Friday, November 15, 2013

Dress Has Always Been My Strongest Suit (but not dressy casual)

Guys, it's happening. A mere two weeks from now, the Pinkerton Academy Class of 2003 will be gathering to celebrate our ten year reunion (along with probably every other class of '03 in the continental U.S., it is the weekend of Thanksgiving after all). 


I was first approached about the idea of the reunion back in March when I got an email from Tim, one of our class liaisons (that's right, because when you go to a school as large as Pinkerton, you need more than one person who agrees in their senior year that they will write updates for the alumni magazine for the rest of their lives, bless their hearts) asking me if I wanted to be involved in the planning of the reunion. My heart cried out "yes!" as I live for party planning, but my head reminded me that I just accepted a job a week before on Nantucket and would soon be moving even further away from Derry, N.H. than I already was. 

I told Tim that while I would love to help, I wasn't sure if it was practical to dive into such a responsibility when I was moving somewhere that required multiple methods of transportation just to return to the mainland. I got no response, until 24 hours letter a message popped up in my inbox that simply read, "I decided. You're helping."

So for months now, myself and the other members of our little committee have been putting together this shindig (thank you, Internet) that will take place on November 30 at the Thirsty Moose Taphouse in Portsmouth, N.H. As happy as I am to have been a part of the experience, there has been one thing that has been plaguing throughout the planning process:

What the hell are we supposed to wear to this thing?

Because I base everything that I am unsure of on things I've seen in movies, I originally pictured a gorgeous dress because I assumed that all reunions take place in fancy hotels. I should have known better, as we had our prom in the gym, but moving on. I immediately thought that I would probably just wear some version of this:


But wouldn't you know, you just can't find any quality marabou trim anymore. 

So I was left only with the minimal guidelines that I was given via an email thread sent out to the planning committee: dressy casual.

Can we talk about what that even means? The only parameters I was given was no jeans. Also, let's remind ourselves that it is being held in a taphouse. What's a girl to do?

So once again, I took to the Internet. I put an APB out on Twitter, contacted my most fashionable friends, reached out to my Boston Blogger cohorts, and stalked the Pinterest boards of super-stylish people to determine what the true definition of "dressy casual" is. It turns out... I still have no idea. There is still no concrete definition of what dressy casual is, just many people's interpretations of it. I am by no means an authority on what everyone should and shouldn't wear, I will leave that to the professionals and the gays. But I do love fashion as a form of self-expression, and when are you more concerned about how you're presenting yourself than at your high school reunion?

So here are some inspiration pictures I put together of some fun ensembles that I would love to see anyone rocking when they roll up at the Thirsty Moose that Saturday. Some of these need some slight modifications to account for New England weather (I don't see how anyone could ever forget the snow on Prom day), but overall I think there are definitely some great pieces that anyone can work into their look, no matter what your fashion comfort level may be.

True Colors


I still don't understand when people tell me that they are afraid of color. Are you also afraid of going outdoors?! Because color is everywhere, and it should be embraced. I'm slightly biased, as I recently left a job in which I was required to wear almost head to toe black and everyday, a little piece of my soul died. That is why I am the number one cheerleader of color and think that every person should have one shade that makes them feel amazing (and no, neutrals like tan, gray and black do not count). If you're shy about it, you don't have to pile on more than one bold pigment like in the middle photo and the one on the right. What I love about the picture on the left is that the rest of the outfit is relatively simple- you can never go wrong with black and white. But you gotta show a little personality somewhere, whether it's a bright lip color or a jewel hued clutch. Start with a basic ensemble and accent it with one (or three, go on with your bad self) piece(s) that really pops for a standout moment.

