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What If We Stopped Worrying About What’s “Flattering”?? – 5 Women on The Outfits That Make Them Feel Great

This week, I was looking for a good comfort-watch TV show – you know, a show where you already know what’s happening so you can pay half-attention and there’s no love lost if you accidentally dose off in the middle – and I landed on What Not To Wear, which I loved as a kid. Surprises! Money! Makeovers! Reveals! I remembered it being so glamorous and fun…but it hit a bit differently as an adult.

It felt kind of mean – every contestant on the show is delivering a master class in “smiling while feeling really sad and uncomfortable” – especially when compared to the makeover shows of today, which are admittedly WAY more about building someone up instead of, you know, ambushing them in an incredibly public place, telling everyone that their friends hate their wardrobes, throwing all their prized possessions in a trash can, and forcing them to stand in a mirrored room while two beautiful folks tell them how “big” and “rectangular” they look.

Every episode really focused on figuring out how to “flatter,” but the rules felt really arbitrary – when one guy wore oversized outfits, they bawked at him and called him “chicken legs,” but when women wore similarly-sized clothing, they were immediately told that it made them look enormous and that they instead needed to be taught how to wear things that flattered them.

That word has always brought up a little bit of controversy here on the blog – because honestly, what is flattering? The What Not To Wear definition was basically “things that make you look smaller and like you have an hourglass figure,” which leads me to be like…with that extremely specific and kind of unachievable definition, NO WONDER WE ALL HAVE SOME SORTA BODY ISSUE. Ryann’s post this Wednesday struck the deepest nerve with me and it seems like a lot of you related, too.

So this week, I wanted to update the 2021 definition – almost two decades after WNTW – and state, for the record, that flattering pieces are the ones that make YOU (or, in this blog case, the EHD team :)) feel best. I look back at all the time in my early twenties trying to draw attention to my waist or trying to make my boobs look balanced with my wide hips and now I’m just like…why???? So some boy who lives with a million roommates and sleeps on a mattress on the ground will notice? Why did I spend so much time concerned with the traditional definition of “flattering” and worrying about scaring folks off if I didn’t wear something waisted? (“Oh gosh, no, this flowy top/dress will make me look like a tent,” – me, 2003-2019ish, forgetting that tents are always fun AF!!!) How many fun pieces did I miss out on wearing? How many parties did I spoil by standing in the corner because I wore something that I thought was cool, but then felt was unflattering? Why did I let 2 TV hosts from 2003 shape my opinion on myself?!?!

To that end, this week I asked the team to show me the outfits that made THEM feel like their coolest, happiest, most powerful self. None of us bought anything new for this post – we just wanted to show you the things that make us feel like we’re on top of the world. The team picked wide, fancy dresses and comfy rompers and tight leather pants and loudly printed pieces and it was just fun for me to see all of us proudly rocking our favorite things, without worrying about some self-imposed fashion rules. LET’S LOOK AT HOW CUTE MY TEAM IS, OKAY?

From Emily

Striped Dress

I call this my “Mrs. Doubtfire” Zoom dress. Here’s why – it’s so cute but so baggy that I can throw it over pajamas at a Zoom moment’s notice (which I do). Then I throw it off and spend the rest of the morning in my PJs. Then I change into my workout clothes and when I come back I often have to throw it back over my workout clothes (including over the t-shirt) for another Zoom call – looking all pulled together. I feel like Robin Williams playing two characters, but I don’t have to take off ANYTHING underneath – just throw it over!!  I’ve worn it probably 25 days since I got it. It has GREAT puffy sleeves, an incredibly good cut that drapes so well with contrasting stripes. I can dress it down (flip flops) and up (mules – if I ever wear heels again). I can wear it in winter and summer (and spring/fall, duh). I wasn’t going to get it until I tried it on at my friend’s house (who works for The Great) and I was like “oh shoooooot”. It’s a splurge, but I know historically I wear The Great’s clothes for years and years (their older stuff was remarkably timeless) and will do the same with this one as well. It makes me feel happy, pulled together, and comfortable.

