Many women consider jeans and a t-shirt to comprise the comfiest outfit imaginable. But I probably wear jeans and a t-shirt twice per year … less if I can help it. Not that there’s anything wrong with that tried-and-true combo, of course. But it just doesn’t work for me. When I wear jeans and a tee, I feel neither comfy nor chic. Jeans fight my figure, tees disguise my assets, and I end up feeling like a big wad of frump.
But for years I thought that casual just meant jeans and tees, and forced myself to wear them and conform. Eventually, I learned that comfy for the majority does not mean comfy for all. And I spent some time honing my laid-back, casual style into one that is at once unconfining, cozy, flattering, and current. And although none of my tools are all that unusual or hard to procure, I’ve had several comments and questions about my weekend ensembles and thought I’d share my not-so-secret secrets to comfy chic.
Let’s start from the ground up!
Yes, I hear you laughing, but hear me out: I love elongating my legs and heels are best for that. But true heels aren’t generally the comfiest of shoes. A platform mitigates heel height AND makes you taller. These 4″ heels feel like 2.5″ heels because of that platform up front. And 2.5″ is thoroughly walkable, if you ask me.
Hark, is that more laughter I hear? Once again, the argument is for both comfy and chic … and wedges provide more stability and support than heels while still elongating the leg. Because of their chunky wedge and sizable platform, these booties are fantastically comfy … well, by my standards, anyway.
I realize that for true comfort, we’re looking at flat shoes only, so here’s my rule of thumb: Flat shoes or boots get worn with higher hemlines (above-the-knee skirts and dresses) OR superlong hemlines (floor-length skirts). They can also work with leggings and tunics.
Speaking of which …
Saw THAT one coming, didn’t ya? Yes, indeed, I live in leggings on winter weekends. But the cropped styles serve me well during warm weather, too. Leggings are the sleek, chic version of sweatpants: Stretchy jersey material, flat and non-squeezy waistband, easy to move around in, and show off your shapely gams. I love, love, love my leggings.
Again, here’s an elegant alternative to sweats: Soft, stretchy, and unconfining but also provides elegant drape and feminine style. My jersey skirts are floor-length, but you can nab them at knee-length during the summer months.
I’d actually wager I’m even comfier in a jersey skirt than I am in leggings. The waistbands tend to be wide, soft, and forgiving and there is absolutely nothing squeezing my nether regions.
Can you tell I’m daydreaming about spring? Sigh. Anyhoo, tunics are a fabulous compliment to the aforementioned leggings, and come in about 70 gazillion styles. I prefer cotton knits myself, or even polyester like this one:
The poplin tunics are so crisp and clean looking, but I have no desire to contend with wrinkles when I’m slumming on the weekend. Stretchy and forgiving are required characteristics, and knit tunics provide!
For a while there, sweater dresses were mainly available in curve-hugging, tummy-revealing styles that made me want to hide in a cupboard. Now, however, I’ve tracked down a handful with nice high waists, plenty of volume, and interesting sleeves. They’re also finally available in HEAVY knits that smooth my lumps instead of calling attention to them.
When it’s too hot outside for sweater dresses, just about any loose, unconfining dress is my next choice … but, as always, jersey knit is my preference. Knit dresses come in everything from empire to drop-waist styles, but since the knit is generally thin and clingy, certain body types may feel exposed in these frocks. Ponte knit is another good bet. A little heavier weight, so warmer, but also better at smoothing out bumps.
Finally, when I DO feel like sporting a tee, I generally pair it with a full or mini skirt. Once again, I feel less confined and more ladylike, so I feel free to make the other elements of the outfit funky or clunky or super casual. This was one of my favorite outfits from last summer.
So, tell me: Do you utilize any of these pieces yourself when crafting outfits for comfort? If not, what are YOUR secrets? Are you a jeans-and-tee gal? Can’t imagine feeling comfy and cozy in a skirt? What comfy-chic garments work best for your body?
{ 47 comments… read them below or add one }
I pretty much live in tees or sleevelss blouses and skirts with a heeled sandal or funky shoe during the summer. It's more professional than teaching in shorts and a tank top, but I don't melt on the walk to my classroom on campus.
he he! I'm not a fan of jeans and t-shirts either. I do like jeans but with fancy tops or tunics not tshirts. Tshirts are for yoga and the gym!
