Details: H&M top (retail), Everlane sweater (thrifted), DKNY skirt (Poshmark)

Thoughts: Ahhh, the saga of this outfit! It all started when I saw the H&M ad on the right in their store a few months back. It immediately triggered my deeply rooted 90s nostalgia. Doesn’t it look like all those cool CK ads from the 90s? I was never cool enough to be a CK girl back then. Kate Moss, c’est pas moi. But my 40s are all about boldly going where my teenage self feared to tread, so I set about trying to recreate that ad photo with a vengeance. The first step was breaking my no-retail rule to buy the extra long sleeved white cotton shirt from H&M. It’s not the worst thing; it’s a versatile base layer, and I know I’ll get lots of use out of it. The next step was acquiring a sheer panel skirt. Sheer is a big trend these days (oop!) but, outside of high end designers, finding a similar skirt proved difficult at first. Oh, I forgot to mention: the H&M version was long sold out by the time I started looking. But then! I lucked out BIG TIME. This amazing, vintage DKNY skirt popped up in my Poshmark searches and you better believe I smashed that buy button hard. Well, actually I made an offer and had it accepted but you know. I got it for a great price, and it’s far better quality than the H&M one, I’m sure. Love that for me, haha! It’s also a more wearable skirt because the opaque part actually comes down to just above the knees; I folded over the elastic waistband here so I could make it appear shorter. I love the extra versatility (and being able to control the sexiness quotient).

Details: White + Warren sweater, Nanette Lepore jacket (both thrifted), Contemporaine skirt (swap), Mia shoes (retail)

Thoughts: This was, of course, an homage to Clueless. I did substitute in a (p)leather skirt for a little extra edge. I also decided to give sheer black tights another try. It’s been years since I’ve worn them, but I feel like they were a 90s thing. I always wear some kind of tights with short skirts, because I don’t love the bare-legs look on myself. I still think I prefer opaque tights, but I might also just need more time to adjust to this version.

Details: Obey hoodie (thrifted), BlankNYC jacket (retail), Chicwish skirt (thrifted), Laredo boots (consignment)

Thoughts: This outfit was all about the juxtaposition and contrast — mixing girly with grunge. I loved wearing this outfit so much! I know Chicwish is basically a small step up from Shein, but I have to say this skirt is great for what it is; they didn’t skimp on the tulle layers, and they give the skirt a lot of volume and depth. I’m actively looking to find it in black as well. I must also give a shoutout to these boots. I was a bit unsure when I bought them because I had been looking for a pair of granny boots and these seemed more masc. But they’re perfect! I love that they have a bit of a combat boot vibe, without being full-on. They work well with skirts and dresses in that 90s kind of way. They’re also great with jeans, of course. And they’re super comfortable!

Details: Ralph Lauren sweater (gift), Gap skirt (thrifted)

Thoughts: The 90s loved their leather — leather blazers, leather trenches, leather skirts. This skirt is from 2000 — that was a GREAT year for Gap. I have a few other pieces from that year, and I love them. Similar skirts are all over the stores right now, and they’re selling for $500 and up. I paid $7 for mine. The burgundy colour is so good for fall. Here, I went really simple — the 90s loved their minimalism too — and focused on the textural contrast between the smooth leather and the chunky cable knit.

Details: Revello top (retail), Mexx cardigan, Vince dress, Fluevog shoes (all thrifted)

Thoughts: Is there anything more quintessentially 90s than this outfit? This takes me ALL the way back. Black and brown is one of my fave “under the radar” colour combos, and I think it has a minimalist vibe that works well in this context. The white provides the bit of high contrast that makes the other colours look sharper.