From Jess

Dress | Sneakers

I am pretty sure I found this brand, Lucy Paris, through one of you and to whoever it was THANK YOU! It’s been a hot minute since I ordered a dress online (or any clothing for that matter) that fit like a glove as much as this dress (and was under $100). Those puff sleeves have just the right amount of volume, the neckline is both modest yet sexy, and I love the length on my almost 5’4” frame. I feel like I could wear this a ton of different ways both dressed up and down (hi sneakers!) which makes it just an ideal purchase that will last me. Honestly, it just makes me feel pretty and feminine which is something I haven’t felt in a long time and I didn’t realize how much I needed it.

Jeans | Clogs

This is by far the most “Jess outfit” out there. I wear a variation of this (switching out t-shirt colors) almost every time I leave the house. Do I dream of dressing in bright colors and fun/cool patterns? Sure. But I think I’m a little averse to dressing “loud.” I think it’s both that I’m a casual person and also that I am afraid of bringing too much attention to a body I’m working on loving as-is (Ryann’s post was beyond relatable to me too). Anyway, my love affair with these jeans is very real. I literally am excited every time I slide them on. I am heartbroken that t-shirt is no longer available and those clogs just make me feel cool. All in all an easy yet stylish enough outfit that puts me at ease. 

From Ryann

Romper | Flats

I am still at home 80% of the time and I just can’t quit being comfy. I bought this thermal romper after seeing it on Ali Tate’s instagram and it really is the perfect lounge-around-the-house-but-make-it-cute piece (but heads up, it runs big so definitely size down). Of course, I am wearing it with my trusty tan ballet flats that I can’t get enough of and when it starts getting warm again I can definitely see wearing this to the beach during sunset (cause I totally do that all the time…HA).

Dress | Loafers

When I tell you I feel good in this dress, I mean I feel BANGIN in it. I love how flowy it is and the sleeves are super cute and whimsical plus I can’t say no to a plaid pattern. I love wearing it with my favorite loafers for a “sophisticated” look but it’s also really cute with sandals or platforms. I can’t wait to wear it all summer long!

From Mallory

Dress | Shoes

I’ve been LIVING in this dress for 2 months now and it’s the perfect winter to spring to summer transition dress because it looks GREAT with tights or boots by itself (I usually wear it with boots that look like this but tbh I couldn’t find them and they’re not available anymore but just so ya know). I was actually really happy with how they looked with these lil heels though and I can’t wait to wear this dress with these shoes to make it more of a summer dinner or a –how do you say– brunchy look 🙂 Anyway, I wanted you guys to know that this dress is great because it’s not tight ANYWHERE but comes in at the waist to make it feel like you’re not drowning in fabric. Plus it’s lightweight and I like that it’s long-sleeved so I can secretly wear my apple watch under it without feeling like I’m ruining my outfit (I love the apple watch but she aint that cute). All in all, I love this dress I love it so much.

Top | Boots

This shirt was an impulse buy and boy I did not anticipate how much I would wear it. It’s super comfy and if your girls are smaller up top (like me!) you don’t have to wear a bra because there’s a lot of fabric up there. It’s comfy AND cute so that’s a real win. I am fully on the leather pant train and I’m not planning on getting off. These pants I bought from a thrift store I think?? I honestly can’t remember but I wear them so much that they’re starting to look uh not great, so I’m considering splurging on a nice pair that will last me forever like this one or this one. Just know I am on the market so if anyone has recs, I’m all ears. Lastly, I’ve had these snakeskin boots for over a year and they’re now formally known as my “walking boots” because they’re in fact comfortable enough for me to walk for long periods of time in (great for bar hopping/sightseeing if I do say so myself).

From Caitlin

Top | Bottom

Shockingly, these are NOT pajamas and I wear this outside (!!!) in front of people (!!!) on purpose (!!!). I think it may because I’m nearing 30, but all of a sudden, I like…really don’t care what other folks think? When I was younger, I never would have worn something like this – my mind would have been a full cacophony of is it too weird? too loud? unflattering? can only thin girls wear this? am I cool enough? – and now, I have a new mantra: IF IT’S NOT FUN, I’M NOT WEARING IT. I love a bold print and a matching set, but this top and this bottom are my personal favorites because they’re made of eco-viscose, which literally feels like wearing a cool, silky waterfall. I just really feel like ~myself~ in this, which is great 🙂

