Details: Ralph Lauren sweater & skirt, Tommy Hilfiger jacket, Laredo boots (all secondhand)

Thoughts: I love watching other people’s thrifting reels on Instagrams, which has only served to reinforce the appeal of the 90s revival. Everyone is into it! Seeing what vintage pieces people are finding, and how they are styling them, has given me lots of ideas. Including an idea about the potential of a red leather jacket. I spent a few weeks looking for one because, while leather jackets abound at the thrifts (seriously, one of the best categories of clothing to thrift), their quality can be hit-and-miss and so can their price. Patience paid off, though, because I eventually found this absolutely perfect, definitively 90s Tommy Hilfiger number for $35 at Goodwill. A bit pricey for thrift, but still great value. So, now, I am experimenting with its potential. I started with a fairly safe combo of black and white, which did not disappoint. Will be trying to add some brown into the mix next time. Stay tuned.

Details: Ralph Lauren turtleneck, Jones & Co jacket, American Eagle jeans, Esprit belt, Coach bag (all secondhand)

Thoughts: As you may be starting to observe, red has been a key colour for me this fall — especially deep red shades. I’ve been adding staple pieces, like this turtleneck, in my favourite shades, and they’ve opened up new styling options for older items in my closet. I love how the colours in this outfit pop.

Details: Babaton turtleneck, Vince skirt, Mackage jacket, vintage bag, Laredo boots (all secondhand)

Thoughts: I’ve been wearing a lot of (almost) monochromatic brown this season, but decided to take a slight left turn with this outfit; instead of a brown jacket, I decided to go with a dark plum one instead. It coordinates nicely, in a slightly less expected way. I “mirrored” the print of the dress in the pattern of the bag, and bookended the outfit with black (turtleneck and boots) to add a bit more contrast. Overall, it’s still a fairly subdued outfit (for me, if recent history is our benchmark) but with tons of details that make it interesting … to me, at least.

Details: Pilcro sweater, DKNY blazer, H&M turtleneck, Do+Be skirt, vintage bag (all secondhand)

Thoughts: I am continuing to test my theory that brown (some shade of it, and there are many) goes with practically any colour. I can now add lavender to that list. It was a fun colour to try, especially in a mash-up with leopard, which I rarely see paired with pastel-type shades. A little bit unorthodox, but I liked it.

Details: M Collection vest, Banana Republic cardigan, DKNY skirt, vintage shoes (all secondhand)

Thoughts: Whimsigoth (kudos to whoever came up with that name) pops up a lot in the thrifting reels the algorithm has been feeding me lately, and while it’s generally an aesthetic that doesn’t appeal to my current sartorial sensibilities, there is one element that has made it stick in my mind. Its 90s flavour, of course. Think Practical Magic and Charmed. So, when I found this vintage vest, I was primed. I had a vision. This was that vision. It made for a very fun and satisfying reality, ahem, outfit. Before you yell at me about one-trick ponies, I am quite certain that this vest has plenty of other potential, which I propose to tap at the earliest opportunity.

Details: Tommy Hilfiger shirt, Ralph Lauren sweater, Brave belt (all thrifted), J. Crew jacket, Zara pants (both retail)

Thoughts: I bought this J. Crew field jacket at the end of the season last year, on deep clearance at Winners, and put it aside for future me. I didn’t have any particular plans for it at the time, but it struck me as a fairly classic piece that would eventually come in handy in a climate like mine. Future me is very grateful because this style has become trendy again, which is a nice bonus, and this colour combo (olive green and dark brown) is perfect for my current wardrobe palette. That corduroy collar … be still my heart.

The current 90s revival has kicked my nostalgia into high gear again. To be fair, it doesn’t take much to do that. If something like immutable character traits exist, susceptibility to nostalgia is surely one of mine. Indeed, I consider it one of the most important milestones of my personal growth that I have reached a stage where the pleasure in looking to the possibilities of what is to come neatly balances the pleasure in looking back at what already came to pass; for most of my life, the uncertain thrills of the future seemed but poor competition to the established delights of the past. But I digress – digression also being something of an immutable trait of mine 😉 With all this sartorial nostalgia floating about, I was struck by a thought: wouldn’t it be cool to look back on what I actually wore in, say, 2000-2004 and compare it to what I’m wearing now, influenced by my memories and ideas of that time?

