How to Dress Comfortably

comfortable outfits

I am completely willing to sacrifice comfort for style.

OK, OK, I am completely willing to sacrifice comfort for style on most days. Or maybe “some days” would be more accurate. And, you know, not EVERYWHERE on my body. Just most spots. Or maybe “some spots” would be more accurate …

Well, regardless of the quantifiable particulars, when I wake up and think, “I need to be comfortable today. And not just for the first couple of hours. All day,” I build my outfits utilizing what I’ve learned about my body, my taste, and my preferences.

Everyone’s comfort-related needs will be different, of course, but having a handle on those needs is key to consistently assembling outfits that are both soothing to your body and flattering to your figure. And since deciphering those needs can be a bit challenging, here are a few suggestions to get you started:

Identify your sensitive bits

Whether you’ve got skin that irritates easily and can only tolerate certain fibers, a bad back that calls for flats, or sweaty pits that do best with absorbent cotton, you should be able to pinpoint which bits of your body NEED to be accommodated in order to create holistic comfort.  Start with the fussiest parts of your physique, and work your way outward.

You’ll be amused to learn that a girl who loves sky-high heels and belts is most sensitive in her feet and waist. That’s right, if I’m dressing for comfort it is imperative that I be beltless and shod in squishy-soft shoes.

Know your irritants

One of my best friends is allergic to all man-made fibers. A co-worker buddy needs shoes with a very slight heel and an inflexible sole or her feet kill. And, personally, I need full range of motion in my arms for real comfort. Stiff, fitted blazers are fabulous, but they make reaching for the peanut butter jar on that top shelf such a pain. Experimentation and experience should lend you some insight into which fibers, styles, and garments will make you the most miserable. When dressing for comfort, avoid them. See how easy?

Know your faves

The tunic/leggings/boots combo is my go-to choice for cool weather comfort dressing. And I know for certain which shoes will serve me well for long days of walking and standing, and which ones will make me want to buy a new pair of feet after an hour. When comfort is paramount, it helps to build your outfits by starting with a few reliable key pieces that you love, that love you back, and that have been road tested for ultimate comfort.

Shop wisely

If you know you can’t tolerate a belt for more than a few hours, DON’T plunk down your hard-earned wages for waist-cinchers. If you have fussy feet, insist on quality shoes … and shop at stores with liberal return policies so you can give ’em a true test-run. If you get a stiff neck or back pain with exertion, think twice before purchasing an oversized handbag made from heavy leather. Comfort needn’t be the primary consideration in every purchase, but it needs to be part of the equation. Especially if you’re thinking of spending big.

Create balance

I don’t subscribe to the idea that all comfortable ensembles must be completely casual, utterly accessory-free, or essentially unstylish. Comfortable outfits can include dressy accents, and mixing elegant items into a casual mix generally works beautifully. If you’re doing jeans and flats, add a long necklace. If you’ve got your hair pulled back to keep it from tickling your face, be sure to wear earrings. If you’re wearing a knit sundress, throw on a scarf or belt. Find ways to style your comfies so that you look chic AND feel fab.

**Disclosure: Actions you take from the hyperlinks within this blog post may yield commissions for alreadypretty.com. See Already Pretty’s disclosure statement for more details.

Next Post
Previous Post
  • I don’t find jeans particularly comfortable. Am I alone in this thinking?

    My go-to comfy faves: In the summer, empire-waist sundresses that skim over trouble bits, yet still allow circulation with flat or low-wedge sandals.

    In winter, soft knits and layers. I know Sal has praised ponte before — but really, it’s amazing. Moves, breathes and stretches!

    • I also think jeans are uncomfortable. They’re stiff and heavy, I hate how the hems get wet when it rains, and I feel ugly in them, so that in and of itself is enough to make them uncomfortable. Not only that, they’re constricting. My must-be-comfortable-area is my crotch. I hate the feeling of having a seam or thick fabric bunching up there when I cross my legs.

      Down with jeans!

    • Kate K

      My mom frequently reminds me of a statement I made when I was 11-years-old: “I hate jeans and I’m never going to wear them! They’re scratchy!” I do wear them from time to time but if I’m looking to be comfortable, I do leggings and a jersey dress/tunic or a long maxi dress.

    • Nope not alone. I hate jeans so much.
      They always give me muffin tops, I have a pear of jeans that are too big for me, and they still give me muffin top. And they seriously interfere with my ability to bend over. And since they are meant to be casual, its not worth the pain. Imo

      Instead I comment fashion blasphemy and wear leggings as pants. 😉

    • Michelle

      I only wear jeans if its almost a “must”. To me they’re uncomfortable and awkward. I hate the stiff material and zipper/metal buttons. I usually stick to dresses and skirts.