Dress

Weird esoteric phobia time: I really DO NOT like bellybuttons (for reasons I still don’t understand today) and so one of my least favorite things is when I wear something form-fitting and get a bellybutton imprint (someone please chime in and confirm that you know what I’m talking about!!!). I grabbed this smocked + sleeved dress for a July baby shower and was a little wary about trying on something so tight – my quarantine 15 and broken back extra 15 are real, and clearly I still have some personal self-acceptance work to do!!! – but the special details, like the puff sleeves (you can wear them up, too), the fruit print, and the banana-shaped beads up top just made me happy and excited to return to the world of in-person gatherings. (And there’s no bellybutton imprint!!) It just feels like a fun celebration/party dress as I start to see my other fully-vaccinated pals again over the next few months 🙂

And there you have it – some of our favorite outfits that make us feel like we can take on the world. I know it’s been a pretty introspective few days on the blog with a lot of self-reflection – and this post was no exception! – but it just felt like a fun and fitting way close out the week. Hopefully, you got some outfit inspo, or read a review of a piece you’ve been eyeballing, or at least got to know the cool ladies I work with every day a little bit better…and now you also know what to look for when you spot us in the wild 🙂 NOW CHOOSE YOUR FIGHTER. WHO IS BEST DRESSED?

JUST KIDDING…have a great weekend. xx

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Karen
20 days ago

Caitlin, I love that both of your prints are fruited!
There is definitely a “you only live once”/“I’m going to do whatever feels good to me” feeling boiling inside me after this last year. Clothing seems like the right place to start showing that feeling to the outside world! Dun-dun-dunnnn!

Sheila
20 days ago

I’ll take this as a suggestion to pay a little no-stress visit to my closet with a “what makes me feel good,” mindset rather than, “OMG, what can I wear that still fits 😬!”
My Zoom dress-up trick is: SCARVES! I’ve got a bunch but rarely wear them because they don’t stay put when I’m running around. But there’s no running on Zoom and they dress up anything from an old T-shirt to a workout tank that I would never in a million years wear in public! These days, there’s always a scarf or 2 draped over the back of my chair.

Rusty
20 days ago

I haven’t been ‘allowed’ to choose my clothes for years (yup, Coercive Control is a real thing, people!) and haven’t worn clothes that are really me for aeons.
However, I have bought a few things in the last 2 years that I love (and got approved) and since my wardrobe is really small now, I’ll only very gradually get more ‘me’ items over time.
A small wardrobe is SO much better!!!

Where I live has been 99% normal living during Covid coz we eradicated it over a year ago, so actual in-person shopping has been no issue…buuuuuut, we’re currently in a 3 day city-wide lockdown due to a case that escaped quarantine and turned into 3 cases. I’m expecting more cases and an extension of the lockdown, but people here generally do the right thing and those who are numb-nuts are fined, e.g. not wearing a mask.

Once I’m “free”, I’ll be learning how to shop in person (I will not support Amazon for many reasons) without a car and I’ll be buying “me” clothes that I love, one piece at a time and then only things that I need andare made from sustainable materials.
It just is.

Mj
20 days ago
Reply to  Rusty

Sorry, I couldn’t get past coercive control! Can you please elaborate??

DeniseGK
19 days ago
Reply to  Mj

Something abusers do. Rusty has been working the past several months towards personal freedom – all while this stupid pandemic is happening. He’s been so strong and amazing.

MJ
19 days ago
Reply to  DeniseGK

Oh my goodness I had no idea — I hope and pray safety and freedom is on the horizon.

Rusty
19 days ago
Reply to  MJ

Thank you.

Sona
19 days ago
Reply to  DeniseGK

I believe Rusty is female, right Rusty?

Rusty
19 days ago
Reply to  DeniseGK

Thank you for the “strong and amazing”. I don’t feel like that. I actually feel quite desperate for peace. xx

Oh… and LOL… I’m female…it’s a nickname. In Australia, we don’t really have Rusty as a name.

