We’re one week out! Christmas Day is almost here! I’m currently in a production of A Christmas Carol, and I’ll confess to having caught the spirit this year (…in fact, I’m PLAYING the Spirits—all three!). I’ve been crying at every holiday movie, lighting Christmas candles every single day, and I cannot wait to watch my fam open their gifts! But I will confess to being slightly burnt out on all the Christmas-related newsletter content I’ve been reading (even though I sent my own gift guide out on Friday, lol). So—if I may?—I offer you a palate cleanser this week. Let’s talk about denim!
A few weeks ago, before the holiday hubbub really kicked in, I was skimming a shopping newsletter by celebrity stylist Angie Smith. Among her shopping recs of the week were a pair of mid-rise, dark blue, ultra wide-leg organic cotton jeans. My rapid thought pattern/emotional journey: 1.) Cutie! 2.) *Inner chuckle,* remember when I thought I really could NOT wear wide-leg denim?. 3.) …Why did I think that? Isn’t a wide leg a universally easy thing to wear?
I grew up in the 90s and the early aughts, when denim was doing A LOT, from a fashion perspective. By the time I got to college, we [the people] had landed, as you may remember, firmly in The Era Of The Skinny Jean. While I have been glad to wave goodbye forever to JEGGINGS (lol lol lol), when I found myself in our current stage of the denim timeline—the return of wide-leg jeans—I discovered I had been holding on to a myth, which no doubt had infiltrated my mind sometime during those years of extremely slim silhouettes. I believed that, as a short torso-ed person with a tush but no hips to speak of, a wide-leg jean would make me look like a sad and droopy rectangle. But A.) who cares?! wear what you want!, and B.) that doesn’t have to be true.
The real question at play was not about denim specifically, or trends and fads coming in and out of style, but about proportion. When I say “proportion,” what I mean literally is: how do different shapes, textures, or colors talk to each other visually in the context of an outfit? And how do I make those combos look and feel like me? If my legs make up, like, 60% of my total body mass (I don’t know, I’m not a scientist!) (sorry Dad), and jeans are a major workhorse of my wardrobe, then the cut, shape, size, and wash of the denim really has a lot of sway when it comes to the total VIBE of an outfit. Relatedly, nothing was affected so much by the shape of the jeans in question as my shoe choice (as you’re about to see below).
In the last year or so the leg size of my denim has gotten decidedly wider. I’ve found some widths and fits that make sense, both for my closet and for how I want to feel as the human inside the pants. And it’s great! Depending on the situation, a wider leg can be lot more comfortable for a full day of *living.* But I still love my slim leg Levi’s, and I’ve had a lot of fun swapping pairs in and out for different reasons and seasons.
This week, I thought I’d do a little compare/contrast between the three pairs of true-blue jeans in my closet: a slim fit, a wide-leg crop, and, my most recent acquisition, a straight-fit full length wide-leg pair of jeans. Let’s talk why I like them, how their proportions differ, and how I style them. Fun? Fun.
The Contenders:

Meet the blues! A wide-leg full length, a wide-leg cropped, and a slim leg, also cropped. Even in this “neutral” presentation, the vibe really changes with the shape of the jean, no?
Also on display here—I have an athletic build, a donk (hey gurl!), but very narrow hips, and so Cannot and Will Not Ever be able to wear low-rise pants. There is nowhere for them to land, and so they move around searching for my hips in vain, which is extremely uncomfortable for me, the lady in the jeans. When I decided to embrace my wide-leg journey, I knew I was looking for pairs that still had a high- or mid-rise fit in the waist. The jeans in the first and second photos fit that criteria, so they got to come home and live with me!
The Shoes:

As I briefly mentioned above, the biggest lesson learned from swapping these jeans in and out was that the shape of the leg had a lot of sway when it came to my shoe choice. Behold the following outfits!—where I try some pairings that work and some parings that don’t, and nerd out a bit on why I think that is. Let’s get into it!
Exhibit A: Boots