    • You’re not alone! I hate jeans. I wear skirts and dresses, bare legs in the summer, tights and leggings in the winter.

      Can’t say enough for ponte. The J.crew Pixie Pant is my best friend.

    • Sal

      So funny. I’ve been anti-jeans for YEARS – anti-pants, in fact – but finally found some that work for me and now I adore them. For me, it’s all about rise and stretch. Low-rise just digs into my midsection, and all-cotton has absolutely no give. My high-rise, stretchy jeans aren’t nearly as comfy as my leggings, but they’re considerably comfier than any others I’ve owned!

    • Nadine

      Hate jeans. I have narrow hips and big muscly thighs (I love my big muscly thighs) and they always FALL DOWN. I hate belts too . . ! This winter (New Zealand, yo!) I have made it through jeans-free so far wearing dresses and leggings with cardis. (I am a dress-wearing maniac.) For me, comfort = freedom of movement. I love the look of pencil skirts and blazers and blouses, but most days I HAVE to be able to move, so it’s all about the knits (jersey) and the a-line.

    • Carol N.

      I am not a big fan of jeans either. But I found some at Talbots that work for me when I do chose to wear them. In the summer it is mostly skirts and sandals.

    • I don’t think I realized how much I hated anything with a front button and zipper until I had to transition to maternity. The comfy stretch band makes me never want to go back to buttons! Haha. The only problem is the ones that cover my entire tummy make me itch.

    • Halo

      I don’t think any pants are very comfortable, so I wear dresses. You’re not alone!

  • I CAN NOT wear heels. Not at all. I love the look of them, but my feet become furious with me if I try for more than a 1″ heel. So I’ve tried to cultivate a pretty flats shoe collection. (also adding to the problem is the fact that I wear wide shoes!) I actually had to ask my sister and mom to tell me off if I tried to buy heels! They’re just so pretty….and torturous.

  • My must-be comfortable area = feet. Painful feet means no fun anywhere above the ankle either. This is a great post, Sal – I esp like the part about creating balance.

  • “I don’t subscribe to the idea that all comfortable ensembles must be completely casual, utterly accessory-free, or essentially unstylish.” Yes!

    I wear flats because my feet and my back hurt otherwise. I hate wearing belts. I won’t wear bracelets or even a watch most days because I’m typing most of my workday.

    Today, I’m wearing a comfortable pencil skirt (without a belt), a maroon jersey top, and a silk red and grey and black printed scarf to up the formal ante. And cheap but comfortable and cute brown flats.

    I also agree with laura that I don’t find jeans comfortable. I’d rather wear cotton or linen trousers or skirts.

  • I’m the first one to give up comfort for style. HOWEVER, over the winter, I wore a pair of pants I LOVED that squeezed me so tight around the middle that it literally gave me stomach cramps! I couldn’t get them off fast enough and as soon as I got in the door of my house those babies came off, got thrown into the trash and then I dumped the morning’s coffee grounds over the top of them just to be punitive!!!! ~Serene

  • Amy

    I used to completely sacrifice comfort for style. Even if that meant coming home with my feat torn to shreds and my soles aching horribly after a night out so that I could wear those cute, strappy, heels!

    As I’ve gotten older I want to look cute and stylish of course, but for me that absolutely 100% means comfort. I think nothing eradicates an otherwise fashionable look faster than someone who looks like they can’t walk normally, who is fussing with straps falling off/down, or who is tugging at something that is too tight or short.

    If I wear anything uncomfortable these days it just makes me feel self-conscious and then that shows through in my attitude/behavior. So, although I miss wearing heels regularly most of all and always having a few extra inches I feel way better most days in my flats, sandals, or boots (depending on the season)!

  • Mary

    How ironic that I was thinking this morning: “Today is not a heels day.” Instead it will be cutout flats, one of those polished-looking t-shirts from Loft tucked into narrow dark jeans, and a big necklace.

  • Katharine

    I almost always dress for comfort, and the few items I have that are NOT comfortable, but extremely nifty-looking or flattering despite that, get very, very little wear. I don’t think that comfortable ensembles need be casual, accessory-free or unstylish AT ALL, although granted my work environment is such that my clothing can be more casual than the average professional bear’s.

