Style Notes: How I choose hairstyles for different outfits

totally no editing here

Some good old fashioned style notes! Talking about hair today. While the example pics are mostly just gonna be my own outfits, the general concepts and approach I use works for any type of hair. So even if you don’t have the same cut or texture as me, hopefully you can get an idea of how you can think about incorporating hairstyling into your looks by considering how it affects your overall silhouette, and the placement of visual interest within your outfit.

The TLDR: if I’m considering whether to take the extra step to do something with my hair, I ask myself whether the outfit could use

  • Negative space around face/neck – Is the outfit getting on the busy or bulky side for my preference on the top half? Would reducing the silhouette of my head help the outfit breathe? Is there already a lot of very dark color around my face? If my hair is loose will it feel like my face is being overwhelmed with overgrown bangs as well?
  • Extra volume on top – Does the hair seem a bit flat compared to a more maximalist look?
  • More styling – Is there so much styling (either in the garments themselves or through accessorizing and layering) in the outfit that my head feels left out? When hair is left out of more intensely themed looks it can often feel more costume-y if your head styling is notable mismatched. Or if I’m looking at the small/medium/large shapes mix to balance the visual interest, would it make sense to add a hair accessory for small shapes, or is there a lot going on already and would having my hair just do its thing and take up a larger area create a better visual rhythm?

On the opposite side, I can ask whether the outfit would benefit from the visual weight being lower around my head, or an undone look better suits a style because doing something would feel too polished or just stuffy.

But I can’t do my hair

“I don’t know how to use heat styling! I can’t even part my hair evenly in half let alone braid it! Which way of the bobby pin goes up?”

Assuming that the reason is more skill related and not that you have a buzz cut: can you put your hair into a ponytail with a hair elastic? You can now do (some of these assuming a certain hair length…)

  • hair down
  • low center back ponytail
  • loose side ponytail
  • high ponytail
  • neat half-up ponytail
  • loose half-up ponytail (i.e. not pulled all the way tight, maybe leaving some of the hair draped over the tops of your ears for a softer look)

That’s already six options! And you can add another five for every different scrunchie or fancy elastic that you have.

On Accessorizing

If you’ve got the length for it, I think having a go-to accessory for days when you just want to throw something on to look more done but don’t have time to put in 36 bobby pins is really helpful. You don’t need to have a whole zoo of accessory types, but I’m always still amazed at how much a medium sized barrette or a headband can make a look feel just as styled as an updo or braids, but with like 1/10th the effort.

You might have to experiment with a couple of options to see what works for you, since not all hair accessories are equally effortless on all hair types. For example I usually need to supplement barrettes with bobby pins so those are not the laziest accessory for me as my hair is very slippery. But I can throw on a headband or a bow paired with an elastic and minimal fussing. Once you find something that works, you can even call it part of your signature style



What even is “chic”? “Cute”? “Cool”??? I find more subjective adjectives harder to optimize for, so when evaluating a look, some variables I consider are:

  • done vs relaxed
  • edgy vs soft/sweet
  • sleek vs textured

And of course these are all spectrums, it’s not all one or the other. Just like you’re not stuck having to pick between full on Blogger Hair or zero styling. And it’s relative. “Textured” for me at most means a french braid. I don’t know how to heat style my hair and I don’t want to get a digital perm. Maybe you’re going for relatively sleek for you and have curly hair, so you put it into a ponytail or bun. But if your words are ‘sleek’ and ‘edgy’ you can also consider bringing in an accessory that works with that like a metallic ponytail cuff. Much more sleek and edgy than just a plain elastic or a floral scarf scrunchie. The adjectives/labels are tools to help you figure out what elements you can bring in, not exclude you from any one aesthetic.

For example, if I want an outfit to feel more romantic, I could describe a romantic hairstyle as “done, soft, textured.” So some styles that fit that are a fancy rapunzel braid or a crown braid.


Again, this is basically just translating a vague adjective into something more concrete. You might be feeling romantic in the sense of frolicking in a field of wildflowers, in which case you might want to go for “relaxed, soft, textured” instead with more naturalistic loose waves (think from wet hair that dried into braids or buns), or maybe just loose but with a floral printed hair scarf to add in the ‘texture’ without having to wield any heat tools if your hair doesn’t style easily.


Another one: Modern –> Done, edgy, sleek –> e.g. one-length bob (this is “done” because it requires regular maintenance to look that sharp). There can be lots of ways to interpret even the more specific description but the idea is just that I find it easier to picture potential styles when there are more contraints.


Instagram cool girl: Relaxed, edgy, {natural hair texture} –> e.g. unnatural hair color but otherwise unstyled

Besides for everyday styling decisions, I think this section is also useful if you’re considering changing up your cut, as some cuts will just be much easier to style to different aesthetics. For example, one reason I have bangs is that it looks fuller and adds some texture and shape and general styled feeling to my head area without me having to faff around with volumizing and setting products.

Now that we’ve gone through that laundry list, I do want to note that I don’t like, sit there and go through a checklist and journal a paragraph on what I want my hair to look like every day. Those are just the sorts of things I’ll think about if I’m troubleshooting an outfit and am trying to understand what it is that I really want out of the hair.


A bit of train-of-thought on why I went with these hairstyles on these days. And remember, it’s not like these are the correct hair for these outfits and everything else is incorrect. Part of it is certainly that I go for a certain amount of balance in every look, but a lot of it is just how I was feeling that morning.

