Gossip Girl Fashion Style in your 20's
Inspiration,  Style

5 Upgrades for Rocking the High School Gossip Girl Fashion Style Like a Grown Up

I have to tell you guys, I’ve been brewing this Gossip Girl fashion themed blog post for a loooonnng time. It sprouted in my mind a few months ago, while I was cycling to work. Going through the otherwise very sharply dressed 9 AM corporate crowd, I spotted a simply unmissable girl!

She was donning a full-on school girl kit- and not as in the mandatory school uniform kind. But more the 2000’s Britney Spears, short pleated skirt-tight white shirt-fishnet stockings look.

Now of course, I am all for everyone wearing whatever they want to, and are comfortable with. But at the same time, I couldn’t help but wonder:

Is there a less jarring way to wear the preppy, high school look if you want to? Can I maybe upgrade this girlish aesthetic, giving it a more sophisticated air? Should I even attempt to wear the high school look well into my 20’s?

5 Upgrades for Rocking the High School Gossip Girl Fashion Style Like a Grown Up.

Well, I’ve decided it’s time to actually answer these questions!

All thanks to a bout of nostalgia that hit me about a month ago, when I started re-watching Gossip Girl. And as always, I couldn’t help but be drawn into their sartorial universe again. I mean, love it or hate it- this series was stilistically iconic for my generation! (any other GG millennial fans here, btw?)

So at that point, it all just felt like a sign! A sign I should try my hand at tackling the iconic school girl outfit, and give it an elevated valence.

Because, first of all, yes! I do think we can wear school girl inspired items even after we are past high school. I probably won’t want to wear them for much longer, but at 28, I feel like I am well equipped to take a very young look and transition it into a more mature, refined one.

And hopefully this helps some of you too! Maybe you’ve been wanting to try this look out, but it makes you nervous. Or maybe you’re literally just finishing high school, and want to seamlessly slip into the next stage of your collegiate look. This post is for you!

Curious to see my upgrades?

Not your typical plaid look

I think the first thing you picture when you hear “school girl look” is plaid. A pleated plaid mini skirt will always be symbolic for this group. But it’s also a wardrobe piece that implies a risk, if you’re trying to look polished.

Because the way I see it, once you’re out of school, plaid skirts have a way of looking very costumey. They are so iconically tied to this period in our lives, that they can take us from fashion icon to cringeworthy fashion victim in a heart beat.

Which means you need to take control, and temper them with the right add-ons (more on that in a bit though).

But my No. 1 solution?

preppy outfit for grown up women

I kept the plaid, and lost the frou-frou pleats!

This straight, buttoned-down dress that hits right above the knee is the perfect compromise between playfully preppy and seriously mature.

The hues are also a bit more muted than the typical red and black uniform combo, which helps add a graceful touch. And even though this dress is basically a full-on print, it’s still less ostentatious than a poufy, loudly coloured plaid skirt.

When in doubt, layer in black

You know how just earlier I was mentioning those add-ons that will help you wear school girl fashion items, instead of having them wear you?

Enter: the black turtleneck and opaque tights!

turtleneck layered under dress

I’m telling you: if you want to dial down any strong look, they are the way to go!

A black turtleneck is elegant and classic. It’s a timeless garment (that also happens to be very much in style right now), and a basic wardrobe must-have. Slip it under a low-cut dress to tone it down, and give it a bit of excitement with multiple layered thin necklaces.

And do I really need to go into why we love black tights? I’ll just say this: pretty much any outfit that’s more revealing than you’re comfortable with can be saved by a quality, soft pair of black tights (at least 80 denier for best coverage).

Girl boss heels for the win

You don’t hear “shoes will make or break your outfit” for nothing. Coordinating your clothes with your shoes will do wonders for enhancing your total look.

Case in point:

Gossip Girl Fashion Inspired LookThis pair of pointy, block-heeled, crocodile-texture Mary-Janes will give any outfit a very grown up and “in-control” air. They don’t whisper demurely or scream loudly for attention- they demand it with ease. They make a completely different statement than say, their round-toed, plain black or brown counterparts.

The latter would have given this school girl look a much younger appearance. Which is not wrong per se, but it doesn’t serve my current purpose of elevating the whole ensemble to a more mature level.

Now the pair I opted for creates a contrast with the otherwise girlish plaid dress. It works to take it from high school uniform to college girl chic- and even to office appropriate. And it does so without straying too far from the classic school girl look, thanks to the ankle strap.

Just think of it as plain Mary-Janes’ older, more sophisticated sister…

gossip girl outfit after school

Headband- but make it current

If you are Gossip Girl fans too, you might remember Blair’s high school obsession with headbands.

And I can’t really blame her for that! Headbands can be seriously stylish if you look at the grown up versions.

To keep the examples short and sweet:

School Girl aestheticThink wide, statement metallic headbands instead of  the thin, plastic ones you wore in middle & high school. Gold, rose gold, silver, copper are all amazing choices if you want to look sleek and chic!

Another personal favorite of mine is the heavily embellished head gear a lot of designers have favored during the SS19 Fashion Weeks. Dare to go with pearls, crystals, 3D flower appliqués- whatever floats your boat.

Or you can always go for the more recent takes on knotted fabric bands! Choose a colour that contrasts beautifully with your hair, and works great with your outfit and voilà! You have the perfect eye-catching accessory.

Because one thing’s for sure:

Head accessories are having a strong fashion moment! And I’m loving every bit of it.

Hold onto your structured bag

And last but not least- if you want to take that Gossip Girl outfit from their high school era to their rulers of Manhattan age, you need a quality structured handbag.

Want to find the perfect purse for you?

I wrote a useful guide which you can find right here. And in it I also mentioned how important it is to match your bag to the occasion you’ll be using it for. structured, elegant bag

So when I want to feel playful and carefree for example, I will go with my cutest, most saccharine purse. Or if I want to be totally unencumbered during my shopping sessions, I will rely on a crossbody, hands free satchel.

But this was not a job for either of them. No, this was the time to let my structured, elegant, plum-hued handbag shine!

Because here’s the thing:

If I chose the slouchy hobo bag, or the soft leather crossbody, or even my feminine backpack for this outfit, the overall impression would have immediately become that of a preppy 18 year-old.

Instead, I wanted it to be that of a refined woman well into her 20’s. Keeping a playful edge, of course! So I let the dress play the younger side, and made the bag do the talking for the chic counterpart. Match made in heaven, I’d say!

high school inspired outfit

Photos by Natalia Bylok

And with this, I hope that I’ve helped you feel more confident and empowered in rocking your own Gossip Girl inspired look! While this look is indeed youthful, and it is playful- it’s up to you where you strike the balance between flirty and serious!

I’m curious to hear if you’ve thought of wearing an elevated school girl inspired outfit- and if yes, have you actually done it? If not, are you more intrigued and inspired to give it a try now?

P.S.: If you haven’t yet, make sure you join The Style Club to receive your free personal style printables and get the most stylish updates directly in your Inbox!

To give you a hand at making your own GG- esque look, I’ve put together the below collection.  If you do purchase an item from it, know that you will be supporting this blog, as I will be getting a small commission- at no cost to you. So, thanks!

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