    The key for comfort for me is fit, usually. One pair of jeans might be comfortable; another might bind at the thigh or waistband. One narrow skirt is comfortable, another is cut a little differently and rides up or twists or is just a hair too breathless across the navel. One pair of heels is comfortable; another, no higher, has a different arch to the last, and makes my forefoot burn after a bit.

    I spend a lot of time in dressing rooms before I shell out my cash. And I’m starting to get pretty ruthless after wearing something for a day and discovering that it is not, in fact, completely comfortable. Some things that are unredeemable I just get rid of. If the problem is something I can alter, I’ll alter the item. But in general, if there is something about my clothes that doesn’t allow me to entirely forget that I’m wearing any most of the time, then I feel just as completely “wrong” as I do in, say, a pastel floral print blouse.

  • I love the way you break it down and give us step-by-step directions!

    Oh, and today–I’m wearing a knit sundress. I’m off to grab a scarf now….

  • These days if I wear an uncomfortable item, as soon as I get it home it goes in the charity pile (well, I will wash it first!). Sitting at a desk all day, I do not want to have something that is totally uncomfortable, and if I can’t even walk from the parking lot to my desk without my shoes killing my feet…they are tossed. You can find cute things that don’t kill. Generally, I wear skirts to work and a good dose of lycra is always desired. I make a lot of my skirts and I am very cognizant of how much stretch the fabric has. They are comfy to wear all day, yet still cute!

  • I think comfortable shoes really should go without saying. I’m sad that we don’t have as many mid-heel options as we used to. If you look at the shoes available in the thirties and forties, they had nice mid-heels, good cushioning and they were made to WALK in. Because not everybody had a car back then.

    One of my comfort go-tos is elastic waist skirts. I have a hard time fitting my butt and thighs and sometimes I really need something that doesn’t bind. If the waist comes with a drawstring for adjustability, so much the better.

  • Belts and Spanx cause me GI distress, heels throw my posture out of whack and hurt my feet. I’m actually not super in love with anything that’s remotely tight, and would rather buy a size up and have it be a little loose than a size down and be constricted. Having clothes that are too loose does negatively impact my polished quotient, for sure, but it allows me to forget that the clothes are there!

  • LinB

    A properly supportive brassiere. Leather shoes with padding in the insoles — flat or with a low heel. Cotton, linen, woolen garments. Shirts and dresses that close in the front, so I don’t have to twist my back to manipulate closures. Adjustable waistlines to accommodate abdominal swelling (okay, overeating). Arms and legs covered against the sun. Sleeves that are loose at my upper arms. Woolen socks in winter. Bare legs in spring, summer and fall (I live in NC, USA.) Pants that hang from my natural waistline. As an adult, I can make these choices. As a child, I suffered from plastic shoes, polyester double-knit, and zippers up the back that were chosen for me. And nylon socks and panties, yuck.

  • D

    I also have a black pair of Tsubo flats, and I wear them A LOT. Definitely a go to for me when I want to be comfortable. I also have a couple of pairs of those New York and Co’s city stretch (I think…I can’t quite remember the name) pants that are basically like classier sweat pants. LOVE them.

  • Laurinda

    Category: IRRITANTS
    I can’t stand back (or side) labels. As soon as I know I will keep an item I cut them off. (It does limit eventual resale, but that is less important than having comfy clothes now). Some brands are now using “stamped” labels, and those are even worse. They are not readable after a wash or two, and become annoying scratchy patches.

    Does anyone have advice on how to remove stamped labels – short of fingernail scraping and tweezers?

    • Katharine

      I think they’re screenprinted. I found this: http://www.ehow.com/how_7649412_remove-cured-screen-printing.html
      but unfortunately, it might not be practical unless you have a vacuum extractor. Otherwise, word on the Internet seems to be “no” and “maybe sand them off, very very carefully so as not to sand a hole through the fabric.”

      I hate labels too. How can they be so ITCHY? I have always cut labels out of my clothing, for years, and in fact will usually go the extra mile and use the seam ripper to pick every trace of the label out. And the side labels are even worse, and more annoying, than regular back of the neck labels, not to mention often being large enough to make the garment drape funny if you don’t remove them.

  • Laura- I 100% agree with you that jeans are not very comfortable. Especially during the summer months in the south where I live, even the thinnest ones.

    I stand on my feet between 8-9 hours at work so shoes are definitely the number one priority for me. This doesn’t restrict me to flat shoes only, but I definitely cannot wear a spike heel. I usually opt for a wedge/platform that isn’t too high if I want something other than a flat.

