Styling modest vintage-inspired pieces to feel less old-fashioned

oregon trail game

Like the How to Look Older in Casual Clothes post, this one is an expanded version of a comment I originally wrote on reddit that people seemed to find useful. Since reddit comments tend just get reabsorbed into the void, I’m crossposting here for posterity with some formatting improvements and extra tips.

The original post by u/bemydarkling was titled “How to pull off “witchy” without looking “homeschool cult”“:

I’ve seen a lot of “witchy” inspiration and I’m loving it. I dig the long skirts and touch of historical/vintage flair, the earthy tones and cozy feel. The problem is, I feel like I look too much like the religious homeschool cults I grew up around in the 90s. How do I balance all that? How do I pull off the shapeless “fashion doesn’t need to show off my shape” attitude without looking like I’m selling purity rings? Or wear the long swooshy skirts without looking like I’m only wearing it because I believe it’s a sin to show my ankles??

(Obligatory disclaimer: This post is all working on the assumption that the target reader doesn’t want to look too conservative or frumpy. That’s not to say that it is the correct or incorrect to dress, or that looking cool and fashionable is something everyone needs to aspire to.)

I generally try to balance old fashioned style items with trendier and/or less modest pieces. A sock bootie (or any currently trendy shoe), bright lipstick, or a slightly deeper neckline can go a long way. Even without showing more skin, the idea is to make the look read “this is for fun” and not “this is because I have to”.

Table of Contents

  1. Examples with my own outfits
  2. Styling choices and the halo effect
  3. Case study: how are prairie dresses styled in stock photos?

Examples with my own outfits

Make it playful

Having multiple cues throughout the look like fun accessories that make the outfit feel fashion-y can help, even if they are not super on-trend.

For example, these outfits are almost the same, and my hairstyle on the right isn’t like, fake slime green roots or whatever the kids are doing these days, but the less severe hairstyle and the addition of some fun green ribbed velvet socks make it read relatively less stuffy. Still a bit vintage-cosplay, but at least to me, it feels more on the “feeling cute, having fun” sort of vibe than a “this is what my mother dresses me in” thing.

If I were to style this by pushing towards trendy rather than playful, I think something like a black or white leather or suede boot with a pointed toe and a funky heel shape, one of those relaxed fit long trenches that have been the trench silhouette du jour, and some gold hoops would look chic. (I do not have any of these things.)

Make it edgy or artsy

In this outfit I have a heavy knee-length smock dress, but I added patterned fishnet tights and patent leather boots, neither of which are accessories that I associate with the purity ring vibe.

For a less goth-costume option, I think a high contrast pairing like white platform high top Chuck Taylors with some colorful funky jewelry could also work to push the monk robes vibes towards artsy instead.

Make it cute/pretty/flirty

Here is a summer outfit with a button-front midi skirt and clogs, but I think the red lipstick, matching silk scarf style headband, fun summery straw tote, and lower neckline camisole help make it read more “wore this to feel cute” and not “I’m not allowed to wear shorts”.

It’s a bit easier to get into the romantic vintage silhouettes thing with tops and bottoms instead of dresses that take up 80% of your outfit’s visual real estate since you have more area to work with when trying to balance it out.

Styling choices and the halo effect

Hair and makeup can also be a huge help. If your face and hair styling clearly reads modern, then that will have a halo effect into the rest of the outfit.

But first, some armchair psychology:

Which audiences do you care about when it comes to all this, anyway? You? Your friends? Your instagram audience? Your coworkers? Honestly, I suspect that demographics who aren’t already  swooning over Zara’s interpretation of trends from the Little Women movie, it’s going to come off as odd to them no matter how interesting or trendy your outfit styling is. It’s gonna be “lol the 70s called, they want their gunne sax back / lol are you dying of dysentery”, so you’ll have to accept that some  people may think of your outfit that way.

