I may have shared my summer take on the 10×10 challenge last week, but given that we’re currently in the throes of winter down under, I wanted to give you a good look at what I actually wore for the winter 10×10 challenge. I should probably mention upfront that Sydney winters are more mild than most. While it might dip down to lows of 4 or 5 deg C in the evening, the coldest I’ve seen the thermostat get during the day is a cool 15 deg C – so if the sun is shining, you can generally get away with nipping out without a coat on. I grew up in Wellington where it wasn’t uncommon to see me wearing a wool coat in summer, so these days I feel pretty fortunate that I’m able to throw on a pair of ankle grazing trousers and bare a little bit of skin even during the coldest months of the year.
A few caveats before I jump right into what I picked for the winter 10×10 challenge. Firstly, I decided to opt for the cosier end of the spectrum, mostly because I work in a relaxed office environment, so I can get away with wearing an oversized knit sweater and a pair of jeans to the office if I so wished – as long as you look relatively put together, not much is off limits, one of the benefits to working in the world of television. While I did include one lightweight jacket, I chose not to count my coats as part of my ten items. I have a couple of absolutely beautiful outerwear pieces and I want to have the flexibilty to wear them as I pleased, while also showcasing how you can completely change up the vibe of an outfit or a set of core items with one piece. And, as mentioned, we’re lucky enough to be subjected to mild winters (and super hot summers), so expect to see the odd bare ankle throughout – I promise I wasn’t cold in the slightest!
My Ten Items
01 | Kate Sylvester Black Turtleneck Knit Top (old but similar option here)
I don’t really know what I would do in winter without this style essential; I love how it pairs on its own, but really for me where it does the most work is as a layering piece. I mostly like to throw this on underneath my mini dresses (with tights too!) to make them a little more winter appropriate – it’s a simple trick that allows me to get so much more out of my wardrobe, and make a few more pieces work year round. Given I’m all about versatility, that makes this a huge keeper for me!
02 | Everlane white linen blouse
Safe to say that there’s been a little bit of a linen craze sweeping the fashion world at the moment, but I’ve been a huge fan of the fabric ever since I was younger. I remember being 10 years old and getting my yiaya to sew shorts from linen fabric that I’d bought from Spotlight, and my linen love is still going strong many years later. I really love this collarless white linen shirt from Everlane, which I actually also have in the pink/white stripe. It’s a very boxy fit through the body, which gives it a more relaxed feel, and I really like the way it looks all buttoned up, or worn with the top couple buittons loose and the sleeves rolled up. As far as I’m concerned, this is a great alternative to the classic white shirt.
03 | Joseph ivory knit sweater
I couldn’t do a winter 10×10 challenge without including this sweater from Joseph (similar here in blush). I snapped this up during the end of year sales and it’s been one of the best investments I’ve made in my wardrobe – absolutely no regrets. It’s a nice oversized fit on me, but what makes this really special is the ribbed detail down the sleeves and centre back. It elevates it from any other knit sweater I own, plus being such a nice neutral hue, it pairs perfectly with everything I own.
04 | ASOS red/white stripe top
This was a bit of a divisive piece in my ASOS Haul video which I shared on my YT channel, but I really loved how effortless this one was to style, plus the weight of the material felt incredibly high quality, despite the low price tag. And I don’t really feel you can go wrong with a classic staple piece like this. It’s a little boxy in shape but I tend to wear highwaisted items, and I really like that visual contrast between something a little more fitted, with a looser piece – it’s a style rule I tend to stick to.
05 | Everlane stripe cashmere sweater
The final top I opted for was another sweater, this time, a striped cashmere option from Everlane. I really rate their cashmere, having had really good experiences with their range in the past; it’s soft, easy enough to care for, and the quality does last the distance. I wanted a top that was still technically a neutral, but had a bit more personality that the other options I chose, and this really fit the bill, plus I love how snuggly and warm it is.
