Pour some sugar on me, 1988.

Okay, guys. I need some help.

It seems that my 20 Year High School Reunion is in three days.

I knew it was coming up. It is. In three days.

This leaves me no time to lose those last few pounds, grow out my hair, or become a surgeon. If nothing else, I’m hoping (with your help, of course) that I can choose The Perfect Ensemble.

The reunion invitation states that dress is casual. However, I think I know better than that. These women (of which I am one! A Woman! I know!) haven’t seen each other in two decades. (Unless, unlike me, they attended the ten year reunion. Or, unlike me, perhaps they have the ability to maintain friendships from their teenage years. I’ve been in touch with no one. NO ONE. In other words, I’m walking into a room of strangers, and the only thing they might remember about me is that I tend to wear fake glasses and I fall down quite a bit.) Where was I? Oh, yeah. These women haven’t seen each other in two decades. You can’t tell me they’re going to be all, “Casual! Great! Honey, where are my cut-off shorts and my INXS t-shirt?”

This is where you come in. I’m about to give you three options. Please tell me which is most appropriate.


Here we have a knee-length denim skirt, a black t-shirt, and a short sleeved jacket thing that originally sold for $116, but I managed to score it for $11. Also, red patent Danskos. Because if I’m going to drink wine and fall down, I want everyone to notice my shiny feet. Not my Hanes Her Way underpants. (Note: Why, yes. I often stand like a flamingo when I’m sipping wine (or Pomegranate juice, in this case). Thanks for noticing!)

Next up? The dress that shows a bit of cleavage.


I purchased this dress for BlogHer, and it’s the most comfortable dress I’ve ever owned. Also, it requires absolutely no ironing! Polyester! With dots! And although I’m sporting black shoes, I think this might look a bit more dangerous with red shoes. Maybe. What do you think? (My grandma gave that stein to Jeff for Christmas many years ago. He keeps it in the freezer, and when he drinks from it, he speaks nothing but German. Obviously, I’m lying. BUT, cool stein. Cold stein, even. Klirrend!)

The final choice is a literal one. If you’re telling me that this event is truly casual, well, this is what you’re going to get.


Ratty jeans that may or may not be too tight, a black tank top that never really makes its way out of my drawer, my Ben Folds Five bucket hat, and my scratched up sunglasses. Also, a big stupid bag of frozen fish sticks, because I have to be holding something or else my hands will constantly be nervously shooting up to my face. (We’ll talk about that next week.)

So, anyway. Help.

Oh, yeah. Get this. Ira Glass is coming to town the night of my reunion. This is a huge conflict for me. If you know me at all, you know that I would drop just about anything to see Ira Glass. Let me just say this: If I have to wait 20 years to see Ira Glass again, I’m going to be So Angry with these people who waited 20 years to see me again. (I realize no one has really been waiting. If this thing wasn’t being held at an Elks Lodge, I’m positive I could do the Fly on the Wall game and no one would even recognize me!) If you live in St. Louis, please go see Ira Glass Saturday night. And while you’re there, pour a little of your drink to the floor and whisper something like, “For my misplaced homey, Fluid Pudding.”

I wonder if I should videotape the reunion so you can see how awkward I am in uncomfortable situations. Do you want me to? Because at this point, I’ll do just about anything for you. ‘ ‘ ‘text/javascript’>

99 thoughts on “Pour some sugar on me, 1988.”

  1. For definites the dress! I love it, and it looks great on you. So does outfit one, btw, but the second one has the little wow-kick to it. You could still pound fish sticks, though.

  2. Definitely No. 1. It’s a great outfit and a little more stylin’ than the dress, which is “nice.”

  3. Option 1 for sure. A dress will make it look like you’re trying too hard. Plus, no one else has to know you didn’t spend $116 on that jacket!

    BTW, nice farmer tan in #3. ;-)

  4. Well, I believe both option 1 & 2 are quite nice…and I see no weight that you need to be losing. I was even considering getting some rugrats so that I could keep the arms from looking like chicken wings, it seems to be working out for you anyhow.
    Option 1 seems to lead more towards casual and option 2 more towards slightly dressy yet casual enough and comfy. I would like option 2 with the mentioned red shoes though for the extra pizazz! Also, does the jacket flatter your slim waist or make it boxy looking? Can’t tell from the side. Love the denim skirt. I think neither option is wrong.

  5. I like #2. Red shoes would be a great touch. I say go with comfort and flattery and as long as the shoes you choose aren’t stripper stilettos, you can still claim “casual.”

  6. Option #1. I just had my 10th this past weekend. I wore jeans and a t-shirt, which was basically what I wore all through high school. But they were NICE jeans.

