Welcome to the first Ask Bee Anything, a series in which I’ll be answering your most asked style questions!
Since I won’t be able to answer every question that came in within one post, I’m planning to break them down into a 3 part series in order to cover as many as possible while keeping the content digestible. There were a few themes throughout the questions I received so I’ll organize the posts that way too.
The theme we’re tackling today is: COLD WEATHER STYLING. I’m dishing out all my layering notes, LOTS of thoughts on boots, outerwear ideas, how to wear dresses when it’s cold, pairing wide leg pants with footwear and hopefully a whole bunch more wisdom that you’ll find helpful.
Right then, let’s dive in!
Quick housekeeping note, this post has a few affiliate links and I’ve noted those with an * to keep things as transparent as possible.
Q1 - The art of layering! I often have an outfit that looks great and then I need a cardigan or something to keep me warm and everything is off balance! Help!
If you’re finding that you regularly need a bit more warmth, then you probably need to factor that in from the start. I personally run cold so if I don’t have a warm material close to my skin (primarily on my upper body) I get chilly.
My basic approach when layering for cold weather is to go for a warm material or a more fitted top piece first (that will help retain body heat), then I add pants in a medium weight (such as a denim or wool), then I add a lighter top element like a button up shirt, soft sweater or blazer.
A simple solution could be to start with a base tank under what you’ve been planning to wear and see how that goes. Alternatively, if you find you’re adding the same cardigan a lot, think about how you might wear that piece in ways that feel more aligned with your style.
I often find it’s when I’m at my desk that the chill sets in and wearing warm footwear and/or having a cozy shawl handy can really help with this.
For additional reading and tips see my blog post: How to Stay Warm and Still Look Chic This Winter.
Q2 - I really like ‘carrot leg’ pants (wide hip, narrow ankle) but having trouble styling them in winter without feeling frumpy. (I think they look good with ankles on show and not so much bulk on top) Would love ideas!
I love this style too and I think they look great with a streamlined boot that’s tall enough to extend up underneath the hem and that is fitted through the ankle. Something like a Chelsea boot would be my recommendation (I have a round up of my top 4 picks for this season below). I styled a pair of tapered trousers with my favourite pair of chunky Chelsea boots in my latest blog post (also shown above).
If you don’t love a Chelsea boot then I would try a combat boot style that laces up the front and stick to an option that has one colour throughout so that it doesn’t disrupt the visual continuity around the ankle.
When it comes to styling a carrot pant shape with tops, I tend to let the pant be the main source of shape and structure in the look and add other elements in to add colour, texture and dimension. I like to go for a fitted top and add a third element like a cardigan, open shirt or blazer. I also like to go for a relaxed fitting knit (or shirt) in a material with lots of drape and either front tuck to create a high visual mid point (to balance the shapes) or choose a cropped length piece that can be left loose.
Q3 - I am always confused about how to dress for winters - coming from a place which never had any winters, dressing has been challenging. So for example, if I wear leggings and then pants, won't I get hot indoors, especially metros?
Welcome to one of the many conundrums of winter in Canada! I’ve spent my life here and have only just started to get the hang of it.
I definitely appreciate that the leggings AND pants approach is not for everyone. It can feel restrictive and bulky and is just generally a bit of a hassle. I only resort to that on the coldest days.
Instead, I often opt for warm, tall socks* that extend up my calf under my pants and always start with a thermal base layer on top. Something like a fitted turtleneck* or long sleeve* in supima cotton is my go-to. Then I will usually wear a wool pant, leggings or jeans, add a sweater over my base layer, and finally top that off with a loose fitting warm coat.
Side note: In the past I found that I would overheat more when my coat was too fitted and all the heat was trapped.
Accessories are also a must for me because I can get away with a lighter coat if my ears, neck and hands are toasty. Plus, those can easily come off if I’m getting too hot.
The bottomline is that dressing for Canadian winter is a bit of a moving target. At least until you figure out a formula that works for your lifestyle and replicate it over and over until spring returns.
For additional reading and tips see my blog post: How to Stay Warm and Still Look Chic This Winter.
Q4 - As I transition to wider leg pants in my capsule wardrobe, what fall footwear would you purchase if you can only buy one pair this season?
