Winter Outfit Ideas

It’s the middle of summer in Sydney, but that hasn’t stopped me from planning out some winter outfit ideas… you know, in anticipation of cold weather in a few months time. I really enjoyed sharing some of my layering ideas in December, so thought I’d come in for round two given the cold snap I know many of my American and European friends have experienced over the last couple of weeks. To mix things up I thought I would give a little more context to each of these winter outfit options here, and explain the styling elements and processes that went behind each one. You can watch the full video via the embed above, or over on my YT channel here.

OUTFIT ONE

Whenever I think of winter dressing, cosy knit sweaters immediately come to mind, so I wanted to do something a little different with this first outfit. The hero piece of this outfit is a navy floral slip dress; a summer piece that I thought could work really well when layered during the colder months. To make this work for winter, I started with my base layers: a fitted black turtleneck sweater, and some tights worn over my heat tech leggings (totally comfortable if you were wondering!). You could easily belt this dress and wear a big sweater with it but I really wanted that floral print to shine so I next added a black leather jacket, which is one of my favourite transitional pieces. This is a great outfit finisher for an indoor winter look, but also an incredible layering piece. For extra warmth you could add some black socks, but I went straight in with some sock boots which fit snugly around my legs, to keep a streamlined silhouette below the hem of the dress. I finished it off with an oversized pea coat (a long black or navy wool duster like this would also look chic), and some winter necessities – a scarf and cashmere gloves.

OUTFIT TWO

My favourite thing to wear in winter are a pair of skinny jeans, and I think you can easily make these work over heat tech for when it’s especially frosty. My tip is to get a pair a size up from your regular size so that there’s room for a layer underneath – perfect to make these really work for a cold weather winter outfit. I tend to gravitate towards dark colours when it’s cold, so I decided to break the mold with this look. A striped Breton top in caramel and white is my base layer, along with socks! Next step was adding a sweater, so I went for a pop of colour with a pink roll neck (similar here ). Complementing my sweater with my outerwear, I wanted to pair this with my Mute by JL coat, which has the same warm undertones as the sweater. For shoes, I went with my Stuart Weitzman OTK boots. I was very late to the party with these boots, and after picking them up late last year, I can finally understand why they’re such a wardrobe staple for so many. Personally, my preferred way to wear them is with skinny jeans, as it creates a different look to what I’m used to. I completed the outfit with camel accessories, just to keep everything tonal.

OUTFIT THREE

For the second denim look I wanted to focus on a different silhouette – the straight leg jean – which I know has become a classic in so many wardrobes in recent years. It’s still a new style for me so I’ve been experimenting with how to make them work, and I really love how they look paired with ankle boots for winter. My base layer for this is a sheer white top, which almost looks like a thermal, and is a piece I reach for regularly to add additional warmth to my winter outfits (especially when I want to wear something other than black!). The sweater I paired with these jeans is my favourite, an ivory wool sweater from Joseph that I picked up in the sales last year. To add some extra depth to the colour scheme of this outfit, I added a deep olive coat – this has a cocoon style and cuts off just above the knee. I like the oversized yet streamlined silhouette, which I think works really well with straight leg jeans. The boots I opted for really complemented that mossy green hue. They’re a rich brown suede, with a chunky heel that is easy enough to walk in, but gives you a nice little bit of bonus height.

OUTFIT FOUR

Another style staple for me in winter is a black leather skirt. I discovered this one from Willow a couple years ago, and it’s become a serious workhorse in my wardrobe. I really wanted to experiment a bit with those OTK boots so I figured this would make for a styled up pairing, that I could build the rest of the outfit around. Again, tights over the heat tech leggings are key here to add another blanket of warmth. To brighten up the outfit, I went lighter with my remaining picks. A pink mock neck top which I layered underneath a camel cashmere sweater (this is a great alternative). To get a little bit of skin – or tights – peeking out between the boots and the skirt, I used a belt to raise the waist, or essentially adjust how high up the skirt sat on my body. Finally I added the same camel coat as before, as I really liked the visual lines that this created as a whole. Topped off with grey and black accessories to keep the outfit looking sleek.

OUTFIT FIVE

I really love winter whites, and I wanted to incorporate them into the final outfit but in a different way to my first layering video, and I loved how this combination turned out – to me, it’s so effortless and easy to wear. The trousers are quite fitted at the waist so I really wanted thin layers; a good ribbed turtleneck was key here. Because I knew my socks would be on show, and I was pairing this outfit with a white boot, I wanted to go for a muted colour that would work well with the trousers – grey seemed like the perfect choice to me. Again I used that same layering trick as with the first outfit, throwing on a leather jacket first (I this this works well with anything high waisted to balance out proportions), and a wool coat second. You could finish off this outfit with a nice scarf and beanie and you would be good to go.

Which outfit was your favourite? x