While cold days are drawing to a close in Australia, American and European readers are heading towards winter. So I thought a Winter Looks post featuring a wrap-up of styles from autumn and winter in SWA, that can also take you seamlessly into spring, might be helpful.
I have to say upfront that for winter looks, your best friend is layering. Winter looks that will take you refreshingly into springtime in the southern hemisphere, or keep you sizzling warm in the north, should be masterfully versatile.
My favourite winter looks have been mostly casual, some with a little design structure, and I’d say that my most interesting outfits have featured colour this year.
To achieve an effortlessly casual effect for winter you need to think about what will go on top of what.
The best Casual winter outfits to keep you snug are compiled with a little thought when it comes to basics, colour, texture and show pony pieces.
Bulky jumpers are not your friend, unless you’re out on a hike. Who wants to feel all trussed up or hot and sweaty (hello ladies of a certain age) with nothing easy to strip off if you find yourself in a restaurant, on a winter’s day, wearing only one big jumper?
But neither do you want to freeze, so putting together an outfit for winter is all about adding suitable layers, and cute accessories.
You might want to refresh your wardrobe for winter to include some new basic capsule items onto which you can add your show pony layers. You might need to purchase the following …
- A couple of new vests, one in white, one in black.
- Ditto long line T shirts.
- One or two long sleeved stretchy shirts in baseline colours
- A blouse with a collar
- A navy pair of jeans, a black pair of jeggings and a pair of ponte pants.
- A pair of leather ankle boots
Table of Contents
How to layer your winter looks
- Start with a T-shirt or a Vest.
- Add a long sleeve top.
- Top with a jumper, cardigan, or jacket.
- Below you might wear jeans, ponte pants or smart tailored pants.
- My favourite winter staple footwear has to be ankle boots.
- If you choose a frock you could wear ponte leggings underneath the dress, and then layer as above.
- Add a scarf or a chunky necklace
- Don’t forget a feature handbag
- Top your winter look with a lovely hat
The trick is to up the ante with each layer you add. You should think about adding interest and versatility to the outfit, especially when it comes to the heat or cold.
The more layers you add, the more chance you have of pulling off a stylish look.
And remember that looking casually put together is a bit of an art, and doesn’t just mean throwing things on. The most appealing winter looks come from thoughtful layering.
Accessories always add interest. So do consider necklaces, earrings, and a nice watch.
Tips and Tricks
Think about the colours you’re wearing – does the scarf or hat you’ve chosen match the base-line colour of your outfit?
Either use a couple of contrasting colours, or keep to complemenary colourways for successful winter looks that don’t clash.
Are your boots going to match your handbag, or will they pick up a colour from your outfit? I’ve loved my suede red boots from Hotter this season, which I didn’t think I’d get much wear from – but they have been super useful for highlighting the red tops I’ve been wearing.
Does the base layer you’re wearing flatter you? If you think you might have to strip off to that layer, then rather wear a flattering T-shirt. It’s no good wearing a skimpy vest that’s gone a bit grey in the wash (!) if that’s the layer you might be going down to if it gets hotter.
Top layers don’t always have to be long sleeved. Think about wearing a sleeveless jacket or gilet for an extra layer in not-so-cold climates.
So what have been my favourite winter looks this year? Read on for some outfit inspiration which I hope might motivate you to have fun layering this season.
Casual Winter Looks
I love the outfit below and have worn it many times this winter.
It’s a Vivid International Hayley hi-low top in Burgundy. Underneath I may wear a lightweight vest if it’s cold, and to top her off I’ll wear a black overcoat.
I love how Hayley has a long-line back which really adds to the movement, as well as covering a multitude of body sins. I teamed Hayley with a black velvet scarf which has cherry detail, red Hotter ankle boots and Vivid’s black ponte pants.

Structured Winter Style
The look below features a Vivid International Fiona faux fur vest in silver with a Polly printed top in moss. Black sunnies, a Travel & Living Collection Hannah bag and black jeggings from Marks & Spencers. You don’t always have to wear a long sleeved top as your final layer. Especially moving into springtime a gilet is perfect.

The look below is structured layering, for a semi formal day out with Mr Mustang Hire. The jacket is soft, but tailored, and layered over a silky top which falls beautifully just below hips and bum.
Underneath I’m wearing a vest. The boots although brown, went together perfectly with the brown leather handbag I was carrying. The necklace mimics the black and white of the overall look. The sunnies add a touch of sophistiation.

Boho for Winter
The cute 1920s style hat below was a warm and stylish addition to this monochrome look. the soft scarf found at a charity shop also complemented the colourways I chose for a light lunch, sitting outside on a wintery day at a local cafe.

The winter looks below and above were all about layering. Below, the base layer was a Vivid International, Macey Merino wool zipper top in wine, topped with a boucle jacket from Millers Fashion and skinny jeans from Marks & Spencers with a scarf from Accessorize. The Macey top in wine also features in the feature image at the top of this blog post.

Outdoor Winter Looks
The simple look below I chose for a sunny winter’s day walk in the forest. Underneath I was wearing a white T-Shirt in case I needed to strip off. The rose gold and dusty pink Nordgreen watch complements the cherry fleecey sweatshirt from Mountain Warehouse.

Below is one of my favourite winter tops. It’s a Maddy merino hi-low top in red. Such a vibrant colour for winter. This look with black jeans was easy to layer with a black jacket, or long line cardigan on colder days. The clay coloured Christin leather bag by Travel and Living Collection has also been a staple fashion handbag this year.

The Vivid, Polly printed top in moss pictured below has been a firm favourite this winter as the colours have been so versatile to match up. Here I teamed Polly with navy slimline jeans, and a Vivid, lined lightweight winter jacket in navy. Ankle boots from Homyped. Just the look for a winter lunch at a winery.

Le Frock for Winter

The Vivid bubble dress in navy has been a real favourite this winter, and I think this look is a little unusual. I’ve put it together with tapered 3/4 length bengaline pants, a maroon cardigan, brown leather ankle boots from FRANKiE4 and a leather tote-style handbag.
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Disclaimer: Thanks for gifted products from the following stockists: Vivid International and FRANKiE4 Footwear and Travel & Living Collection. This post contains gifted products, and affiliate links from which I stand to earn a small commission if you buy from them – but at no expense to you. Lifestyle Fifty Website is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to Amazon.com.
Your winter looks are fabulous. I love winter clothing because of the layers and colours I can wear. Merino tops are very handy here in NZ which I wear daily. I have a “vegan” black leather vest which I adore and an array of colourful merino cardigans to drape over the base. I also wear jackets often.also in many colours- leather, tweed, denim etc
I love colour,ankle boots and colourful scarves to bring it all together!!
Enjoyed your blog today.
I’m so glad you enjoyed my blog post today Gaye. And thank you for your own thoughts and tips too :). Yes Merino is a great wool to look out for.