Smells like Team Spirit


I can't ever resist a good theme. If you find yourself feeling fashionably uninspired, look no further than the PA's classic colors. Not only is red, white and black one of my favorite color combinations (always chic, in my opinion), but you can never go wrong paying homage to the Astroman at a school function. The look on the left is super on trend with the leather mini, but a striped long-sleeved shirt is the "casual" to the skirt's "dressy." As with many of these skirted options, you might have to thrown on a pair of black tights, but this brightly hued coat will keep you warm on that sure to be chilly New Hampshire evening while making you easy to spot across the bar. Win win. If you don't have a pair of red pants by now, you need to get off the computer and go get a pair now.  I'm serious- you can finish reading this later. I am obsessed with my red pants, and I got them at TJ Maxx for $16 when I was weary of the longevity of the colored-pant trend. They can be worn in a multitude of color combos, like with this Dalmatian print top or later with a more nautical scheme (my other favorite). The girl on the right is definitely a little more formal, but again, with a pair of black patterned tights and some ankle booties, this look can be dressed down to be taphouse appropriate. 

Crazy Pants


Ladies, want to ensure you're not totally overdressed? Wear pants. Pants are by default, a more casual look than a dress or a skirt. Now sure, you could go and throw on a pair of black trousers that have been kicking around in your closet since you got a job at Applebee's, or you could live a little and mix it up with one of these fun patterns or bold hues. If the leopard is channeling Peg Bundy a little too much for you, go for a more attainable pattern like polka dots. And maybe the harem-style slacks in the middle aren't your cup of tea, but the drapeyness takes away a bit of the formality (and it's sort of like wearing socially acceptable pajamas, if you really think about it). The one thing that all these looks have in common is that everything else is super simple- when you break it down, these are neutral tops and a solid pair of heels. So don't be afraid- WEAR THE PANTS and show them who's boss.

Liquid Leather


Another trend I'm super excited about right now is (p)leather leggings. Let's be real. As much as I love clothes, I spend the good majority of my days off in leggings, and even when I am in real clothes, I spend 100% of my time thinking about how I'd rather be wearing leggings. Am I the only one? So when I got a pair of these, I was super excited because a) they are amazingly smooth and I couldn't stop running my hands across them, and b) they are just like regular leggings, but are acceptable to wear to the bar. Target has some great hybrid pairs right now like the ones in the photo on the left- half shiny, half regular stretchy material. I love all the different ways you can dress these up- just look at the three different options here! A sequined moto jacket, a neon coat, or a white tuxedo blazer are all winners in my book. Just please ladies, follow the cues of the stylish women in these photos and wear a shirt or blazer that is long enough to cover your ass. I beg you. In fact, do this with all forms of stretchy pants. I don't care how fat or thin you are, it just needs to happen. Let's all raise our right hands and swear on our 500-page yearbooks, okay?

Sparkle Queens


I don't know if I can even express how in love I am with these looks. A little sparkle is always a good thing, and even more sparkle is like, the best thing ever. J. Crew has been all over this lately, which is perfect because I think it is the definition of dressy casual. What's more dressy than a sequined skirt, and what's more casual than a worn-in chambray? The knit hat can obviously go, we are going to be inside, after all. I like how both the outfits on the left and the right work in a colored shoe and a statement necklace. As for the middle photo, I get it- none of us are Blake Lively. She is an Amazonian-ly tall freak of nature that could probably do a high kick over my head. I chose this picture because I am all about dress shorts for events, especially in the colder months with a pair of tights underneath. I like how she balances out showing five feet of leg with a slightly over sized blazer and button down that have more of a men's cut to them. 

Sweet Tartan


While I love that we were never forced to wear uniforms at Pinkerton, there is still a soft spot in my hard for a good plaid skirt. It's like a little school girl, a little L.L. Bean, and a little early 90's grunge. But wouldn't you know, plaid is totally in right now, and like sequins, it's all about working it in with a contradictory element. A plaid skirt could totally go all Baby, One More Time on you if you pair it with a boring button down, but a chambray shirt gives it a more casual feel (accented with a good pair of heels and a few baubles to keep it from going too woodsy). While Hermione's look is a little more formal than what we are going for, I like how she paired it with a cropped leather jacket. If you're thinking of wearing a dress to a reunion and it feels like you're too done up, especially depending on your location, a cute biker jacket is a great way to take it down a level and make you feel a little less princess, a little more rock and roll.

