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BACK TO SCHOOL- 12 Back To School Looks That Will Get You An A In Fashion

We interrupt your regular scheduling to bring you something a little different…

Every once in a while, I like to create posts that just make me smile, in the hopes that they will also make my readers smile too. We all remember the baseball caps post, right? Well, the time has come for me to have a little bit of unscheduled fun with fashion, which is why I'm really excited to talk about back to school style. While I'm far too busy with my five children to actually go back to school (although I would never rule it out – especially now that I have the back to school wardrobe down) I still wanted to have some fun with some make-believe back to school outfit scenarios. Because isn’t life more fun when you don’t take yourself too seriously?

I don't know about you, but I loved going to school. As much as I adored my summer vacations when I was a teen, I really enjoyed high school and college. From hanging out with my friends to playing all the available team sports to learning new things (yes, really – you know I'm a history nerd, but I also loved art and science too!) and naturally, experimenting with fashion, I was a fan of it all!

High School Fashion

Of course, if I was to look back on my high school and even college wardrobe, I would probably cringe at over 90% of it, because who can honestly say they would wear their high school and college outfits in the present day? Having said that, I went to school in the 90s and 00s, and many of the best trends have actually come back in full force (hello scrunchies, slip dresses, and overalls) so maybe the kids of today will actually think I was pretty fashionable. Who knows…

Back To School Fashion Trends 2021

Since all five of my kids started school at the end of August, I started thinking about what I would actually wear if I had the chance to go back and do it all again. Paired with the joy of having my whole closet back since moving into our new home in Texas after all these months of being on the road, this fantasy scenario was something I was really committed to. Please take this post with a grain of salt and indulge me as I playfully explore some back to school fashion trends – which is even more fun as the season is changing from summer to fall and I can mix and match everything in my closet. 

Think of this post as a mix between back to school fashion, some Halloween outfit inspiration (for years I always wanted to dress up like a Manchester Prep girl from Cruel Intentions, just because I loved the school uniform, so this post subconsciously has been a long time coming) and teaser to the upcoming summer to fall transition post that I am currently working on. (Spoiler alert: it's super fun, and I'm really enjoying putting these looks together!)

But for now, it's all about back to school fashion. From preppy chic to faux school uniform and even revisiting and reimagining fashion trends from my lazy college days, I think there's a little bit of everything in here. Take a look at some of my favourite back to school looks that I have playfully put together. Expect a lot of plaid, white shirts, and a few little surprises along the way.

Preppy School Girl 

Look 1

Preppy Style Aesthetic

When I think of the phrase 'back to school' from a fashion trends perspective, I always think of the Clueless movie. And to this day, I still can’t figure out why no one has invented Cher's computerized outfit selector. Can someone please make this happen? Cher Horowitz was the epitome of schoolgirl preppy chic, so I wanted to channel her by rocking some plaid (a schoolgirl essential!) but also mixing it up by adding some modern and slightly edgier twists.

I've teamed my plaid skirt, which I think is the real hero piece of the look, with a sheer pink buttondown to keep with the girly aesthetic, and then added some edge by way of a black velvet corset (maybe if they ever revamped Clueless, Cher 2.0 might adopt this style too). I finished it off with some retro tube socks and Chanel sneakers, to make the look a little sportier. You never know when you might need to play an impromptu afternoon game of softball…

Look 2

Plaid Perfection

What's the first thing that springs to mind when you think of classic schoolgirl attire? For me, it has to be plaid – especially plaid skirts or plaid dresses – so creating a back to school look with this blue plaid mini dress was an absolute no brainer! (Ps, this isn’t the first time I’ve been obsessed with plaid. Or do I mean tartan? I think I mean plaid… check out this post if you want to know the difference between plaid, tweed, and tartan, because it can get pretty confusing!) 

Women's Plaid Skirts

To make the back to school look fall-appropriate, I’ve teamed my blue plaid mini skirt with a drop sleeve cream colored cardigan, which can of course be taken off if the weather isn’t quite cold enough, and finished off with my Stuart Weitzman 5050 boots. The black over-the-knee boots might not be in everyone's schoolgirl vocabulary – even less so if the weather is still screaming summer – so accessorizing with preppy women's ballet flats, white tights and brogues, or even ankle boots for a more meet-in-the-middle approach, could also work.