Do you have any tips for styling wide leg jeans with shoes? I love the look of them but haven't figured out how to style them with anything but heels. I don't want to own a pair of jeans that require me to fuss with heels every time I wear them. Thanks!
What shoes are best for wide-leg jeans in colder months? Boots seem weird?
Lots of questions like this came in so I’ll do my best to answer them all together.
If I could only wear one pair of fall footwear with wide leg jeans I would have to go for a black Chelsea boot that has a streamlined shape and a substantial sole (roundup of Chelsea boot options below.). I like that the shaft of a Chelsea boot extend up the leg a fair amount so even if your wide leg pants are slightly cropped there is overlap.
As for flats with wide leg pants/jeans, I also love the look of a high top sneaker or a simple white sneaker. If you want to wear them with more of a dressy flat, I recommend something with a long shape like a pointed toe, to visually extend the foot and leg. Here’s an example of how I styled wide leg pants with flats this spring.
It may help to check out this recent post in which I styled a pair of wide leg trousers and wide leg jeans and you might also find my post on how to style a pair of wide leg trousers more casually helpful as well (all the looks would work with jeans instead of the trousers).
Q5 - I initially found your blog from your Blundstone review a few years ago. Would you still recommend and how do you style?... Also, a Chelsea boot roundup. Thank you for sharing all that you do!
I still love my Blundstone boots and wear them often (more as the weather gets cold). If I was buying them today I’d probably go for the 2274 Winter Thermal Black Original High Top instead of the 1392 Thermal Rustic Black Dress Boot. I find now that I live out in the woods I need more grip and tread than the dress boot offers.
I also have an entire Pinterest board on Blundstone Styling ideas.
Here are my top 4 Chelsea Boot picks at the moment:
The Cortina by Maguire, a Canadian brand - I’ve had the Cortina and the Corticella in suede for many seasons now and really like both. I wear the leather Cortina with shearling lining the most since they’re so warm.
The Decade Chelsea* by Poppy Barley, a Canadian brand - These were gifted this season as part of a collab and I’ve found them so comfortable. Plus the brown accent is a unique detail that warms up the look.
The Mora by Maguire, a Canadian brand - This style is a more refined option that I would opt for if I didn’t need a grippy tread.
The Skye Boot by Dear Frances - If your budget allows, these are probably the most perfect, minimal Chelsea Boots I’ve encountered.
The Chelsea boot is such a timeless style so there are a lot of options available if these don’t speak to you.
Q6 - Source for resoleable shoes/boots for women? Seems like they exist for men, harder to find for women.
Here are a few boot brands offering women’s styles that, to the best of my footwear knowledge, can in many instances be resoled:
Anfibio (Canadian brand)
Poppy Barley* (Canadian brand)
Q7 - Do you have recommendations for winter hats, scarves or gloves that are Canadian made?
My favourite hats have been from Bare Knitwear, Canadian designed and Peruvian made and I just ordered two from Ana & Zac (another Canadian brand to know) that are Alpaca wool from Peru. However, a couple of years ago, I gave Dave a toque from La Tisserande MTL via ETSY and it has served him very well. Great quality yarn and construction.
My suggestion would be to hop on ETSY and search for the accessories you’re after and filter by “ships from Canada” to find Canadian makers. I’m sure you’ll come across a few great options.
Q 8 - You have a lot of great tips on how to dress warmly for the winter. I am always looking for tips on how to pair pants and boots (mostly ankle boots, and no heels) *for work* (no denim). I have yet to find the right combination of pant leg style with boot style that looks good and is comfortable for me. Do you have any tips for how to pair different boot styles with different styles of pants?
The #1 thing that confounds me is a basic formula for how to match pants with shoes. I like playing with different silhouettes, but it's also important for me to keep an edited small closet. In other words, what is the fewest number of shoe styles I can get away with to match the most amount of jean/trouser cuts/lengths/silhouettes? thank you!
