Woah, we’re almost halfway through November already and I didn’t post Random Outfits for September or October. Yikes, sorry! I’ve been pretty busy at work, having just launched a brand new e-commerce website for the company I work for. The site had to be built from the ground up, which meant lots of computer time, and quite a few later nights towards the end. So as you can imagine, I didn’t much want to come home and sit in front of the computer to work on editing photos or writing much. Anyway, I managed to put together over 20 Random Outfits between September and October, both of which were fun-filled months (yes, even with the new site launch at work). So here we go… two months of Random Outfits!

September 5: Floral & Leather

I’d been dying to wear this outfit since seeing it on Loop Looks, and when September finally rolled around and it cooled off a little, I decided to go for it. I paired my thrifted leather skirt with a swapped semi-sheer floral top (with a grey tank under for modesty’s sake). Instead of doing strappy sandals or dressier shoes, I went with my black cut out booties. I wore grey ankle socks under the booties to echo the grey tank. I kept my accessories light, wearing just my Michael Kors watch, my “Rachel” necklace from 9thandelm.com, my ShopBevel earrings, and a midi ring.

I liked this outfit, but it was rather uncomfortable. The skirt is a smidge too tight, and when I sit, the second button at the waist tends to pop open. It was a really good deal, and it fits my hips nice, but between that button popping thing and the length, I’m not sure how much longer I’m going to keep this skirt around. This was the first time I wore the top, and while I like it, I’m not sure it’s for me either. I know why it caught my eye at the swap, but I think I’ve found something a little more me to replace this one with.

September 7: Craft Fair

On the 7th, two girlfriends and I headed to a craft fair in the city. We walked around, looked at some really fun, interesting, cute things, ate Puffs of Doom, and just generally enjoyed each others’ company. I didn’t buy anything at the craft fair, but that’s ok… it was a fun day regardless.

It was a nice day out, but a little on the chilly side in the morning, so I erred on the side of being to warm and wore a pair of Lauren Conrad ankle jeans, cuffed with my cut out ankle booties. On top, I wore my black bralette with a peasant-inspired top that I picked up on clearance at Old Navy before the Jimmy Buffett concert. I added on a few necklaces, some rings, my awesome Benjamin Black Fingernail Ring and Double Midi Ring, and threw my hair in a bun.

This was a good mix of city-chic and boho-music-festival looks, I though. I surprisingly liked this look quite a bit, even though it’s not really as rocker as I tend to feel comfortable in. It worked though, and while I haven’t worn the peasant top since (it’s cooled down enough where I’d feel a little silly in it), I’m looking forward to playing with it in late spring and summer. These LC jeans are pretty much the same as my pink ones, and I like them quite a bit. I wish they were a tad longer so I didn’t have to cuff then, but they’re nice for wearing with ankle booties, flats, or even Chucks in warmer months.

September 9: Yikes, Stripes!

I got these killer studded shoes at Kohl’s on clearance and just had to wear them to work, even though one might not consider them workwear. I figured if I paired them with a longer pencil skirt, a more casual top, and some fun accessories, I’d make them, well, work. So that’s what I did. I pulled my green and black pencil skirt out of the closet and opted for a cream and black striped top on top. I added a green fox bracelet, my midi ring, and my go-to earrings, and that was it.

This outfit really worked! I loved it entirely. The bold stripe in the top with the simple, thinner, colored stripes on the skirt played very nicely together, and the shoes added a nice texture to the look. In fact, I got quite a few complements from coworkers on this look, which always makes me feel nice. This skirt was a semi-impulse buy–I got it off the Forever21 clearance rack a couple days before a conference because I thought I could make it work with an ugly, pale green plaid shirt I was required to wear–but it’s so easy to wear and works with so much in my closet that it’s quickly become a piece I really enjoy wearing. And what’s funny? I probably never would have looked twice at it if not for that ugly shirt!

September 11: Go Sox, Go!

Now, I’ll readily admit that I’m not much of a baseball fan. My husband and his family are Cubs fans, quite a bit of my family are Sox fans, and I generally just don’t enjoy baseball. But when my new boss offered me sixth row tickets just off the Sox dugout, I jumped at the chance and took my parents and brother along. But not before I bought myself a Sox shirt!  I paired said Sox shirt with my Rock & Republic sequin skirt. I didn’t want to have to worry about changing after work, but also didn’t want to dress down so much at work that I felt uncomfortable. So I wore the skirt with sheer tights and my cut out booties. I had a jean jacket, but it was such a beautiful day and evening, that I didn’t need it at all.

Here I am waiting for my train into the city, with my tickets. Like I said, awesome seats!

When we got to the game, I was actually pretty comfortable. I felt a little overdressed, but not to the point where it was awkward. In fact, when I ordered my food, the girl at the concession stand professed her love for my skirt (not that I can blame her).

Oh, and if you follow me on Instagram, you likely saw just how great our seats were. If not, here’s a pic and a video demonstrating just that. I gotta say, when you’re that close, baseball is actually pretty exciting. We all had a great time at the game!

September 15: Grungin’ It

This was one of those days where we didn’t get ready until way late in the afternoon, and it was largely because I wanted to run to Target and check out the Phillip Lim line. But I didn’t want to dress up, and it was cooler out… I just wanted comfort and not much else. And because, thanks to Monroe and Main, I’ve discovered that fleece lined leggings are like sweatpants, only not as sloppy looking, I decided to throw on a pair of teal ones I picked up at Discovery, along with a grey tee and an oversized J.Crew flannel I snagged out of the men’s section of Goodwill. A messy bun, a few random necklaces, and combat boots finished off the outfit nicely, and off to Target we went.