Look 3

School Uniform Inspired – With A Twist

Another effortlessly smart casual look that I would totally wear to high school or college. I've been doing my research, and it turns out that berets and hats are very popular in other countries where school uniforms are essential until college. Can you imagine having to wear a school uniform until the age of 16 or sometimes even 18? I'll let you in on a little secret – while I now love the idea of a school uniform, I really loved wearing my own clothes to school, as I loved being creative and expressing myself through my outfits. Nothing new there! Believe it or not, my school once floated the idea of school uniforms and I was really against it. Luckily it didn’t happen, and I was able to freely roam the campus in my fun and creative outfits every day, which I am eternally grateful for. Quite a few of my friends weren’t too opposed to the idea though, and I can definitely see why. After all, it could avoid wardrobe mishaps and being eternally embarrassed of your old school photos based on the things you used to wear. 

I wanted to incorporate a hat in one of my back to school looks, and felt like my slouchy lieutenant cap was a fun and slightly more casual alternative to the more traditional school uniform hats. I teamed it with my flare jeans, a white buttondown and black knit tank to sharpen the look up, and my Veja sneakers to bring it back down just a touch. A true mix and matched smart casual back to school look!

Look 4

Classic vs Preppy Style

Do I look like an extra from Harry Potter or The Princess Diaries? Or with any luck, like I belong at Gossip Girl's Constance Billard School For Girls? The shape of this black velvet mini dress gave me cute schoolgirl vibes even before I started planning this article, especially when teamed with the right layers, so I knew I had to dig it out for the occasion.

Teamed with an argyle short sleeve sweater I really do think I've nailed the smart, classic yet preppy unofficial schoolgirl aesthetic here. Just to make things a little more fun and edgy, I've finished the look off with a coral shimmer blazer, which adds a touch of maturity to the look, while also complementing the colors of the argyle sweater so perfectly I can't believe they didn't come as a matching set, as well as my Chloe Franne boots, and Dior sunglasses.

Look 5

Summer Schoolgirl Casual

No, this isn’t a traditional summer schoolgirl look. But it should be!

I think some cute Bermuda shorts like my French Terry ones are perfect to wear in the height of summer in high school or college. A stuffy classroom with broken AC is definitely not the best learning environment, and I think it's perfectly acceptable – encouraged, even – to wear longer and more conservative shorts like Bermuda shorts in the height of summer. Teamed with a navy ribbed crop top, Hermès Oran denim sandals, and Chloe sunglasses, I think this is a well-rounded, casual but not too revealing summer look that would work for school and college students with ease.


Look 6

Let's Not Forget Teachers And Officeworkers

It isn’t just kids and teenagers who are going back to school. Teachers are often overlooked when it comes to back to school fashion, which is a shame as there's so much fun to be had with smart yet comfortable and fashionable looks. For teachers, and even office workers who don't have strict skirt suits and pantsuits guidelines (or even just for casual Fridays) there are so many outfit combinations to choose from – and I think choosing an elegant dress, or a matching top and skirt set with modest necklines and hemlines is one of the best routes to go down. Plus, something in a bright color or exciting print might cheer the students up a little, and might make learning just that little bit more fun.

If I was a teacher or working in a fun office, I would wear this bright floral skirt set, teamed with my Free People brami (that's half bra, half cami for anyone who doesn’t know; and I am obsessed with them! They're such handy pieces for layering, and I have no shame in admitting that I own them in at least four colors), and my YSL sneakers, just because I assume being a teacher involves a lot of running around. Much like busy mom life.


What Should I Wear To The Office?

Look 7

Smart Officewear

Despite some rules being a lot more relaxed than they once were, the COVID restrictions still haven't been lifted enough for everyone to return to the office. Most people I know are still either working from home full-time, or going into the office (with masks and only if they have a negative COVID test) every once in a while (two or three days a week, I'm told) which got me thinking about how officewear has changed over the years – and over the past 18 months in particular. I know I don't work in a conventional office and my five children are definitely not conventional co-workers, but most people I know have told me that the novelty of working in pajamas and loungewear has now worn off, and they actually like to dress up while working from home. And naturally, this got me thinking about smart/casual office outfits, and how to make them a little more exciting…

I love sharp and tailored outfits commonly associated with officewear, but I must confess that I would get very bored very quickly if I had to wear a black suit and a plain white shirt to the office every day, which is why I would like to offer a more fun approach to the traditional officewear. Because officewear is a kind of uniform, is it not? I've chosen some plaid tailored pants, which are still very smart but offer something a little bit different, and teamed them with a chic white blouse for maximum smartness, and Swedish Hasbeen clogs, which are perfect for pants of this length. Brogues and loafers would also work wonderfully with this look, but the clogs are just so super-fun and different aren’t they? Who wants to look the same as everyone else? I finished the look off with my Chanel flap bag – it's so timeless and iconic and goes with absolutely everything!