A lot of getting comfortable with fashion is just repeatedly wearing things further out of your comfort zone until you don’t give a fuck anymore when social consequences of wearing something weird are inconsequential (i.e. grocery run, or going out for brunch or to read in the park vs a job interview or funeral).

That said, it’s always nice to have some concrete things to try and make yourself feel cooler or more comfortable or whatever when wearing a piece that you’re into but a little hesitant about.

Edgy styling

If you, physically, give off a vibe that is more punk or stylishly modern or whatever, that will carry through your clothes. In a more extreme example, think of people who have a lot of tattoos and blunt bangs. Or buzzed hair and heavy eye makeup. No matter what else they’re wearing, whether it’s a linen sack dress with sneakers or minimalist bizcaz, they’ll have an edgy vibe.

Of course you don’t have to go all permanent body modification or extreme haircut to get that effect. You can incorporate a more edge or modern vibe as easily and temporarily with things like

  • black nail polish (or other relatively offbeat colors)
  • makeup (an easy one if you’re not committed to doing a full ~look~ is adding some bold lipstick)
  • loud fashion earrings, rings, or hair accessories
  • additional clip on earrings
  • or even other faux piercings if you want to go that route.

Personally I don’t want to have my ears stretched, but I like these gold faux gauge for a different take on gold hoops (though standard gold hoops would also work great for moving a fit away from a buttoned-up vibe).

Conventionally stylish styling

(I really didn’t know what else to call this section.)

I always come to this conclusion and hate it, but honestly if your goal is to look conventionally well-dressed, then having your hair and makeup on-point and wearing a trendy piece of jewelry or hair accessory is really what makes it more than almost anything else you could wear. As you might expect, it’s pretty hard to find photos of folks wearing bolder things with truly nonexistent makeup and dgaf hair styling, but I like to use the power of imagination and think about how critical it is to  a look to have cool hair, or a particular hairstyle or length, or well-applied makeup when going through inspo outfits like the ones below.

Striking a balance

The more you look like you are actively invested in your appearance, whether that’s by having fresh from the salon balayage or undercut or incorporating multiple well-chosen accessories, the more likely anything you wear will come off as intentional rather than misguidedly awkward or forced. Think “I made an active choice to look this way, you don’t get like this via inertia”, no matter which particular aesthetic you prefer.

Additionally, I find that one way that any given outfit can feel more cohesive is if all its components are all similar levels of extra. The prairie dress or an aggressively romantic-witchy sort of getup is a bold clothing choice. It can provide a good canvas/infrastructure for bold peripheral pieces (shoes, outerwear, hair styling, bags, sunglasses etc). For example, chunky hoop earrings vs minimalist gold post earrings.

On the other hand, if you want to keep from looking like a cosplay for Little Women, you can choose accessories that while bold, are from a tangential aesthetic, e.g. lug sole platform docs vs granny boots.

Case study: how are prairie dresses styled in stock photos?

I fully admit that I am not the most fashion-forward person to give examples (nor do I have an infinite and fully up-to-trend wardrobe), so when thinking about this sort of thing I’ll often browse more youthful or trend-oriented shops and recent vogue/cosmo/marie claire/etc images and mentally take note of the types of shoes, accessories, and hairstyles that show up repeatedly.

Since these are ecommerce stock images, if it isn’t the shop’s look, they’re probably not gonna choose models with tattoos and other body modifications or really crazy hairstyles, and they’ll want a makeup that goes with a variety of their stock items. But I feel like most people don’t have extreme body modifications or hair styles and aren’t planning to change that for the sake of a trendy dress. And if you do, you probably already know how it affects your outfits anyway.

The following photos are all from ASOS, Anthropologie, or a Cosmo street style article, and you can find them and their sources in this Pinterest board.

But in the meantime, there are shoes. I feel like shoes are a pretty approachable way to foray into the world of more visually intense outfits and they pretty reliably appear in stock photo outfits, so I’ve grouped some inspo photos according to types of shoes that I often saw used to style long, ruffly and/or long-sleeved dresses. I also noted some other styling choices in the looks.