06 | Dr Denim skinny jeans
There was a point in time where I felt like these jeans no longer had a place in my wardrobe, but I’m glad I actually ended up hanging on to them. I picked these as they are so versatile, and I think one of the most flattering pairs of jeans that I have in my closet. I love the faded black wash, and I think the style works quite nicely for both a relaxed office environment (thank goodness for our casual dress code!), and also for the weekend plus they go with absolutely everything.
07 | FRNCH b/w polka dot maxi skirt (old but similar here)
I don’t think that capsule wardrobes or ‘edits’ necessarily need to be basic, and one of the easiest ways to elevate your style options a notch is with a timeless printed piece like polka dots. This skirt just grazes the ankles which makes it a great one to layer over tights with a pair of ankle boots peeking out underneath. I also like the elasticated waistband, especially as my diet is much richer in the winter time (think lots of casseroles and hot chocolates…).
08 | ASOS navy grid check trousers
I wanted to include these trousers as they literally feel like wearing pyjamas. The fabric is soft and stretchy, and they have a loose fit through the leg that tapers in at the ankle. I will admit, there are probably more flattering styles out there, but I love this take on a classic style, as the grid print makes the trousers feel a little more modern. I’d love to look at investing in a more expensive pair in a wool or cotton/linen, so am now keeping my eye out.
09 | Workshop khaki utility jacket
My style tends to be a mix of classic pieces in feminine and masculine styles, and this jacket definitely errs on the latter side of the spectrum. It’s quite boxy fitting through the body (it is a unisex jacket!), but I love that you can cinch it in and add a bit of shape by tightening the drawstring at the waist. This is relatively lightweight, and I love the khaki hue.
10 | Everlane black wrap mini dress
The last piece I wanted to include was a dress, and I wanted something that would be versatile enough to wear at least a couple of different ways. It’s a huge reason why I really like this dress from Everlane – it looks great thrown over different tops (and I’d also say.. a thick snuggly sweater), in addition to doubling up as a ‘skirt’, when you want to throw another layer over the top.
Coats
While I didn’t explicitly include any coats as part of my ten items (one of the flexibilities of doing this challenge), there were five that I switched in and out depending on my outfit. I’m the kind of person who likes their coat to be complementary to the whole look, so it seems less an afterthought and is more the final touch to your outfit. There are two coats that I probably reach for the most on a daily basis; my navy wool ‘edith’ coat from Stella McCartney (also here and this is a great affordable dupe) and my camel cashmere robe coat from Mute by JL (I also like this option). On days when the weather is a little warmer, I’ll reach for my globe coat from Wilson Trollope; this is a lovely lightweight option and I adore the pale lilac hue. Alternatively, I’ll cycle in one of my trench coats. I have two on rotation currently: my beige trench from Everlane (which I’d admittedly like to upgrade to a Burberry… one day), and an old navy cropped style from Karen Walker with gold buttons (I found the beige – pre-loved – here!).
The Accessories
If you took a look at the bags I usually reach for on a daily basis, you’d probably note that there isn’t much variety, but I wanted to try and mix things up for this challenge and force myself out of my ‘handbag rut’ – if this is even a thing. I bought a velvet zodiac bag a couple months back as I wanted to test out the Prada cahier bag style without splurging on the actual designer piece, and it’s actually become one of my favourite bags to throw on as it is such a statement piece. The other smaller bags that I reached for throughout this challenge include my Celine trotteur bag (affordable option here), my Chanel chevron leather boy bag (similar style here), and my Phillip Lim mini pashli bag, the last of which I can’t wait to wear more once the weather warms up, as I usually like to pair this with my spring/summer wardrobe. Then the two bags I used were my Cuyana black leather tote, which has become a major favourite of mine, and my Linjer tan leather tote, which I equally adore.
There are three scarves that I use regularly, which I tend to rotate depending on the base colours of my outfit. I splurged on a grey Acne Studios canada scarf a couple years back which I loved so much, that I bought a second one in a beautiful caramel hue as a birthday treat to myself in February. I also have a darker charcoal grey cashmere scarf from Mia Fratino which is the definition of winter luxury – this one feels a little lighter than the other two and I like to wrap it over my shoulders at the office if I’m feeling a little cold.
