A/W Style Switch Up
A/W Style Switch-Up  |  Little Henry Lee

I’ll be honest, proper winter dressing is completely foreign to me. Although I complained about winter in Sydney every year, Toronto is on a whole other level, and it’s still technically autumn! In Sydney I would essentially wear my summer clothes with a pair of tights and a coat over the top, but that doesn’t really fly over here, so I finally understand the need to have distinctly different summer and winter wardrobes. In the interest of literally not freezing to death, I’ve had to push myself to try some new things when it comes to my personal style because Toto, we’re not in Kansas anymore! What this means is most of my style “uniforms” that I’ve been relying on are pretty new to me, and they definitely aren’t things that I was wearing last year.

A/W Style Switch-Up  |  Little Henry Lee


I’m determined to keep wearing skirts & tights until the temperate drops below 0 because I know not being able to wear them anymore will seriously restrict my wardrobe options. But those days are coming up fast, and although jeans are definitely outside of my comfort zone, they’re something I’m forcing myself to try and get used to. I know everyone loves them and thinks they’re the most comfortable, failsafe thing in their wardrobe, but I don’t feel that way at all. I’m far more comfortable in skirts and dresses, but since that’s not really an option in properly cold weather, I have to suck it up. Who knows, maybe by the end of my first winter here I’ll be converted?

I didn’t have it in me to trawl through the shops trying on pair after pair, so I just took Anna’s advice since she lives in denim and bought the latest pair she’d fallen in love with, the Topshop Moto Raw Hem Straight Leg Jeans. I can’t remember owning anything other than skinny jeans since about 2003, but I needed something that wasn’t too skinny so I’d be able to fit thermals underneath, and straight leg seem to be the in thing at the moment anyway?

A/W Style Switch-Up  |  Little Henry Lee

I really didn’t give it too much thought if I’m honest, I just heard Anna talking about them and they’re a brand I was able to see in person and try on before buying, so I bought a blue and a black pair just to get it over and done with. Even though I bought them in the same leg length, I feel like the blue ones are longer, so I like to roll up the cuffs a little so they don’t feel so baggy. I’m thinking about cutting them a little shorter though, since they’re raw-hem anyway. When I saw people wearing jeans with cropped hems I always thought their ankles would get cold, but if it’s so cold your legs are numb then your ankles aren’t going to be any colder than the rest of you – right? Although I say that as someone who is very inexperienced with cold weather so I may be proven wrong come January.

A/W Style Switch-Up  |  Little Henry Lee


Beyond jeans, I have a couple of pairs of black pants from Uniqlo which I bought back when I was working on building a work-appropriate wardrobe, and surprisingly I don’t hate them. I don’t feel comfortable in clothing that’s even remotely corporate, but these Smart Style Ankle Length Pants are great.

They’re super comfortable, have an elastic waistband at the back and are cut in a really classic, tailored way that could look corporate if you wanted it to, but can just as easily be dressed down with an oversized knit and Vans. They’re slightly cropped and look really cute paired with a striped Breton and flats, which is how I was wearing them when the weather was warmer. If you hate black work pants as much as me then you might like these because I never thought I would, but I do!

A/W Style Switch-Up  |  Little Henry Lee

Oversized Jumpers

I know the whole jeans/pants + oversized jumper formula isn’t anything new, but it’s not a style combination that I’ve ever relied on in the past. Oversized jumpers are pretty hard to style unless you’re wearing pants, and since I’m a skirt and dress kinda girl I never bought them because I knew they wouldn’t see much action from me. But now that I'm forced to wear pants, the easiest (and crucially – warmest) combination I could think of was to pair them with oversized jumpers. They’re both something I’m not used to wearing, but if it’s a staple for basically everyone in Europe and North America, then it seemed like a safe bet.

With my hourglass shape I always felt like what flattered me most was skater silhouette clothing with a cinched in waist, which is not what oversized jumpers are known for. But life isn’t all about what’s “flattering” or what we’re told suits our body shape. I’m a person who feels the cold pretty easily, and a big part of getting out of my style rut is challenging myself to leave my comfort zone and try new things.

Oversized jumpers are one of the easiest ways for me to feel comfortable wearing pants, and I don’t think comfort has to come at the expense of style, so as long as I choose jumpers that I love then I can still feel cute with this combo.

A/W Style Switch-Up  |  Little Henry Lee

A few of my favourites have been this western themed one from Zara because I’m all about that cowgirl aesthetic. You can see Carrie wearing it here – it’s always so validating when you buy something and then one of your fave bloggers gets it too. I also picked up a great tomato-orange-red jumper from H&M after looking for one in that colour for a while, and I have an absolutely massive cream one from J Crew that’s 100% wool that I found second-hand for $10 - bargain!

Depending on the shape of the jumper I like to either slightly tuck in the front, or perhaps tuck in the very end of the entire hem and make sure the bulk of the jumper is hanging loosely down over the top of my jeans.

Because the Topshop jeans are properly high-waisted, these two styles of tucking work really well and add a bit of flair to an outfit that might otherwise make me feel really frumpy. I also like rolling up the sleeves a few times to avoid looking like I’m too swamped in material.