The outfits you've put in this post (apart from the platforms and heels – I always wear flats because although I'm short my legs are long and heels look funny on me), are pretty much this Yoginis' casual wardrobe too!
Three cheers for leggings of all lengths, tunics, sweater dresses and skirts
I agree with you. I've grown to love my black skinny jeans, but it took about two years to get them to the point that I love them.
I'm far more comfortable in dresses – I love jersey dresses and somewhat shapeless dresses (I love that they're not restricting, and that a belt can give them a different silhouette if I feel like it). For me, that's the big thing I can't cope with – being forced into one shape or silhouette that, on many days, is not the one I want to take.
And tees really do nothing for me, so when I wear them I usually pair them with a blazer or sweater of some sort and they instantly feel more like me.
Spring still has not reached your part of the world? Tsk tsk. I am excited to see your spring looks.
And yes, I agree with all points here. Especially on the platforms
Love these ensembles, especially that top one! Fabrics with some "give" and breathability are what I go for these days. I do love my jeans, but go for the ones with some lycra… much more comfortable and they don't bag by the end of the day.
Great post, Sal! I'm not very comfy in jeans myself, so I've loved reading your tips
Oh, I am totally WITH YOU about jeans– I find them so uncomfortable that I have a hard time believing that other people actually honestly do. I feel like it is a grand mutually-agreed-upon delusion that jeans are the best, most comfy casual wear. I wear skirts pretty much all the time. I am wanting to try my hand at leggings-based ensembles and I've really appreciated your examples.
Sal, I have been wearing leggings since the 80's with no hiatus. Even when those beeyotches on the block made fun of me. I was a dancer when I was young, though, and now no matter what kind of shape I am in or have been in, I just feel comfortable with my body in leggings like I am still in my leotards and tights.
Anonymous: Kick ass! It took me a while to warm up to leggings, but now I can't imagine weekends without them. And, like you, I'll be sporting 'em LONG after they've lost their trendy edge.
I live in jeans and cords. In fact, I have a really hard time varying my daily wardrobe beyond denim. I'm recovering from an eating disorder and very self-conscious about my body, so wearing dresses and skirts (really anything that shows my legs) is challenging. Your blog is so inspiring to me – I really admire you for your creativity and going outside the typical fashion box. Thank you for continuing to inspire me!
I am a total j and t girl but am trying to move away from them. My question is are there nice opaque leggings that do not cost $40? That's just a little too pricey for a layering peice to me.
nestra: I get my leggings at Target (under $10), Old Navy (around $15) and American Apparel via Amazon (http://www.amazon.com/s/ref=nb_sb_noss?url=search-alias%3Dapparel&field-keywords=american+apparel+leggings&x=0&y=0). The AA ones are the best quality, and you can nab them from Amazon for around $10 a throw.
My summer uniform consists of v-neck, short-sleeved, fitted tees (most flattering – love GAP and Three Dots); a-line or full skirts; the current iteration of Born wedge sandals (which I wear TO DEATH); and big ol' earrings. I feel feminine and sassy, and since 98.3 percent of what I'm wearing is cotton, jersey or both, I'm a cool, comfy customer.
In winter I wear jeans on the weekends (but only ones with stretch), and black jersey pants to my business casual job. I top it with some variation on cute jersey top + funkily tied pashmina + cardigan + belt (drawing great inspiration from the ladies at academichic. I truly *want* to rock Katharine Hepburn button downs and pressed trousers, but they a) make me look like an accountant, and b) they wrinkle, leaving me looking like an accountant left in the dryer too long.
Hi Sal, I live in jeans and tee shirts because I am lazy. Thanks for giving me other ideas and thanks for adding in some warm weather ideas too like the shorter leggings.
Best. Lesa
I am with you on the shoes! I think a big wedge or chunky heel is more comfortable than my ballet flats because they offer so much more support (and I'm just used to being in heels 90% of the time). Jersey, especially maxi skirts, are heaven sent – I seriously feel like I'm in the world's comfiest pajamas but still look presentable!
I love your platforms! I've been looking for a pair like that. Do you mind sharing where you got them?
kateherself: You bet! The brown strappy platforms are John Fluevog Haights. The black wedges are Alice + Olivia for Payless. Neither are available in stores anymore, but keep an eye on eBay!
