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What Do I Wear There? Back-to-School Milestones


When I started writing for CF one year ago (can’t believe it’s been that long!), my very first post was about what to wear to your first day of classes. While that is definitely an important day, I realized there are many other days in that first week that’ll have you tearing apart your freshly-full closet!

Therefore, I wanted to cover three of those days for this article–move-in day, the first day of classes, and your first night out. This way, you can breeze stylishly through your first week at school and reserve your worrying for the important things (like decorating your new room)!

Move-In Day

What to wear on moving day in college

Product Information: Top:, Shorts:, Sandals:, Bracelet:, Messenger Bag:

Deciding what to wear when you move back in to school can be tough–it’s your chance to make a first impression for the school year, so you want to look great, but you also need to be comfortable enough to lug heavy suitcases. All that lifting may also make you sweaty and disheveled, factors to consider when doing your hair and makeup.

I recently saw a friend wearing this army-style, slightly cropped shirt and thought it was such a fun piece for a casual day. Paired with dark denim shorts, it’s a great twist on the trendy military style that will also be ultra comfortable and airy. I love these sandals as well; besides looking great, they will stay on securely even if you are running up and down stairs.

This chain-link bracelet is the perfect accessory, as the detailing continues the look’s tough girl vibe, while the pearls add a feminine touch. For hair, I similarly went for a style that will add some girlish glamour, choosing a sweet, simple pulled-back hairstyle that will look even better as it gets slightly mussed from unpacking.

Finally, be sure to carry a sturdy purse for move-in day and keep it on you at all times; this will ensure you keep your new keys, ID, documents, and other dorm essentials safe!

First Day of Classes

What to wear on the first day of class

Product Information: Dress:, Blazer:, Necklace:, Wedges:, Socks:, Eye Refresher:

For the first day of classes, go for a look that shows you are focused but also fashionable! First, since purple is one of the hottest colors for fall, go for a vibrant dress in a purplish/indigo hue. Top that off with a smart boyfriend blazer for a classic look, and then toss on a mixed chain necklace for an updated twist on a classic.

One of the fall fashion statements I’m most excited about is over-the-knee socks worn with dresses, so I figured since the first day of school signifies the start of fall, it was an ideal time to try it! I went for ribbed gray socks, paired with nude wedges, as the gray-ish, floral-adorned bow on the shoes ties in perfectly with the socks. This look is a great way to bring summer favorites (like a tank dress and open-toe wedges) into the fall!

For beauty, go with whatever hair and makeup you are most comfortable in so you can feel completely confident and unconcerned during class. I do suggest using an eye-brightener before your makeup, though, since waking up early for the first day of classes may leave you with puffy, tired eyes!

First Night Out

Fashion for your first night out in college

Product Information: Top:, Jeans:, Curling Iron:, Ring:, Eyeshadows:, Heels:, Self-Tanner:

There’s nothing as exciting as your first night out with your new roomies and all of the college friends you haven’t seen in months! So I wanted to create a look that would be effortlessly cool and allow you to fit in anywhere from a frat party to a bar (if you’re legal!), to your much-missed late night pizza place.

I love how fun this bright top is–it will definitely make you the center of attention wherever you go. I paired it with dark, skinny jeans (to balance out the loose top) and some killer wooden heels. The contrast of orange and turquoise is amazing and unexpected, so go for a large cocktail ring adorned with turquoise stones.

If you spent your summer locked up in an internship rather than lying on the beach (as many of us college students unfortunately did), fake your tan with a sunless glow–start doing this before you even go back to school to develop a gradual, natural color. Highlight your faux-glow with a shimmery, nude smokey eye in bronze tones.

Retro-inspired hair is huge for fall, so ditch your beachy waves for more tailored curls. I’m currently lusting after the Conair Infiniti curling iron, as its clampless design makes creating perfect curls seem so much easier!

What do you think?

First things first–are you excited to head back to school? Nervous? Which of these looks is your favorite? What styles are you excited to try for the fall? Are there any other back-to-school events you’d like “What Do I Wear There?” advice on? Let us know in the comments!

Posted on on August 19, 2010 / Filed Under: Fashion Tips / Tags: , , , , , , , , ,

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42 Responses to “What Do I Wear There? Back-to-School Milestones”

  1. 1
    August 19th, 2010 at 6:13 pm

    The third look is definitely my favorite! I love the orange :)

  2. 2
    August 19th, 2010 at 6:13 pm

    This article gave me some good ideas for move-in day and first night out. I like the idea of a casual/unusual top for moving in since it can easily show your style without making you look like you tried to hard. And I really like the bright top with dark pants for going out your first night – i LOVE bright colors!
    the only issue I had with the article was the first day of classes outfit. My first day of classes will definitely call for something cute, chic, casual, and COOL as in the temperature. It’s going to be hot for the first couple weeks for most colleges so I think the over-the-knee socks seem unrealistic. And with all the walking around campus and trying to find classes I think the Wedges, though adorable, would hinder you from gliding across campus.
    Otherwise great post!

