Back to School Lookbook

Back to School Lookbook (2019) - www.cozyrebekah.com 23 outfits, made from 10 simple clothing pieces that anyone could have in their wardrobe.

For some of you, school has started up already, but it’s still a couple of weeks away where I live, so I’ve decided to make a back to school lookbook. I have to admit though, as a previously homeschooled teen, I haven’t been back to school for a few years.

All of these outfits follow the dress code I had when I was in school, which was as follows:

  • No skirts, shorts, or dresses that end above your fingertips
  • No tank tops that have straps thinner than the width of 3 (or 4) of your fingers (unless a sweater or shirt is worn with it)

All of these outfits are made from 10 pieces of clothing (plus various accessories), so that the outfits are versatile no matter how small your wardrobe is!

Here are the clothing pieces that I used:

  1. Cream sweater
  2. Oversized red sweater
  3. Beige sweater dress
  4. Black blouse
  5. Beige camisole
  6. White t-shirt
  7. Dark wash skinny jeans
  8. Mom jeans
  9. Corduroy pants
  10. Black leggings

All of 23 of these outfits are organized by what I was wearing as the top, so let’s get right into it:

Cream Sweater

A cream sweater is the perfect item for a more studious look if that’s the kind of thing you’re going for.

In the first outfit, I’ve paired the sweater with some ankle boots, dark wash skinny jeans, and white browliners, for a timeless look.

In the second outfit, the sweater is tucked into a comfy pair of mom jeans, for a silhouette that emphasizes my waist line. I’ve kept the white browliners and the ankle boots.

In the third outfit, I went for a retro style, inspired by the fashion of the ‘70s. The cream sweater is now tucked into a pair of corduroy pants, and though you can’t see them in this photo, I’ve swapped the ankle boots for some white loafers. This outfit is incredibly comfortable, and cozy!

Red Oversized Sweater

An oversized sweater is such a cozy, comfortable, and warm outfit, which is perfect for any day of school.

In the first outfit, I’m wearing black leggings with the sweater, as I like the juxtaposition of the tight fabric of the leggings mixed with the oversized nature of the sweater. I’ve added some red heels to this look, since the sweater on its own is pretty casual.

In the second outfit, I’ve exchanged the leggings with some skinny jeans, for a similar but more polished look.

In the third outfit, the sweater has been tucked into a pair of mom jeans, which creates some waist emphasis. I’ve kept the heels, as I like the contrast between them and the casual look of the jeans.

Sweater Dress (+ Variations)

Sweater dresses are one of my favorites, since they’re a combination of two of my favorite types of clothing pieces (sweaters and dresses).

In the first outfit, I’ve gone with my ankle boots from before, a pair of thigh-high brown socks, and some clear glasses, to give this look a monochromatic feeling.

In the second outfit, I’ve switched out the boots and the clear frames for my white loafers and browliner, so add a pop of contrast against the shades of brown.

In the third outfit, this sweater dress has been paired with some black leggings, along with my ankle boots, for a more modest look. I’ve also gone back to the clear frames.

Lastly, I’ve added a black belt to this fourth outfit, which cinches in the waist, making a flattering and feminine silhouette.

But wait, there’s more! I have a couple of variations of the sweater dress, in which I’m wearing it as a sweater instead of a dress.

In the first variation, I’ve tucked the dress into my skinny jeans, but only at the front of waistband. Then I tied a chevron scarf as a belt around my waist, and added some pops of white with my loafers and browliners.

In the second variation, I’ve gone with mom jeans, since I can easily tuck the entire dress into them, and the waist emphasis provides a flattering silhouette.

Blouse (Buttoned)

A buttoned up blouse can help give you a formal look on the first day of school without going over the top.

In the first outfit, I’ve gone with my corduroy pants, a pair of black dress shoes, and some black frames, to add some contrast to my look.

In the second outfit, the blouse has been tucked into the mom jeans, to give off a more casual vibe.

In the third outfit, I’ve swapped the mom jeans for the skinny jeans, to create more fitted silhouette. I find that the sleek look gives off a polished vibe.

Blouse (Unbuttoned)

If a buttoned up blouse is a little too formal for your taste, you can always leave the blouse unbuttoned and wear a cute camisole underneath it.

In this first outfit, I’ve tucked the camisole into my corduroy pants, but left the blouse untucked and unbuttoned, to create a very casual silhouette.

In the second outfit, I’ve gone with the skinny jeans instead of the corduroy pants, which I find gives this whole ensemble a very sleek look.

White Tee

Next up we have a very basic piece that pretty much everyone has in their closet: a white t-shirt!

In this first outfit, my white tee is tucked into my skinny jeans, and I’m using a chevron scarf as a belt to add a pop of interest to the outfit. My white loafers and browliner ties in with the white t-shirt and the chevron scarf.

In the second outfit, I’ve gone with the mom jeans for a more ‘on trend’ look.

And lastly, in the third outfit, I’ve gone with the corduroy pants, which help tie in the shades of beige on the chevron scarf.

Layered Tee

Last, but not least, we have some layered looks, for a fun and casual vibe!

In the first outfit, I’ve tucked my camisole and t-shirt into my skinny jeans, and I’ve opted for no belt to make this ensemble as casual as possible.

In this second outfit, my camisole and t-shirt are now tucked into some mom jeans for a playful and retro look.

Lastly, for the third outfit, I’ve gone with my corduroy pants. The shades of brown add a bit of visual interest, and the white of the t-shirt, glasses, and loafers adds polish to the look.


And that’s all for this post! In case you’re here from my body types posts then you might want to know that I’m a soft classic. Some of these outfits aren’t exactly soft classic outfits though.

If you enjoyed this post, please leave a like or share it with someone else who’d enjoy it. Thanks, and I hope that I’ll be seeing you around!

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