Dressing Room Adventures

Anatomy of a "try-on" date

Getting true time to myself is a rarity these days. A whole afternoon of uninterrupted, solo time requires serious planning and orchestrating.

When at last those sacred hours I’ve booked for myself (during daylight and business hours!) arrive, the hardest thing, in fact, is figuring out what to do with them. Do I tackle the neglected errands buried in the near-endless scroll of my to-do list? Do I take my laptop to a cafe and write to my heart’s content? Do I book myself a yoga class, or some studio time at a sewing shop?

Most of the time though, all I want is some fresh air and the freedom to be idle. As such, I’ve found myself abandoning productivity goals for the pleasure of wandering around my favourite neighbourhoods—usually involving an overpriced caffeinated beverage and a trip or two to the fitting room. It feels indulgent, sneaky even. But it’s become a necessary ritual to keep me level-headed amid life’s stresses. To help me cling on to the deteriorating concept of “me time”.

I’ve always enjoyed in-person clothes shopping as a recreational activity—one I usually conduct alone, sometimes secretively. In the past, I’ve gone off the rails with accumulating to excess, but I‘ve since come a long way in minimizing my need to own everything I find pretty, cool, or see potential in.

In line with my resolve to browse and buy less virtually, physical stores have once again become a primary outlet for me to explore my enthusiasm for textile design, my sartorial wanderlust. Even if I almost always come away empty-handed—satisfied by the petting zoo experience of dancing my fingers across beautiful garments I have no business bringing into my messy, casual life.

Some “unsuccessful” try-ons over the years. I liked all these pieces, but have no regrets about leaving them behind.

I don’t have the time to shop on a whim like I used to: after work hours or in between meetings. But when the opportunity presents, I like to make targeted trips to track down pieces I’ve spotted online (though I don’t support the practice of using local, independent stores for trying-on, only to buy the thing from SSENSE), or try my luck with secondhand and vintage.

These outings can be a chance to physically interact with garments I’ve fallen in love with through a screen (often bursting that bubble of perceived desire). Or a continuation of a patient hunt for my fashion unicorns. Successful or not, I always learn a lot from these excursions—about clothing quality, fashion history, and my personal preferences.

Here’s my approach to executing the perfect “try-on” date:

1. Prepping the “Wishlist”. For me, this exists as a physical list on my phone that I like to prune whilst riding the subway. There are particular pieces (Toast roll-neck sweater) and unspecified desires (a vintage wool coat). Everything from short-term needs (rain shoes) to long-term maybes (selvedge denim). Being detailed on ideal qualities and criteria for each item helps finetune the radar. Currently on my list is a pair of pleated trousers: made of wool or thick cotton; with a dark stripe, herringbone, or check pattern; slightly cropped; slightly wide-leg; with functional pockets.

2. Mapping the Route. I like to situate the try-on date in the context of a good walk along an interesting stretch of the city. Clothing-wise, there’d be a few independent boutiques, vintage stores, and specialty stores—maybe an upscale consignment shop or a humble thrifter’s paradise. I like to hit up 4-5 places maximum, cleansing my palate in between with coffee breaks, snacks, and a poke around a bookstore.

3. Dressing to Undress. For these occasions, I like to wear simple clothes that are easy to disrobe (no overalls, no unnecessary layering or accessories) and could pair well with whatever I may be trying on (no dresses). My go-to outfit for the fall/winter has been a nice plain sweater with jeans and ankle boots.

4. Collecting Try-on-Worthy Pieces. Sometimes I make a beeline for the specific items I’ve viewed online (and made sure was in stock), blazing through this step in under five minutes. Other times I like to let my eyes wander and really comb through the racks, open to discovering things I may not have been looking for. When it comes to what I advance to the dressing room, I like to be very edited in my choices; I generally never try on more than three pieces at a time, and often exit without trying on anything at all.

5. To the Dressing Room. Dressing rooms are usually poorly lit, cramped places, sometimes downright dingy with a flimsy curtain that barely conceals. Yet they are magical places, too—a time machine to another era, an adult-sized dress-up box. Once my eyes have adjusted to the harsh overhead lighting, I get down to business. Here is where I try on each item, carefully scrutinizing the piece and running through my assessment rubric. I pay attention to the quality: the feel of the material and the construction of its parts. I take note of the fit: how it looks and feels on my body, doing a few aerobic exercises if necessary to gauge how it moves. I look at the design from all angles, picking up on details that could never be conveyed through a two-dimensional image.