  7. My first choice: skip the reunion and go see Ira Glass. Seriously, who are these people anyway?*

    My second choice: I was going to say the dress until someone pointed out the farmer tan. now I am totally behind option #1.

    *I also speak to no one from high school. Not a single soul. And I am happy that way. I didn’t care for these people then, I really don’t care to know what they are up to now. My best reunion story: I attended my 10-year reunion stag (in 2001). One of The Popular Boys from high school hit on me and asked for my phone number. I let it go on for awhile before I held up my hand to shut him up and said, “What’s my name?” Total silence. I turned and walked away. Perfect reunion moment. No need to ruin it by going to my 20 year.

  8. I agree with Amy in KC, ditch the reunion and spend the evening with Ira. And wear outfit #1.

    My 10 year reunion was fun, the 20 year was not, aside from looking at the photo album that Larry the cross-dresser brought to show off his more feminine side. I’d still rather have been with Ira…

  9. I vote for either 1 or 2, either way w/ red shoes, for all reasons mentioned above. You may get a bit chilly in the dress if you’re anything like me.

    Also, seriously, you have no weight to lose, you look gorgeous. You’re going to kick butt at your reunion.

  10. Number one! And do I spy a tupperware thing of knitting next to the fireplace? But really, I love the dress, but outfit #1 wins for its sassy awesomeness.

  11. Though they are all quite sassy…I would go with number 1 because it hides your slight farmer’s tan lines.

  12. I vote #1 with a black skirt. Or the dress with a better bra and red shoes, black = too predictable. Feed your eyebrows some iron (or pencil em in), the anaemic things need to be brighter and bushier-tailed– you’ve got beautiful eyes and a more emphatic marquee is called for. Look at your daughters! Gorgeous eyebrows. Please don’t hide yours. Your weight looks perfect.

  13. Option #1! With the fishsticks, of course.

    Of course, I have to ask, if you haven’t talked to anyone in 20 years, why bother? Go see Ira Glass!

  14. I was originally going to say the dress but I am on board with #1 now. A thought – jeans with the top and shoes from #1? Then you don’t need to worry about falling down and pulling a Lindsay.

  15. Option 3!!! No, probably option 2. Or 1. I’m no good at deciding.

    I skipped my 20 year high school reunion this summer. Mostly b/c it was held over a weekend and it was far away. If it had been closer and just an evening I would have gone just to see how old we all are… so sad.

  16. I was going to say “dress,” too, but seeing that the jean skirt and red shoes combo is winning — what do I know.

    (I am the last person to give fashion advice, by the way.)

  17. I vote for outfit #1. I recently attended my 15 year reunion (who has those?) and ignored everyone’s advice and wore a dress. It was really flattering and I had the perfect shoes to go with it, but I was very overdressed. I don’t usually mind that, but I was overdressed by a lot. There were a couple of other skirts there, but very casual skirts. Most women were in blouses and nice pants. If I had to do it over again, I would still err on the side of overdressed, but would have left the dress for another occasion.

  18. I’d go with the dress. At my 20 year reunion just a year ago apparently the cool thing to wear was a dress with boots (the just below the knee kind of boots, and not flat either… with heels).

    I wore nice slacks and a nice sweater and boots. If someone had told me I’d have worn a dress with boots… cause just like 20 years ago I wanted to fit in.

  19. Skip the 20th, go see Ira Glass and go to the 25th reunion.

    No, really. REALLY.

    I skipped my 20th, having just had a child three days before. I went to a cocktail party for the 25th but not the whole weekend. It was fun and just enough reunion without being too much of Those People.

    If you have to go to the reunion, though, then outfit 1 is the winner.

  20. I’m voting for #1 just because I think it might be a little more Elk appropriate. I’m not sold on the shoes… love that they’re patent red, but not that they’re Danskos. I do love that dress. Add some pearls and you’re good to go.

    PS – My 5 year reunion was at the Fiddler’s Association. Yeah, I passed on that super opportunity.

  21. Your best bet is to listen to the opinion of the most judgmental bitch in the room. Since that would be me, here’s the perspective of someone who would be sizing everyone up and guessing their yearly income and level of happiness based entirely on their outfits.

    That being said, #2 looks amazing on you. It shows off your perfect figure (shhhh it really is) and shows you stayed in shape all these years, even after 2 kids. That’s big in the bitchy reunion world.

    It is elegant and casual at the same time. It doesn’t pigeon hole you into any income category. It doesn’t say you’re a corporate woman or a stay at home mom. It’s about as neutral as possible and still very stylish and just slightly sexy.

