Why do we persist in thinking that effortless fashion is a thing? Why?
It’s not. And yet we still seem to believe that if we can’t just throw something on and look good, then there’s something wrong with the clothing. Or with us. Or that we’re failing at fashion.
Maybe you don’t feel that way. But I do sometimes. Even when I pretty much know what I like and what looks good on me. Even when I know the direction in which I’d like to take my personal style. And even with a closetful of clothes that mostly fit me and which I mostly like.
So earlier this week, when I was struggling to style a new piece that I’d purchased, I was grateful to hear my style mentor Allison Bornstein say in a recent TikTok video, that “fashion is not easy and it is not effortless.” And when we get discouraged, we should be cheered by the thought that “it’s not easy and it’s not effortless for anyone.” I can’t tell you how grateful I was for that reminder.
I’m sure you know, because I waffle on about her all the time, that I am a big fan of stylist Allison Bornstein. I’ve been following her for a couple of years now, ever since I discovered this YouTube video about her closet editing system.
In her recent video, Allison recommends analyzing an outfit that’s not working, and then using trial and error to find one that does work. She uses the tailored vest as an example.
“Trial and error,” I thought. “That’s what I normally do.” But this past week for whatever reason I found myself uncharacteristically defeated by my clothes. Defeated, coincidentally, by a tailored vest.
I’ve been looking for a vest for a while, and finally found one I liked at Aritzia. By the time I saw Allison’s video, I’d already tried the vest with three or four outfits. And I was NOT in love with any of them. “Good thing I left the tags on the vest,” I sighed, “because it was going back to the store.” Then, after watching Allison’s video, I decided that I’d have another go. All told, I tried and took photos of seven outfits. Trial and error on steroids, people.
Let’s have a look at all the outfits, shall we? The good, the bad, and the exceedingly ugly.
Consider, first, the outfit above. Sadly, these black dress-pants were the reason I wanted to buy a vest. I imagined the fitted vest with a cami underneath, the loose dress-pants, and flat sandals for summer. And in the fall, the vest with a tee shirt or long-sleeved shirt underneath, the pants, and sneakers or boots. But here’s the thing. The different fabric of the two pieces, the way they each reflect the light, means the black vest makes the black pants look navy. They don’t look good when worn together. Plus that old white cami is doing me no favours at all.
So I scrapped my original plan of wearing the vest with the black dress-pants. I own other black bottoms that I wear in the fall and winter. Namely a black faux-leather pair of pants and a black faux-leather skirt that might work, so I wasn’t giving up the black on black idea just yet. I still had possibilities for fall outfits.
But could I find some way to wear the vest now?
Ha. See below the answer to that question.
Those wide-leg Levi’s Dad jeans, above, look dreadful with the tank top and vest. It’s the proportions, the open vest, the tank top… something. I prefer a slouchy top with these jeans. Or sneakers and a blazer. But not this. And the shorts combination is just as bad. Maybe if the shorts were white. Ugh… maybe not.
I’ve learned a couple of things from looking at these photos. My black Everlane tank should now be relegated for exercising and camping only. In its third season, it’s stretched and faded from washing. I need to order a new one. The second thing I’ve learned is that maybe I am not a “Dad jeans” kind of girl after all. I want to like these jeans. But somehow I keep putting them on, and then taking them off before I leave the house. That’s a sign, people. Ha.
The Frame straight-leg jeans, above, are better. With the black Vince tee shirt under the vest. While this outfit is not groundbreaking, nor even very current, I’d still feel comfortable wearing it for a library run, or to meet a friend for coffee. The cream cloth tote bag with the dark grey lettering lightens up the look of the outfit. I bought this bag at Shakespeare and Company in Paris in 2015.
One Vince tee shirt lead me to trying my other Vince tee shirt. See above. I think the white tee works with the cream cargo pants when they are separated by a black belt. And keeping the accessories (like belt, bag, and sandals) chunky works with the heavy cargo pants. I tucked the tee shirt in tightly because a slim, neat tee seems to work better under the neatly tailored vest. I like this outfit. I’d also wear it with sneakers instead of the sandals, or maybe even black ankle boots in the fall.
The outfit above is a work in progress. It theoretically works. The vest buttoned over the dress pants is a look I like. But I need a better black camisole, or perhaps my Vince tee. And the pants are heading to the tailor this week. They’ve always been a bit too large. I’d sized up when I ordered them back in 2021 because I had gained a few pounds. But now that I’ve lost those same few pounds, the pants are falling off me. So I will get the tailor to take them in, and hem them again. I should have had them hemmed shorter the first time. Not sure why I didn’t. When the pants have been altered, we’ll see if what I believe will work in theory does so in reality.
Above is the outfit I tried last. And which I wore shopping earlier this week. This is when the tags finally came off the vest. Ha. The black vest works with the black cargo pants, even though they are slightly different blacks. I like the Everlane lilac tank top under the vest. I rolled the cargo pants to make them a bit more slouchy, and went for the more delicate sandals instead of my chunky Birkenstock-style ones. Somehow the chunky sandals threw off the proportions, and made the outfit look bottom heavy. For jewellery I wore my big silver hoops, a small silver chain, and a black cuff with silver trim. The straw bag lightens up all the black a little.
I felt great in this outfit. Effortlessly chic, one might even say.
I mean how hard can it be to throw on a tank, with a black vest, and black cargo pants, then buckle on flat sandals, and grab my favourite straw bag? And it only took six failures to get an outfit that I wanted to wear and in which I felt most like me.
Oh, it’s so easy to bandy terms around like effortless fashion, effortless style, effortlessly chic, isn’t it? It’s so easy to envy the women who look as if they just rolled out of bed, reached blindly into the closet, and pulled out a fabulous outfit in which they look great.
I’m not talking about the women who wear head-to-toe designer looks, accessorized by Cartier or Tiffany. Like the ones you can see on IG lately, in all those “street-style” posts. Ha. I have no idea where these streets are, but they’re not in my neighbourhood.
No, I’m talking about the women who look chic, but a teensy bit thrown together, in just the right way. Nothing too overdone, or fussy, with the proportions just right, and the fit just right, mixing oversized with tailored, the pieces not too matchy-matchy. Looking wonderful. Effortlessly wonderful.
But like Allison says, let’s not forget that achieving those effortless looks takes effort. Sometimes more effort than at other times. For all of us.
Of course, fashion can be effortless. Sometimes. Eventually. Once you have done all the trail and error, and put in all the hard work. You’ve done your research, and purchased something you love, that fits, and which you’ve tried and liked with several other pieces in your closet. Once you’ve found a few outfits that you love, then it’s effortless to pull those pieces out of the closet, throw them on, and head out the door. Easy peasy.
But this time, for me, fashion felt anything but effortless. I know there are other looks I could have attempted, different camisoles, more jeans, different sandals, different tee shirts, whatever. But trial and error is, well, a trial. And tiring. Usually by the time I’ve tried a few outfits, my hair is stuck up, my mood has plummeted, nothing looks good, and I long for a nice cup of tea and a good book. On the second day, by the time I had hit on my final combo I was done like dinner.
I have a theory as to why I seemed so short on patience with my clothes this week. I’ll share that with you another time.
But, let’s not talk about me anymore. Let’s talk about you, my friends. What is the most onerous thing about fashion for you? The most effortful part of your style journey to looking like you want to look? Have you purchased a piece lately that you love, but which required hard work to style?
P.S. Here are some vests that I like, that I didn’t buy. Have a look if you’re interested.
P.P.S. The links in this post are affiliate links. If you make a purchase after clicking my link I will earn a commission which helps to pay for the blog.