(The level of detail really devolved as I went through all the pics, but hopefully there’s still some inspo in here)

1 – Just for reference, one where my hair is down. This outfit was super fun, but it’s also getting a bit into precious/twee territory with the floral print and layered babydoll dress and white shoes. So I just left my hair loose to keep a more relaxed vibe.

2 – I wanted to emphasize the cool shape of the cape jacket, so I put my hair up. The aesthetic here is more like vintage a la Audrey Hepburn, so I went with a bun rather than a ponytail, as I associate ponytails with later decades unless it’s like, a ponytail tied with a bow. I also liked that it added extra volume so my head didn’t feel tiny next to the jacket and baggy jeans.

3 – This outfit is basically just a single color+fabric dress and shoes. But each of those items is on the dressy side, so I thought it would suit it if I did a more styled look. The whole thing was making me nostalgic for early some 2010s styles, so I did a poofy high bun. Babydoll dresses can also lean very youthful depending on the styling, so I also liked that this style felt more mature than say, a braid.

4 – A summer playsuit look with matching separates! I wanted my hair up cause it was hot, but also felt that a bun by itself without careful ‘just so’ disheveling felt stuffy up for this. I added a playful element with the satin scarf style headband.

5 – This look I think would be really cool with my hair down. It’s about waist length now, so I think the contrast would be striking and also play into the 70s hippie vibes. But I’ve also been watching a lot of style videos from youtubers who do the ~effortlessly chic~ minimal aesthetic, so I wanted to play at that with a low bun. Of course that’s hard to photograph in mirror pics so you can’t quite see the whole effect here, but I did like the contrast with the loose/loose look. There’s a lot of ease in these pieces, so there’s still enough of a balance of polished and chill for my style compared to if I was say, wearing fitted jeans. It was also nice to show the full neckline of the blouse, since it creates a cleaner negative space shape to contrast with the relaxed fits.

Another reason I don’t often do low buns is that it just feels too plain and minimal. I generally like volume. But I thought it was nice here to show off the blush and cute star puff earrings.

6 – Embracing the science camp vibes, I just went with a basic ponytail. It felt kind of plain compared to the outfit though so I threw a colorful hat on since I was going outside, otherwise I think a scrunchie would have worked.

7 – Knit separates, so pretty chill, but the skirt is definitely A Look. With the dressier shoes, I felt that to keep the top half of the outfit from feeling too relatively blah, I should style my hair. I just did a half up so nothing too done since I still wanted a kind of casual summer weekend look rather than a Going Out look.

8 – This cardigan is pretty ‘designed’ (intricate cabling, sleeve structure) and the derby flats are slightly dressy, so again I felt that doing a little something for head styling would keep the look cohesive. I didn’t want to get into old fashioned librarian territory or too school girl though, so I went with half-up instead of a bun or braid. I ended up going with the outfit on the left, which just used one large clip to secure the ponytail in the back. The right side outfit has two small clips just behind the ears but without extra pins, so it’s a looser look (that would require restyling or just get wilder throughout the day) that didn’t feel neat enough.

9 – Hat and ringer tee is a lot around the face, so I didn’t want to add loose hair to that. I thought side braids would suit the countryside + childhood nostalgia vibe.

10 – Was feeling fancy so I did a bubble ‘braid’ for a rapunzel look.

Mostly just throwing this one in to show the hair idea. To do this you just need to do a half ponytail about 1/3 up your head, a second half pony with a portion of the remaining hair 2/3 down your head, and then as many more sections as you need to get to the end of your hair. No braiding required!

11 – This outfit is quite heavy on the bottom with the giant flounce and the chunky boots so I added a headband for a bit of extra volume and detail at the top. I still wanted to keep the hair down for an overall soft look.

12 – This skirt is a bit extra (vs say a plain denim mini) so I accessorized so that the top half of the outfit wouldn’t feel like it was pulled from another outfit that was way more casual.

13 – Again, wanted to add a more ‘finished’ feeling since the core items are basically pajamas. I did clips for a bit of sparkle but still keep things relaxed.

14 – My new favorite hairstyle, space buns! I love these because (1) they’re great for getting greasy hair out of the way and (2) they take any super casual outfit from blah to A Look. For example, this goes from normcore to like, well, still normcore, but The Cool Babysitter normcore. So I tell myself.

15 – Likewise, this is a pretty basic crunchy look with the Tevas and grocery tote. Nothing wrong with it with just a ponytail or hair down, but the more youthful hairstyle with the crop top adds a little sass.

16 – Truly, even the most IDGAF today outfits can be quirkified with even messy double buns.

17 – Or on the other hand a more esoteric outfit can feel cohesively esoteric with the quirkier hairstyle.

18 – I didn’t really get into braiding my hair for practical purposes until last year but I’ve found french braids more practical for workouts than ponytails! They get slightly disheveled over time, but I don’t have to keep pulling the elastic up, and it doesn’t pull on my head as much. Since it’s also a more styled look than a ponytail (at least to me, since I didn’t grow up with braids being a practical look. My mom has a totally different hair type than me so we never did much to my hair.) it also always makes me feel fancier in activewear looks.

19 – I wanted to show off the fun ruffles here, so I wanted hair pulled back. I didn’t want to do anything too polished as the woven blouse + denim was already a lot for me but I also didn’t want my head to feel left out, so I did a loose braid (basically my default when I want my hair kind of done but not done done).

What are the most common ways you style your hair for outfits? What criteria do you use to decide which style to go with?

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