R
20 days ago
Reply to  Rusty

Hearts to you Rusty, and I hope you have a plan in place to get out of your current situation safely

Rusty
19 days ago
Reply to  R

Thank you. I have a plan and then about 3 contingency plans… for me and my scruffy dawg. Less than 4 weeks to go… the most dangerous time…

Elise
19 days ago
Reply to  Rusty

Just a few more weeks until freedom, right? All of us here will celebrate with you virtually. Finally getting out of a bad relationship/marriage is the best feeling!

DeniseGK
19 days ago
Reply to  Elise

Yes! I’ve been thinking in the back of my mind “it’s soon right?” I hope so!

Rusty
19 days ago
Reply to  DeniseGK

It is soon, but it’s scary.

Rusty
19 days ago
Reply to  Elise

Yup, less yhan 4 weeks.
Today’s only just started and he’s being horrendous.
Tick….tick….tick….

Marian
20 days ago

Caitlin, your style is probably closest to mine, which is why I MUST tell you to check out Nooworks. Their prints are amazing and each one is designed by different artists. Their jumpsuits and dresses are so so so comfy, like wearing pjs out of the house. Just trust me, ok?

kk
19 days ago
Reply to  Marian

OMG NOOOWOOORKS!!! I am now obsessed! Thank you !

Amanda
20 days ago

Caitlin – where are your black shoes from? Love!

Sarah
20 days ago

Killing it.
Jess! Please could we have a regular on your fashion?!?
I’m getting those sneakers. Now!

KD
20 days ago

I work in PR and I’m often asked “what should I wear for (insert public appearance / event / speaking opp. / media interview here)?” My reply: “Wear what makes you feel great!” I’ve learned that stuffing someone into a blazer/jacket/suit when they hate wearing suits is the worst thing you can do. Everyone knows what makes them feel confident and, most importantly, what still feels like YOU…and that always comes across better than wearing what “should” be worn.

Christie
20 days ago

My zoom trick is a blazer over my PJs hahaha. I strategically tilt the screen. But lately I’ve been going all out in the cropped target fleece Em recommended and love.it. Like obsessed. No hood, quarter zip, and not too long like the sweatshirts of the 90s/00s. Thanks for the rec, my new spring go to piece!! All of you ladies look lovely, and I think Em is the most relatable to me with the zoom clothes over PJs lol!

R
20 days ago

Love this! I definitely feel that there is an idea out there that as a woman I owe it to society to try to look as “attractive” as possible (with a very narrow definition of attractive) all the time. For a few years I’ve been trying to focus instead on clothes that feel like they take care of me and are not constantly on the verge of betrayal. For me, this has come to mean wearing a lot of men’s clothes because it’s so much easier to find quality, simple clothing made out of good material and not overly trendy. Just throwing that out there as an idea.

Susan S
19 days ago
Reply to  R

What is the “betrayal?” I am curious because it is such an interesting notion. I think a lot of men’s clothing is beautiful. As I watched the retrospectives of Prince Philip’s life I was struck by how beautiful and timeless his casual clothing was. I would happily wear some of those outfits. I also think that there are clothing lines for women that make clothes that feel really good on me, attractive, but not at risk of “betrayal”.

R
19 days ago
Reply to  Susan S

Some examples that come to mind are, skirts that might get caught in the wind and blow up, shoes that get uncomfortable quickly, or a bikini that threatens to fall off. I think it mostly comes down to clothes that make me adjust my movements to accommodate them, instead of the other way around. But no judgement to anyone who likes skirts and heels! I’m also coming to see that I just prefer a more androgynous style and of course that’s not for everyone.

Alison
18 days ago
Reply to  R

Love this so much. But also, biker shorts under all dresses and skirts forever.

StephanieZ
18 days ago
Reply to  Alison

yes always!!

Caity
20 days ago

I normally never click on the clothing posts because as an extremely petite woman I can basically never wear shoes or clothing recommended online. I have basically discovered that size 10/12 in boys basically works great for me in terms of cute sweatshirts or button downs. That said I can’t wear girls or boys bottoms because of the hip/waist issue. Cute shoes are basically not possible for me (I’m size 4.5). In the winter I wear nice boots with two pairs of socks to make them fit, in the summer I wear flip flops. But I really loved this post from just a human loving humans perspective (not for shopping purposes). I really loved seeing you all so happy and confident, and Ryann’s posts were pretty sexy IMO! And I mean that in the most non-creepy way a stranger commenting on a pic of your body on the internet can be lol! Our society tells us our worth is defined by what our body/face/hair looks like, but I say we define our worth for who we are inside and also the power of what our bodies can do. Our bodies can literally grow and birth other human beings. Our bodies… Read more »

Evee
19 days ago
Reply to  Caity

Caity – check out Sam Edelman shoes. As a fellow small shoe size gal, that’s the only store I find shoes in!

