo! I sat with this comment for a minute and can’t thank you enough for these words. Your words made me feel even more seen as the transition out of ballet continues.
Hands down my favorite Week of Outfits to date. I am positively riveted by the bits and pieces of Samantha’s story – her incredible fashion sense is the icing on the cake. As a fellow (brown) adoptee in an all white family, I empathize with the search for true identity. Thank you for your candor, Samantha!
this is one of my all time favorite “week of outfits” I love Samantha’s style so much and feel energized about re-looking at my own wardrobe and mixing pieces up differently. love love love. i immediately hit follow
My favourite as well!
Wow, Samantha has this magnetic draw that pulls me in and wants to know everything about her. Saying that she is beautiful seems so shallow. It’s like I can feel her energy, her spirit in photographs alone. Everything she said has inspired me to thrown down my shlubby ways and pull together outfits so that I can shine more brightly!
Gosh, she is so stunning! Chic, accomplished, confident. Can I be her in another life??
Love her style and the story behind the window tattoo!
I love self-expression through clothing and body art! I love that you’re freed from a routine that no longer service you, and that you are sharing your beautiful stylish flare with women looking for how-to’s in the steadily evolving world of fashion.
Ahhhhh she is so cool!! I’d love to see an apartment tour too
one of my favorite COJ posts by a million miles! samantha, i would read your memoir in a heartbeat ♥️
Love this so much. Thank you for sharing your style and inspirations.
Samantha, I loved your story about finding freedom, confidence, and belonging in your next chapter of life. Beautiful!! Loved your wonderful, inspiring outfits too! Very much relate to the looser, less constricting feel of things these days. I’ve just put on my double denim look, and I’m off to the farmers market. ;-) XO
Is it coincidence that I just subscribed to Samantha’s Substack yesterday and then saw this post or is it meant to be? I felt a similar relief when I quit my career in classical music. The pressure is just so intense. Also, I’m in St. Louis and it is a regrettably casual town :(
Loved reading this!
She’s beautiful – love her style and whole vibe!
Love, love, love. Every outfit is just yes! And the stories and feelings behind your approach to dressing, it is artistry.
I love this one! I would wear all of these outfits!
MY HEART IS FULL. Thank you for this feature and THANK YOU ALL for the kindest words and messages. The younger version of me who longed for community feels so loved by this one on Cup of Jo.
Love it all – the clothes, your story, your thrifting advice!
Love this! Style feels sophisticated and accessible. Basically want your whole wardrobe! Love the career shift too.
I always search vintage wool sweaters in the mens section! TBH, I’ve been starting to shop more mens clothes in general because the sizing is more consistent.
Thank you!! The next time I go thrifting I will check out the men’s blazer section. Not trying to generalize, and I’m sure many, many men read COJ, but if there is a woman shopping the same section, I will ask her if she’s a COJ reader!
Samantha, When my daughter quit ballet she said “I need to run” – your running horses on the beach analogy is perfect. Such a feeling of FREEDOM!
LOVE LOVE LOVE – superb style and I’m inspired to go thrifting with a one-hour-long playlist :))
Love her style!! I’m expecting a baby in early November, but after that I plan to also commit to dressing myself every day. I’ve worked from home for about 5 years and I am SO sick of leggings!
Maybe you’ll embrace the house dress? One of life’s little pleasures!
She radiates style. I want to recreate her looks!
Best thrifting advice ever: an hour long playlist! Gorgeous style – thank you, Samantha!
BRB, gotta thrift some men’s blazers…
Thank you, Samantha. You’re inspiring. I am adjusting to big life shifts in the last 18 months, newly widowed, cross-town and downsizing move, goodbye to my 17 YO pup, at 68 merged law firms and am rebooting my work world, chopped my grey hair. Just about to update my (now ill-matched, overlooked and tired wardrobe) starting today. So many good thoughts from you about freedom, being the “only”, choosing with care and honoring your feelings. Lovely. And yes, a denim post please! And a week of outfits from a chic 60s girl would be great!
So many changes! I wish you the best in this new chapter!!
I hope you find some new threads that match your next chapter of life – exciting! Those are huge life shifts you’ve had and sending you a virtual warm hug/compression blanket wrap style. I like following @lindavwright Linda Wright on IG for her stylish looks (I think she’s in her 70s) and there’s a beauty post here on Linda Rodin who has some great style. Take the time to treat yourself nicely and hope you have fun doing it.
Thank you Susan. Give yourself grace in the process of refreshing your wardrobe. I pray you find moments of joy throughout and wish you the best as you navigate this new chapter.
My absolute favorite Week Of Outfits. While my style doesn’t align with Samantha’s I feel like I could step into everything she’s wearing and feel great about it. I also enjoyed her story around the influences of her style.
Love the look. Loose fit has a chic vibe that fitted doesn’t. I agree with blazers. Thank you for the tip. I will check out the men’s section for blazers.
