Help needed for outfits for class reunion: Casual Friday night ( picture heavy)

I will soon be attending a highschool class reunion and want to look my best without looking overdressed or like I'm trying too hard. This is billed as casual and is in a very small city on the wind-swept plains. The weather is supposed to be dry with highs in the 80's, lows in the 60's.
Below are some outfits I'm for the first evening of an informal dinner, visiting and possible float building. The first are inspired by gorgeous Karen's summer sweatshirt look. Each include a pair of Aeropostale faded jeans worn rolled as probably my most flattering jeans and DV black ankle strap flats that are very comfy.
1/2: closest to Karen's outfit. Top is a Talbots oversized striped top.
3/4: Target plaid sweatshirt. I usually layer a shirt under this sweatshirt.
5/6: another Target mixed media sweatshirt. I could layer a button down under this one too.
7-10: dark red H&M jeans with possible toppers if it is colder than expected.
11-14 various white out possibilities with BR ivory skinny jeans sized up
Do any of these look especially good?
Someone suggested that I wear school colors. Maroon ( burgundy ) is scarce in my closet. If the weather is cooler Friday night or Saturday morning, I could wear burgundy H&M sized up skinny jeans. Do any of these toppers work? I have on a BR chambray button-down and Me Too Adam Tucker loafers but would probably wear short black or brown boots not yet brought out for the season as it's still too hot. Do any of the outfits with the dark red jeans look good to you?
I would really appreciate your input and your eye. Please give me your honest opinions. Tell me if you think I should go back to square one if none of these look right. I have plenty of other options and can shop tomorrow if needed.
I will post more possible outfits for other events in there own theads.

This post is also published in the youlookfab forum. You can read and reply to it in either place. All replies will appear in both places.


  • Sal replied 4 years ago

    Have fun at the reunion.

    I like 5 and 6 the best. While I also like 1-4 I think they read more casual, and maybe some people won't realise that they are fashion forward. I don't know if that makes sense! I think 5 is very smart casual and comfortable too.

    I do like the burgundy jeans too, in preference with the lighter top.

  • Suz replied 4 years ago

    I am with Kiwigirl here. I really like 5/6. The top reads as just a touch more polished while still being casual, and like Karen's outfit, it is cohesive with your personal colouring while also bookending the shoes. The first two tops read as much more casual to me. I think your style, like mine, veers to polished rather than super-casual, and just speaking for myself, I'd feel a bit TOO casual and maybe even "trying too hard" (as in trying to be youthful) in the first two outfits. Not at home -- for at home, they would be FAB! (And you look fantastic, let me hasten to add. This is not about how great you look!) But for an outing, 5/6 has that special bit of polish that feels better. 

    I like the burgundy jeans on you, too, but feel the outfits are somehow less current. 

  • jackiec replied 4 years ago

    I was going to say 3/4, but after reading Suz' response I agree with her. :)

  • Nebraskim replied 4 years ago

    I have it in my head you're from Nebraska, like me. I totally vote 5/6. You will shine.

  • Firecracker replied 4 years ago

    Of the outfits with your faded jeans, I'd go with 5/6. I agree with Suz that this outfit looks a little more polished and typical of you. I do really like the plaid top in 3/4 and the stripes in 1/2. To me, those outfits could work better for this occasion if paired with a darker wash jean or with a white jean. Maybe white wouldn't be ideal for float-building, though.
    The burgundy jeans are great on you, too, Joy. My favorite topper is the plaid jacket. Maybe a short-sleeved top underneath would work better than the long-sleeved shirt, if it's going to be warm. And perhaps stick with the loafers? Showing skin at the anke or foot will help keep the look--and the feel--good for the warm weather. The other looks with the burgundy jeans look a little more geared toward cooler--true fall--weather.

  • Joy replied 4 years ago

    Kiwigal, that makes lots of sense. It is about looking good rather than fashion forward.
    Suz, you are right. I do want to look polished and have trouble putting a really casual outfit together. Thank you for your help. Jackie too.
    Kim, you are right. This reunion is in western Nebraska. :)

  • Joy replied 4 years ago

    Sharan, we must have cross posted. I could wear darker jeans. You post also reminded me that I left out a whole set of photos with ivory BR skinny jeans. I will add them. I was trying to create a white-out look but will probably avoid getting into the float building if I wear white :)

  • Zibbets replied 4 years ago

    What Firecracker said!

