Today I’m back with another instalment of Ask Bee Anything, a series in which I’m answering all your most asked style questions.
If you missed Part 1 the theme was Cold Weather Style Advice and if you live somewhere chilly you’ll probably find some helpful insights in there.
This time I’m answering all the question that came in under the theme of Style During & After Change. This one covers a huge range of topics from changing jobs to retirement, maternity to post-partum, style after surgery and how to make sweatpants presentable. We’re also getting into the question of whether a closet can ever be complete and how living at Steep Hill has changed my relationship with clothes.
I’m honoured that so many of you trusted me with these questions and hope that my responses will offer helpful style ideas and more!
Quick housekeeping note, this post has affiliate links and I’ve noted those with an * to keep things as transparent as possible.
Q1 - Hi Lee, Since retiring I've greatly simplified my wardrobe and jewellery to a capsule - high quality, limited number of pieces, limited colour palette. Wardrobe is now more casual (business suits gone). I am struggling to add a new piece or two for wearing out to dinner, to an event or a party. What's your approach to styling up a basic, more casual wardrobe to get an event look that is classy and polished? Thanks!
I think the first thing to determine is what items make you feel more put-together and polished?
I have a very casual day-to-day wardrobe as well and then I have a handful of items that I love to pull out for dressier occasions like dinners and parties. At this time of year, I love a wide leg pant or dark jeans with a drapey top, and a heel (like the first look here or this outfit) or I like a sweater dress or silk dress with a pair of tights and tall boots (like this look or this one).
Sometimes however, it’s as simple as adding one piece like a silk scarf or a beautiful blouse that you can pair with a simple black pant or your favourite jeans. I also think a really great little bag that you can carry to your events or dinners is all that might be needed. As long as one element in the look feels elegant and special you’ll feel more polished.
Q2 - My style is a lot about nice textures—silk, wool, etc—but since having a baby it’s rarely feasible to wear things that don’t machine wash well. Any suggestions for how to get nice texture combinations with machine-washable fabrics? Specific textiles, combos, pieces—any suggestions would be great! Thanks so much!
This is such a good question. I’ve had success with Everlane’s Washable Silk* styles, Eileen Fisher’s Crepe Silk* is washable (it has a matte slightly nubbly texture). I would love to try out Quince’s Washable Silk but they don’t ship to Canada. However, a Canadian washable silk shirt brand on my radar is NUMI. I also heard that Elizabeth Suzann’s Silk Signatures are in the works, and those are by far my favourite (seen most recently here and here).
For a silk alternative, I love Tencel (aka Lyocell) as it offers a similar drape and movement but has more weight and durability. Everlane uses this in many of their drape styles like the Way High Drape Pant*, which I love. Vestige Story (Canadian) also uses lyocell in their Prose collection.
For softer fabric with a silk-like drape, bamboo is a great option. I have the bamboo bras from Free Label (Canadian & size inclusive) and love them, plus it looks like they do more styles with bamboo and other luxurious natural fibres that are machine wash friendly.
I love Supima cotton for its smooth and elegant hand feel. It doesn’t have the same stiffness as regular cotton. These* are my go to for base layers in the winter and I always machine wash and dry those.
I also love a Jersey or Modal for lots of flow and ease without the preciousness. Eileen Fisher does beautiful stretch jersey styles (which are largely made of Tencel) and I love Encircled’s Comfy Wide Leg Pant* (use LEE10) in Modal.
Of course linen is highly durable and feels great on but if you’re not into the rumpled look it can be a nuisance to iron.
Wool is less precious than most folks realize too. It has antibacterial properties which means it’s naturally self-cleaning and its also stain repellent thanks to the structure of the fibres. If you are open to a bit of spot cleaning (I just use dish soap and warm water) I think you can probably still wear your favourite wool pieces.
If you want the texture and warmth of wool but need to know you can wash it, I would consider Tradlands* or KOTN* for cotton knitwear styles. I also really love the soft and cosy feel of Power of My People’s flannels (use STYLEBEE10).
As for mixing materials, I tend to pair something smooth with something more textured as a general rule of thumb.