I would love a post about Samantha’s job! I’ve never met a stylist IRL—it seems like a job people only have on TV/movies. What is it actually like? What does it entail? As a fellow Chicagoan, I’m also really curious about what it’s like to be a stylist here. Chicago has always struck me as a casual/comfort kind of town (one of the things I love about it). What’s the styling/fashion scene like here? How does it compare to other cities?
Same! Also would love to know good places to thrift in Chicago. My very favorite place in Logan Square closed down and now I live in Edgewater and have found finding a new place challenging.
Wally, not sure about clothes, but the Brown Elephant in Andersonville is supposed to be a lot of fun. I like Elliott Consignment in Lakeview. Prices are higher than thrift, but good quality stuff!
Ditto! Esp someone who has relatable style and not too high fashion.
Thanks, Erin. I was disappointed by the Andersonville brown elephant – maybe should try it again.
Wow, LOVED this one!!! Selfishly, I like how these Week of Outfit posts help me think about my own style. This one has me planning my next Goodwill hunt for blazers!
I’m bookmarking this one, love her style! Appreciate the thrifting tips too. More from Samantha, please 😊
Wow, this is my favourite week of outfits ever. she’s not only stunning and the most stylish person I’ve ever seen, but I love that fashion functioned as resistance and is such a core way of expressing identity for her. I love it. House tour?? More of her words, please.
Love her story and the care that radiates through her attention to details and accessories. I get the feeling of a whole, genuine person, and it shows in her style.
I LOOOOOOOOOOOOOVE this series. and this one is so great! love these outfits, and such a lovely story to read. that window tattoo is so good.
This woman has style, wow! Thank you for sharing!
Wow, that jacket! I adore it. Samantha, you are fashion inspiration. I love to see people who are comfortable in their own skin. Wishing you every success in whatever you do and thanks for sharing your wardrobe and your thoughts. x
“When you understand denim washes, you can make denim-on-denim look effortless.“ please! I want to understand denim washes! this could be its own post.
Love love love
I loved this. She feels wise beyond her years. Joanna, I love how these week of outfits also give us insights into the person behind the outfits. I found it so, so interesting to read about how Samatha came to care about fashion (committing to dressing herself every day) and how she chose to dress in this style (wanting to be far from a leotard). I just loved this whole post!
Cheers to the freedom you feel now, Samantha! The feeling of horses on the beach!, and the freedom to express yourself with your hair, clothing, and tattoos. Your style has inspired me. Thank you for your thrifting tips too! Would never have thought to check men’s blazers and now I just really want a spare hour and a great playlist!
“ I’d find patterned blouses with massive shoulder pads and pair them with my Jordans.” You were this cool in MIDDLE SCHOOL, Samantha? Clearly destined to be a stylist.
Wow amazing style and stories! Loved hearing about her reflections on ballet. Awesome tattoos too! Can we get a house tour from Samantha soon?!
Ok i am confused about large button downs in everyday life. A photo posed in a way where there’s a certain position or things are scrunched up or pulled to the side, looks great. But esp as a petite person, how are you actually wearing them and how does it fall? Half tucked in the front? untucked and open in the front? buttoned? i’m confused…
I think you just embrace large button downs not necessarily being flattering at every angle / in every pose – whatever “flattering means.” That you embrace them because you wanna wear them and you feel comfortable and don’t have to think about it. Whether it’s half tucked, etc I would try different options and see what works for you. Or, if you’re not comfy with it, maybe it’s just not your style and that’s OK. As a full figured person who is 5’9, I would imagine it’s easier to make this look good on a petite person … think the Olsen twins and their oversized clothing being chic.
i’m petite (5’3″) and I pretty much treat big button downs like a cardigan – untucked, sometimes buttoned part of the way down from the top, kind of how Samantha has it. Sometimes I knot at the waist if it feels like too much fabric at the bottom. I personally have never been able to make a half tuck work, it always ends up looking messy on me. :,)
I am almost in a large mens button down. I wear them in so many different ways – as an oveshirt opened over a t-shirt or body suit, buttoned up all the way with baggy pants etc. I’m a busty woman with a very small frame and I tend to love things oversized and not close to the body, that are not necessarily “flattering” because who cares about things being flattering anyways?
I like unbuttoned and open, it’s comfy and unfussy. Any garment that requires a special tuck (or a special anything, like ‘this top can only be worn with this bra’ kind of thing) is a no for me. I love all of Samantha’s button down looks! That denim, dang
and I totally agree with the others, f*ck flattering! A nonsense term
There is also a shirt called The Big Shirt that Ralph Lauren sells, you can find a lot of them on eBay. It’s like the perfect oversized fit for women (they also make it for men). I have a denim one in M that is like a men’s size L in that it is huge, but it’s proportioned slightly different and is so so perfect. Recommend!
I’m 5 feet tall and love an oversized button down. Things I look for are a drapey/ softer fabric (vintage/ second hand usually takes care of this since they’ve been washed and worn more) that hugs your shoulders rather than stiffly standing up and straight hems rather than shirt tail hems so they don’t seem as long proportionally to your body. Also try buttoning just one or two of the middle buttons and leaving the rest unbuttoned. Hope you find a way that feels true to you!
