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
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
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.
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
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).
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
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.
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
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
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
The post What If We Stopped Worrying About What’s “Flattering”?? – 5 Women on The Outfits That Make Them Feel Great appeared first on Emily Henderson.
from Emily Henderson https://stylebyemilyhenderson.com/blog/5-women-on-the-outfits-that-make-them-feel-great
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