Sharp Boots

Fitted suede block heel boots, slightly textured bob with choppy fringe, minimal but finished makeup.

Tall cuban-heeled pointed toe boots in a shiny finish (can’t quite tell if that’s patent leather or not). Trendier higher shaft on the boot. 70s shag sort of hairstyle with heavier but muted tone makeup.

Ass-kicking boots

A traditional complement to fun floral dresses.

Very “done” looking hair, makeup is not minimal  but in more natural colors. Combat boots with extra hardware.

Combat boots with a heel and extra hardware. Large rhinestone heart hoop earrings.

Funky Shoes

Very minimal/natural hair and makeup, large thin hoop earrings, artsy sandals

Trendy padded headband, flatform loafers (seriously, how often do you see these? we should see them more, they’re awesome), dressy purse. This dress is also in a non traditional pattern (rainbow leopard!).

Tall high-heeled snake print boots 💥

Trendy / Fun Sneakers

Dad sneakers, long nails with white nail polish, low-key hair, medium natural toned makeup.

Mismatched high-top sneakers (though I think this would still be cool even if they were worn as matching shoes), trendy headband, “finished” trendier but loose hairstyle

Chunkier sneakers with retro style crew socks (feels a bit like fun pattern mixing with the dress polka dots), loose, trendy, finished hairstyle, hoop earrings, medium natural makeup.



And there you have it! I hope that was interesting or helpful. I always feel like these sorts of things boil down to “google image search for recent outfit photos and write down all the reoccurring styling details”, which seems pretty “does that need an article”, but based on my experience on reddit, it’s still helpful to discuss specific examples. Since so many people are quarantined or working from home these days, this whole write-up felt a bit moot. But this won’t go on forever 😬 and a little time musing on outfit formulas is a nice distraction to have anyway.


  1. ‘A lot of getting comfortable with fashion is just repeatedly wearing things further out of your comfort zone until you don’t give a fuck anymore when social consequences of wearing something weird are inconsequential’ – words of total wisdom! I think this is such a good way of thinking about it. It’s easy to forget that in almost all situations it doesn’t matter than much what you’re wearing, so you may as well have fun with it!

    Love all your outfits, especially the black artsy ones, as I think that’s further from what I’d normally wear – definitely need to push out of my comfort zone!


  2. Oregan Trail was like the best game! There was a Yukon Gold Rush Version and a Amazon River version but I could never get past the tree from one on the Amazon trail – I need to look it up now!

    This is a really fantastic post. I always feel so grumpy when people start in about the “looking like flds or homeschooling” when it comes to these dress – those are such intentional looks themselves and most people aren’t going to hit it. Even with your first outfit of the tee and the skirt doesn’t look “religious sect” because the tee fits through the body and is note of a fashion tee and the skirt looks quite intentional – it makes me think more of someone who’s building their style than grew up homeschooling. (I’m not coming at you!! I’m just ranting about the people who think they’re accidentally going to look that way when in fact it’s a look that’s very currated in it’s own way.) I love that you showed how footwear makes such a difference,modern and trendy shoes really do a lot. It’s such a great trend with the prairie dresses and the Victorian influences going on in styles right now and the modern takes on twee – I personally really like the cottagecore(I think that’s what they’re calling this version of twee Noe?) and all of the romantic fabrics and silhouettes. It’s a nice change of pace from the minimalism and plainer cuts/looks that were so dominant.


    1. Thanks, Katie! Yes, that’s a great point that the full on conservative-homeschool look is also extreme enough that it’s hard to completely hit it. I think on the spectrum of things though, it can still be pretty easy to end up more towards awkward than intentional, even if it doesn’t read “religious sect”

      I’m also enjoying the current takes on romantic dresses! I feel like it’s a little easier to style in different ways than the standard twee silhouettes with the shorter skirts and fitted tops. I keep reading that puff sleeves will be sticking around for a while longer which makes me really happy, there are so many options!


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