Lastly, I find myself reaching for the same few jewellery items day in and day out. I didn’t really wear a watch over the ten days but the one I did reach for was my ‘aki’ watch from The 5th. For earrings, I wore my spiral hoops from Reliquia, my editor hoops from Mejuri and a pair of oversized wavy earrings from Anthropologie.
Shoes
I love a statement shoe but day-to-day I will always choose practicality over style – though thankfully I have a few pairs of shoes which incorporate the two! One of my favourites has to be the two tone pumps I have in a charcoal/black from Vaneli. This is my second pair, which I bought after enjoying my beige/black ones so much. My other pair of flats that I love for winter are these Gucci dupes from Sam Edelman. I love a good loafer and the gold horse bit detail across the vamp is just a little bit extra, plus they look great with tights. For a little bit of height, I tend to alternate between the Everlane day heels and my black suede pumps from Charlotte Olympia (similar affordable option here). The latter are a little bit special with the gold heel, and I love that they provide some height which elongate the legs, but they’re still easy to walk in. I also have a pair of Maxmara heels which live under my desk at worn, which I’ll often throw on if I’ve walked to work in a more casual shoe. Finally, I’ve got two pairs of black leather boots which I alternate between: the Everlane boss boots (full review here) and these buckled boots from Jo Mercer.
The Outfits
1 | red/white striped top + faded black skinny jeans
I started my challenge on a Friday, just to be able to maximise the number of more relaxed outfits that I could wear throughout. Trust me when I say that this is the best way to start this challenge. Our work dress code is pretty relaxed most days, so I try and keep things casual but looking smart. I opted to pair the red and white striped top with my skinny jeans, and for shoes I wore my two-tone pumps. These are super comfortable for walking long distances in. It was cold so I wore my Mute by JL coat; I love the rich caramel hue of this classic piece, plus I think it really helped to make the red striped top pop.
2 | red/white striped top + black wrap dress
Most weekends are spent at home working on my blog and Youtube channel, and while I didn’t have anything to actually ‘dress up’ for, I really wanted to come up with a playful way to style the Everlane wrap dress. I decided to wear it over the red and white striped top (nothing wrong with wearing the same item two days running…), and I think it turned out looking pretty cute – though probably not something I’d generally wear day to day. To add a bit of height, I wore my Everlane day heels, and then I grabbed my Chanel chevron boy bag – because this bag was such an investment, I like to try and use it as often as I can!
3 | striped cashmere sweater + faded black skinny jeans
So… I have this thing with stripes… and on Sunday I decided to pair my striped sweater with my skinny jeans. This is such a comfortable outfit, and was perfect for a day spent at home editing. I did need to nip out to the shops to pick up some groceries, so I threw on the same shoes from Saturday, my globe coat from Wilson Trollope, a scarf and my mini pashli bag.
4 | white linen shirt + navy grid check trousers
Because I have quite a long (walking) commute to the office, I tend to warm up pretty quickly so if I won’t layer up too much unless I really need to. Thankfully, it was a pretty mild winter day. I opted to pair the white linen shirt with my navy grid check trousers, and to tie in the colour scheme, I wore my navy trench coat from Karen Walker. I adore this piece because while the style is ultimately a classic, the tailoring makes it unique to anything else I’ve ever seen. I swapped my bag out for my Cuyana tote, and went for a lower pair of shoes – my pointed toe ‘lady’ shoes from Charlotte Olympia (similar). The final details were my cashmere scarf from Mia Fratino, and my ‘aki’ watch from The 5th.
5 | black turtleneck + black wrap dress + khaki utility jacket
I decided to reach for the wrap dress again on Tuesday, and wore it how I would typically style this piece, with a black turtleneck underneath. I think this combination looks really chic, especially when worn with black tights and some pointed toe boots. I also threw on my utility jacket with this one, and keep the same tote as yesterday.