    If the room is too warm, you won’t be sweaty. If it’s too chilly, you can throw on a sweater. It’s low enough to have a hint of cleav but not so low there’s a threat of a nip slip.

    If I was a stylist dressing you for this event, I’d insist you wear #2. The first is too casual and the last isn’t appropriate. Then I’d chain smoke and demand my 1 thousand dollar fee.

    But please bring the bag of fish sticks to fall back on in case the conversation lags.Breaded frozen items can be an excellent conversation starter.

  22. Either #1 or #2 (or something in the middle of the 2). Be super careful w/ those Dansko clogs though–everyone I know finds that they turn their ankles more often in Danskos–and that would be really embarassing at a reunion.

  23. As a person who’s recently done the 20 year thing.. #2. “Casual” at a evening event never really means mean denim when it comes to this kind of thing.

  24. Did the “casual” 20 year reunion thing this summer myself – went with tan capri’s & a black tshirt – but some of those people do not know what casual means. Ahem.
    I’m voting option 1 because denim invokes casual & those shoes are close to the ground which means any tipping over will happen quicker and make less of a scene.

  25. Option #1 is casual enough so that you won’t feel out of place if it is indeed casual, but also lovely enough that if it’s dressy casual, you’ll fit right in.

    I had a similar dilemma this weekend when my husband told me that we were invited to a “casual wedding.” The. Day. of. the. Wedding.

  26. I say skip it and go see Ira Glass. You’d be happier. I haven’t attended ANY of my class reunions (20th was last year). I don’t talk to a single soul from my class and up until 5 years ago when I started sending my daughter to a private parochial school did I see any of them. My daughter school functions? I steer clear of them. Yeah, I’m antisocial like that. BUT back to your original question, if you really feel the need to go, I vote for #1. It’s totally the shoes.

  27. The dress! The dress! But with black heels, not the red shoes. (But that’s easy for me to say. Those aren’t my feet I’m punishing with that decision.)

    What ever you decide you’ll look fabulous! And maybe you’ll run into Ira Glass afterwards at a quaint, late-night diner.

  28. Another vote for #1. Those Danskos seal the deal.

    #2 is lovely, but at a casual event of any kind (even one like a reunion) it’s trying too hard

  29. I’d probably wear #1. But I wouldn’t decide until the day of and I’d obsessively try on all of them until I left. I maybe chose #1 because I love red patent Dansko clogs. But seriously, wear whatever you feel most fierce in. I find that as long as I’m feeling my best, I’m the happiest person in the room. Tomorrow we have an all day meeting with a leadery type of group. I’m wearing my fiercest heels and my (on-sale) Brooks Brothers shirt because that’s how I feel most empowered or something. Knock em dead!!!

  30. Outfit #1, it’s great! Just be careful with the clogs. Everytime I mix my Danskos and drinking, a horrible falling scene ends the evening. Clogs are not drinking shoes.

  31. Delurking to throw in my two cents. These days when I get a “casual” invitation, I assume it means business casual. So I vote the dress as well, because it covers the dress up-down spectrum so nicely. And I would love to see it with red shoes. The other outfits are very cute, too.

  32. I am brand new to your blog, and came across it due to the “pour some sugar on me” tagline…great song. While I was here, I decided I would look at your outfits since my 20 year was last year…I say #2, however, my fashion style consists of jeans, t-shirts and Birks…I am just saying.

  33. Mutha Mae, all the way. ‘Zactly what she said.

    And the dress could be ok with red shoes, as long as they’re not those Danskos. I think I’d prefer black shoes, though. Pop in some color with accesories, if you like.

    Don’t get me wrong, the Dankos ARE cute (helloooooo red patent), but with jeans only. Or maybe brown cords. BUT THAT’S IT.

  34. Love the dress- it looks great. I think is shows you to a great advantage.

    IMHO- stick with black shoes, red shoes with the dress for this event might look “trying too hard” while as it was photographed it looks “effortlessly fantastic.”

  35. Delurking to say #2. It is totally classy and yet isn’t saying you were trying to show up every other woman in the room (the women who dressed dripping in diamonds at my 25th this year – No, I didn’t go but I saw the photos – were totally trying to do that), it fits your gorgeous figure, I agree you should stick with the black shoes and the MOST important point is that you said it is the most comfortable dress you’ve ever owned.

    What’s more important in an already uncomfortable situation than something you FEEL good in?

    That’s only if you really decide to go. I’d totally skip it for Ira Glass. There’s always the 25th. (I’d totally skip THAT to dog sit for a friend. Which I did, in fact…)

  36. Mutha Mae and Blackbird have told you all you need to know. I won’t even add a reason (except that you look just byootiful in that dress).

