I have quite a few much-beloved pieces of clothing in my closet, but while they all bring me a lot of joy, they don’t necessarily form the backbone of my wardrobe. I could rhapsodize at length about my favourite pieces, but it might be more useful to talk about something slightly different: to wit, the most versatile items in my wardrobe. Even if your style is nothing like mine, you might find some inspiration from seeing the potential represented in these pieces.

Of course, this is still a subjective exercise – as anything fashion-related always is. Don’t take those “Ten Must-Have Items For Every Wardrobe” articles literally; there is no such thing. Clothing needs are never universal unless we are talking generalities like “pants” and “shoes”. And even “pants” are debatable (says the woman who wears skirts and dresses 80% of the time).

With that being said … here’s my list.

1. Zara crop top/vest

I’ve had this top since 2018, I think, and it’s certainly one of my most worn clothing items. It can be worn as a top, as a vest, or as a general layering piece. The faux leather front panel give a bit of edge to outfits, often creating a nice juxtaposition with more luxe materials. It can be dressed up or down, and work with anything from glam to rock ‘n roll to witchy styles.

2. Kimchi Blue side zip ponte culottes

This is a bit more subjective a choice, because not everyone likes wide-leg cropped pants. As someone with an almost-petite length inseam, I find that cropped pants work best for me; a modest wide leg feels like a more current cut than the old cigarette style I used to wear. But regardless of silhouette, the key details here are (1) the side zipper, and (2) ponte knit material. The side zipper helps to streamline the fit, eliminating extra bulkiness around the waist, which in turn makes it possible to wear these pants under dresses or tunics, hence increasing their versatility (if that kind of layering is your jam). A thicker ponte material helps to give the pants some structure but also stretch – great for comfort.

3. Mesh turtleneck

This is probably most worn layering piece. It works so well for transitional weather, adding some extra coverage without bulk. It’s also great if your style skews a bit goth/dark romantic/witchy.

4. Topshop polka dot pinafore

Pinafore style dresses are inherently quite versatile because they can be worn alone or over any number of different tops – it’s like a new dress each time. I am very partial to this particular dress because I find the cut to be very flattering but also comfortable, and because the black-and-white geometric pattern is very easy to mix and match with both solid colours and other patterns – minimalist or maximalist, whatever your preference.

5. Re/Done tee

This is a cliché, but a good graphic t-shirt can be super versatile. You can dress it up with a pencil skirt, dress it down with jeans, and lots of other things in between. I love the retro vibes and colours of this Re/Done tee, but the choices here are endless. I do recommend picking a design with a colour palette that complements the rest of your wardrobe.

6. BCBG peplum belt

I find belts to be an easy way to change up the silhouette of an outfit, particularly anything involving dresses. I initially got this belt because of the shape (reads designer even though it isn’t) and was a bit hesitant about the colour. Turns out, the colour is a huge part of its appeal and versatility. Black is a common default “accessory” colour, but I’ve discovered that white can be equally versatile whether your colour palette is monochromatic or rainbow (like mine).

7. Cartonnier fur collar jacket

This piece is a little more niche, but in looking back over my outfits of the past 3-4 years, this jacket crops up again and again. It’s a moto-style jacket, but it’s slightly more unusual being a knit material (not leather) and having a faux fur collar. Again, it’s an item that has served me well as transitional outerwear in a variety of outfits, from preppy to boho to punk-lite.

8. J. Crew check vest

I love vests as “completer piece” in outfits. Vest are inherently versatile; you can wear them with pants, with skirts, and even with dresses. Of all my vests, this J. Crew is probably the most versatile. The neutral colour works well with a variety of other colours, while the subtle pattern adds visual interest without pulling too much attention to itself.

9. Gap striped sweater

Patterns are not for everyone, and stripes are certainly not my favourite type of pattern, but this particular sweater somehow manages to work for almost everyone. I’m pretty sure I’ve managed to “sell” this sweater to at least a dozen people in the last 3 or 4 years, which is definitely my most successful “influencer” achievement. It’s a colourful sweater but not so colourful that it overwhelms. I find that it works equally well with monochromatic outfits as with more colourful ones. And being a relatively lightweight knit, it can even be layered.

10. Poncho

This one came out of left field, so to speak — surprising me with its versatility. I had never paid much attention to ponchos in the past, but I bought this one because the colours attracted me. Turns out, it’s a great “3rd piece” to throw on whenever in doubt; it works with pants, skirts, dresses, you name it. I think the key is finding one that has a nice weight and drape to it, and a colour palette that complements the rest of your wardrobe. The warm tones of this one works well as a contrast to the cool colours in my wardrobe (green, blue) and complements the warm ones nicely.