This is another common question and my most basic rule of thumb when it comes to pairing pants and shoes is: “Intentional gap or overlap”
Meaning, if there is an intentional gap of a couple of inches (2-4 inches) between your shoe top and your pant hem, for instance a white sneaker and an ankle length jean (like this), then you’re good. Otherwise I like my pants to overlap my shoes enough that there is no awkward sliver of leg in between (like this, same jeans with boots). This might mean the pant leg is long enough to rest on the top of my foot and graze the floor OR the shoe I’m wearing extends up the lower leg enough to tuck under a shorter pant leg.
If you’re finding your pant/boot combos don’t offer this overlap then I suggest a black dress sock to visually close the gap.
I tend to prefer a looser fitting pant over a slimmer fitting ankle boot. The Style Journal has DOZENS of boot and pant styling references to explore.
I think when it comes to the fewest number of shoes you can get away with it will vary person to person but versatility is critical. To me this is achieved three main ways:
1 - Design simplicity - So the fewer bells and whistles, the more range a shoes style will have.
2 - Restraint in colour and texture - So that the shoe is visually streamlined as this will help the shoe pair with more items in your wardrobe.
3 - Balance of form and function - Is the material durable and easy to maintain, but also visually pleasing? For instance suede might appeal sartorially but a pebbled leather is actually much more forgiving and will look good longer. Is the heel height walkable for your lifestyle? 4 inches looks great in outfit photos but 2 inches is much more conducive to daily life.
You didn’t ask this exactly but it may help to clarify shoe styles for you. If I was reducing my footwear collection to just 2 styles a season they would be:
Spring: Tall rain boots & High top sneakers
Summer: A neutral, sturdy sandal & Neutral heeled sandal
Fall: Chelsea Lug Sole Boot & Block Heeled Glove Boot
Winter: Snow Boots & Cosy Slippers
Q9 - What is your all time favorite warm but fashionable boot?
My all-time favourite warm but fashionable boot is definitely the Cortina Shearling Lined Boot from Maguire (Canadian brand).
Q10 - Hi! Thanks for doing this. Any suggestions for professional winter footwear that would be appropriate for a city commute? I live in Chicago & it’s about to get cold & snowy. Thanks!
I suppose it depends if you plan to wear the boots all day at the office or if you’re just planning to commute in them.
I always point folks to Maguire for a winter boots and Anfibio does beautiful weatherproof boots (made in Canada). I also really like the look of the new Summit Boot* from Poppy Barley. Otherwise, you can’t go wrong with a pair of Blundstones.
If you’re simply planning to commute in them and wear something else at work then I think BOGS are a great (affordable) option to trek through snow and slush in. They’re lightweight, warm and highly functional. Then I’d switch to something more sleek for the office.
You might also want to explore My Current Winter Boot Collection.
Q11 - I recently bought a gorgeous long dress secondhand and now that it's getting colder, I'm struggling to wear it. The dress is not only long but also has long balloon sleeves. And a long cardigan only makes it feel old somehow. It works best with my short jeans jacket but that's not warm enough for autumn.
You could start with a base layer underneath your dress and pair that with tights and tall boots. I’d also explore the option of a knit vest to wear over your dress. Gillian Stevens (a Canadian designer) recently released some lovely knit vest options like the Eleanor or the Briar (I have one from last fall and love it). Then you get the effect of the dress sleeves still but a bit of warmth on top.
This blog post covers more tips on how to wear long dresses in the winter.
Q12 - What outerwear (for Canadian cold weather) are we wearing with wide leg jeans & pants?
I personally prefer a long coat with wide leg pants. Something that hits at least at just above the knee or even mid calf. This helps to keep cold drafts from venturing up the pant leg. I think it also works well with a wide leg pant to balance the visual weight of a wide leg silhouette.
I love my London Coat from The Curated (gifted years back & styled here) and my ReWool Long Peacoat* from Everlane (linked to the latest option & styled here). When it’s super cold I wear a long puffer. I bought the Petera Long Parka from ARC’TERYX last winter during a family & friends event and it’s incredibly light but still very warm.
Q13 - Hi, love your content! Long term follower here from the Scottish Highlands. It's cold and wet here for six months of the year. Any ideas for warm evening wear for events at cold country houses?
