How to Dress for Back to School

We’re all too cool for school, and yet we find ourselves going back every year anyway. Sigh. Is it really that time again?

Well, if you’re going to hit the books again, you might as well do it in style. The first day back is always a decisive moment in the school year – it’s the day you talk about that amazing trip you took and that surfer you met, but it’s also about making a brand new impression. If dressing is a form of self-expression, what you wear tells a story about who you are. If you want to revamp your closet to better scream you, there’s no time like the present.

With our buy-sell-trade motto, Crossroads is a great place to revolve your closet by trading your old duds for some clothing better suited. If you don’t know which way to go, here are a few key trends we think will help you own that first day back.

1. Muted tones. Brights are still alive and kicking, but this season they’re accompanied by their quieter friends.  We understand the bright look wasn’t for everyone (whaa? You didn’t like the green-red-blue ensemble?), but are betting the muted colors seen this fall–mustard, jade, rust, –will be much easier to digest. I like how this outfit incorporates a pair of softly colored cords as opposed to loud bright jeans; same message, different season.

2. Sleek sneakers. Do you know what one of my worst fears was when I walked in my high school graduation? Tripping in my heels. There are numerous ways to keep your feet looking polished on the first day that don’t include putting yourself at a questionable height. I like these leather sneakers,  but why not try a pair of patterned oxfords or lace slip-ons? Do your best to stay grounded.

3.Chunky sweaters.Can you tell we love them? A staple for any fall closet, a sweet chunky sweater is a great throw-on top if you miss your alarm the first day…or hell, any day. 

4. New school denim. Or old school denim, depending on how you look at it – try being just a little fashion forward with a pair of flares, wide-legs, or some high-waist jeans instead of skinnies.

5. Tote bags. I was a fan of totes instead of backpacks when I hit college – a slightly cuter, more mature way to carry your books around campus. Easy to find for cheap in any Crossroads store and easily DIY’ed to look how you want it to, they also transfer seamlessly to (a) the beach (b) picnics (c) pretty much anything.

6. Backpacks as accessories.  For those who aren’t convinved they can carry it all in a tote, backpacks have gone from being boring and drab to crazy tribal prints, denim and all-flowered-out. This fall there’s a cute backpack out there just a’calling for you…or maybe five or six.

7. Midi skirts. We’re fans. Short enough to be kept off the floor and fashion forward, these skirts aren’t just wholesome, they’re wholesome hot. Then confuse people by wearing a mini on the second day, ha!

8. Menswear. Another trend-become-staple we like, give the prep school boys a nod in your school outfit. Of course, that doesn’t mean it has to be a manly outfit…go girly then add a blazer like the outfit I made!

9. Be yourself. No matter the occasion, the one thing that never goes out of style is being comfortable in your own skin. Back to school is a time to make wardrobe changes and it’s great to challenge yourself.  Don’t feel like yourself in flares? Take chances, but don’t stray too far from who you are — there’s the weekend for that!

So what are you planning on wearing for your first day back?

Images via our Polyvore

About Sarah

I'm a recycled fashion enthusiast, as well as the official Crossroads Trading blogger. I have a penchant for cameras, pumpkin flavored-anything, midi skirts, throwback TV shows, music festivals, and beaches.


  1. I like the ideas of 1, 3, 5, 6,7 ,8 and most of all 9. I feel like without 9, being yourself, then what is the point of even attempting any of these outfits. I want to wear all of these outfits, especially the 3rd one. I am a sucker for Midi skirts because they keep me looking tall compared to full maxi skirts or super mini skirts.

    Either way, you’d get an A for style with any of these looks. LOVE THEM!

  2. wow! These are some awesome items!

  3. All summer long, I’ve been on a quest to find cute clothes at an affordable price. I’m not quite too sure what I’ll be wearing on the first day back, but I’d sure like to pair my outfit with a glittery necklace!

  4. Sneakers (esp. those brown converse) and a Chunky sweater is a back to school MUST!

  5. Catherine says:

    thanks for this post – it was really helpful.

  6. Loves the outfits~

  7. John Lenon revival.

  8. going back to school for the first time in, well, a long time…..guess I better reenlist the grand tradition of “back to school shopping” ….all great stuff up there!

  9. I specifically love outfit sets 1, 3 and 4! Colored jeans, ankle boots, chunky sweaters, nice sunnies, durable backpacks, boyfriend blazer and a WATCH are truly must-haves for school especially this Fall! This blog post is very helpful!!! I love Crossroads! Stay awesome you guys! 😀

  10. Laura Orea says:

    I l0v3 all the outfits they are sooo cute! :) The hangbacks,clothes, and jewelry are to die for. Lol good ideas of how to dress n back to school shopping

  11. so looking forward to this school year! chunky knits + menswear!

  12. So excited to go back to school! I love wearing oversized sweater. They are an essrntial for any roll out of bed a d hurry to class college students. The dress in the last outfit set is lovely. The cut, ruffles, and color are all extremely feminine and absolutely would be matched well with a blazer. Loving this post. I suggest you revisit this topic about what to wear to school when winter comes around so students can go shopping for cold weather essentials during their winter vacation.

  13. Love it!! I totally needed for me cause I really don’t know what else to wear and its already a week for me!! ha ha ha

  14. Well that cheered me up after a crappy first day back.

  15. Diggin the first and last outfits

  16. oh my gosh. this is perfect for school. thank you so much!!!

  17. this is a really helpful post. thanks! now i need to go shopping!

  18. i love the first outfit so much. it looks so comfy yet really trendy

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