Many women like to feel comfortable in their clothes. For some, comfort is their number one driver when dressing (and sometimes it shows, as often comfortable translates to sloppy). So how can feel comfortable but look stylish at the same time? Well as you’re about to see with these 10 outfits I’ve put together, comfort is about choosing fabrics that move with you rather than constrict you but also, adding accessories to add the icing to your sartorial cake.
Now these 10 outfit looks are ideas that you can copy or take elements of, to copy from your own wardrobe.
Use them as inspiration for putting together those comfortable but still stylish everyday outfits that allow you the freedom of movement you crave, but still say that you are put-together.
1. Tunic and Leggings


2. Jeans and a Sweater

3. Loose Harem Pants and a Stretch Knit Jacket

4. Caftan and Flat Sandals

5. Jeans and Cardigan

6. Knit Dress and Boots

7. French Inspired Stripes

8. Knit Dress and a Denim Jacket

9. Knit Skirt with a Tee and Leopard accessories

10. Yoga Pants with a Stretchy Top

Casual Dressing Tips
Smart Casual Decoded: How to Dress with Confidence (Even When the Dress Code Is Vague)
8 Ways to Look Stylish in a Casual Environment when Jeans are Not Your Thing
Want to learn how to accessorize more successfully? Well grab a copy of my ebook The Finishing Touch.















Jeans are not comfortable for me.. 🙂
loved the outfits above, they present inner harmony and there is always a hero piece to make it stylish!
Thanks again! So many different takes on comfy casual outfits. I don’t wear jeans or slacks. I wear mainly dresses, daggy skirts, tunics and leggings and you have presented such a wide range. Some Yin and some Yang as well I think.
Every one of these is right on target for me. Thanks for the ideas!
The most comfy thing for me to wear is a linen or cotton button-down shirt.
Love the outfits you have put together. I’m a huge fan of comfortable clothes 🙂 Rachel xx
I love the options presented here. We all have different levels of comfort. Jeans are not comfortable for me (too stiff), but khakis are. I love the outfits you pulled together. I love your style.
Imogen, do you think one could swap the flats in these outfits for wedges (high wedges)? I’m a petite V, and I prefer to wear heels most of the time (wedges for casual wear). I almost always feel better/more self-confident in them, and I think I look better in them too!
You can always swap out to a wedge – I try and put lots of flats in pics as I know lots of people don’t wear (or can’t wear) anything but flats. You can always add a heel!
I’m 70 and retired (artist) and live in a small remote village. I have a left over business wardrobe and grubby reno clothes. I am low color contrast and medium value and H shape. I feel a need to look better just for myself. Any suggestions?
P.s. I love color and have pinks, yellows, turquoise, and lime green!