Details: Re/Done tee, Gap blazer, Gap belt, Oak & Fort jeans, Modern Vice shoes (all thrifted)

Thoughts: Last but not least, this outfit was inspired by the one and only Winona Ryder. Her street style, to be exact. Was there anything cooler in the early 90s? Anyway, speaking of leather and 2000 Gap things, this blazer: it’s so good. Just the right amount of oversized, a classic cut. I don’t even remember how much I paid for it anymore, but it was under $30. Good luck finding anything like that in stores now … well, unless you’re hitting up the thrift stores. Which you should 🙂

The r/FemaleFashionAdvice sub-Reddit has never been a destination for incisive fashion discussion, but it does, among other things, offer a good sampling of the Average Person’s secret fashion worries. FFA abounds with posts asking for advice on whether one looks too old, too young, too fat, too skinny, too rich, too poor … and how to look more or less of those things, depending on the poster’s mood and unacknowledged biases. It’s kind of exhausting, tbh. And that’s not all. Another topic about which posters fret an inordinate amount is trends. What’s trendy, what’s not. Looking dated, along with being old (a moving target generally positioned around age 30), is possibly the Worst Fashion Sin one can commit as far as the FFA commentariat is concerned. The flip side of that conviction, and equally fiercely held, is a devotion to certain trends.

Spend any significant amount of time on r/FemaleFashionAdvice and you will encounter the phrase “they can pry my skinny jeans out of my cold dead hands” with almost reassuring regularity.

It was so ubiquitous for a while that “cold dead hands” became something of a meme, not only on the FFA circlejerk sub-Reddit, but also on the main sub-Reddit as well. At least millennials have a sense of humour, right?

Perhaps it’s a measure of how little I love jeans relative to other people, but I found the transition between jean trends fairly painless. I’m not bragging, honestly. Trend transitions in general should never be a cause for fretting. The process looks something like this:

1. I spot a new style of something. Jeans, shoes, doesn’t matter. This might be on a runway, on a Fashion Girlie’s Instagram, in a magazine, in a store, or on the streets of my town. There are many phases and entry points to a trend as it ripples out from the centre. Unless you’re working in the fashion industry, it doesn’t matter that much when you become aware of a trend. If it’s late in the game, it’s worth considering how much you want to “invest” in that trend (financially and emotionally, hah!).

• I may not be sure if I like this new style. If it’s not an immediate “yes”, I sit with it before I reject it. Sometimes the eye needs time to adjust to something new. Other times, on calm and measured reflection, it’s just a “no”. Not everything is for everyone. This is ok. One is not any more or less stylish for not adopting every trend out there.

• Okay, maybe I do like it. Off to the thrift stores to see if I can find something similar to experiment with.

• I got it and I love it. Time to stop buying the old style and focus on the new.

• New style is fully embraced, but always with a light grasp. No cold, dead hands. I enjoy what I love, but I’m always open to new ideas.

I also don’t immediately throw out all the existing items of the old style in my closet. If I have several, I might pare down to one or 2, but I keep the best versions (best quality, best fitting, etc.). Trends are cyclical, always. It might take a long time in some cases, but things come back. Just look at bootcut jeans. If you have storage room, keeping good quality clothes (that fit you well) past their current “trend date” is a good approach in terms of sustainability.

I have been on the wide-leg denim wagon for well over a year now, and I still have a couple of pairs of skinny jeans in the back of my closet. And let me tell you an even darker little secret: I still wear them sometimes.

Here are some thoughts to chew over.

One.

Skinny Jeans As Outfit are currently “out” of fashion. That is to say: if the outfit is centered around skinny jeans, and skinny jeans are the first and maybe only thing you notice about that outfit … it’s out of step with current fashion.

But Skinny Jeans As Style Building Block are a different, much more fluid story.

People get very hung up on the idea of things looking dated. But it’s always a combination of items that looks dated – in the sense of being suggestive of an era that isn’t currently trending – not necessarily the items themselves. I’ve done enough wardrobe remixing in my time to know that the same piece can be used to create outfits reminiscent of very different eras.

I promise you that you can wear skinny jeans in Our Year of The Lord 2023 and absolutely not look dated. Will you look trendy? No. But you can look cool AF in a way that isn’t tied to any particular trend or era. That’s called personal style.

I saw a male-presenting person on Instagram rock black skinny jeans with a majorly oversized chunky knit cape thing and tall platform shoes in a way that referenced both Rick Owens and Lenny Kravitz with a healthy dose of Gen Z “no f*cks given” attitude, and let me tell you: that was fly as hell.

Two.