SarahT
19 days ago
Reply to  Caity

So true, Caity! (And I’ve found that Target’s Cat and Jack boys size 14 husky fits on my hips and my smaller frame. The regular doesn’t. Might be worth a try for their size 12 husky plus their jeans are recycled materials 🙂

Lola
17 days ago
Reply to  Caity

Check out The Real Real for shoes in size 4.5, they have lots of options. Even if you don’t find a great pair, it will at least introduce you to designers that make that specific size.

Jacki Manley
11 days ago
Reply to  Caity

Yes girl. I’m 4′ 10″ and size 5 shoe. I feel you. I love Matilda Jane because I can wear their girls size 14 and they have such beautiful things 🙂 shoes are always a struggle, but I’m currently loving my kids toms 🙂

Monica
20 days ago

Very nice post! I am trying to raise awareness that we need to #helpindia NOW! We need to persuade the Biden adminstration to release critical supplies like oxygen and vaccines ASAP. The most extreme words we have cannot express how devastating the situation is there at the moment. Please upvote and EHD team, please consider a post or a link tomorrow. Thank you! And please share: https://www.bloomberg.com/opinion/articles/2021-04-24/india-s-covid-19-crisis-means-the-pandemic-is-far-from-over?utm_medium=social&cmpid%3D=socialflow-twitter-view&utm_campaign=socialflow-organic&utm_source=twitter&utm_content=view

Rebecca
19 days ago

Who knew working from home entailed so many wardrobe changes?? Loved Emily’s idea of a dress to throw over anything. I generally go from pjs to something decently respectable for preschool drop off back to pjs or sweats to work out clothes and maybe a nicer top thrown in for the Zoom meeting. That dress could cure at least a couple rounds of costume changes.

DeniseGK
19 days ago

Caitlyn, there are adhesive belly button covers out there. You can also use adhesive nipple petals/patches or the small round bandages.

Michelle
19 days ago

This may seem like an unlikely combo but I am half a tee/jeans/birks kind of person and half eccentric-art-teacher/Mrs.-Roper-from-Three’s-Company (well, maybe I’m realistically not that out there but she is who I envision as eventual style goals). After living for over a year only exercising my tee/jeans side due to the pandemic, my Mrs. Roper side has been awakened by Caitlin’s fabulous two-piece outfit so she gets my vote!

19 days ago

I’ve come to despise the word flattering and all it represents, because it’s rooted in fat-phobia. The fear that looking any larger than you are, or not as small as you could, is the ultimate thing to avoid. We were/are so terrified of this that we spend so much money, time, and energy trying to camouflage or create an illusion. It’s ridiculous when you think about it. Why does big equal bad? Who decided that? Anyway, now I focus way more on texture, color, and pattern with my outfits and it feels so much more fun and creative to get dressed. (Although I definitely still battle with overcoming my own internalized fat phobia – it’s so ingrained!!)

dianne
19 days ago

What I loved most about this post was the smiles and expressions on the faces of each of you when you wore something you love.

Eve
19 days ago

Hi guys! As per usu, I loved the post-I always find new great brands from these, and most are accessible for most of us…however, if I could make one suggestion, it would be when you post about an item/brand if you could also post what sizes they go up to. Several times I have gotten really excited to check an item/brand out only to be sad that they don’t go, let’s say, past size 12 or 14. Some of us are 16 and up. If I know they won’t have my size then I can choose whether I want to check it out anyway and also not get disappointed. Hope this could be possible to do in future posts? Thanks-love you all!

Janis
19 days ago

I love that you all posted your favourite dresses, I must say great choices, all of you look great.

Jess
19 days ago

Great post that definitely has me rethinking some things! Love what this blog is doing.