The Jumpoff


Hear me out on this one- I know a jumpsuit is like, WTF, as it is one piece and how are you supposed to go to the bathroom? But I think there is something so chic about this, and you could not ask for a ensemble that requires less effort than this. Think about it- there is only one thing you have to put on! No time spent trying to figure out which top and bottom go together, or whether you should wear a skirt instead. It's easy breezy, put it on and you're ready to go. Well, not without some fun jewelry, because as you can see, many of these jumpsuits are super simple. I bought a strapless black jumpsuit and every time I put it on, I feel like I am channeling Bianca Jagger at Studio 54, without the ridiculous drug use, of course. These short ones might be a bit scary if you're new to the jumpsuit thing, because you have to have just the right shoe depending on where the bottom of your pant leg hits. I personally prefer the wide-leg version, as it makes you feel like you are floating across the room with every step. Just make sure they are hemmed correctly- I haven't worn mine in forever because I took a horrible digger in them when a heel got caught in a seam of my pant leg. The things I'll do for fashion.

Winter Whites


Did you guys know we can wear white after Labor Day? Yeah- turns out it was just a rouse all those years by our mothers, who were sick of trying to wash stains out of our clothes. Now that doesn't mean that you should wear your white linen beach cover up out and about in December, but it turns out, it's not so much about the hue as it is about the fabric. Go ahead, wear white freely all year long, just take cues from your environment. You should not be traipsing around in January in a pair of strappy white sandals (as a matter of fact, you probably shouldn't do that during any month, ever). However, it is socially acceptable to wear your white jeans with boots and a cardigan or stock up on sweater dresses in shades of cream and ivory. Or take a cue from this lady on the left and work it on a night out with a sparkly top. Add fun accents like leopard accessories and shiny gold jewelry.

As for my ideal reunion ensemble? I actually have no idea. In looking at these photos, I actually felt overwhelmed with options because I JUST WANT TO WEAR THEM ALL. And short of doing Academy Awards host-style costume change every hour (don't tempt me), I need to narrow down my options a bit. But seriously, take these suggestions with a grain of salt. Be yourself. Show off your assets that make you feel amazing and downplay what makes you feel eehh. Really, just wear what you want. As long as it's not jeans. 

Oh and guys? I didn't forget about you. But I can't tell you how to dress, because half of you could care less and the other half are dressed by their significant others. Since you're not supposed to wear jeans and it's a little unnecessary for you to show up in a full suit (unless you are dying to, then hey, go for it), your options are slightly more limited. Here's a little inspiration for you too:


Yes, I understand. You are not a male model, and therefore will not look like this in clothes. That's cool, because like I said, none of us are Blake Lively. So I guess we're all even. But there are definitely some elements that you guys have to work with. Like the ladies, I encourage you not to be afraid of color. Did you know there are other shades of pants besides khaki? My husband has recently acquired a few primary color shades of pants (red, blue, yellow) and he gets compliments on them all the time. I'm serious- it's hard to go places together because he sometimes appears to be better dressed. Add a pair of fun patterned socks women will think that you spent hours putting together your outfit. And I'm not saying you have to wear a scarf, but it will be almost December, and some sort of cardigan or sweater over a button down is like, the epitome of men's winter style. Jackets aren't necessary, but definitely gives off the vibe that you put a little more thought into it than the average Schmo. And finally, I get that it's Movember, and you might be excited to show off your scruff that you may not have had in high school, but try giving the facial hair a quick trim before heading out for the evening, eh? 

That's all for now- see you at the reunion! 



  1. I love that someone else is trying to figure out what to wear to their reunion. Mine is of course tomorrow! And i have decided just to rock out the lace dress and heels. Go big or Go home! Even though ours is in a nice Irish pub in Foxboro

    1. In the end, I just decided to wear what I felt the best in at the time. You can easily overthink it, but it's best to just be yourself and represent your style! I bet your lace dress looked amazing!