How to wear shoes with jeans
Seems simple, but it isn't!
Hi and happy Friday!
Something’s in the air because as I was wrapping up this newsletter yesterday, Anna Gray’s Things I Would Buy If I Didn’t Have to Pay Rent popped up in my inbox and lo and behold: jeans! Great minds and all that! In it she says the following:
"Jean trends are funny because they make sweeping generalizations (“The skinny jean is dead” et al) at an attempt to lasso the widest swath of audience but I argue that once a consumer’s style and fit is found, most people stick with their preference."I wholeheartedly agree! I was going to talk a bit about how absurd jean trends are but just go read her newsletter and I’ll get to the styling of the things.
Seeing Anna’s name is even more serendipitous because our time at Object Limited partly inspired today’s newsletter. Long ago, we put together an IG show called, “How to Wear Stuff” wherein we would take style conundrums from our customers and try to help resolve their issues by showing a few ways to wear said conundrum. One such prompt was “How to pair the right shoes with pants” which seems like the odious jean trend cycle in that: wear whatever you want. But that prompt, coupled with a friend recently telling me she also had trouble picking shoes to wear with pants made me take a beat to consider this may be cumbersome for many people.
So I figured I’d take the most ubiquitous pant in the world and show you what shoes to wear with it!
As with trends, these are not hard-and-fast rules. Wear whatever you want! But if you’re looking for guidance, here it is. Also, as an aside, if you read Anna’s newsletter you’ll note she loves a student-fit Levi’s so I found two options for us all here and here.
The looks below are listed in order of width so we’ll start skinny and finish wide with a touch of variety in between.
Let’s get to it and happy shopping!
p.s. Items marked with an asterisk received a lower offer after adding it to my liked list
p.p.s. Don’t forget to click to expand the email - it’s a long one!
Skinny Jean
Ah, the skinny jean. My home away from home. As both a hippy and wide lady, these are the only jeans that don’t make me feel bigger than I am. Thus why I take such umbrage with the idea of jeans trending in and out - should we not just dress for our body type and what makes us feel best? I guess this is a lesson learned and earned in your 30s, but I have no qualms with wearing these. And how would I do so? These ones pictures cut off right above the ankle which makes them the perfect candidate for a delicate shoe. Visually you’re not burdened by any extra pant width so you can stay as slim as you like. A flat, a loafer, a classic brogue are all perfect for this cut. You can also do a chunky shoe (just balance the weight with a bulky jacket or sweater up top) but this is the easiest pant to wear your visually smaller shoes with.
Top it off with mixed pinstripes and you’re good to go!
Straight Leg Jean
You’re a vision in brown, darling. With a slightly wider (and often stiffer) cut than the skinny, a straight leg jean is also great with slimmer shoes, or as I recently found, a slim ankle boot:
I just found these Stuart Weitzman boots and they’re giving 90s knockabout in the best way. The key is a slim ankle on the boot because otherwise you’re looking at an imbalance of visual weight when there are better jean options to wear if that’s the look you want. A straight cut jean is sleek and wants a sleek shoe, too.
So for the coordinating outfit I tried to find you the same boot! Up top I love the color combo of this mint green and brown. If it’s cold, add a white turtleneck underneath and a camel coat on top, if it’s mild, wear the top as-is and just throw on your metallic liner jacket.
90s Tapered Jean
The 90s taper! Seen ‘round the world and nearly everyone’s tried it. Me? I personally like to lean into its roots and style the jeans as you would in the late80s/early 90s with a cowboy boot. A thick ankle here is the point and for cold weather it’s a good one. Because the jean starts wider and then tapers to a smaller width, having a heftier shoe helps balance the visual distribution of the jean.
For your outfit I say go all-in on the 90s and wear a killer western brass belt, a thrashed 90s band tee and then this cropped blazer jacket to keep people on their toes!
Flared & Cropped Jean
The flared crop is a favorite cut of mine because you can really show off your shoes. The bell shape is almost a spotlight on what’s happening below it, meaning you should make it count! Add visual interest with some laces or a print but make sure it has weight to it. Depending on how wide the flare is, you need to visually weigh down your whole look with a heftier shoe. This is specific to a stiffer denim flare, though! If you have, say, a flared cropped plisse pant, that silhouette is slimmer in general which means you could wear a daintier shoe.
For the outfit, why not try this chic little vest/blazer combo and really keep it interesting with this incredible diamond print coat!
Ovoid Jean
A shape of denim I always admire and daydream of wearing! This silhouette is basically a super exaggerated version of a taper. It usually has a tight, high-waist cut, then balloons out on each side, finally tapering slightly toward to ankle. They always feel like fashion jeans, so let’s do right by them! Because the entirety of the jean is wider, a slim shoe like a flat will make your whole silhouette feel like it’s going to topple over. The wide cut when tapered is still wide so it needs - say it with me - the visual weight of a heavy shoe to anchor it. I love these suede flatforms because the mirror the odd energy of the pants - they’re both a touch off kilter and thus perfect for each other.
Styling-wise, I do love adding more weight to this kind of jean, so I found the best mohair cardigan…ever? to throw on top. The color! The stripes! An oversized sweater would look cool with this, too, but for me I want some bodily definition so I added this angora tee to let the sweater and jeans sing while still adding more texture and intrigue to the whole look.
Wide Leg Jean
Such a chic cut! These in particular go all the way to the ground which means your ankle is completely obscured so the rules of heavy visual weight don’t really apply here. Instead of weight you need extension. Something that extends past the pant leg. It can be a flat like I’ve chosen or a boot or a heel, but you want a shoe with length. A pointed heel is an easy win, but sometimes an extreme squared toe will do the trick, too. I would steer clear of rounded shoes because then it looks like your pants are swallowing your feet and snubs the silhouette you’re looking for. If you had a wide leg that was cropped, though, then visual weight is back in the game and you’d want chunk and heft to anchor your silhouette.
To pair with the above pants, I went slouchy and cool with a big oversized sweater but threw in an angora tank for underneath in case you get hot! Toss on this Nina Ricci bag cross body and you’re calm, cream, and collected.
Please know you should wear your clothes however you want, whenever you want! Like art or a well-designed room, though, it’s helpful to know the “rules” so you know exactly how you want to break them! I also know that for people who don’t think about clothes and fashion all the time (unlike me), this stuff can get confusing and we all just want to feel confident about our style and ourselves, so I hope this helped in some way.
One last thing that is wholly unrelated to denim: I wanted to share this dress I found and listed recently. It’s slinky, it’s sexy and it has a cut-out with an attached necklace AND a thigh slit with another gold ring for good measure! In case you were looking for some va-va-voom in your wardrobe. Here’s a full pan video and click below to shop it!
Thank you as always for being here and have a great weekend! Please comment if you liked this kind of guide or share it with your friends! And don’t forget to email your reps every day for a ceasefire, and here’s a link that fill out your emails automatically. It takes 15 seconds! xx Maggie
we love pants !!!!
Fully influenced my on the Donald Pliner shoes with the wide jeans. Really love your outfit compilation pics. Great post!