    OH, and I love that you talk up Prairie Underground! I use to intern for them when I lived in Seattle a few years ago and it’s a great little company 🙂

  • Go-to comfort is jeans, a T (preferably quirky), and a light scarf. Scarves are like little security blankets.

    The only non-negotiable comfort consideration — how tight pants are around the waist and where they “sit”. I’m tall and all legs so my waist and curves sit higher than what most clothes are made for. If pants or skirts hit me at the wrong spot it’s not only uncomfortable, but it visually adds 10 lbs because of how the clothing squashes my body. I’ve always found that Theory clothing is great for my body type.

  • Aziraphale

    I think about this one all the time! Because, really, walking around in my pjs all day would be the ultimate in comfort, but you can’t do that, right? Combining comfort and style always seems like finding a happy medium. Shoes are a big factor. They don’t have to be flats, but they need to be comfy. Fluevog and Tsubo are good for this. I am also far more comfortable in a garments that end at my waist and are structured, like jeans or a non-stretchy skirt, provided they are not too tight. I feel slightly uncomfortable in loose dresses that skim your waist, weirdly. Maybe it’s because such dresses, while wonderful for temperature control on hot days, make you think you’re wearing a nightie, which makes me feel a little out of control. I like the support a waistband provides. I loathe the feel of elastic waistbands, though.

    I’m also sensitive to any fabric that is itchy. Some will even make me break out in a rash — yikes!

  • Kaitlin

    If I’m not comfortable, I’m so cranky and cannot focus (I guess I’m highly sensitive) so I’ve had to find work appropriate comfort. For me, that’s usually a wrap dress, or Jersey skirt with a dressier blouse of jacket and low heals. Accessories are my addiction and they dress anything up!!!

  • If I’m looking for comfort (like I often do these days) I go for looks that are a little baggier than usual, perhaps a little more on the androgynous side of things. Comfort doesn’t mean t-shirts and sweat pants to me; it all comes down to fit and the materials. This summer it has been all about maxi skirts and dresses for me. Shoes do play a huge role, too.

  • Since I am generally chilly, even in summer, I live in pants (or capris, on those occasional hot days). And my go-to pants are jeans, snug-fitting, straight or skinny leg, dark-wash, as they can be dressed up or down. I really don’t have any ‘dress’ pants, and looser fit/wider leg/ lighter fabric generally adds to my feeling cold. I also wear t-shirts more than button-ups, again, as they feel warmer. And cardigans, cotton in summer-wool in winter, or blazers, smooth cotton in summer, corduroy or wool in winter. I really love natural fibres, (I can take a bit of lycra in my clothing), but polyester makes my skin crawl! I wear flats, or a lowish wedge heel in summer (generally), but I truly love boots, as my ankles often feel cold. And we won’t even talk about winter outerwear, as it is more about pure survival, rather than fashion. I do love earrings and necklaces, but find that bracelets and rings ‘get in the way’.

  • I am mad for knits, not in the sweats/PJs way, but in the soft T-shirts & jersey way. Pretty much all my tops are knits, & I’ve sworn off crisp button-downs bec. I finally realized that no matter how much I like the look of them on other ppl, something about the way they feel & fit on me is a non-starter. Knit tops make me feel super comfy. And they look sharp with a fitted pencil skirt, jacket, & heels for work or jeans & flip-flops for weekends.

    Also, sweaters. Damn, but I love sweaters! Except for certain 100% acrylic & 100% wool — itchy! Cotton blends are my fave, silk blends are delightful. But I might be the only woman in the world who finds 100% cashmere a bit itchy too 🙂

  • Sara

    Love this one!

    Sal, coincidentally my go-to comfort item is a “pretty” hoodie as well. It’s a wonder they’re sort of hard to find, as I know several ladies who love the idea.
    This is mine! http://www.anthropologie.com/anthro/catalog/productdetail.jsp?navAction=jump&id=20237970&parentid=SEARCH_RESULTS

    • Sal

      Sara, so PRETTY!

  • Jeans are my ultimate comfort clothing. I’ve even been known to put on jeans and go to bed when I am sick. Jeans, earrings, flat boots, and a knit/stretchy top and I’m good to go, feeling confident and comfortable.

  • Rachel W.

    I’m wearing jeans today in a naive effort to convince myself that I don’t hate them. This attempt failed fantastically: I’m going to change into a skirt first chance I get!