6. Making the Decision. The vast majority of things I try do not end up going home with me (my friends in the dating game seem to share this experience). Often, the rejection is swift; there is something about the piece that is uncomfortable, off-putting, or simply underwhelming—and I can’t wait to get it off my body. There are also situations where I fall in love with a piece I’d already mentally committed to buying, the try-on just serving as a confirmation step. Everything else falls into a bit of a grey area, where my decision could go either way. I have to weigh my in-situ desire for the item against its cost, anticipated usefulness, and the prospect of holding off for something better. In this scenario, I usually end up walking away, giving myself the option to come back for the item should it continue to haunt my thoughts, or keep it on the wishlist for future consideration if it’s something I don’t have to worry about selling out.

7. Documenting my Trials. My advice: always take pictures. If it’s an item I want to keep pondering, I make sure to photograph the tag with the brand, name of the style, size, and price. Otherwise, I still find it valuable to document pieces that may not have been for me, but were noteworthy in their splendor, or left me with takeaways about my wishlist criteria or clothing preferences in general.

My Fall/Winter Try-on Diary

Here’s a selection of things I’ve tried on recent months and the thought process behind my decision: to buy or not to buy.

Vintage Yellow Sweater - December 3, 2024

• Preface: A vintage varsity-style sweater has been an unwavering obsession of mine for the past year. I’ve stalked and bookmarked many online, but the ones I like tend to be in poor condition or insanely pricey.

• Assessment: I loved the fit of this sweater, and the buttery yellow felt rich and cozy. However, the itchiness of the material was a dealbreaker; it also felt like acrylic—not the pure wool I was hoping for. While the price was very affordable and could have easily been an “experimental” purchase, I knew that eventually I’d be saddled with the burden of removing this not-quite-right version from my closet after just a handful of wears.

• Decision/Takeaway: I only have room in my closet for sweaters that will work hard for me, so I’m holding out for something that betters meets my expectations. But I am grateful to have found this piece, which has confirmed my interest in this style of knitwear.

Trippen Black Loafers - December 15, 2024

• Preface: I do currently have a pair of beaten-up secondhand loafers—they get the job done, but I’m always on the lookout for a more comfortable and sightly upgrade.

• Assessment: Trippen is known for its avant-garde, architectural footwear—the kind of stuff your cool ceramicist aunt might wear. I’d seen this pair online, but was skeptical about the unconventional form. While trying them on for fun, I found myself reluctant to take them off. They were a perfect fit for my wide feet and I liked the kookiness of the platform sole (not pictured). They’re not a traditional loafer by any means, but feel sharp enough for professional settings, though I’d mostly wear them casually. The only thing halting me from purchasing them right there and then was the eye-watering price tag.

• Decision/Takeaway: Sadly, I couldn’t justify buying them, but at least I now know my size. While they are out of my budget currently, I would seriously consider getting them if they went on deep sale (in fact, I nearly did buy the red version of these which were marked for clearance).

Vintage Men’s Wool Coats - January 11, 2025

• Preface: My pursuit of the perfect wool coat is over a decade long at this point; I’ve thrifted a couple during that span, but none left me quite satisfied. Now, this isn’t a need—I have sufficient outerwear options, albeit none that are really my style—but I feel like the right “smart” coat would give my cold-weather wardrobe a serious boost.

• Assessment: I couldn’t resist slipping on these gorgeous men’s coats I spotted at one of my favourite vintage stores. Neither checked off all my boxes—the dark one was too oversized in the shoulders and I was lukewarm on the light camel shade—but they were two of the nicest coats I’d ever encountered. Both were made from thick, luxurious blends of wool and cashmere, with impeccable, intact silk linings. The style of these were exactly what I’d envisioned: raglan sleeves, mac collar, long length, single breasted, warm but not too heavy. For the condition of these older garments, I thought they were priced reasonably—between $200-300 CAD.

• Decision/Takeaway: The hunt continues. A positive takeaway is that I’m now fully committed to buying vintage for my wool coat. I know I won’t get same value for money on something brand new in 2025.

NARU Green Sweater - February 9, 2025

• Preface: I was vaguely craving something green for spring; in my mind, I’d concocted visions of prancing around in a crisp poplin skirt, the colour of dewy grass.

• Assessment: This sweater was pulled from the sale section at a local store specializing in Japanese brands. I really liked the colour and quality of the wool, but felt like the drapey, oversized shape evoked the frailness of an elderly Joan Didion on my frame.

