How to Look Stylish Yet Be Super Comfortable


How to Dress Comfortably and StylishlyLee wants to know: looking stylish and be comfortable as well – I often wear VERY comfortable clothes at home but they aren’t stylish at all.

1. Quality – ensure your pieces have still got good wear left in them. That they are not pilled, old, stained, faded or just plain worn out.

2. Fit – make sure your garments fit correctly.  Often when we go for comfort we go bigger and baggier than necessary.  Do your clothes skim and not cling, but also not appear boxy or baggy.

3. Outfit – think about putting together an outfit, instead of just stepping into whatever is the closest, easiest thing to put on.

4. Accessorize – a scarf, a necklace, a stack of bangles.  Take your comfortable outfit from plain to interesting with a small edition.

5. Fabrics – polar fleece is not stylish, practical yes, but stylish no.  Cotton ribbed knits will often bag and sag quickly, look for t shirts with a smooth finish and some elastane in their fibre content for a smarter look.

You can see what I wear when I want to be comfortable in the outfit pictured above:

  • Jeans with LOTS of stretch in them – but in a dark denim.  Dark denim is more dressy than lighter or more distressed denim.
  • T-shirt – but a smooth knit with elastane to hold its shape.  Here I’ve worked with a navy to create that slimming column of colour too!
  • Knit waterfall cardigan/jacket – it’s comfy but skims over the lumps and bumps and adds a bit of style and colour
  • Soft viscose scarf to create a focal point and add some interest
  • Slipper style shoes – I can run around all day in them as they are flat and comfortable
  • Soft makeup – a dash of mineral powder, some blush and mascara and a lashing of lip gloss

What do you love to wear to feel comfortable but still look stylish?



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  • Personally, I don’t believe it’s necessary about the garment itself that is the main problem with our clothes, its our own comfortzone, personality and sometimes the occasion or surrounding.

    I dont find fleece and jeans comfortable at all, not because necessary because of the fabric because Im someone who is more dressy in nature who tends to dress up even when it’s not necessary.
    I prefer to wear office-inspired wear like office dresses, pencil skirts, blouses, fine knits and conservative low heeled leather shoes but in a more dressed-down way. I kind of dress somewhere between “smart” Casual without jeans and business casual (E.g. Sheath Dress + Cardigan + tights + Riding Boots). When I wear jeans its mainly for errands or ocassions that isnt important to me, like I would feel a bit awkward wearing a somewhat dressy dress to the supermarket or dentist. 😛
    With shoes, comfort is a more important factor because Ive an ankle injury from childhood. I cannot slip into ballet flats (high foot arch) and pumps (heel aggrivate my calves) no matter how “smart” they look, I still need to wear my more sporty athletic flats and boots. I wont sacrifice health for being “stylish” and I dont think anybody would. 😛
    I rarely wear leggings in puplic because Im sleeping in that at home and it would feel like Im going out with my PJ’s. Funny thing but Im actually scared of looking too casual and wear exercise clothes in puplic, because it doesnt mesh with my comfort zone and personal style. The same thing goes with more “sexy” garments and trendy items. No matter how fashionable is, I wouldnt wear it if it doesnt goes with my personal preferences. I do wear shorter skirts and sheer blouses, ocassionally, but it has to be in a more layered way like for example mesh tops, I wear mainly as layering pieces to add interest, if skirts are shorter than 2″ above the knee, I need to wear spandex and tights because otherwise I would keep tucking it down all the time imaging people would stare at me. I just cant concentrate if its something I dont wear often. x’D This person wear the skirt the same way as I do: so it doesnt really look that “too revealing” as a whole outfit.

    If the person is someone who are in jeans and hoodies all the time and prefer to look more casual, I doubt the person would be comfortable in pencil skirts and blouses even if they are made of the most comfortable fabric in the world! 😛

    Fit is different matter – I wouldnt go out in clothes that are hanging down on my butt or if they are skin-tight. One problem with jeans is that many of them are made in a slim fit cut and fairly low rised so Ive problem finding the right pair because they dig into my hipbones because Im so “buttom-skinny”. But Highwaisted Stretch Jeans are supercomfortable because they doesnt rub my boney hips. LOL

    • Lina – your version of comfort is quite different from many of my readers. Your personality has to be comfortable, whilst many have to feel comfortable in their body (ability to move and stretch). Shows just how different people are!