  3. 3
    August 19th, 2010 at 6:27 pm


    -Baby Showers
    -Wedding / Bridal Showers

    I have a baby shower coming up. I want to be super comfortable for all the sitting around “Ooohing” and “Awwing” that will be going on. But I also want to look cute, so I wont feel shy, but instead feel confident, meeting all my friend’s girlfriends. So would you please help me put an outfit together. It would be much appreciated.


    P.S. Some shoes that are easy to slip on and off at the door, would be super helpful. :)

  4. 4
    August 19th, 2010 at 6:32 pm

    I love this! It makes me even more excited for school to start! Only a week until I begin my sophomore year. Yay! :)

  5. 5
    August 19th, 2010 at 6:33 pm

    The shoes for the first day of class might not be the world’s most practical..

  6. 6
    August 19th, 2010 at 7:00 pm

    loved the move in and first night outfits…
    i would love to see a more practical first day outfit. maybe something with jeans or a more casual dress…

    but keep the fall outfits coming! i leave soon && need more inspiration!

  7. 7
    August 19th, 2010 at 7:10 pm

    I love the move-in and first night outfits! But as other posters have said heels and high socks aren’t exactly ‘first day’ material. I would love to see some outfits for classes during the couple of ‘hot’ days in the beginning of the year. Though the purple dress is simply stunning :)

  8. 8
    August 19th, 2010 at 7:27 pm

    While I appreciate the topic & the effort & usually really like your suggestions, I have a few problems with the first two outfits. In no particular order:

    1) The shoes for both are way off. Those sandals are way impractical for hauling stuff for move-in day. Stubbed toes are imminent… and the other shoes are way too high for a first day of class, for shlepping stuff around & possibly getting lost & walking who-knows-how-far between classes.

    2) Though the start of school signifies the start of fall mentally, it’s usually still August, which means it’s a billion degrees. Sweaty socks stuffed into too-high shoes? Not a great first impression.

    3) This sounds mean, I guess, but I basically always mentally make fun of people who get that dressed up for class, first day or not. I don’t think that outfit says much about smarts; it mostly says “I aspire to get out of class & go get drunk.”

    I like the third outfit a lot, if that counts for anything?

  9. 9
    August 19th, 2010 at 7:28 pm

    The outfit could use a little of Cleobella’s Gypsy Jewels…

  10. 10
    August 19th, 2010 at 7:40 pm

    First Day of School Outfit- That just way too dressed up for the first day of school. really though? A blazer? That last outfit should be for a first day of school outfit.

  11. 11
    August 19th, 2010 at 8:44 pm

    This was a really good idea. I think #1 is spot on (though I wouldn’t wear a crop top, it gave me ideas for what to wear now – though, a little more cas than yours). #2 is interesting, but I dont think I’ve EVER seen ANYONE wear ANYTHING like that to classes (even first day) before. I want to look good for the first day, but not over the top – then you get labeled as the stuck up girl who thinks she’s the shiz. #3 is perfect – love it!

  12. 12
    August 19th, 2010 at 8:48 pm

    Just for ideas for next time…. (sorry for filling up the posts).

    First Day of Classes:

    – Purple Dress shown
    – Silver gladiator(ish – if no likey gladiator) sandals
    – Black tote bag (one of the really cool, nice ones you find)
    – Mutli necklace that isnt so fancy
    – small dangly earings
    -matching, kitchy(ish) bracelet

  13. 13
    August 19th, 2010 at 9:15 pm

    Yay! This made me so happy! I’m still a high school student and therefore don’t have a new, exciting college experience in the immediate future but, this excited me nonetheless.
    The first outfit is sartorial perfection. I seriously keep scrolling up to look at that military inspired shirt while I type this ;) I’ve fallen completely in love. The whole outfit gives me one of those warm belly feelings you get when you see (or buy, or drool over) really good fashion.
    Oh, and for the record I totally adore the “First Day of Class” outfit. Sure, it may be a little too hot for some climates but, in my opinion, the point of this post is to draw inspiration, not wear exactly what she tells you to. And while we’re on the subject I think there’s nothing wrong with dressing up/ making an effort for the first day of class or class in general. Since when is it wrong to look like you care about fashion and actually made a slight effort with your appearance? I think dumbing down (if you will) your style for class is just plain silly! Just be who you want to be, sartorially or not. But, I disgress…
    Anyway, Colleen, I absolutely love this post! Anything that makes me get the aforementioned warm-belly, good- fashion feeling is such a pleasure to look at :)


  14. 14
    August 19th, 2010 at 9:37 pm

    Great ideas, although I found the second look to be a bit pretentious. I’m a student at SCAD and even us Fashion Majors would think that’s too dressy. When I go back to school the weather will still be hot and humid so a blazer would be a bit iffy. I think the dress would be perfect paired with a vest, some flats, and a cute bag.