    YLF in all of these. I would like a darker or white jean w/ the first few, #5/6 are my favorites the way you have styled them. Ten is my favorite with the burgundy jeans, but I think I would try a lighter color for the shirt. I agree that the loafers are nice for warmer weather.

    Have a wonderful time and please let us know what you wore!

    ETA: I LOVED the plaid shirt/white jean combo you had on the other day, an Angie ensemble, I think. That was ka-POW gorgeous. I hope I commented on it then!

  • columbine replied 4 years ago

    I prefer the burgundy skinnies for this occasion. School colors and super flattering. What about the sweatshirt from 6 and the burgundy skinnies together ?

  • Joy replied 4 years ago

    Thank you, Zibbets and Columbine, for your comments and ideas. I will try dark and white jeans as you recommend. I also added some white jean idea photos that I forgot.

  • MsMaven replied 4 years ago

    I hate that I accidentally clicked away and my post was lost. Just a brilliant analysis gone.

    Okay, I like all the outfits--but the burgundy ones I like the least. I like the striped top, but it does come across as a bit casual. You look drop-dead gorgeous in the cream outfits, especially #14, but they may be a bit dressy and TTH for the casual occasion.

    Speaking from my own experience attending a casual picnic the evening before the more formal (and more expensive) official 50th reunion dinner, I'd say go with 5 & 6. Comes across more sophisticated than the stripes or plaid. 

    Joy, my dear, no matter which one you wear, you are going to knock 'em dead, or at least bowl them over. 

    I actually dug out my old class pin and wore it both evenings to my reunion--thus inciting a certain amount of envy in the folks who didn't think to do it. 

  • Sal replied 4 years ago

    Oh wow the white ones are great too!  I guess it depends if you want to do the float building or if you want a good excuse to get out of it.

  • Caro in Oz replied 4 years ago

    Haven't read the other responses. I LOVE the white outfits & you need to wear them at some point imo but if you are float building then probably not a great idea :) #1 is my next pick - very chic.

  • jackiec replied 4 years ago

    Coming back to say the white outfits are amazing! You can do no wrong, Joy.

  • Debbie replied 4 years ago

    I have not read the other comments but I like 5/6. You look confident and polished. Any of them are fabulous but that is my favorite!

  • catgirl replied 4 years ago

    Not reading any other responses, I LOVE the white outfits - 11 and 12 are beyond belief.  Next I like the stripes.  But please wear the white!

  • columbine replied 4 years ago

    Wow! I really love the white outfits, all of them. Sorry I'm no help! I still like the burgundy over the denim, for this occasion but if you can wear white, and not worry about the float, you look awesome in white.

  • bj1111 replied 4 years ago

    it depends on the message you want to send.  

    5/6 is the most put together, but i'm not trying to hard look.
    3/4 is very fashion forward, i know i keep up with the trends, now how are YOU doing?
    1/2 is my personal favorite, it just looks so comfortable and stylish and effortless.

  • Beth Ann replied 4 years ago

    You look amazing in all, but, for your occasion, I like 5/6 and 12/13 best.  My husband is from Pratt, KS.  I know all about those small towns on the windswept plains!

  • unfrumped replied 4 years ago

    I Lso like the mixed media sweatshirt outfit. I like the slightly dressy but comfy shoes. Also could try top and shoes with burgundy jeans.

  • Aubergine replied 4 years ago

    My favorites are #1-2 and #5-6 -- both effortlessly stylish and casual! Also like #3-4. The ones with the white jeans look absolutely great, but I wonder if they might feel a little conspicuous at something like this?

    BTW, my husband's family is spread out through a bunch of places in Nebraska, although nowhere really far to the west.

  • shemarie replied 4 years ago

    I absolutely adore your white-out outfits, Joy, and whether or not you wear them for this event, you MUST wear them sometime. So chic!!

  • shevia replied 4 years ago

    Wow! I pick 5/6 but every one of these are terrific. The pointy flats and the loafer flats are both perfect. 

  • Joy replied 4 years ago

    Wow, I am humbled by all who have taken time to look at all this and comment. I' still not sure what I will wear but am thinking of taking 5/6 for sure, maybe the burgundy jeans and the white jeans, which could both be worn with the mixed media sweat shirt in 5/6. I may also toss in a white top and the jacket just in case.

  • Angie replied 4 years ago

    #3, #13 or #14. LOVE. You look INCREDIBLE, and will know everyone's socks off, Joy. xo

  • texstyle replied 4 years ago

    I immediately thought #5/6 when I saw those and thought about all you said "not wanting to look like I tried too hard" , "building a float" etc. I also like #13 a lot.

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