I sometimes wear Skinny Jeans As Outfit. I mean, I don’t post about it on Instagram because it’s the equivalent of that brunch plate nobody really cares about. There are times when function triumphs over style, though, and skinny jeans are damn handy when the snow is a foot deep and I need pants that I can tuck into my quilted winter boots. They’re also handy when I’m gardening in the fall, and I need long pants that won’t flap around or get easily damaged and will protect my legs from rogue thorns and other hazards.

It’s good to recognize the utilitarian value of clothes. Even as someone who generally looks at clothes as a tool of creative self-expression, I know there is more to it than that. Just because something isn’t trendy, doesn’t mean it hasn’t got a place or purpose in one’s closet and life.

I leave you with these parting thoughts:

Love the things you love. Wear the things you love. Use them as tools of authentic self-expression. Use them as practical tools for living.

Know there are other tools out there. Some useful to you, some not. Sometimes, you won’t know which until you try.

Honour the tools that have served you well. They may serve you well again. Be prepared to put them down from time to time. It will be okay, I promise.

Details: Rebel Sugar mesh top (gift), Zara top (thrifted), BCBG belt, Carven skirt (both Poshmark), selfmade necklace

Thoughts: I love this outfit a lot and I can’t believe I didn’t think to pair this skirt and belt before. Long-line skirts like this one remain one of my style obsessions. Some people might think the extra length would only serve to overwhelm me — I am not especially tall (5’7) with short legs — but I think it actually makes me look taller (which I love, for the same reason).

Details: Emmy Deveaux bodysuit, Vero Moda blazer, Nicole Miller skirt, BR belt (all thrifted), J. Crew shoes (retail)

Thoughts: I wore this outfit to the office recently. Yes, I went into the office for once. It was nice to see everyone but the commute was awful. Once again, thankful I’m WFH … even if it means nobody usually gets to see my awesome outfits. Well, apart from all of you. Anyway, I had put this blazer away last year, as I had stopped reaching for it. It doesn’t really suit my Historian or (summer) Bohemian avatars. But I’m glad I held on to it because as soon as I thrifted this skirt, I knew this was the first outfit I wanted to try. They’re made for each other! I also think this blazer might serve me well with some 90s-inspired outfits so it’s sticking around for a bit longer.

Details: Club Monaco turtleneck, Gap sweater (both thrifted), Banana Republic jeans (retail)

Thoughts: How perfectly does this turtleneck match up to this sweater? It creates this cool trompe l’oeil effect that looks like I’m wearing a rainbow vest over a striped turtleneck. But, actually, the sweater has sleeves! That’s it. That’s the whole reason for this outfit. I am easily amused.

Details: Oak & Fort top, vintage vest (both thrifted), Ralph Lauren skirt (gift), Rafael Alfandary necklace (eBay), Holt Renfrew belt (retail)

Thoughts: This was a pretty literal translation of a runway look from (IIRC) Chloe. Or Celine. Sorry, I can’t remember anymore. But this is basically my Fall 2023 Bohemian avatar come to life. Big “Jo March” vibes. I loved it. Easy and simple and comfortable.

Details: H&M x Moschino sweatshirt, Philip Lim skirt, Only & Sons jacket (all thrifted)

Thoughts: I dusted off a couple of pieces I hadn’t worn in a while — this skirt and this sweatshirt — because I thought the jacket would bring them off together into a cool, casual outfit. And I was right! Sorry, that sounds insufferably self-congratulatory, doesn’t it? But I felt great in this outfit, and I continue to be impressed by the versatility of this jean jacket. I haven’t worn jean jackets in a few years, but the combination of the men’s (oversized) cut and the colour make this particular jacket feel really fresh and fun to me.

Details: F21 sweatshirt, Woolrich vest, BDG jeans, Fossil belt (all thrifted), Converse x Woolrich shoes (eBay)

Thoughts: This is the kind of outfit I never felt cool enough to wear as a teenager. Or had the money to purchase, for that matter. I loved wearing it this time around! These jeans were a calculated risk on my part; it’s definitely a cut/design that’s out of my style comfort zone, but I dig how they look. And they are comfy AF.