College Girl Outfits

Look 8

Casual College Vibes

This look is almost definitely how I would be attending college lectures if I was going in the present day – especially in this current weather. I don't even need to play dress-up and pretend I'm going to college to wear this look, because I've actually been wearing it right now in this confusing September weather. The calendar says that fall has begun, but the temperature here in Texas is still very summery, which is why I love the idea of wearing cool, summer pieces, in slightly more toned down and autumnal colors.

I think this look is effortlessly sophisticated yet not too formal and restrictive, which makes it perfect for a day of education. I'm still repping the schoolgirl aesthetic with the plaid mix print maxi skirt, and adding some class and sophistication with some Louis Vuitton loafers. Choosing the right shoes often dictates the style of the entire outfit, and as far as this look goes, adding some sharp loafers instead of a more casual pair of sneakers or even sandals is what makes this look school-ready in an instant. I've finished off with a ribbed crop top, Cartier sunglasses, and a Bottega Veneta Jodie bag to carry all my essentials.


How To Dress In College

Look 9

Art Major Vibes

Can’t you just imagine taking an art degree and turning up to college in a selection of fun, casual overalls every day? I clearly chose the wrong major, (I was pre-med, in case I never mentioned it before) because I could live in overalls every single day if I could! This is another effortless look that would be perfect for high school or college, and also heading to the mall, coffee shop, movies with friends straight after.

Grey French Terry overalls teamed with a crop top, Chanel sandals, and a Burberry cap is the ultimate casual, comfortable, yet still cute (if I do say so myself) look that being a young and carefree kid is all about. (Side note, remember how we thought we had problems as teenagers and now we laugh about how miniscule and insignificant they were? Oh, to be that young again…)


Look 10

Boho Chic

Boho chic was very popular when I went to college. I don't know why, but this ruched floral boho midi dress instantly transforms me back to my college days, so I just had to include it in this edit.

I probably went a little more casual in terms of accessories and footwear when I went to college, but on this occasion, I wanted to show how it can be dressed up and made classier. Teamed with Chanel slides and an attention-grabbing pink Gucci bucket bag, I think it would work really well as a smart casual office or college look, and again, think it's great for this very confusing time of year weather wise.

Look 11

Mix And Match Summer To Fall Look

As most kids go back to school in September, I know they can be faced with the dilemma of having to anticipate the weather before they leave the house. In some states, the seasons are easier to understand and dress for than others. In Texas, fall weather has yet to be seen – which is great for getting the most out of your summer wardrobe, but less so if you want to put everything away and start layering with your fall favorites. Plus, no one likes pumpkin picking in the blistering heat; am I right? Anyway, I think I've found the perfect solution to the confusing summer to fall weather – and it essentially involves wearing everything all in one go, so you have the choice to take off and put on layers as the weather dictates.

I've decided to start with a summery floral slip dress, and team it with a fall-ready oversized gray sweater vest. The reason I included this look in this post is because this vest has always given me preppy schoolgirl vibes with a splash of bohemian; does anyone else agree? I've also added a sheer purple layering top to this look, to prove it can be worn when the weather gets even colder, and added marled boot socks and Golden Goose mid star sneakers. Maybe this look isn’t for everyone, especially in this current season, but I love it!


Mom on the School Run

Look 12

Mom On The School Run

Another person sometimes overlooked when it comes to back to school are the moms and dads who are doing the school run. And this is exactly what I would wear when picking up my children at the school gates. It's effortless, it's super-flattering, and smart, and I love it!

The truth is, I took a picture of this dress when I wore it a few weeks ago, and just wanted an excuse to share it with you. Yes, it is great for the school run, and to be perfectly honest, it's so versatile and would also work for a smart casual teacher or office look too. It's perfect for this type of weather too; a 3/4 length sleeve embroidered midi dress teamed with summer sandals – that's the beginning of fall in Texas for you! I teamed my Empire waist embroidered midi dress with the Hermès Oran sandals I wear all throughout the spring/summer season (and evidently the start of fall too) and added my Gucci sunglasses.

Thank you for reading and indulging me while I bring you this unscheduled, hopefully very fun back to school fashion post. Would you wear any of these preppy schoolgirl looks in your day to day lives? Perhaps I’ve given you some inspiration for Halloween? I’d love to know your thoughts over on Instagram at @Lily_Tracy.  

‘Til next time! 

Love, Lily x x