    Disappointed about Ira! Just (yesterday) told the husband all about your love affair with all things Glass. But Ira will return, and “the 20” will not!

  37. The dress for sure. It looks great on you and “casual” is over-rated. It isn’t too dressy, just right enough.

  38. I’m going w/the second option, minus the black heels and plus some cute red shoes. And accessories. And maybe a cardi to throw on if it gets chilly? To me, “casual” means “business casual”, so I wouldn’t wear denim anything. And those clogs? NOT with that dress. I’d always rather be slightly over- than under-dressed, kwim?

    Have fun at the reunion, and good on you for going! I’ve skipped both my 10th and 20th, and have no intentions of making my 30th, either. ;)

  39. I say option #1. It’s cute and fashion forward, so though you may FEEL awkward, you’ll LOOK relaxed, casual and together!

  40. I vote #3 but only if you bring the fish sticks. I really wanted to see Ira Glass Saturday but we are broke and I am sad. I will join you at his next local show.

  41. Agreed, #2 w/ red heels. I would love to see Ira Glass, but I already have plans to see Jim Gaffigan at the Fox. My best friend and I are so excited we keep talking about how “Jim Gaffigan will make us laugh again.” And my mom wanted to know when I’d seen Jim Gaff before, since we were seeing him again.

  42. I went to my 20 year last year. It was way better than the 10. Really enjoyed talking to people with whom I’d had little in common in h.s. (when I was kind of a prissy nerd) and finding that we have lots in common now (books, kids, wine, etc.)
    I vote for #2 (really adorable on you), or #1 with a black skirt (fun and hip – but not too out there) – depending on whether you want to blend, or strut it a little more. Also – looks to me like WW did you right – I don’t see any weight that needs losing.
    If you go – have a great time! I didn’t regret it. Ira Glass will come again in six months- next reunion is 10 years away.

  43. I went to my 10th and 20th reunions and had a ball at both. Not because I as at all popular either. For a writer it’s like someone threw 6 months of research in a room and gave it to you. From that experience I say that dress + red non-Danskos = reunion GOLD! If the tan issue gives you pause bring a wrap or sweater.

    Have fun!

  44. Both 1 and 2 look fabulous, but since you mention that you’ll be feeling awkward all evening, I think you’ll feel altogether more comfortable in #1.

  45. I own that dress you wore to BlogHer, in a (cough) larger size. It’s totally comfortable, and won’t do anything unexpected.

  46. That sassy little number in the first pic is fantastic and I would love to see you add the accessory of the fish sticks, please? It would totally complement the red shiny shoes.

    Have fun!

    Ira is coming here in November. Want to just come visit me and ogle him together?

  47. I really like the cleavage one (not in a weird way), and I’m such a dork I’d probably end up wearing red clogs with it, so don’t listen to me. Since you asked (I think), if it were me I’d totally go see Ira Glass instead of going to the reunion. But that’s just me. I had my 20-year reunion this summer and apart from connecting with one long-lost friend (which in reality could have been accomplished by picking up the phone), I really could have skipped the whole shebang and saved tons of money (dress, shoes, hair, nails, serious undergarments, makeup, therapy) and stress for something else. But have fun!

  48. I’d be more likely to wear 1, but I say go for 2 simply because you look fantastic in it. And I have to agree, unless you can read your keynote blog at the reunion, (that would get things going) go see Ira Glass!

  49. Fishfingers in my culture, people. Fish FINGERS. Thank you.

    Otherwise, I can’t see the pics, but going on the description alone, I’d have to say #2. Reunion will be blogging gold. I await.

  50. i have a ticket for ira,but can’t go since i have a child attached to my breast. you have to pay for ‘everyone’ at the pageant. ridicule!!

    i like #1 since it seems more you. the dress is cute, though, so i won’ t be mad if you wear it.

  51. What 10 lbs? I like both 1 & 2 so wear what makes you feel comfy – cause they both look good. Definitely bring the fish sticks.

  52. Seriously, you don’t have 10 pounds to lose, you gorgeous woman. I like the dress the best. With a pair of red heels, if you have them.

  53. The first concert I ever went to was Def Leppard’s Hysteria tour…in Casper Wyoming. I remember the smug superiority I felt when, afterward, I was at a dance and watched a girl singing along with the song, crooning, “my love for sure!” instead of the accurate “one lump or two?”

    I really think I pitied her. Candidly…I think I still do.

  54. All of the outfits were boring, except for the jeans. You look older than you probably are. Find you a smoking hot outfit that everyone wished they had on. Try a younger outfit. something sassy.

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