    While I have picky feet and a horror of synthetic fibers, mental discomfort still bothers me more than most physical discomfort: if I bend over in these low-rise pants, will anyone see more than I want ’em to? Is my shirt going to be rolling upward all day, and I going to be rolling it back down? Do my bra straps show at the edge of this scoop-neck? The sort of fiddling required to keep everything in place adds a subtle anxiety to my day. Comfort, for me, centers around clothing that doesn’t require any thought to wear.

  • Kate K

    I have major issues with shoes, mainly because the shoes being touted as the ultimate in comfort make my feet miserable. Birkenstock’s arches are too high, as are Danskos and Chacos. My feet don’t sit properly in Privos so that doesn’t work. The only exception? I have a pair of Clarks wedges that have been quite comfy and don’t make my arches protest. I need flat, squishy shoes–those make my feet happy. (This creates issues because if I complain about a pair of shoes and my friends give me advice, I usually have to take it with a huge grain of salt. Also, people don’t believe you when you say “Danksos make my feet hurt.”)

    Beyond that, comfy for me means scarves, jersey dresses and a cardigan that I can button (loose, flowy cardigans tend to flap in the wind which just makes me annoyed.)

  • My only absolute is no low rise, and no leggings. I like the idea of leggings, but having really skinny legs means that they will either be waaaay too tight in the waist or really baggy in the legs. So I just gave up. Low rise cuts into my hips. I feel like I always need at least a kitten heel. It helps me stand up straight. Flat shoes tend to hurt my back after awhile.

  • bluemoose

    Jeans are my #1 go-to clothing. Used to be that was true ALWAYS. Now it’s true only if the temperature is below 85 or so. I’ve finally discovered a love for easy summer dresses with sandals or flats — one piece, no effort, and yet, you look professional. My current favorite (I try to wear it only every other week) is a jersey maxi dress with a nice twist/cross detail in the neckline/waist. It feels like wearing pajamas, skims everything, covers unshaved legs, and looks amazing.

  • Comfortable shoes, especially if I have to walk. Necklace/earrings for interest but no bracelets as they get in the way and annoy me. And except in summer a giant pashmina scarf I throw over everything and can take on and off as I wish. I have them in about 20 colours.

  • Let’s see, I hate wearing tennis shoes, or any shoe that requires socks for that matter (except my boots) because I hate feeling like my feet are constricted. I can’t wear bracelets in the summer, I sweat and they stick to me! I can’t wear jeans or shorts if I have to bend a lot because guess what, no bum = the bottoms aren’t staying! Even with a belt, I have to tighten it to the point of discomfort, and I promise, the pants aren’t too big. Oh, and frankly, I hate bras.

  • Cass

    Default comfy outfit for me is thick sweater over a light shirt or blouse/tee and light cardigan depending on weather, skinny jeans, and ballet flats, with no makeup and only earrings for jewelry. Snug enough not to get in the way, just loose enough not to feel tight, temperature adjustable, no worries about a skirt riding up, no need to be sure to have shaved, no bits to fiddle with or mess up, and no need to worry about smudging anything.

  • I don’t mind being squished (I “burrito” up at night, so I like close fitting clothes) but I cannot stand fabrics that are itchy, rough, or scratchy. Exposed elastic makes me bright red instantly (hello cheap bras, I’m looking at you). I try things on and if they itch AT ALL, they go right back. Period, end story. Because they do not get better. And it’s sad because I LOVE sparkle, but a lot of sparkly clothes use very itchy/scratchy materials to get the sparkle.

    Also, when I had long hair, I couldn’t stand loose sloppy pontytails, but too tight ones gave me headaches…it was an all da war to wear my hair up.

    On my easy days? I love cotton dresses with a pair of flats. Dark wash jeans with a great tee and a bolero. At work it’s a short sleeved sweater, slacks, and heels.

  • Pingback: LadyMags Links of the Week | Fashion Pulse Daily()

  • Halo

    I’ve learned to avoid cute flats because they invariably dig into my feet at the big toe joint and/or have too short toe boxes and/or don’t accomodate my third toe, which is as long as my first two.

    My other rules: nothing must squish my midsection, skirts need to hit the top of my knee, and I have to wear a bra that fits well. Violating any of these means I’m constantly adjusting my clothes and feeling both cranky and unattractive.

  • Pingback: Friday’s Featured Blog: Already Pretty @ Divergent Musings()

  • Great post!

    I completely agree – the word ‘comfortable’ is not synonymous with ‘drab’. I tend to bear that in mind when shopping.

    My issues: feet that require some arch support and cushioning, garments that breathe, and range of motion. My OTBT slingback mary-janes are great, cotton is queen, and cardis in lieu of jackets.