A/W Style Switch-Up  |  Little Henry Lee


I've always been an over-dressed rather than under-dressed kind of person, so I never used to get much wear out of t-shirts. But now I like to wear them under my jumpers for two reasons: firstly, every place you go has the heating on full-blast, so you usually have to remove at least one layer. I like wearing something I'm happy in underneath in case it gets too warm, like this Zara one that looks awesome half-tucked into black jeans with my pointy boots. The second is that it’s much easier to wash a t-shirt than a huge wool jumper, so the t-shirt underneath is going to absorb any sweat and body odour (soz, TMI) so your jumpers require washing way less often.

A/W Style Switch-Up  |  Little Henry Lee


I used to shy away from anything with a high neck, especially if it had long sleeves, because with my bigger chest I thought they made me look frumpy. But actually turtlenecks are awesome and I’m so glad I realised that because they’re a total staple for me now.

Before we left for Toronto I picked up a few from Uniqlo and wore them a bit in Sydney as it got cooler, and now that the cold weather has come to Toronto I’ve gotten so much wear out of them.

A/W Style Switch-Up  |  Little Henry Lee

While I can still get away with wearing a-line skirts with tights I’ve been pairing them with turtleneck sweaters and my ankle boots or Vans and I think the combination is super cute.

The Uniqlo ones are pretty hard to beat – they’re 100% merino wool, come in a range of shades and they’re only about $40-50 each, depending on which country you're in. I have black, burgundy and cream from them and I couldn’t recommend them enough.

As well as those, I have a beautiful grey cashmere one that’s vintage that I scored for $45 in perfect condition, and I also have these black and grey sweaters from ASOS that aren’t strictly turtlenecks, but they have a high neck with a little ruffle and I think they’re adorable.

Although I’m not overly inclined to wear tighter knits with jeans as I feel like everything is too form-fitting for me, pairing knits like these with skirts or layered under pinafores is totally my vibe. and I've been wearing that non-stop this autumn.

A/W Style Switch-Up  |  Little Henry Lee


My jackets haven’t seen much of a shakeup because I already owned lots of ones that I love and have been wearing for years – a few vintage letterman jackets, the perfect fringed leather cowgirl/biker jacket, and a beautiful vintage faux fur. But this year I branched out into to denim jackets – I picked up my blue one in SF back in Feb and have worn it to death since then. I customised it with a Leonard Cohen back-patch and a bunch of cute pins and it’s one of the most “me” things in my wardrobe.

My other favourite jacket, and one that I bought more recently, is this pink corduroy ASOS one with faux shearling. It’s a perfect blush colour that goes with so much in my wardrobe, and can easily be layered over my aforementioned jumpers and turtlenecks. I was desperately looking for a black denim jacket with white shearling and for some reason they are nowhere to be found this season. Eventually I tracked one down on ASOS and ordered it to my parent’s house so my boyfriend’s parents can bring it over for me when they come and visit in December.

It seems like a lot of effort but I’m really not keen on paying customs duties in Canada because we don’t have to deal with them in Aus! Oh, and if anyone was concerned that I think denim jackets are going to be good enough for winter here, don’t worry – I’ve bought a North Face parka which I’ll probably be wearing over every outfit once it starts snowing.

A/W Style Switch-Up  |  Little Henry Lee

Longline Cardigans

I remember owning a few longline cardigans years ago and eventually feeling like they weren’t my style anymore, so when I was looking to try one again I didn’t want to get anything too pricey in case I didn’t love it.

I spotted these at H&M and picked up the grey one because it’s exactly what I was after and it was really affordable. I’ve been fairly picky with my knits and for the most part have preferred to buy wool, but since this is more of an outerwear item (I’m hardly going to wear it without anything underneath) I’m not all that fussed.

In fact, I was so surprised by how warm the grey one is that I picked up an oatmeal/blush shade so I’d have some variety. As long as the weather is over about 5 degrees Celcius, one of these over a cool t-shirt like the one above and a pair of jeans is definitely warm enough. So not only are they warm, cosy and comfortable, but they give me some extra ways to wear jeans that maybe I wouldn't have been doing before.

A/W Style Switch-Up  |  Little Henry Lee

Ankle Boots

Ankle boots are nothing new for me, but I’d fallen out of love with the ones I owned back in Sydney and donated them before the move, so I had my eye out for a new pair. My little heart was absolutely pining for the utterly perfect Acne Jensen Boots, but since I’m not in the habit of spending $700+ on myself in one go, I went with a really similar pair from Urban Outfitters that I got on sale for about 10% of the price. They don’t have the cool cowgirl metal tip or the designer label, but they’re real leather and they look pretty close. I was prepared to spend a fair bit more than $70 but didn’t see anything that I could get my hands on that looked similar enough, and I actually bought these UO ones in store which meant I got to try them on first. For the record, I went for a full size up from my normal size based on the reviews and they fit perfectly and are super comfortable.

A/W Style Switch-Up  |  Little Henry Lee

Vans Old Skools

As with skinny jeans, since leaving behind my emo days about 10 years ago I wasn’t in the habit of wearing anything resembling a sneaker. But I’d asked for a pair of white Converse for Christmas last year and have worn them to death, so it was about time to invest in a pair of Vans Old Skools. I’d wanted them since I realised how much I liked my Converse but only just got around to picking them up and I love them so much. I feel like white Converse don’t look that great with black tights, so they’re better for summer, whereas Vans go with basically anything and I’ve been getting so much wear out of these bad boys.