Relaxed style: how to dress for comfort without looking like you don’t give a shit

Relaxed casual. I think for me this is the holy grail of everyday fashion. It’s those awesome Pinterest women in their striped tees and rich-girl hair, looking all tousled and super-chilled out and fabulous.

It’s such a tough one because when you want comfort, you can sometimes end up looking like crap because you’re wearing your husband’s old tee that is all faded and a pair of baggy sweat pants that are super soft from so much washing. And then you can’t leave the house because you look like a hobo.

So how to dress for comfort without looking like you don’t give a shit?

It all comes down to finding clothes that are loose fit, but are the right size for you. If you buy clothes too big so they are comfortable, they generally just look ill-fitting. You don’t want anything itchy or grabby or that cuts in anywhere. Plus they need to be made of really great fabrics that you want to wear. And of course they need to be low maintenance wash and wear garments. When you are feeling a bit low-key and going for comfort you’re clearly not going anywhere near a bloody iron.

Here are my key tips:

Find a pair of jeans you love

Make sure they aren’t too tight anywhere. Well fitting jeans will hug the right places and be flattering, no matter what size or shape you are. You will need to look around though, there are so many jeans on the market but it may take some hunting to find the most flattering and comfy fit for you.

Buy good quality t-shirts

Nikki Parkinson at Styling You offers a whole lot of fantastic advice on her blog about the basics and good quality wardrobe staples in this article. The great thing about tees is that there are so many out there, you are bound to find some that suit your shape and style. Once you find a shape you love you can buy them in white, black and grey and wear them all year round as a layered item.

Go sports luxe

Okay, so we all know leggings aren’t pants, despite how comfy they can feel. But there are some awesome jeggings and ponte leggings on the market that are fabulously comfortable and suck everything in like your running tights, but are a bit more everyday-wear friendly. Team them up with an oversized shirt and trainers you’re talking extreme comfort with an edge. I’m a massive fan of pleather jeggings but according to our Facebook community, many of you fear sweaty-crotch syndrome. I don’t think I’ve personally experienced this but I’ll let you know if it comes up.

Look for great knitwear

Find knitwear that is relaxed and loose, without looking baggy and bulky. Go for lighter types of materials such as cashmere which will give you more shape. Knitted scarves are always brilliant for creating a really chic look as well. There are a gazillion tutorials out there on how to wear a winter scarf.

Get into boyfriend shirts

I love a good tailored shirt worn buttoned up or open over a tee with leggings or jeans. Again, look for the right shape for you. I am very busty so I have to make sure the buttons are in the right place and that the shirts aren’t too boxy. I prefer lighter more flowing cottons and denims that aren’t too stiff. And I don’t buy them super baggy, I make sure they just skim the body, that way they are relaxed fit but not unflattering.

Choose the shoes

Get yourself a pair of flat boots and a pair of everyday trainers. You want to find something super comfy but with a fashion edge. Flat man style boots are big this season and you can never go wrong with a pair of white converse or something similar.

Comfort Dressing Pinterest Panel (1)


1. Country Road Denim Shirt
2. H&M Conscious Striped Tee
3. Witchery Long Cuff White Shirt (all proceeds of white shirt sales go to ovarian cancer research at the moment)

4. Surafina Grey Knit in Styling You shop
5. Country Road Cashmere Knit (ON SALE AT THE MOMENT!)

6. Witchery Ponte Splice Legging
7. Cotton On Skinny Mid Rise Jeans
8. One Teaspoon Bleu Milke Weekenders
9. Frankie4 Jenni in Midas Gold
10. Frankie4 Jamie Boots

Are you a fan of relaxed style? What are your tips for getting it right?

Written By

Gillian is a marketing savant and brand strategist with over 20 years of experience in above and below the line marketing, digital strategy and creative direction. She is an exceptional people person who loves to collaborate with clients every step of the way to achieve the best possible outcome. Gillian is also a successful makeup-artist and make-up obsessive who loves to share her tricks of the trade and help women to look good and feel great.


    • Well Nikki, you are the absolutely queen of beautiful simple style and I love how you have all the tricks for the best basics wardrobe. I was really inspired after Saturday and think I need to have a big wardrobe overhaul! And you are so already a Pinterest girl 🙂 xxxx

  • Oh you are so speaking my language! I’ve been working on this exact thing since becoming a school mum this year. I love the idea of looking like I give a shit, but like it took no effort for school drop offs and pick ups! I also work from a home office (not mine – someone else’s) so it’s a casual vibe there too. Still, I know that for me to not feel like a frumpy lost cause I need to strike a balance. My fave go to is a great leopard print tee from Sportsgirl and some distressed jeans. I put a little effort into some neutral make up and a couple of easy accessories and I feel like a comfy million bucks. Yay!

    • PLEGGINGS! God yes I’m all over those too, love a pair of pleggings. Glad to hear you aren’t crotch-sweat challenged hahahaha. Good luck on the hunt for the knits. Check out those Country Road ones xxx

  • You have completely nailed my everyday style! I’d love to move into skirt & dress territory but now the weather’ cooler I can procrastinate about it until next Summer!!!

    • Oh wow, you’re on fire Shan! But you always look amazing. I have inspired myself with this post and I’m getting around all comfy but looking OK I reckon! MWAH x

  • Loved this post – I think that I want this to be my style. I think that I might have lost a little of myself in being pregnant and breastfeeding and being pregnant and breastfeeding and being pregnant once again… But I think that I am going to cull my wardrobe just before we move and only take the pieces that fit into this style {because life is too short to wear clothes that you actually don’t like that much}.

    • Hear hear Shari. Couldn’t agree more!!!! And love your quote, life definitely IS to short to wear clothes you don’t like! xx

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