Q3 - Hi Lee! Two years ago I went from working a typical 9-5 job to being self-employed as a wedding photographer. Since then, I've struggled to feel stylish in my day-to-day life without having Zoom meetings and other 'professional' events to dress for. Most weekdays are spent sitting at a computer editing photos and doing a lot of solo work, so I've found myself lacking creativity and inspiration with my outfits, thus feeling a bit down on myself. I'm hoping you can help provide guidance on daily outfit inspiration. I'm looking for something that is casual and comfortable but leaves me feeling good and put together (i.e. minimal sweatpants and leggings!). I live in the Northeast, so I find this is more of an issue in the winter when it's chilly. So I'd love some ideas for the chillier months, as I feel like it's way easier to get dressed and feel cute in the warmer months (sun dresses are the best!).
This scenario definitely resonates as I tend to be at home behind the computer a lot myself. I’ve found that the most reliable and low activation solution (meaning minimal decisions and energy required) is having a few very comfy but still refined loungewear sets that I can wear around the house but dress up with a cute pair of sneakers or boots, a nice coat and accessories. A matching set looks intentional and put together and then you just need to add a trench, wool coat or quilted jacket and maybe some warm accessories to make it presentable for the real world.
I also find that if I treat my loungewear a bit more like my “good” clothes then I don’t feel as though I’m in sweats. For me this simply means folding them nicely or even hang them up so they don’t have wrinkles or creases.
For minimal lounge sets I would look at:
LÉZE THE LABEL (Canadian brand, size inclusive)
Encircled* (Canadian brand, size inclusive, use LEE10)
Vestige Story (Canadian brand, size inclusive)
Free Label (Canadian brand, size inclusive)
Colorful Standard* (use STYLEBEECS10)
Another thing that might boost your styling inspiration is planning your outfit for the next day and setting it out the evening before. It might still just be a lounge set but having it ready to wear always elevates the experience of getting dressed somehow.
Q4 - I start a new job in the City on the 4th December. I have worked in a business-casual office for the past 8 years. My new office is more business than casual (no jeans and trainers). I need affordable, warm, work ideas!
Congratulations on your new job!
This post and this post both have some very warm office appropriate outfit ideas.
I would start super lean with my business workwear additions. I’d go for one pair of really good black pants and a blazer (either to match or in a neutral plaid) that you can add different tops and shoes to. I’d pick up a few lightweight knits in different colours to pair with the pants and blazer. I also love a sweater dress with tights and boots in the winter because it’s cozy, comfy and still polished.
I’d be looking at Everlane*, Banana Republic*, Sèzane, RW & Co., Aritzia* and KOTN*.
Q5 - I am getting a long awaited and anticipated breast reduction surgery soon! I am very excited but nervous because I know how to dress my body in its current state and am both excited and nervous about dressing my "new" body. Any insights/thoughts/advice/words of wisdom?
Thank you for sharing this exciting and impactful change. I hope that everything went (or goes) really well and your recovery is smooth and swift!
My best advice would be to take your time figuring out what works for your new figure and try not to rush any big purchases or decisions about your style. Maybe stick to one addition at a time and see how each item really feels.
Apart from the physical differences you’ll need to get used to, I can imagine you’ll likely find that a lot of underlying emotions come to light when it comes to how you think about and see your body. I’d consider keeping a journal handy to write down how you’re feeling and what you’re noticing as you embark on discovering your personal style in this new chapter.
Sending lots of love and healing energy your way!
Q6 - Thanks for doing this! My question is: I’m officially in my thirties now and my wardrobe feels like I’m stuck in my twenties. I love basics but I’ve been wanting to upgrade my style a little. Do you have any ideas how a lover of a plain white tee and jeans can elevate their everyday look, apart from jewellery? Your thoughts would be much appreciated. Thank you!
Blazers are a great way to elevate jeans and a tee and if you don’t love wearing structured pieces, opt for a soft option like this one* featured in my latest blog post. I also love an oversized button up in a colour or stripe, worn open to add some dimension. I think a great pair of shoes can also work wonders. I’d opt for a leather Chelsea Boot or a chunky loafer to add some polish to the base.
Q7 - Hi! I am currently 18 weeks pregnant, which means I'm no longer able to wear my usual favorite styles (high-waisted jeans with shirts tucked in). I'm struggling with trying to find a new style that works with my changing body while also still feeling fashionable and like *me*! Any advice?
I’ve just had several friends go through their first pregnancies and navigating the changes that the body goes through sounds confounding for sure.
My advice would be to start by shopping your closet for any pieces that do still fit and feel like you. Chances are there are a few things tucked away that could give you a bit more runway in terms of fit.