  15. 15
    August 19th, 2010 at 10:08 pm

    To Mika: Since you’re still in high school (and yes College is a BIT different) you might not totally understand yet – in high school (or at least mine) the goal WAS to look super fashionable and something like that would make heads turn and other girls covet your outfit while secretly hating you for being so cool (though, that’s mine.)
    And yes, nothing wrong with dressing up/making an effort for class – we’re just stating thats a little MUCH for college classes (especially if the fashion student is saying they’d think it’d be a bit pretentious!). And I hope you aren’t stating that the rest of us don’t care about fashion or don’t make an effort for our classes … I for one know I don’t “dumb down” my apperance in college….
    So even though we were just letting the writer know our feelings – we didn’t attack her or anyone else commenting here like you possibly did (though I’m sure that wasn’t your intention).

  16. 16
    August 19th, 2010 at 10:27 pm

    Great! I would totally wear the third outfit. I don’t see anything wrong with the second one, either; personally, I’d rather be fashionably overdressed than wear something less original that doesn’t fit my personality just to not stand out. I am all for dresses and towering shoes at school, as well as blazers in August. Good job on all three looks. :)

    I’m excited to see your note on retro-inspired hair too- I wear pincurls all the time and I can’t wait for that sort of thing to be more popular!

  17. 17
    August 19th, 2010 at 11:20 pm

    Hm… The second outfit isn’t my favorite. For one, it won’t be cool enough where I go to school to wear an outfit like that until well into November. But I think the footwear is more of a problem. I love the socks. I love the shoes. I’m just not sure that those socks go with those shoes… I don’t know what it is, but some little voice in the back of my mind just screams at the thought of wearing socks with wedges.

    Otherwise, I absolutely adore the second outfit. And retro-inspired hair is the best. On curling irons, though, I’ve found that just ignoring the clamp on a regular curling iron works just as well as buying a second, shmancy clampless one.

  18. 18
    August 19th, 2010 at 11:39 pm

    Lizzy: Oh my gosh I didn’t mean to hurt your feelings or personally attack you or anything! I’m so sorry if you took my comment that way. I was just expressing my personal philosophy on fashion and personal style and it’s completely understandable that it doesn’t coincide with your beliefs.
    My moral was basically: dress how you want to dress! And, in my opinion, there’s not much more to it than that.

  19. 19
    August 19th, 2010 at 11:40 pm

    On move in day my freshman year I wanted to look nice and make a good first impression… I didn’t wear anything super nice but I still wore a real shirt instead of a t shirt and everything. By the end of the day I was so sweaty and gross. This year I just stuck to athletic clothes and tennis shoes and didn’t care how I looked and I felt much better.

  20. 20
    August 19th, 2010 at 11:55 pm

    I love the first outfit but those shoes wouldn’t be too great for lugging around heavy stuff for half the day.
    I can definitely see what other posters are saying about the second outfit. Other than it not fitting too well for most climates in the U.S. in August (and nobody wants to be remembered as that really sweaty girl), it looks like its sorta trying too hard to me. While I may spend hours mulling over my first day of classes outfit, I’d like it to appear effortless and chic.
    I guess I picture more of that (and I apologize for this terribly overused term) “model off duty” look.

  21. 21
    August 19th, 2010 at 11:59 pm

    the second outfit seems a bit too ‘night time’ to me.

  22. 22
    August 20th, 2010 at 12:03 am

    I am dying to go back to school. I feel like I have been living in my work uniform and I can’t wait to dress up and wear normal clothes again. I love the idea of the second outfit- yes the blazer and knee socks may be a bit warm for early September, but is definitely looking ahead to fall’s cooler days. But, I don’t think I would pair the socks (a look I am definitely going to try this fall) with the wedges- a bit over the top for my style, but one would definitely turn heads with that look! I would try out that trend with the dress, but boots instead. Great inspiration! These outfits really got me thinking about what to wear my first week back :]

  23. 23
    August 20th, 2010 at 12:55 am

    I love #1 and espeically #3! The orange top is so cute! :)

  24. 24
    August 20th, 2010 at 2:07 am

    Hey guys,

    I appreciate all the feedback, and it’s good to hear that I have helped inspire some of your back-to-school picks.