6 | black turtleneck + black polka dot maxi skirt
My black turtleneck is a great multi-tasker, and I wore it on Wednesday as a pared back piece to let my polka dot maxi shine. I switched up the boots and threw on a buckle pair, just as they come up my leg a little higher, and I wore my camel coloured coat to add an extra layer. Because I wore my hair back, I wanted to jazz up the outfit with accessories, so I wore the biggest pair of statement earrings I own from Anthropologie. These look like they’d be super heavy, but they’re actually pretty comfortable to wear and I think the folded wavy design is really special.
7 | ivory oversized sweater + navy grid check trousers
I’ve worn this sweater from Joseph so much this winter – it just goes with absolutely everything. I chose to wear it with my grid check trousers, and wore my Stella McCartney coat (on sale!) to tie everything in. I actually spotted a great dupe for this if the designer option is out of your price range, which you can shop here. I had an event on in the evening so pared back my belongings so I could take my Chanel bag out for a spin.
8 | striped cashmere sweater + black wrap dress
Now I told you that the wrap dress was a versatile piece. For Friday, I wore it with a grey cashmere sweater thrown over the top. I tucked the sweater behind the bow slightly, just to add some visual interest and avoid any bulkiness underneath the sweater. The jacket I wore is a trench coat from Everlane – this is a coated cotton so it is waterproof, however after having it for a couple years, I think I’m really to upgrade this to something more substantial and that has a little more structure – Burberry is the obvious option, so for now I’m saving my pennies until I can invest in it. I ended up wearing this outfit with my Maxmara heels which sit under my desk at work, so to give you a better picture of how this looked I wore my Isabel Marant pumps.
9 | ivory oversized sweater + faded black skinny jeans + khaki utility jacket
This sweater and jeans combo is probably my most worn outfit of the moment. I’m not afraid to repeat outfits, and if I find a look I love, I’ll keep it on rotation for days when I don’t want to think about what to wear so it’s probably little surprise that this is one of my favourite looks from my winter 10×10. My Sam Edelman loafers are a great pair of shoes for every day, and an option I usually pick on the weekend just because I can dash about in them, but they also look incredibly chic. I paired this outfit with my utility jacket again, and to complement the colour palette, I switched my Celine trotteur out for my Linjer soft tote bag.
10 | striped cashmere sweater + polka dot maxi skirt
My last outfit of the challenge was probably my least favourite, but I really wanted to wear this maxi skirt again and wasn’t feeling how it paired with the Joseph sweater. In saying that, it’s still 100% a look – who doesn’t love to print mix a little bit? I wore the spotted skirt with the striped cashmere sweater, tights on my legs and my CO ladylike pumps. I spent most of the day at home but when I was cold, I did drape my Acne Studios scarf around my shoulders for an additional layer.
Are you going to do the winter 10×10 (or summer) challenge? I started this a little early but wanted to say a huge thanks to Lee and Caroline for hosting again this year!
Hi there – I love the https://www.mutebyjl.com/collections/cashmere/products/jl033-camel-coat but have never seen any pictures of it actually done up with the belt. What does it sit like…. I worry it’ll be a little “sack” like?!
I wish I was as good at remixing clothes as you! Still love that Prada-dupe bag (trying to find it and I can’t, haha!) and that Stella coat is soooo gorgeous!
http://www.closet-fashionista.com/
Hi Jamie – love your youtube channel and blog. Especially watch your videos all the time!!! Just wondering what size your utility jacket is?? I have a small frame, but am tall and am wondering whether the small size is going to be too big for me. Thanks for letting me know.
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Thank you so much Tanya!! I got the utility jacket in an XS – it’s still oversized on me, but I like the way it looks. For a good size reference, have a watch of the video if you haven’t as it should give you an idea of how it drapes on me 🙂
Thank you!! That is very helpful 🙂
Wow, I love every single outfit. I actually quite like the polka dot maxi outfit at the end, but it is a bit of a different look for you so perhaps it was out of your comfort zone?
That acne scarf is such an outfi-completer. I’m a sucker for their printed logo and love how it shows in the pic.