Then I would prioritize comfort and what makes you feel most like yourself. Sounds like jeans with a visually cropped shirt is a go-to for you so you might try a pair of maternity jeans (I‘ve heard good things about Madewell*) and a couple oversized shirts or knits that could easily layer over top. Otherwise, I might opt for a fitted base, like a black legging and fitted tee with an oversize shirt or cardigan left un buttoned on top I can imagine this would work post-partum too. I also love a black cotton or fitted knit dress over black tights and cute tall boots for a dressier look.
You might also find this post by the very chic Rosie Ann Butcher on her approach to pregnancy style helpful.
Q8 - I am looking for a versatile outfit formula that will take me from teaching at a university in the daytime to semi-dressy dinners with work colleagues at night. Maybe a sweater dress? Thank you so much!
Yes, I love the idea of a sweater dress for comfort and ease during the day, while still being appropriate for dinners with colleagues in the evening. SÈZANE* has lots of lovely knit dresses and so does ARITZIA* (I still wear one I got from there over 7 years ago shown here).
I also like a classic black trouser with a lightweight or ribbed crewneck sweater (similar to this look). With a pair of sleek and comfy boots and a few pieces of simple jewelry you’re all set.
Q9 - Hello, I have a question about finding my style again post-pandemic. I've been back at the office for a year now, but honestly still don't know how to dress myself. My office is super casual (jeans are fine), but I like to look slightly more put together -- or rather, maybe a little more styled. Over the course of the pandemic I invested in good-quality loungewear and comfy clothes. I'm not sure, now, how to make it look like I tried harder with those same clothes when I leave the house. So I guess my question is about taking flowy, soft, leisure & athleisure pieces and making them look a bit more sharp or intentional -- if that's even possible! Thanks!
I think a lot of folks are finding themselves in a similar situation so I’m really glad you shared this question.
My advice when it comes to making causal items feel more put-together or more styled is to pick one casual piece and pair it with more structured elements. If jeans are okay, then I would maybe start by wearing those with a sweatshirt with a cute sneaker or boots and a few pieces of jewellery to add some polish. Jewellery goes a long way to give casual items more sophistication.
Alternatively, if you wanted to wear a flowy lounge pant to work, I would pair those with a chic sweater and maybe layer an oversize blazer on top and pair the look with a sleek heeled boot.
I also try to keep the palette monochrome or limited to three or less colours, to instantly elevate the feel of a look.
Q10 - My Hi Style Bee! My name is Anna and I live in New England. I’ve been following your content for some years which inspired me to start being more intentional about my closet and to explore things like a capsule wardrobe. It’s been a process of many years and I’ve definitely made a lot of positive changes from mindless shopping and a closet full of clothes with nothing to wear. Most recently, I went through another closet clear out focusing on removing anything that was uncomfortable and also realizing that it was time to let go of clothing in the colors that didn’t really suit my own coloring. When I did this closet clean out, I found myself feeling both extremely excited and spacious, as well as finding a ton of gaps in my closet. What started as a positive experience, then turned into a flurry of trying to fill those gaps. I am now at a point of having a fairly well-rounded wardrobe, but I wonder is there ever such a point of completion? I guess I always feel like something is missing or my style is evolving, or with the seasonal change there are multiple wardrobes to focus on. Would love your advice on this feeling of incompletion, and that idea that one day my wardrobe can be truly complete.
Hi Anna, Thanks so much for your longstanding readership and for sharing this question about the elusiveness of closet contentment.
I used to let my perceived wardrobe gaps guide my wish list planning, purchases and even my perceptions of my own personal style. But ultimately it only led me back around to feelings of lack rather than feeling like I’d achieved something.
From the sounds of it, you’re in a really good place with your wardrobe and style right now. I think if you shift your mindset away from what’s missing and more towards what you have to work with you’ll feel a lot closer to a sense of completion in your closet.
I also recommend unsubscribing from or unfollowing some of the sources that are contributing to your sense of needing more. Within a short time I’d bet you’ll find a lot more contentment with what you have. This practice has been hugely beneficial to my own sense of satisfaction in my closet and within my personal style. It doesn’t mean your style will become stale or stagnant either. It will simply give you some space to actually wear your clothes and see the potential within what is already there.