Jersey skirts, jersey skirts, jersey skirts for me. Or even cotton skirts with a zippered yet unconfining waistband. With supportive-ish sandals in summer and flattish boots in winter. I gotta say I can't do much more than walk from my desk to the coffee maker in most of the footwear you have posted, even though I might wear similar when that's all the ambulation I'm going to have to do that day. I actually tried on those black booties with all the buckles, and hell N-O.
They might have been ALMOST as uncomfortable as jeans.
My suuuper should not be seen in public comfy look is my yellow track pants and my huge 80's sweater…
Otherwise, I actually have been feeling very comfortable in skirts. The winter slack makes my pants pinch a little, so I'd rather feel nice all day than think about the pinch.
Your "casual style" looks a lot like my "dressed-up style," since I teach & am not bound by office attire. I'm glad to know that about platforms–I've always shied away from them because they LOOK difficult to walk in. I'm just now learning to wear shoes that aren't Earth shoes or flats, and have trouble thinking any heel or dress shoe is truly comfortable.
Hi there-there is great outfits here, I'd like to find a long maxi dress or skirt for a change too. I'm a jeans girl, I like to wear them with different style jackets.
I've always thought a dress or skirt was getting "dressed" up, but have loved watching your posts and you are inspiring me to ditch that old idea and brave more skirts and dresses for my casual life. I do think I look better in skirts and dresses, but the shoe/hose issue always trips me up. Without giving my age away (teehee), if you are over 50, can leggings look childish or inappropriate?
artlover: It's totally a matter of style, taste, and personal comfort, in my opinion. I've seen women over 50 look amazing in leggings, and women over 50 who clearly feel awkward and wrong in their leggings and therefore can't quite pull it off.
One look I love is ankle-length leggings, a dress or tunic, and ballet flats. It's not the most leg-elongating look in the universe, but it's comfy, chic, and current. And, depending on the style of the dress, can work for a woman of virtually any age.
Glad to hear I'm slowly convincing you that skirts can be worn on non-dressy days!
My confy dressing avoids all sorts of trousers and jeans at all cost – just because they are not comfy! I go for leggings and tunics/big knits, or alternatively, I pick a skirt and combine it with a simple sweater and tights. Jersey knit does it, indeed! As for comfy shoes, I tend to go for flats, but platforms and wedges can be surprisingly comfortable, too!
I agree… my jeans tend to be the kind that aren't meant for lounging. I'm an enormous fan of cotton and jersey dresses, especially in the summer.
After resisting leggings for many years (having experienced them the first go-around) I finally gave in last year and have been in love ever since. I wore leggings on my most recent flight to Florida and felt like I was in sweats. It was wonderful!
I love tank tops and cardigans for the top layer as comfy basics.
On the bottom- there isn't anything more comfy than pajama bottoms lol. However, I do like relaxed fit carpenter style pants.
I'm a sahm so most of my wardrobe is comfy. I've just started trying leggings with tunics. I have a huge fear of looking pregnant so that is a big step. I like leggings with a skirt though as I run around the house without shoes one whenever possible which is not good for tights. I'm also loving embelishing tees this year. I have ruffles, flowers and such. I make most of mine so they are sized to fit me well.
As for jeans I've gone designer. I have a pair of joes jeans which are comfy and soft. I also have Kut from the Kloth jeans, cords, and slacks and they all fit me well and are super comfy.
All that said come spring/summer I'm a skirt girl all the way.
I also find that the jeans/tee combo isn't really the most comfortable. I love my soft jersey knits, leggings, and tunics. And now this post has got me thinking about sweater dresses as something I should keep my eye out for as all the wintery items get deeply discounted.
I lovelovelove your first outfit! I like wearing jeans and tees most days, but I prefer tees with an unusual bit of detailing or an interesting neckline, and I like layering camis underneath. It just elevates the outfit from "I threw on the first clean items I found this morning" to "Yeah, I actually put some thought into my look."
Love jeans. They're the only thing that make my butt look good.
Love this post, Sal–great ideas and photos! I too love leggings and I was wondering if you have a favorite brand or place to get them? American Apparel's version isn't quite stretchy enough for me, but I have other brands that are way too spandexy and cut into my stomach–not comfy OR chic. Anyway, I'd love to hear your suggestions!