It would be SO cool.

Sadly, that’s all this thought was destined to be: a cool idea. The concept of photographically documenting one’s daily outfits (as a non-celebrity) is a progeny of smartphones and fashion blogs, neither of which yet existed back in 2000. Sure, I have photos of myself from before 2010, but they were usually taken on special occasions and rarely focused on what I was wearing. So, goodbye, cool idea.

However, I hate giving up. Settling for “something vaguely similar” is, in this case, a preferred alternative. And that’s how we end up here, with this post. In lieu of 2000, I present you 2011 and the beginnings of my fashion blogger era.

I chose a sampling of outfits that felt accurately representative of what I was wearing in 2011. Obviously, the 90s did not figure strongly (or at all) in my sartorial inspiration at the time. It was too soon, for one thing. For another, I was in my “figuring out colours and proportions” phase. Well, to be honest, I was in my “figuring out fashion, period” phase. At a first glance, I would say that the middle outfit is closest to something I might wear today – though not in that exact silhouette. Indeed, I was rather pleased to see myself even wear brown 13 years ago; I had forgotten all about it, in the wake of the intervening corporate goth era (2017-2019).

That being said, most of the clothing I’m wearing in these outfits are things that, for one reason or another, I wouldn’t wear today. They include:

• Thin cardigans with cap sleeves
• Knee-length pencil skirts
• Low rise pants
• Baby-doll style tops
• Peep-toe shoes

The black shoes, white shirt, brown cardigan, and brown belt are items I would still wear today, if I still had them, which I don’t. I would also wear those jeans, were it not for the almost-certain fact that they were low-rise, just like the black pants. I do like the bootcut style, which is all the proof you need that denim silhouettes are eternally cyclical. The leather jacket is almost another “yes”, but the ruched collar frill thing kinda ruins the vibe for me.

Can we just take a moment to appreciate how god-awful low-rise pants look on me? Visually, they cut my body in half, as perfectly illustrated in the middle outfit. I’m sad to say, the relevance of the fact I have a long torso and short legs remained lost on me for almost another decade.

Anyway, I thought it would be interesting to compare each of these outfits to a current-day equivalent.

The main difference here is silhouette and proportions. Longer hemlines and a higher waist help me to achieve an impression of (extra) height, which I appreciate. You will also note that the sleeves in the current outfit, while still short, are different. The triangular effect they create on the top half of the outfit nicely balances the fluted silhouette of the skirt. Most of this stuff is, of course, a question of preference not objective value. I’m not here to rain on your pencil-skirt-loving parade.

Once again, it’s a question of silhouette and proportions. The pants are higher-waisted and have a menswear-inspired pleated cut. The shoes are also more masculine in style, and chunkier. Also, the current outfit offers a juxtaposition of vibes – casual chambray with preppy corduroy blazer – that makes it more interesting, imo, than the 2011 version.

In some ways, this side-by-side offers the least jarring contrast. Sure, my current jeans have a wider leg and higher rise but, to my eye, it’s a difference that whispers rather than screams. The proportions of the jackets are surprisingly similar. Obviously, it’s the tucked-in shirt that represents the biggest difference. The baby-doll top is probably the piece that feels the most “dated” (i.e. of its time) but, ironically, is probably closest to making a comeback as the fashion trend cycle continues to churn, getting ever closer to the late 2000s as a source of inspiration.

Well, that’s it. If you thought this post was building up to an interesting thesis of some sort, sorry to disappoint. Like a lot of nostalgic exercises, this one offers no special insights, its sole reward being the pleasure of remembering what was, and marvelling how different it has since become.

Let’s do it again, yeah?

Details: J. Crew shirt, vintage vest, Gap jacket & belt, Twik skirt, Tommy Hilfiger bag (all thrifted), Mia shoes (retail)

Thoughts: I don’t wear a lot of black these days but I do enjoy a black-and-brown combo. Whiskey, in particular, looks really sharp paired with black. This outfit has a dandy vibe that pleased me a great deal. Ties are a trend for womenswear this fall, and I’ve been experimenting with it off-and-on, but sometimes it feels “too much” and also too cumbersome (since I haven’t learned how to tie a proper tie knot, and require assistance from my husband). This bow pin is a rather perfect alternative for me; thanks to the striped fabric, it has a flavour of tie about it, but it’s much easier to put on and feels jauntier and more me.