When it comes to jeans and boots, that iconic combo, I find that the more substantial the boot, the slimmer I want the jeans to be. If I combine a wider leg with a heavier shoe, I tend to want a little visible ankle for contrast. Check out how bottom-heavy the pairing is in the first photo. I don’t dig it! The wide leg of the jeans make a sort of shapeless puddle around those big chunky boots. By contrast, in the second version, the slim, pointy toe balances the wide leg and puts a nice button on the whole outfit.
Even though these black lug boots carry some weight, they have a nice slim ankle, and so I prefer them with the slim-leg cropped jeans in the third photo. Given that these are my heavy winter boots, I’d probably throw a white crew neck knit over that black t-shirt (plus some gold jewelry) to head out the door/seize the day.
Here are the same black boots with the wide leg cropped jeans. Unlike the full wide leg, these jeans end with enough room to catch that slim ankle on the boots—so we lose the puddling/shapelessness I didn’t love from before.
Exhibit B: Heels
This category came with some surprises! Going in, I assumed that the general rule would be similar to the boots: the wider the leg—> the slimmer the shoe. But rules are made to be broken!
Interesting, right? I thought I would like the platforms with my slim jeans the best. Turns out, that was my least favorite combo—I felt they were too clunky next to such a slim fit. Because the shirt in the first look is also oversized, I thought it gave off a kind of dumbbell effect—heavy on the bottom, slim in the middle, heavy on the top. Totally my personal preference in the moment, but, to me, those proportions were odd.
Alternatively, the platforms and the wide leg jeans have a harmonious size and weight, which made for a more streamlined shape. I think it’s worth noting that my concert tee has a lot less volume than the oversized button up—and I think a more fitted top with a baggier jean generally makes the whole thing feel a bit more sleek. (If I were instead to pair the oversized button up with the baggier jeans, I would only do it with a skinny, bitchy shoe, like the following:)

Shoe swap! The slimmer the shoe, the more versatile, IMO. And I love a 2-inch heel these days! So fun, so easy to wear for hours on end. I used to be a 4-inch queen, but I no longer want to traverse the streets of New York in stilts, and I am too cheap to call cars all night long. (Let’s just say those velvet platforms above are from another time.) Anyhoo! I feel fucking great in all three of these looks. See how a pointy-toed shoe works in every version? Much wears!
As a side note: I’m noticing that I tend to skip the belt if the shoes are really giving a moment, like these bright red ladies. I think I’m not generally a fan of competing elements—but one of my style words is “ease,” so there you go.
Exhibit C: Flat Shoes
When it comes to pairing shoes + denim, this was hands down the easiest category. Similar to the heels above, a slim shoe tends to work with any cut of pant—it adds a little something, but doesn’t compete with other shapes. Potentially that is why flats are coming back with such a vengeance.
Because they are naturally so versatile, I find there’s typically room to add a flat shoe that’s a little unexpected—which keeps the whole look fresh and playful. Color, texture, interesting details all welcome! As far as this Mary-Janes-and-socks combo (which, yes, I am committed to, it is very cold in MA!), the cropping of the jeans matters in that the length shows more or less sock, thus giving more or less schoolboy vibes. Cheeky!
This may not be seasonally appropriate, but quickly, while I’m on the topic: a little sandal works with almost everything too, for the same reason. Plus, there’s some subtle-but-fun shock value with a wider leg and a delicate sandal—like, “Aaaah! Toes!” (Unfortunately, I have no actual sandals here to demonstrate this with, but the third photo is to aid your imagination with that full-length wide leg.)
In the end, personal style is what you make it, and everybody (and every body!) is different. IMO, that’s what makes this all so fun! And, in the sense that it can be a tool and not an obstacle, thinking about proportion is a cool way to embrace the visual art of it all, and try out new shapes and trends in versions that work for YOU.
And das it! No big style talk next week for the holiday (though I may sneak into your inbox just to say Merry Christmas!), but I’ll be back in two weeks to talk the granddaddy of style holidays, New Year’s Eve. Tra la!
Sending you love, Costume Change Fam!
A probably unnecessary Editor’s Note, but: my hair is in this slick bun/braid in all my photos lately because I wear it in a bun for my shows! But I am a proud member of the curly girl club, and the curls will be back soon!
Costume Change is a styling newsletter (vs. a shopping newsletter). None of the above shopping links are affiliate links. As always, I hope that Costume Change first and foremost provides you with inspiration to shop your own closet, rather than tempts you to buy a bunch of new stuff. Thanks for reading, and Happy Holidays!