As a fellow lover of neutral colors with loose silhouettes, I love this! The way she puts outfits together is perfect. I’m inspired!
Omg! Hiiii, Sam!! I worked part-time at the dorm at Boston Ballet while Sam lived there. :) So fun to see her pop up here! Loved reading about your journey! :) – Janae
This is crazy! Hi Janae!!! I hope you’ve been well. So funny we cross paths again here.
This is so gorgeous and the layers are so complex yet complimentary, I mean this in the materials she wraps herself in and the presence of her true self. Thank you for sharing her outfits and thoughts with us. I love hearing about and seeing other women find themselves through fashion and life, it makes me feel part of a greater community.
All the layers, materials wise and identity wise this is an incredible ensemble. Thank you for this story, it’s so gorgeous and touches on so many things that define style and class.
I have been loving the oversized tops lately (like that Everlane one, swoon!!) but I have the hardest time figuring out which size to order when I’m shopping online. I wish retailers would add a separate size guide for an oversized fit! I don’t know if there is a solution to this but if anyone has tips – do share!
Sometimes a retailer will have the garment’s measurements. If you know your own measurements, then you can tell just *how* oversized the shirt is. I also read the reviews (if there are any) and if folks are saying it’s WAAAY oversized or not oversized enough, then that is also information that can tell me how much bigger to go or not. Hope that makes sense.
Oh my gosh, she curates a Pinterest board every week called “everyone’s invited”!! It’s a vibe ✨ https://pinterest.com/samanthaaelise/everyones-invited/ I love everything about this interview. Thank you for sharing your story and your style! The analogy about feeling freed after being tied to ballet for a lifetime resonated with me.
“Everyone’s invited”?! Will absolutely be checking weekly. Thank you for sharing💕
Ooooh thank you! Totally following!
Thank you! This is what true style is all about! Following now!
This board is stunning! She has such vision.
Love her vibe and her style!
I really love your style, Samantha. You look chic and comfortable and confident. And I feel you so much on having to do a hard pivot away from ballet aesthetics. I also grew up in that hard core ballet world and I mostly loved it but to this day can not participate in any balletcore trend. No ballet flats for me ha. Thanks for sharing your inspiring thrifted ‘fits!
She’s so coooool!!! love the fits.
Oooooh she is fabulous in EVERY WAY! this is a really inspiring post (they all are but…) she’s a stunner. The ballet parts were fascinating. And Boston actually is a hot bed of interesting dressing, for sure! We spent a week there this summer, (my tween girl & I), from the LA area, and we lovvved people watching, on the metro, on the waterfront, all the tourist haunts and also the college areas. Great thrifting there! Boston has a lot going on! Thanks for this gorgeous look at a very cool girl. She’s going a long long way!
Great content! Leaves me wanting to know and see more!
I loved the discussion of ballet. There seems to be something about dance that really consumes a lot of childhoods and then leaves people reeling after. Also, love seeing clothes pulled together in a real way that looks wearable and not mannequin perfect. I wish I had her skills!
Samantha is gorgeous! Her style is so cool…love the button down shirt outfits. She makes it all look effortless.
I actually copied this quote because I loved it so much: “You know that TikTok video of horses running free on the beach? That’s how I felt the moment I stopped dancing. About two weeks after leaving the program, I chopped my hair off. To meet the company uniform standards, I’d had to heat train my hair, which left it damaged. I also started getting tattoos and committed to dressing myself every single day. Back then my #1 thing was resisting anything skin tight. It felt too similar to a leotard, and I wanted nothing to do with that.” I just love this – maybe because I am obsessed with videos of caged animals being freed, those break my heart into a hundred pieces but then, just knowing that people care so much that they dedicate everything to this freedom, well it puts it back together. I kind of feel like that after reading this! Thanks for sharing.
What a babe! Great style and inner za-za zoom!
“Inner za-za zoom!”…what a great turn of words. I love that and now want to find a way to capture my own za-za zoom and find an opportunity to use it to compliment a friend!
I love your style and the way you tell your story. I wonder if you miss dancing… you probably still do actually! Can I recommend a french movie, about a ballet dancer at the opera who has an accident and changes her life. Sooo inspiring. In English it’s “Rise”, by Cédric Klapich. Love from Paris
I love hearing from a former ballerina. It’s such a shock to move from ballet being your whole life to it being… nothing.
I feel like all these types of posts have transitioned to Big Salad and I miss them!! This was wonderful! Thanks for sharing your style and point of view, Samantha!
week of outfits is 100% a Cup of Jo column, always has been, always will be! we just did sharon Beesley’s the other day, too: https://cupofjo.com/category/style/fashion/
Now here is a stylist I would take advice from! So many stylists I see online are too over the top for every day wear. But Samantha’s style is bold and unforgettable while still being subtle. Love her strategic use of pops of color.