Details: Club Monaco turtleneck (retail), Ralph Lauren blazer (thrifted), Cartonnier pants (thrifted)

Thoughts: I love, love, love this outfit. It perfectly encapsulates one aspect of my style — the Historian. It’s, like, elevated dark academia? I don’t know, I’ve always been bad with style descriptors. I like that it’s a little bit history professor, a little bit maybe-villain. I enjoy outfits that allow me to imagine myself in the middle of a murder mystery (let’s say) while also being wearable for my actual day.

Details: Only t-shirt (thrifted), Liz Claiborne dress (thrifted), BR belt (thrifted).

Thoughts: I can’t wait for spring and summer. I’m practicing at home till I’m ready to bust out my summer wardrobe properly. This outfit was fun and the perfect amount of “dressing up” for one of my days off. I really like how the graphic of the t-shirt works with the dress.

Details: Topshop dress (ebay), Oak & Fort top (Poshmark), Manolo Blahnik shoes (thrifted), selfmade necklace (thrifted and upcycled).

Thoughts: I wanted an outfit to showcase my newly upcycled necklace, made from 2 thrifted necklaces. Yes, sometimes I pick the jewelry first, then the outfit around it. I thought the polka dot pinafore would be a great pairing for this fun, asymmetrical geometric necklace. Plus, any excuse to wear one of my fave dresses.

Details: Motions top (thrifted), Troubadour skirt (consignment), Debew poncho (thrifted), Lena Bernard necklace (thrifted)

Thoughts: I mentioned before that I love 3-piece outfits, and this one is great for WFH. I feel dressed, but also comfortable. The mossy green velvet top adds extra richness to the colour palette – much better than a black top (my old default).

Details: granny square sweater (thrifted and upcycled), Inc International pants (thrifted)

Thoughts: Hot pink culottes were one of my best buys last year. That’s basically all I have to say. Oh, and I love my granny square sweater made from a blanket I thrifted by the wonderfully talented Prairie Trail Goods.

Details: Wilfred sweater (thrifted), J. Crew blazer & shoes (retail), Babaton skirt

Thoughts: I had this blazer up for sale for a while, but no buyers, so I decided to give it another try. I’m probably going to keep it. It’s just too much of a classic to give up completely, and it will work for the Historian outfits. The skirt is a recent thrift purchase. I love the design, but the fit … oof. It’s a size 10 which I thought would be safe, even with Aritzia sizing (always fits small on me). And it’s snug! It must be why the previous owner donated it, practically brand new; inconsistent sizing is the worst.

Details: Twik mesh top (thrifted), vintage velvet waistcoat (thrifted), Isabel Marant belt (thrifted), H&M pants (thrifted), Fluevog shoes (thrifted), selfmade necklace

Thoughts: Another outfit I adored wearing. I like to think of it as the off-duty Historian. Plus, I am obsessed with moon-themed clothing and jewelry, and this checked so many boxed.

I will be turning 42 this summer. This is my 3^rd year of working from home, and the first working part time. I’m slowly realizing that I’ve arrived at a bit of a crossroads in my sartorial life. But, this time, it’s not my aesthetic preferences that are changing – it’s my lifestyle needs.

I am having a harder time grappling with the resulting shift than in the past when changes in my closet where being dictated solely by the evolution of my personal taste. I’m not sure why that is the case; perhaps it’s a reflection of the complicated feelings I have about this stage of my life in general. Somehow, it seems like the pandemic and the loss of my mom accelerated me into a phase that I didn’t expect to enter so soon. It’s not that I feel old, suddenly. It’s just that, after the slow build-up of my 30s, I feel like I have suddenly, unexpectedly, finally, come into my own power as a woman. I can’t explain it very well, but it is a turning inward, finding strength and joy and inspiration within as opposed to outside. It is a good thing, but it is an adjustment and it requires me to figure out a whole new way of being.

But let’s talk practicalities.

I don’t expect that I am ever going to go back to working in an office, certainly not on a full-time basis. In addition, for at least part of the week, I am living the life of an artist/stay at home parent. And last, but certainly not least, my body is starting to change too. Now, admittedly, this is something over which I have some measure of control and, indeed, something I’m working on – eating healthier, trying to increase my activity level. But the reality is that the body I have now is not the body I had at 30, or 35, or even 39. I want to be kind to myself, and dress my body in a way that feels kind to it; dealing with chronic health issues that have worsened slightly over the last few years makes it more important than ever.

I’ve become so good at dressing myself in a certain way, which suited the previous phase of my life, that un-learning is hard. A lot of the outfits I like to wear don’t make as much sense for my current lifestyle. Now, there is always going to be a certain amount of “dressing up” in my life, because that’s how I’m wired, but I need to figure out what that looks like now, as opposed to before. I am always going to be a little “over the top” compared to the average – whatever that is – but the how of it is what I need to get a better handle on.