Details: Toni T dickie, J. Crew sweater, Ralph Lauren trench, American Eagle jeans, Gap belt (all thrifted)

Thoughts: I loved this combo of red stripes and tan trench. It felt classic and effortless. Now, these are objectively meaningless terms, so what I’m saying is that this is what classic and effortless looks like to me — or at least one version of it, at the current moment. Easy, relaxed, but also polished and elegant in an understated sort of way, and trend-neutral. The trendiest thing here are the jeans, a category of clothing that is often the most obvious clue to an outfit’s era. Something to think about in that, eh?

Details: Northern Reflections sweater, Ungaro vest, Donna Karan belt, Mondi skirt (all thrifted)

Thoughts: Plaid on plaid is a fun way to do pattern mixing, and in this case, it solved for me the problem of choosing a colour palette for an outfit built around this skirt. Red-and-green plaid is tricky given its tendency to come across Christmassy, and the choice of accessorizing colours can often play that up. Here, by adding another red-dominant plaid that doesn’t prominently feature green and doubling-down on the red, I think I managed to avoid looking like someone who puts up her Christmas decorations immediately after Halloween. Which, for the record, I am not.

Details: H&M shirt, Ralph Lauren sweater, Eddie Bauer pants, Fossil belt (all thrifted)

Thoughts: I was so excited to find this brown striped shirt. Brown shirts are relatively rare, have you ever noticed this? But now that I have one, I could finally put together a monochromatic version of this favoured outfit formula: oversized striped shirt, menswear-inspired pants, contrast-colour sweater. So simple, so good.

Details: Club Monaco sweater, Gap jacket, vintage skirt, Ann Marino shoes (all thrifted)

Thoughts: Also simple is this 90s coded outfit animated by my love of contrasting textures: leather, chunky knits, chiffon. Minimalism has certainly infiltrated my sartorial aesthetic — it’s part of the DNA of the kind of 90s style that appeals to my nostalgia — but I am still me, and I still need visual interest in my outfits, or else I end up feeling very blah. I cannot do blah. If an outfit feels blah, it is not worth wearing. Luckily, colour and texture are most effective tools to zhuzh up minimalist outfits (which, to me, means any outfit that doesn’t involve more than 3 pieces and at least one statement accessory).

Details: Jeanne Pierre sweater, Ralph Lauren jacket, Fossil belt (all thrifted), Zara pants (retail)

Thoughts: Brown and yellow, who knew? This is a combination I tried thanks to the influence of Instagram; I guess my mindless strolling does occasionally pay off. Special shout-out to this blazer, which is probably my best thrift find of the year, if we are going by prestige alone. It’s a Ralph Lauren Collection wool and cashmere blazer that probably originally retailed for $3,000CAD+. Ralph Lauren Collection is the highest tier in the RL brand universe; the fact this non-vintage blazer was made in the USA is an obvious giveaway of that. Anyway, it feels pretty darn luxurious, which might seem like a “duh, obviously” statement given its retail price, but honestly isn’t a given these days even for higher-end designer brands. I don’t have the budget for $3,000 jackets, so I am happy I got to have this experience for the thrift-queen price of $25. As a PSA, I should mention that I found this (undeniably women’s jacket*) on the men’s blazer rack, which is a reminder that you should look at every section, even in a cursory way.

*I can tell it’s a women’s blazer because it has zero inside pockets. As far as I can tell, the pocket-looking slits on the outside are also merely decorative. A men’s jacket would NEVER.

Details: Danier jacket, Jones Collection vest, Talbots skirt (all thrifted)

Thoughts: I’ve mentioned how much I’m loving navy and deep red as a colour pairing lately, so this vintage (made in the USA) Talbots skirt was a no-brainer buy. I knew it would look smashing with this navy wool vest, but I surprised myself in choosing the 3rd piece. This burnt orange suede jacket wasn’t my first choice, and I only ended up adding it to this outfit because it happened to be hanging nearby when I was weighing up my options. Turns out, this shade of orange looks great with navy! Noted. I will be exploring the possibilities later. I decided to add one more thing to this outfit — minimalism plug-in not detected! — because my neck felt a little bit naked, and went with an extra special piece: my mom’s Hermes scarf.