Look Book: Back to School Outfits for Every Style

For a lot of people (myself included), classes start once again this Monday, and you don’t know how much it pains me to write that.

Seriously, though; didn’t we just get let out for the summer, like, two days ago? No? Okay then.

Anyway, with all my shock of time flying yet again aside, the start of school also means the start of the search for the perfect first day of school outfit.

My quest for said outfit has been entirely via Pinterest, as it is ever year. And also just like every year, it has been entirely to no avail. This is because, as we all already know, there are just soooo many pretty images on that darn site that after about three seconds of searching, it instantly becomes impossible to choose. So, yeah, I’m still at square one, even after about a week.

This struggle I’m having, though, has made me want to help others out in their own quests for the perfect back to school look. So what I have done is chosen some of my most favorite fashion pictures that I’ve seen on Pinterest thus far and put together some outfits inspired by them. I tried to pick one outfit for every type of style I could think of, that way more than just people who dress like me can find this useful.

Hopefully you like everything, and hopefully this helps you narrow down a look for this upcoming week, thus making your first day of school garb a little bit easier to put together than mine.

In general, though, whether you find this helpful or not, good luck to you in both your first day dressing and your actual school year, and let’s begin.

Look Book: Back to School Outfits for Every Style:

For the Simple Girl:

If you’re a person who likes to look good yet hates going all-out, then this look is for you.

Lazy summer outfit with the white crop top, light grey shorts, messy braids, and layered necklaces

^The inspiration

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^My actual look

A simple, sightly loose-fitting shirt paired with any sort of soft, comfortable, streamlined bottom will instantly make you look effortlessly put-together.

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Whether or not it makes you feel like you’re wearing pajamas, though, is a whole other story.

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A major key in making an effortless look work is not going too crazy with any colors, fits, patterns, cuts, etc. If you’re going for loose (which you should in this case), make sure none of your garments are baggy; they should be an odd mix of fitted yet also not, that way you don’t look like you’re swimming in your grandpa’s clothes.

Playing around with a neutral color palette is another great way to keep things effortlessly cool while also not getting too out of control. I chose white and black with pops of red (as you will see soon), but mixing any neutral shade together is fine (even if it’s the same one). And, yes, that does even include navy and black.

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In general, though, just have a nice balance between everything, and all will be well with your casually cute, naturally cool, and incredibly easy to wear outfit.

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See? A pop of red!

As for accessories, I opted to keep it as simple as possible, for that’s what felt most right with an outfit of this style. I only wore one necklace here, but I actually suggest choosing two or three of different lengths (but same thickness) and layering them. You can even do a mix of silver and gold; it’s just layering in general that would be killer.

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Please excuse my chipped toenail polish.

For shoes, I chose my knockoff Birks, partly because they tie the colors of my clothing together but mostly because they are just incredibly comfortable and only take about 1.5 seconds to slide on and off. I mean, we are trying to keep it simple here, after all.

You can honestly pick any shoe of your choice, though, whether it be comfortable sandals or not. Just make sure they don’t look odd, of course.

(PS – I just kicked a whole glass of water over onto my computer case, and the inside of it isn’t even wet. Now that is what I call protection!)

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As for hair and makeup, I chose to keep things just as simple as the rest of the outfit. A braided ponytail is both cute and easy to maintain, and the no makeup makeup look is perfect for letting you not have to worry about whether or not your face is melting off in front of all the strangers. Hooray for simplicity.

For the Quirky Girl:

Peter Pan collars; mixing and matching deep, colorful hues or unique and classic patterns; sweaters layered on top of patterned button-downs; a good, old, classic oxford: If those are on your list of most favorite things to wear, then you are most definitely a quirky girl, which means that this is your outfit.

Tweed Ride Hat

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Apologies for my unflattering posture.

Perfect for going between chilly classrooms and the great outdoors, layering a cape on top of a cute dress is a very unique way to go about on your first day.

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Mixing neutrals is once again part of the keys here. The trick this time around, though, is to do so with garments that are cut a little bit differently than our simply styled outfit; more out of the ordinary shapes — such as a hooded cape sweater and a collared, fit-and-flare dress — will give the quirky feel that you’re looking for.

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As you can see above, while still pretty darn cute by itself, a cape sweater isn’t necessarily the most flattering thing with me. Why? Because my top half is smaller than my bottom one, that’s why. #bigbootyproblems

If it was the other way around, however — or if I was just skinny everywhere — then the loose, flowy shape of the cape actually would work because it would serve to either mask a larger top or add oomph there where it’s small, thus, in both cases, evening me out. With a bigger lower half, though, it just takes away all concept of my body even having a shape, and so it does noting more then make me look like a walking, plaid-covered blob. How exciting.

But the good news is that said blobiness can be fixed!

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Yes, by wrapping the cape around my arms as if it is a, well, wrap, I suddenly am proportionate once again. Yay!

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^I just really liked those two shots.

Speaking of shots I like, here’s an image of my sick-looking hem:

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(I was going to make an alcohol joke there, but I don’t drink, so I couldn’t think of any. Darn.)

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These shoes were featured in my last look book, but I decided to use them again here simply because they’re super quirky and thus kind of make the outfit.

Plus I ❤ them.

Note that for extra spunk, I didn’t lace the shoes all the way up. If the shoes you plan on wearing have laces, too, feel free to copy this idea.

