Style Notes: Outfits with pleated jeans

Another one by user request! One of the jeans I purchased after having to size up due to 2020 weight gain was a high-waisted black acid wash pleated pair from Target. One of my signature pieces from 2018-2019 was pleated corduroy trousers, so it’s been nice to have that silhouette option again! Since that time my style has leaned more to the casual and modern side with more sneakers and tees, so going the denim route helps blend my more “storybook style” pieces with the “crunchy casual” stuff. If you’ve gotten caught up in the pleated pants style but are feeling a bit stuck on what to wear them with, here are some examples of how I’ve been wearing or plan to wear mine.

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In general, I find these work with more romantic style items I would also style with a vintage style trouser, such as button-down blouses or sweaters, but the acid wash denim aspect lends the piece to outfits that lean into the 1980s look. In this first outfit I’ve blended the two with a true vintage teal graphic tee and the more classic leather accessories of the derby shoes and purse. To accentuate the more modern style of the shirt and the white type, I went with a Casio digital watch instead of a leather wristwatch.

Vintage Quotron graphic tee via eBay, Madewell Zip-top Transport Tote, Trotters “Lizzie” derby flat, Casio watch

With retro style sneakers the whole vibe definitely leans more 80s throwback. I’m into the old school nerd look so this works for me! For a slightly less Steve Urkel look I could have adjusted the cuffs to sit lower but I wasn’t feeling that high-effort to re-cuff them for each photo here. Personally I’m in the camp of if you’re going for a dorky look, it’s more fun to go all-in anyway.

New Balance Classics sneakers

Another styling option that lean into the retro-casual vibe is a high half-ponytail with a scrunchie. I used a gingham one here along with a cropped slightly drop shoulder sweatshirt. Since the top and jeans both have more poof going on, I went with more fitted sneakers to add a sharper finish to the silhouette.

Levi’s Diana sweatshirt (XS), Converse Chuck 70s High tops

Now more into the romantic-vintage-academia-farmers-market-run sort of aesthetic with a milkmaid style eyelet blouse and the leather purse and shoes, this time with a coordinating watch for that can’t-go-wrong neutrals combo. These pants are very high-waisted on me, so when paired with a lower neckline top and no belt (which would shorten the proportion the pants take up in the outfit) it’s quite a leggy silhouette. It’s a little on the extreme side for my preference, but with the current trends and my preference for feminine silhouettes, I’d personally rather end up slightly too high waist than slightly too low.

Anthropologie blouse

Compare to this monochrome example with a crewneck blouse and a belt closer in color to the top, which downplays the high-waisted cut a bit more. I like how the acid wash adds more texture to the all black/gray, and I paired it with other high-texture pieces: a waffle-knit gigot sleeve blouse (gigot sleeves are also vert 80s!) and metallic derby shoes.

Free People “Tasha” thermal via Poshmark, Anthropologie belt, Louise et Cie “Adwin” loafer

This styling with the ultra pointed toe boot and contrasting belt feels slightly western to me, very much like something @carokolbe would wear! With the dressy boot, the ruffle blouse, printed headband, and belt this is more glam and accessorized than I usually go for, but this was fun to try out! I think it would look cute with some rings or a minimal gold pendant necklace (mine is still somewhere in the remaining moving boxes).

Anthropologie belt, Intentionally Blank “West” leather bootie, Anthropologie headband

A lineup of variations-on-a-theme to show how color contrast, neckline, top contrast, and tuck-vs-crop change the torso:leg proportions. Even though the center outfit is also mostly black, because of the midriff line and thicker band on top of the belt, it has a lot more horizontal emphasis and the top section reads more separate to the jeans.

An easy-peasy-pinterest-breezy oversized turtleneck sweater tucked in outfit. I’ve found I prefer chunkier sweaters feel more natural tucked in to more relaxed fit bottoms like this vs trying to stuff them into the instagram influencer version of hammerspace when wearing fitted bottoms like skinny jeans. This sweater also has a pretty strong drape to it (it isn’t stiff), which helps it flow more naturally when worn tucked, and I always feel very chic in it especially in movement.

Free People “Softly structured” tunic sweater in XS via Poshmark

A less blogger-y pose.

In the same color palette, an more more warm weather friendly option.

Free People “Moonriver” cardigan, H&M rib-knit cami, Birkenstock “Mayari” sandals

With a crop cami for more colorblocking. For milder extra casual days, I like longline bra / crop cami combined with a cardigan for a more gentle take on the bare midriff style.

I love the balloon silhouette of pleated trousers, so I usually go for cropped or tucked options for tops. But even then, because they’re relaxed, I think they work nicely with pieces that have a slouchier or casual vibe. It results in more of a free-spirited/romantic feel than a true 1980s preppy look.

From vintagedancer, a great resource for learning about true vintage styles

So for a button-down shirt option, I think it works well for my style with this cropped statement collar blouse. It’s not so long that untucked it creates a more rectangular rather than pear shape (again, I gravitate towards feminine silhouettes, but that’s a personal preference), and it has an air of old timey storybook adventure style especially when paired with granny boots. I wore this one with a french braid, to have an element of “done”ness within all the slouchiness. Way different vibe than the look above!

Vila petite long sleeve statement collar blouse, Comfortiva “Cordia” booties

And it’s not raining this week, but just for fun I tried a rainy-day spring look with my gingham trench and platform docs for a less twee styling. I really liked how this turned out with the full value range monochrome + print, and the balance of structure (cuffs, collar, boots) and relaxed fit. I am eagerly awaiting the next rainy day so I can wear this in the wild!

Columbia gingham trench rain coat via Poshmark, Dr Martens “Leona” platform combat boot

The particular jeans I’ve got are the “Women’s Mid-Rise Straight Acid Wash Jeans” from Who What Wear at Target in a size 12, although it’s currently sold out except for size 22. More casual-trendy oriented brands like Urban Outfitters/BDG, Topshop, Madewell, or ASOS will carry similar options, but you’ll find the most variety in pleated jeans from vintage resale – you can filter an eBay search for “women’s pleated jeans” to used and check double the item measurements against a pair of jeans that you know fit you.

A few currently-available options in a similar style with most of their sizes in stock (which look cute but I haven’t personally tried) are

Abercombie & Fitch High Rise 80s Mom Jeans

Madewell Baggy Pleated Tapered Jeans in Springdale Wash

Shein Plus High Waist Fold Pleat Mom Cropped Jeans

Just for fun, let’s end with some behind-the-scenes pics:

doing my best avant-garde / editorial / tortoise impression

If you own pleated jeans, how do you like to style them, now or the first time they came around? Let me know in the comments below, or leave a comment on whether you found an aspect of this post helpful or interesting. I love feedback!


    1. Haha the 80s came back! Yes, these are definitely thinner than the average non-stretch jean, IMO it feels more like a trouser. A lot of the reviews mentioned it being more of a summer weight and I think it’s a little easier to style with soft pieces because it isn’t so structured.

      Liked by 1 person

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