    I just wanted to address the class outfit since it seems to have stirred up some comments. What to wear to class has definitely always had a lot of debate on CF (luckily, we all seem to agree on the “golden rule”–no pajamas!).

    When I create outfits for CF, I want to bring in different styles that college students may not think are attainable for their daily lives (such as wearing high socks to class) due to their lifestyles or budgets. Therefore, I want it to be something more inspiring that you can use to help you with your daily look–something that you can see and then think of what you like and dislike to help you find a new look!

    I was so excited to hear how some of would change the look, as that is exactly what I hope to inspire you to do! This is a look that would fit into my particular lifestyle as a student and fashion intern in New York (who also happens to love heeled/platform shoes for any and all occasion ;] ), but obviously everyone at CF has different daily lives that they need to dress for.

    I just wanted to address this since it seemed to be getting a lot of comments, and I was sort of unhappy to see how some of you were responding to each other’s comments in a derogatory way. Some people prefer more buttoned up blazers and heels for class; others prefer loose knits and boyfriend jeans, that does not mean anyone is wrong! I love so called “messy” style one day and “pretentious” the next–fashion to me is all about expression, so let’s keep this a forum in which we can all feel free to express ourselves =]

    xo Colleen

  25. 25
    August 20th, 2010 at 2:40 am

    Very classy colleen! I love how cf always incourages positivity :) since unfortunately its going to be at least 90 degrees in the first month of school for me I will not be tryong out knee socks or wearing blazers for a few more months. I will definitely be storing that outfit in my mental catalogue for later though :)

  26. 26
    August 20th, 2010 at 9:14 am

    for move in day, thats kind of too unrealistic. its gonna be hard lugging boxes, refridgerators, and microwaves in and out the buliding. there will be long lines to get to the elevators and some schools dont even have ac, like mine didnt. as for first day of classes, that is a pretty outfit, but most students legit live in their sweatpants, hoodies, and uggs. by mid first semester, you just dont give a .. but nice clothing though?

    can you guys do an article for curvy girls..i dont mean kim kardashian cause no one looks like that, but i mean REAL sized 8-16 girls..theres really not a lot of options for us. thanks

  27. 27
    August 20th, 2010 at 12:36 pm

    i have seen your blog, its really good, i am also working on fashion. keep updates

  28. 28
    August 20th, 2010 at 8:47 pm

    I agree with Shanee 100% I would love to see a plus size 8-16+ fashion for college girls + I’m not ‘model thin’ myself (a proud size 12-14) and i would like to see a blog that give inspiration to that-just a thought :)

  29. 29
    August 21st, 2010 at 6:47 pm

    Move in day outfit is definitely a cute, relaxed and chic look…something I would wear on any day of the week!

  30. 30
    August 21st, 2010 at 8:37 pm

    You would be the laughed out of class in the first day outfit! Wear the moving day outfit for the first day, but no more dressed up than that unless you have a job interview or internship interview. Seriously, it reeks of desperation. I am not saying you should wear pjs or Uggs, but please.

  31. 31
    August 21st, 2010 at 11:38 pm

    Honestly I don’t see why people seem to think the first outfit is impractical. You’re right, it probably will be hot lugging around suitcases and boxes. But what better way to keep cool than shorts and a cropped shirt? As for the shoes, I personally think they are a good idea. Obviously with all of that carrying and walking around (most likely going up and down stairs), you are going to want flat sandals for comfort and too keep your feet cool, and you because of the straps and buckles you wont have to worry about them coming off. I definitely give the first outfit an A+, it gave me a few ideas on what I will be wearing for move-in day as well :)

  32. 32
    August 22nd, 2010 at 4:17 pm

    I love the looks, but I personally have been completely unable to find a pair of wedges I could comfortably walk in for long periods of time. I just think flats would make the look easier for readers to replicate.

  33. 33
    August 24th, 2010 at 3:55 pm

    I 2nd Faith’s idea of a WHAT DO I WEAR THERE? SHOWERS post.
    Bridal/baby showers are one of these occasions which i try to avoid because I never know what to wear =S I’m always either overdressed or underdressed! Could you please help me with some outfit ideas?!

  34. 34
    August 24th, 2010 at 11:29 pm

    I really liked the Moving In Day outfit but the First Day of Classes look was my favorite out of all three.

  35. 35
    September 3rd, 2010 at 11:11 pm

    The outfits are not that creative and don’t really show any sort of individuality. For my first impression, I’d want something that represents me, not a mimic army top. Sure they’re cute, but why all the hype??

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