Q11- I’m currently breastfeeding and am struggling with finding clothing options that I feel good in that are also breastfeeding accessible (eg buttons, zips etc at the front). Would love any ideas! Love from Australia
I love all my button up shirts from Power of My People* (stylebee10 for 10% Off anytime). Another one I think could be good is Daughters of India (I love my Kira Dress and would say it’s breast-feeding friendly (also Australia-based). Sèzane* has some lovely blouses and knitwear with buttons and I also think POSSE*, which I believe is an Australia-based brand, has some really beautiful linen separates with button up fronts.
Q12 - I'd like to know if you have any tips to transition easily from "home outfit" (leggings) to something a bit more dress up, to go run some errands , without having to change entirely.
Depending on the weather, I usually throw on a relaxed fitting jacket (like a trench or a wool coat) and some white sneakers or black boots and either a baseball cap or a toque to run errands when I’m not planning to change out of my leggings. If it’s summer and hotter outside, I’ll layer on an oversize linen shirt, cuff my leggings so they are a bit cropped and pair that with a chunky sandal and a tote.
Q13 - I'd like to know how your style, and relation to clothes has evolved since moving to steep hill cottage full time ? Do you have a "workwear" capsule : D ?! Thanks again for your style wisdom
I love this question because this topic has been on my mind a lot since we moved here. In a practical sense, my relationship to clothes has become a lot more focused on function over form, which used to hold more value when I lived in a city. I also feel as though I need far fewer clothes now. It took me a couple of years to accept that most of my closet was going unworn. After my latest closet edit I’m just taking my time and trying to add carefully so that anything that comes in serves a very clear purpose.
In a more theoretical sense, my relationship with what holds value for me has changed a lot overall. In large part with living in a more remote location, but also with age and life experience. Things that I used to think mattered a lot, like how I look and what I’m wearing, hold much less value now than how I’m feeling, where my energy is going and how my decisions are leading me to what I really want in life.
I still love style and clothes but my reliance on them to demonstrate my value has reduced and I’m grateful for that shift.
I’ve been letting my workwear capsule come to life organically and just making do with what I have. Luckily Dave is a contractor so we have heaps of t-shirts and hoodies that I can throw on when I need to get seriously messy.
Q14 - Hi Bee, I too live in a rural setting. I have things I wear for walking the dog through places with no path, and for various forms of outdoor work, and also for art making. There is some overlap with what I wear to town. And then sometimes I need to be dressier. And sometimes, rarely, but sometimes I have to go to a wedding or something and it’s a challenge to have the right thing to wear. So please what are your thoughts? Thanks!
I faced this exact conundrum this summer. When it comes to looking presentable for trips to town, I usually go for a comfy pair of pants and either converse or boots with a fitted long sleeve tee and a relaxed fitting coat like my trench or vintage houndstooth.
For weddings and more formal events, I tried renting dresses from Fitzroy Rentals this summer and had a great experience. Would definitely do that again in the future.
Q15 - How can the "coastal" look be tweaked to be a "mountain" look?
To me the “coastal” look features flowy linen, slip on shoes, soft colours and stripes or woven accents.
Whereas the “mountain” look is more about functional footwear like a lug sole, lace up boot with a more fitted cotton pant and maybe a fleece under a rain shell.
To shift the coastal look more mountain I would go for a cute but functional boot, a relaxed pants (like these*), a flannel shirt under an oversized knit or fleece, a beanie and a tote bag.
Q16 - How can I make sweatpants look presentable if I wear them out to run errands?
It depends on the exact sweatpants but generally speaking if you pair them with a cute sneaker or chunky ankle boot and layer a long trench or relaxed coat over top with a crossbody leather bag and a baseball cap or toque, you’ll be plenty presentable!
For an example of what I mean see this post, this pin and this pin.
Thanks to everyone who submitted their questions and to you for reading! Lots of style ideas to absorb across lots of topics and hopefully some helpful insights.
Next time we’ll be digging into a more eclectic mix of questions like my thoughts on luxury goods, selling clothes online, finding a tailor, how to mix metals in a look and lots more!
Have a wonderful Sunday and I’ll be back with a new Friday Digest this week!
Sincerely,
Lee the Bee
Great assortment of insightful questions; many of which I could relate to. Your answers were excellent and your inclusion of examples super helpful! Keep up the great work!
Thank you for this great article. : )
I'll keep it handy to read and read again, because there is a lot of usefull info and style wisdom for issues I can relate to, or that I may encounter later on.
I am currently breastfeeding, and indeed, I was living in button up shirt this summer ! I have now switched to big chunky cardigans worn over simple long sleeve breastfeeding tops.