Melissa
19 days ago

I’m sorry, but I think this is just a bunch of hooey coming from someone in the design/aesthetic field. To me, it’s like saying having a too small rug or high water drape doesn’t affect the look and feel of a room. Proportions matter. And yes, I think you can have it both ways- dress for your personality, keep your overall vibe but still work your best angle.

Kristin
18 days ago
Reply to  Melissa

I think that’s the wrong analogy. It’s more that sometimes you just love the cozy chair (or throw or pillow or art by your child – pick your emotionally-attached decor item) that’s not the most attractive but is comfortable and well-loved. Sometimes the look isn’t the most important thing, in decor or in fashion.

Jessie
17 days ago
Reply to  Kristin

I also think it might be like walking into every room as a designer and telling the homeowner they’re doing it wrong unless they’re doing everything they can to make it feel big, bright and airy. Maybe your style isn’t big bright and airy? Maybe you want cozy and eclectic? Maybe you just want to buy what makes you happy and not worry about whether you’re maximizing the size of the room? The right size rug and right length drapes are more equivalent to buying whatever clothing you’re going to buy in a size that really fits you, and has less to do with whether it’s the right rug/dress to begin with. No matter what you buy, fit is important – but the clothing itself doesn’t have to be designed to make you look as thin as possible in order to fit you correctly.

Kristin
19 days ago

I really enjoyed this post. This is something I’ve been thinking about lately. I grew up with a mother who was (and still is) all about what’s flattering, or more precisely, what *her* idea of what’s flattering is (and she feels free to comment on it – at Easter she spontaneously pulled me aside to tell me my dress was “great – better than anything else you’ve worn for the past few months – seriously” – not really the compliment she thought it was, by the way; sadly it make me like the outfit a little less, as that thought hadn’t entered my mind until then). It’s taken me to my 40’s to realize that dressing in the most flattering way isn’t always the goal, and sometimes you just love the comfy tent-like dress.

Sara
18 days ago

Team, you are SO ON POINT this week. Every post I’ve exclaimed to my husband, they did it again! Bravo. After 3 kids and minimal contentment with my bod, I have no clothes that I feel that genuine spark of “YES this is me” in. So sad. And I’m ready to change it and seek out not what is most flattering but what truly makes me feel lost alive. Thank you for this inspiration and your vulnerability. You’re all the best.

Sara
18 days ago
Reply to  Sara

*most* alive not lost, but alas 😂

Alison
18 days ago

I remember reading this article with Stacy London a million years ago and realizing even she didn’t like the fact that they handed out rules on how to dress. I really have appreciated her honesty and evolution over time, and she has fantastic, bold fashion now in how she dresses. Big fan.

Kelly Kestler
17 days ago

I would like to submit my own version of this: the Athleta Presidio dress. My husband calls this my mumu, but the fabric feels amazing, it never wrinkles, doesn’t attract dog hair, and I did not take this off during my pandemic summer of 2020. I have since purchased a second one so that one can be my “house dress” and one can be my “going out dress”.

Alec
17 days ago

So some boy who lives with a million roommates and sleeps on a mattress on the ground will notice?”
I shrieked out loud at this. I wish I could go back to my 22-year old self and just be like “THESE BOYS ARE NOT WORTH IT”

Cheryl
17 days ago

I was watching Amber Lewis in her cute but cropped and boxy white pants over on Instagram. The video really captured her funky style and her pants looked fresh and flattering. But the still photos were way more awkward. There wasn’t a really flattering shot in the bunch. Some clothes have a vibe and an energy, you can’t capture.
I sometimes am struck by photos of myself that make me cringe, like, does that outfit really look like that? Usually nope.

Erin
16 days ago

It’s so true. I look at my closet of work clothes (that I LOVED) from pre-pandemic and just think WTF?!! Why did I ever put myself through all that weird discomfort and performance (and TIME, and MONEY)? I don’t think there’s any doubt we’re going to look back at this as a huge moment of cultural shift in women’s clothing… maybe it’s because I’m in my 40s, but there’s just no universe in which I’m willing to go back to all the uncomfortable things… And it turns out I am just as professional and competent and good at what I do without heels and a silk blouse and blown-out hair….

Jess
15 days ago

OMG BELLYBUTTON IMPRINTS DRIVE ME BONKERS

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