      • Well, I guess Im thinking a bit different because Im alot younger as well (early 20’s, but I dont know how old your readers are). Older women (30+) dont seems to be bothered by what other people think while girls in their teens and early 20’s are pressured by it . My parents and relatives wouldnt care less if they showed up jeans to a restaurant , while I freak out (worried) if I dressed up too much or wore something too “racy” for the occasion. “Is this outfit too dressy/low-cut?” LOL

        I don’t think its about my personality but about how I grew up. Always been that kind of person who struggling with finding a comfortzone and not being stuck in that “shell”. Clothing wise, Ive only concious about for a few years when people pointed out I was dressing up too much for the beach restuarant. and when I get treated like a high school kid because Ive a babyface.
        Thats how I got interested in clothes and changed my point of views on it in a good way. 😛 Now that I start to wear more office-inspired outfits (formal cuts but otherwise fairly casual), people dont treat me as “ignorant kid” anymore, I couldnt even order juice at a bar longue with my parents without a passport (looking young isnt a bad thing, but it can be, if people treat you like if you are 10 years younger…).

        Im not sure if thats the same for people who are bit older, changing your clothes due to experiences and if they care about opinions from others.

  • Sorry, if my comments are too long, I just cant summarize my comments. haha Beside cannot review them before submitting them, they feel shorter when you write them but then they appear so long. LOL 😉

  • And how many times do we just put on anything first thing, then have something unexpected happen which means we have to jump in the car and go out. Then we run into somebody, even a neighbour in the driveway and feel so caught out:-)
    This used to be my major sin! Now I hang two sets of clothes somewhere for putting on first thing in the morning and I make myself put on minimum makeup. For me its eyeliner that makes me feel soignee…(Two sets because clothes worn around the house attract stains!)
    So for me its not the comfort level of clothes but making some effort to compose an outfit. You can keep the day’s jewellry in a container near the front door, together with going out shoes eg ballet flats and make a quick change on the way out the door.

  • My “go to” super comfy everyday outfits are a knit dress and sandals or linen pants and drapey knit top. I am incapable of leaving my bed room without earrings and a slick of mascara and blush. My mother instilled into her 5 daughters that you must get dressed for work. Raising children and running a home is important work. Dress appropriately.

  • Boyfriend jeans, tee in an interesting color or neutral, cool sneakers, a classic jacket (peacoat, moto), and a man’s scarf.

    + long gray hair in a braid.

    Pretty much every day, unless I’m going to the gym. Comfort in style is the new normal.

  • This topic seems to be all over the blogs I read. Style with comfort is surprisingly not all that easy to find, especially for the 50+ woman – yes that’s me. Clothing manufacturers often load up on stretch which clings to everything rather than offering a cut that fits and flatters. Many of the ‘comfortable’ styles that use better quality fabrics are targeted to the young and slender who can pull off a looser look, for example Vince which goes up to size 10 – that’s their Large!! That said, I think it’s worth the effort because once you have your comfortable and stylish clothes you can relax and just get dressed and get on with life.

  • Speaking of comfort: I’m huge on comfortable shoes, which meant no heels for quite a few years now. I have recently found that changing into heels at the office, where I know I won’t be doing much or fast walking, is a great outlet for enjoying some pretty heels. They’re still not very high, but higher than I like for walking down the street. I can imagine changing into heels to enjoy the style in any circumstances where not much walking is expected.

  • Definitely I would agree with your thoughts Imogen. Its feels good when your in fashion and at the same time your comfortable enough on your outfit. Being resourceful is a good help by adding something that glitters or something you want to add for a twist on your old clothes in your closet will do. 🙂

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