So, lately, I’ve been working to break down the how. I’m taking my time, observing and getting in tune with my needs, and making mental notes as certain conclusions begin to crystallize. Here are a few of them.

Blazers

I’ve been trying to break up with blazers for 2 years now, with some but not enough success. The reality is that, as much as I don’t feel “dressed” unless I’m wearing (at least) 3 pieces, blazers are not something I ever really want to wear at home even when I’m working. I’ll make exceptions for some – knit ones, or loose/unstructured ones that feel more like housecoats – but most traditional “business suiting” blazers are out. I do love wool blazers as outside coats in spring and fall, but don’t need very many of them because I have other coats I like to wear as well, and those seasons are fairly short-lived in this part of the world.

Re-focus: Because I still love the look of 3 piece outfits, I am looking at other things that might replace blazers in my closet: knit vests and waistcoats, duster-style coats, wraps and ponchos. I wouldn’t say that I am actively looking to buy specific pieces, but when I thrift, I try to orient myself to these types of things as opposed to blazers.

Special Pieces

Okay, this one hurts me a bit. I adore over-the-top pieces: tulle, sequins, the more drama the better. While there will always be room in my closet for these things in small doses, I have to figure out how to infuse drama into my closet in a way that is more wearable for my current lifestyle. Right now, colour and volume seem like the way to go.

Re-focus: Thankfully, voluminous “nap” dresses are still having a moment. I love them. Bold colours and patterns are never in short supply in thrift stores, and they always cheer me up. And I’ve been looking more and more at vintage pieces (mostly 80s and 90s stuff) which can be quite unique and fun but in wearable ways – like funky sweaters for example.

Jeans

This might seem counterintuitive given that my life is more casual these days, but I am having a hard time with jeans (and pants in general, let’s be honest). Primarily, this has to do with my health issues; bloating is a common symptom, which makes jeans a tricky proposition. I hate low rise jeans because they emphasize my long torso in a way that I don’t like, but high rise ones can unexpectedly become uncomfortable if I’m having a bad day … and since bad days can happen out of the blue (fun!), well … you can imagine.

Re-focus: This is highly specific, but ponte knit, side zip culottes are my Holy Grail pants of the moment. I want them in every colour. They’re comfortable (no waistband, stretchy) and can be dressed up or down (and layered under dresses or tunics) so easily. Mid-rise culottes or palazzo pants are also good, as long as the waistband sits lower on my torso and the fabric doesn’t squeeze. And, lastly, leggings. I have been slowly building up my athleisure collection, which I wear around the house in the evenings and on weekends, while gardening, and when going for walks. Leggings are also great for layering. The key is finding ones that are stretchy without being constrictive.

Shoes

I don’t really wear heels anymore, and certainly not anything over 2ish inches. But letting go of my old ones is hard; I’ve been slowing chipping away at my collection of heels, but once I’m down to just the old favourites, I don’t know what I’ll do. Some I know I save for my daughter (think Louboutin, Manolo Blahnik, etc.) because it looks like she will have a larger shoe size like me. But I need to make room for shoes that better suit my current needs, so at some point, I’ll need to sacrifice my nostalgia and just say goodbye to a large chunk of my old collection.

Re-focus: Flats, flats, flats. In the summer, I wear Birkenstocks, slip-on sneakers, or my favourite Ash wedge sneakers almost exclusively. In the winter, flat boots and booties (I recently thrifted a pair of OTK flat-heeled boots and I was ecstatic). I love colourful shoes, however, and would like to replace some of my old, beloved J. Crew colourful pumps with a similar, lower-heeled alternative. Because I do appreciate a little height boost, I would like to find some kitten heels; I know they’re not considered trendy or cool, but IDGAF. My current Holy Grail is a shoe similar to the Manolo Blahnik kitten heel slingback (or slides) but in funky colours like red, pink, or blue. Just to have options when I want to dress up a little.

Bags

I am slowly getting back into bags, but I realize that my tastes and my needs have changed in this department. I don’t need large tote bags anymore because I’m not schlepping to the office every day. And high-end designer “status” bags don’t feel right for my current lifestyle, where my outings are limited to running errands and visiting with friends. I’m keeping my old collection for my daughter, but I don’t think I’ll be adding to it again.

Re-focus: I’m loving small purses – crossbody bags and bucket bags especially – in all colours. I’m mostly looking at lower end designer brands (MbMJ, Coach, Dooney, Ralph Lauren, Tignanello) where I can get decent quality without the “prestige” mark-up, even if it means buying older or vintage styles.

If you’ve experienced a similar lifestyle change in the past, how did you navigate it, style-wise? Tips and reccs are welcomed as always.