As for hair and makeup (which I didn’t include a picture of this time due to me looking absolutely disgusting in all of them), I kept everything the same except for adding a nude-pink lipstick.

For the Professional Girl:

There are tons of people in this world who like to dress as if they’re a CEO on their way to go slay a board meeting (myself included). So if you enjoy looking powerfully pretty, too, take a look below:

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I feel like this is an incredible outfit to use in a few weeks as a transition to fall, whether or not you end up wearing it on the first day. Just be warned, though: This much layering isn’t 90-degree-weather friendly. :/

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The key to mastering a professional look is proportion: If you have a fitted bottom, go for a looser top. Likewise, if you have a looser bottom, go for a fitted top. Just don’t be completely loose or completely tight everywhere; remember, you’re being professional, not a sketchy hooker/frumpy grandma.

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See? Proportion keeps things streamlined and thus modern and attractive.

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As for mixing patterns and colors, keep things simple. Have one bold pattern or a few fairly tame ones, but don’t go mixing every single pattern in the world together — unless you want to walk around school looking like a hot mess, of course. Likewise, with color, definitely choose a specific range to work with; whether it be navy, white, and red or shades of brown and beige, having a set palette will once again keep things streamlined yet fun rather than fun yet hideous.

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Since I’ve layered a sweater with a collared shirt, I thought it would be a nice touch to add a statement necklace to the mix. In general, statement necklaces under collars are, classically, aesthetically pleasing, so, to take your look up a notch, feel free to add one.

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While I could have easily went with strappy, neutral heels (that I don’t actually own, haha ha…) I instead opted for some more ankle boots, reason being the following photo:

They be the illest.

So, naturally, I wanted to partially emulate them.

For the Girly Girl:

I think “girly girl” is pretty self-explanatory:

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Basically, anything that embodies the 1940s and 1950s is the epitome of the modern girly girl.

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For this outfit, I chose to do the most feminine thing I know of: mixing and matching classic patterns in classic colors.

Why is this the most feminine thing I know of? I don’t know. But what I do know is that every single time I do it, I look super girly, which means that it must, then, be the most feminine way to dress. (Horrible logical fallacy, I know. Calm yourself.)

Of course, though, bows and such help, too,

To keep everything looking sleek still, despite my mixing, I made sure that none of my patterns were overwhelmingly large; while the stripes are big, they’re only at the very bottom of the skirt, and while the dots are everywhere on the shirt, they’re also fairly small. Having this type of balance is absolutely necessary, for it keeps you from looking like a walking interpretive art piece, the thing we definitely do not want.

The same thing goes for colors: Just make sure you have a good balance.

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As for getting that classic, girly, hourglass shape, tucking your shirt into a fit-and-flare skirt (or simply wearing a fit-and-flare dress) will do the trick no matter how curvy you are in real life. To add even more oomph, layer with a cardigan and tie the ends at the smallest part of your waist.

Here’s some detail shots of everything I just talked about:

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And here’s my accessories:

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I simply chose to stack a few bracelets that tied the colors of the outfit all together. I’m not really a jewelry person, though, so while this is enough for me, it may not be enough for you. Feel free to go as all-out as you want.

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Above are my shoes. I liked flats better for this because of the color-blocking I was doing, but if you want heels, then you do heels. As my homeboy Wesley would say,

as you wish

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For my hair, I simply changed the ponytail into a bun, and for my makeup, I just added some red lipstick. Simple and easy yet also cute and girly; it can’t get any better than that.

For the Trendy Girl:

Finally, I have an outfit for all those girls who like to be on top of the most fashion-forward, cutting-edge trends:

Victoria Roll Neck Sleeveless Crop Top - $8.00 | http://ninjacosmico.com/15-ways-grunge-crop-tops

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Right now, being trendy is all about the crop top, the high waist, and the flatform sandal.

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Why is this type of look so in right now? First of all, it’s incredibly flattering for the female shape, accentuating every body type in all the right places. Second of all — and what I say is most important of all — it’s incredibly simple, which means that’s it’s also incredibly easy and comfortable. Who wouldn’t go for that?

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To keep this outfit from looking too young (because a crop top and skirt can definitely run the risk of doing that), I kept to another very neutral, clean palette, opting to spice things up only with a simple, basic, modern stripe.

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^I look like I’m expecting to be slapped across the face. Not my best…

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^And this is when I realized that I left my bow in my hair from the last outfit.

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In general, just keep your proportions balanced and your color/pattern range clean, and you’ll hit the trendy nail perfectly on the head.

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For hair, I kept the same bun that I had in the previous outfit, (partially) minus the hair bow; a top-knot is just another sleek hairstyle, so it pairs well with an outfit of this sort. For my makeup, I simply switched the lipstick again, this time to a bright, matte magenta. One of my most favorite lipstick/clothing pairs is black-and-white with magenta, so I simply couldn’t resist. Feel free to add some black eyeliner to your look if you want, too. I just didn’t have the time.

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And to top it all off, I whipped out these bad boys. Any flatform sandal is going to make you look like you just stepped out of a Vogue editorial page. Or out of NYC. Or Seoul. Or anywhere else fashionable in the world. So if you’re a trendy type of gal, make sure you have flatforms.

If you don’t, though, then any type of shoe with thick, black straps is a good replacement.


Well, that’s it! Like I said at the start, I hope this helps you out with deciding how to dress this upcoming first day of school, whenever it may be for you. Thanks so much for reading, and have a great school year!

Until next time! ❤


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