THOSE WEDGE BOOTS ARE RADICAL!!! I AM SCREAMING! i love them.
well sal, im the opposite, jeans and a tee are my go-to combo to feel comfy, chic and sexy. i have more of a 'boyish' figure so it works for me! i also love a long boyfriend sweater over skinnies with boots. can't beat it!
I live in the desert, so the summer is all about cotton knit skirts with a loose tank or tee and flipflops!
I've realized that I absolutely love wearing dresses and skirts. Jeans and tees are great, but the amazing comfort of a dress is unbeatable. Especially now that tights aren't necessary.
I love your shoes in that last one!! Where did you get such lovely amazing shoes!?
WOW!!! you packed soo much into this post. i love it. thank you!! love your creativity and you always inspire me to think about piecing things together in new ways.
btw, vera wang leggings at kohls are pretty good too! and reasonable!!
daddylikeyblog: Hmmm, have you tried Target or Old Navy? My Target leggings are definitely the stretchiest, but they're also a bit on the thin side. I must say I've only tried those two brands and AA … I'll have to experiment a bit more!
General Jinjur: Thanks, kitten! Those are Dansko Marcelles. A classic – Google that name and see what kind of a price you can get. Don't forget to check eBay and Amazon, too.
I am SO with you on this. I own one pair of jeans. They are, in my opinion, the perfect pair of jeans for me, but I never choose them for comfort.
My comfy chic consists of a very worn-in pair of khaki pants and a sparkly necklace. I've always found chino fabric to be softer and more flattering for me than denim. The jewelry is effortless and fun, two of my favorite things.
Sal, what do you wear under your skirts (when you aren't wearing tights)? Do you wear shorts or one of those split slips, or do your thighs not touch so you're comfortable wearing nothing but undies?
My thighs rub, and I hate wearing pants, but especially in the hot summer months it's a constant battle to figure out what to wear under a skirt. I walk 3-4 miles on my commute round trip, too.
Great post! I was just thinking about this subject yesterday. A friend of mine came over to take photos and borrowed a sweater dress of mine and remarked on how pretty and yet comfy it was! Which is why I like it, because it feels nice enough to sleep in
Leggings are my comfy-pick of choice. They look good and feel good, as long as they aren't too tight around the waist or constantly falling down.
I used to be a jeans and a t-shirt girl but since I started reading fashion blogs and being inspired, I've toned it down. Now I only wear jeans to paint in (I'm an art major) or when I'm trying to make them a bit more fancy.
Oh, I just love love love those wedges!
Also just my $0.02, I have a pair of leggings from Target that fit perfectly and aren't very thin at all. My only complaint is that they're not very long–I'd like them to be longer and less stumpifying
I used to be a jeans and t's only girl – but I started working with this adorable girl at my last job who rocks skirts and footless or capri tights with cool shirts, and completely fell in love with her style.
I've been slowly revamping my wardrobe ever since! Since I now live in Hawaii, I'm always looking for ways to keep cool, and skirts/dresses are waaay more comfy than shorts to me.
I completely agree with all your "comfy" choices.
As for jeans, I found that if I stay away from skinny jeans, and go for the widelegs, then things get comfy again. If I want the skinny look, I go for leggings.
Platforms are superbly comfortable, as are wedges; they both give lots of support and stability.
Like you, I have yet to find a pair of jeans that really fits me right, and tees – oh, please don't get me started. The unisex/men's cut ones are bulky and hide the curve of my waist: with very few exceptions, the shrunken ladies' styles are too short, especially once my bust gets involved. Crew necks are Not My Friend, either.
I'm with you on the comfy-casual wardrobe, though: leggings, knit dresses, skirts, jersey tops. I'm also in total agreement about the wedges and platforms: I actually find most flats terribly uncomfortable (they usually don't have enough arch support) so I keep an eye out for rubber-soled, sturdy-heeled shoes with good footbed construction. Just about the only exceptions are true athletic shoes such as sneakers and hiking boots!
Jealous!! I find it's very difficult to wear skirts where I'm from because it is always very windy and ranges from hot to cold. If I ever try to wear a dress or skirt, it always blows up and/or leaves my legs freezing, even if I'm wearing leggings or tights under it.
I find jean material is the perfect material to keep warm against the wind!! I must admit it does get difficult when it's warm out … sigh, no winning!
This blog makes me realize the energy of words and pictures.I am grateful that you let us look in! Keep coming up with ideas.