Hello and thank you! I would go for knitwear sets or sweater dresses with tights and tall boots to stay cozy and still look a bit dressier (example here). Sézane* does some really lovely long knit dresses that could be perfect dressed up with heeled boots, jewellery and a great bag. You could layer a relaxed blazer on top as well for added warmth.
Q14 - Layering! I live in the uk, and work primarily from an office. Our dress code is pretty casual, but in winter it’s dark when I leave for work and get home, and cold and wet, and I’m lucky enough to be able to commute on foot. But the office is pretty warm, especially when there’s lots of folks in! So office appropriate layering is required, and I feel like my daily wardrobe is a bit uninspired! Any suggestions?
This is a tricky one but here’s my two cents:
If I worked in an office I’d be keeping my style very simple and would probably have a few long sleeve merino, cotton or cashmere ribbed knits to wear with black or dark trousers and an oversize blazer or two to mix and match. Then I could take off the blazer if gets too hot.
I would keep a pair of cute shoes at my desk (if I had assigned seating) to swap my warm/rain boots for when I’m in the office. I’d also bring/leave a cosy scarf that could double as a shawl at my desk for when I need some warmth but don’t want to be too committed to it.
Sometimes a little style creativity can go a long way to inspire a closet that may feel tired. Try using the following styling prompts to build looks next week and see what happens:
Monochrome (dress head to toe in one colour using a variety of tones)
Fancy Casual (pair something you consider dressy with something more relaxed)
Three colours only
Bookends (match the top item in your look with your footwear)
Off season (pick an item you wear often in the spring and see if it can work now)
Q15 - Hi Lee! I'm on the hunt for a classic knee-high, heeled boot. Brown or black leather. Basically a true wardrobe staple! Around $250 CAD (or less), ideally. Thank you!
Ah yes, an icon! I will warn that $250 CAD is going to be tricky to stay under for a good quality knee high leather boot. If it’s within your means a timeless style like this is worth spending a bit more on so that you can have them for years to come.
However, if venturing above $250 CAD is non-negotiable, I would check out ALDO’s Satori, Tanerdy, Alers and Equine styles (they all come in genuine leather in both black and brown).
I love my knee high leather boots from Everlane from a few years back and they recently released an updated version*. Poppy Barley (a Canadian brand) released the Toujours Tall Boot* this season, which is similar too, however both are closer to the $500 CAD price point. Madewell’s Monterey Tall Boot* is also a beautiful, minimal option (very similar to the boots I have) and rings in closer to $450 CAD.
If I were buying a pair of heeled knee-high leather boots today, I’d be on the waitlist for Maguire’s Lorca Boot. This boot rings in at $330 CAD and I know the quality will be top notch and the design is on point. They just get proportions so right and I love the little band between the leather upper and the sole. The black version is also available in wide and x-wide calf options.
Q16 - I'm looking for a casual fall high top sneaker, something that I'm not afraid to tromp through the fall/early winter in but looks put together enough for work/going out.
I personally love my black 70’s Chuck Taylor High Tops* from Converse and find that they work with everything from jeans to trousers to wide leg pants. I also love the new olive suede option (they’re water repellent). The Vans Sk8-Hi Mono in black or olive suede is a similar elevated high top style.
If you want something more sneaker forward I would try the New Balance 650, ON’s Roger Spin Clubhouse or VEJA’s V-15 Sneakers.
Q17 - What shoes or boots can I pair with a midi length leather skirt with middle slit?
This sounds like such a fun piece! My inclination would be to style it with a sleek, fitted, knee high (or over the knee) boot in the same colour but a different texture, like a knit or suede so that you have some textural contrast without breaking up the colour. Something like these boots* could work. I’d wear them over a black stocking if you don’t want to have any bare leg exposed.
WHEW! That was a lot of winter style and boot talk but I do hope there were some helpful notes in there. Thanks to everyone who submitted their questions and to you for reading!
Next time we’ll be digging into questions around the theme of Style During & After Life Changes and I’m excited to explore those topics with you.
Have a wonderful weekend & I’ll be back with a new Friday Digest next week!
Sincerely,
Lee the Bee
So many good recs!! Just added the waterproof converse to my cart 🛒
This was so great and chock full of useful advice! Thanks for sharing your wisdom!