• Decision/Takeaway: Oversized sweaters without structure are definitely not my preferred style, but this try-on helped catalyze the purchase of another green sweater (more to come on that).

Vintage Grey Cardigan - February 9, 2025

• Preface: I guess I’m not as impervious to being influenced as I thought—lately I’ve been coveting a boxy little wool cardigan in the style of the ever-popular ones from Nikki Chasin and Babàa.

• Assessment: This 50’s wool cardigan didn’t exactly fit the bill, but I thought it was such a sweet and well-preserved piece. It looked home-knit, featuring dark pearlescent buttons and short raglan sleeves. Adorable as it was, I wasn’t sold on the light grey or the price. In this economy, I just don’t have a spare $100 to spend on clothes I don’t completely love.

• Decision/Takeaway: It was a painful “no”, but I haven’t completely closed door on this, yet. I might revisit the shop in a few months to see if it’s still there, but I know I’ll be fine without it in my possession.

Cawley Georgia Wool Trousers - February 9, 2025

• Preface: Cawley is a major aspirational brand for me, and their Georgia trousers were my idealized version of the tailored, pleated trousers that top my wishlist. Their price point is a huge barrier for me, but when I saw that they were available at a local store for 60% off (still a massive amount of money), I thought to myself, “just maybe…”.

• Assessment: Off the bat, these trousers are literal works of art. The fabric choice, construction, and thoughtful design were even more impressive in person. Unfortunately, the shop didn’t have the dark bouclé wool version in my size. I still tried them on, a size up, but they puddled around my lower half. The pair they did have in my size was rendered in this unappealing split pea soup colourway that not even the very charismatic salesperson could convince me was complementary.

• Decision/Takeaway: While I loved the fabric of the first and the fit of the second, I wasn’t bummed that I’d missed out on my “dream” pants. In fact, I felt like they were too nice to belong in my world; I would very rarely have the opportunity to wear them without driving up my blood pressure. Instead of falling desperately in love with these trousers on sight, I got a reality check about lusting after luxury pieces that don’t suit my lifestyle—an invaluable lesson in itself.

Vintage Pierre Cardin Red Sweater - February 21, 2025

• Preface: A red chunky sweater is something I’ve hemmed and hawed about for a long time. My closet isn’t short on pops of red these days, but this elusive piece remains a distant want on my wishlist.

• Assessment: I adored this shade of cherry red, the ribbed texture, and the cropped fit of the sweater. I was pretty tempted to bring it home with me—until I read the 100% acrylic label.

• Decision/Takeaway: I thought about letting my insistence on all-natural-fibre knitwear slide just this once; I know that vintage synthetics can be higher in quality and aren’t always bad news. But with so many sweaters already in my collection, the bar is set pretty high for any further additions. So a pass it was.

Vintage Pendleton Plaid Skirt - February 21, 2025

• Preface: Similarly, a wool skirt isn’t really an item I’m prioritizing for my wardrobe, though I would like to get back to wearing skirts more often.

• Assessment: I found this plaid wool Pendleton skirt at the same vintage store as the previous sweater. The subtle pattern, straight shape, and side pockets were all in line with my style preferences, but I could barely zip it up.

• Decision/Takeaway: An easy rejection, and I feel no burning desire to add a wool plaid skirt to my current wishlist. That said, if the perfect one (that fit me) were to cross my path, I wouldn’t say no.

Vintage Blue Flare Pants - February 21, 2025

• Preface: When browsing vintage or secondhand, there’s always the danger of stumbling across a heart-stopping treasure—unplanned, unforeseen. A pair of faded blue 70’s flares was nowhere in the vicinity of my strategic wardrobe plan, but I was simply awestruck by this piece, lured by its charm.

• Assessment: The fit was great: neither too loose nor too tight, though I could cinch it with a belt for more waist definition. The length was perfect as well: a rarity for my short stature. I’m a sucker for a slubby fabric with bits of contrasting threads poking out, so the textured wool blend material was right up my alley. Overall, I found these pants to be such a cool, unique vintage find—and one that could be very wearable, given that I wear pants most days.

• Decision/Takeaway: I got them! They’re not the fancy pleated trousers I wanted to manifest, but they do align with my goal of incorporating fun pants that aren’t denim into my wardrobe. While I don’t see myself wearing these all the time, putting the kind of mileage on them as my everyday workhorse trousers, they are a statement bottom I could see myself having a long-term relationship with.

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I hope you enjoyed this peak into my dressing room forays, as well as my thought processes behind the try-on snapshots. If you have any great dressing room stories or tips of your own, please do share!