I got a couple things from the Phillip Lim line, so the trip was a success, as was this outfit. It was everything I wanted it to be, but I still felt put together. I could live in this, easy.

September 16: Phillip Lim for Target Leopard Skirt

This wasn’t one of the items I had originally had my eye on from this line, but when I saw it in the store, and didn’t see some of the other stuff I’d wanted, I figured I’d try it on. It’s nice and flowy, without being too thin, and, turns out, it fits me really nice and flatters my body. So I got it. I paired it with a simple black turtleneck, black lace tights, my old OTK boots (which have since been donated), and threw my Monrow and Main varsity jacket on for a little warmth. I also wore my Rachel necklace, since it added just a little bit of sparkle.

Success! I loved the texture the tights added to the look, and how the oversized leopard looks on. It’s a really fun skirt, and one I’m working on styling still. It’s not like anything else I own, and is a big of a challenge because of it. But I love the way it fits and looked on.

September 17: Phillip Lim & OTK Boots, Round 2

And another piece I hadn’t planned on getting at all was this buttondown shirt. In fact, of the 4 pieces I wanted, my Target had 2, and I was underwhelmed by one and told I looked like a Japanese flight attendant in the other. But I loved this pattern, and while I usually don’t like sheer buttondowns (I always have trouble wearing them, since I’m often cold and can never seem to layer them right), I figured I’d get decent wear out of this one.  Plus, I figured it would replace the floral top from above nicely.  I wore it to work and opted to dress it down a little by pairing it with the same teal leggings I wore Sunday, my OTK boots again, and a black tee. Simple and understated, as well as comfortable.

This was a good look, though it felt a little strange to be wearing something nicer with fleece lined leggings. But that was more of a “how the oufit feels” thing, rather than a “how the outfit looks” thing. I like this shirt, and am glad I got it. I have some plans for it, oh yes.

September 22: Farnsworth House

On the 22nd, hubs and I decided to take a drive down to the historic Farnsworth House to check out the architectural marvel. I wanted to look cute, so I wore a thrifted vintage Express skirt with a black Calvin Klein pullover, sheer black tights, black OTK socks, and my new black OTK boots. I added an olive vest for another layer, since it was a little chilly out.

Sorry, no detail shot… I wanted to show off a little of the house for you. Neat, huh?

The outfit was a success! I loved the way this looked, and while I feel like the skirt’s a little short for work, it’s perfect for fall, or even winter, weekend days where I want to wear something comfortable but a little nicer than fleece lined leggings.

If you’re in the area, or even if you aren’t, the Farnsworth House is totally worth the drive. You can buy tickets for the tour (which is the only way you can see the house) online or when you get there. It was so neat to see such an important piece of architecture and hear the story behind it. If you have a chance to go, you should!

September 24: Pattern Mixing

Very rarely do I find an entire outfit somewhere, in one trip, but that’s what happened here. I stopped into Kohl’s to see if they had marked down any pieces I had been eyeing (because I never pay full price for anything there), and because I had a 30% off coupon.  I managed to find these tribal print Rock & Republic jeans, this Princess by Vera Wang long sleeved tee, and this sleeveless plaid flannel. When I grabbed them all, I didn’t think about putting them together, but when I got home and was hanging up my new purchases, I thought “this is cute with that… and with that!” so I decided to wear all of it the very next day. Again, with my new OTK boots. Kind of obsessed with them (which is good, because I don’t regret the purchase or the subsequent donation of the old pair).

This is such a random mix of patterns, but somehow it totally worked. I liked it quite a lot, and have fought just rewearing this exact outfit a couple times. I like the juxtaposition of the flannel and the jewel design on the tee, and the texture the pattern on the jeans lends to the look. The jeans, while, well, jeans, are ones I actually feel ok wearing to work too, which is kind of nice. It’s another option that doesn’t feel as… shleppy as regular jeans do. No idea why that is, but oh well.

September 26: Grey is Great

Towards the end of September, fall was here, but it was that perfect fall where you could wear a cardigan over a dress with tights and be perfectly comfortable.  I really wanted to wear these grey flats, which were a new purchase, with black tights, and when I was looking for something to go with them, this dress jumped out at me.  It’s short sleeved though, so I tried on a few cardigans with it and this olive and cream one just worked.  I added a black scarf to balance the black tights and went minimal with accessories and makeup.

This outfit worked nicely, and was great for work.  The only issue I had with it was that the cotton dress stuck to my tights, which made me feel a little odd.  I might just have to get some short slips or something–this isn’t the first time I’ve had this issue.  Anyone have any recommendations, or should I just buy a slip and shorten as necessary?

September 28: Welcome to the Boat Show

Hubs and I drove up to The Abbey in Fontana, WI (on Lake Geneva) for a vintage boat show on the 28th.  It was pretty cool to see all these vintage wood boats fully restored.  Some of them were just incredible–fully customized and gorgeous.  For the trip and walking around the show, I wore a black, slightly oversized buttondown with a military vest (that I added some studs to along the shoulders) on top.  I wore denim cutoffs and olive tights, and then added these great grey Jeffrey Campbell boots I scored at Plato’s Closet.  They filled a nice void in my closet and were a really awesome deal.  I’m carrying my black fringed bag as well.

I rather liked the name of this one (and because of it, you don’t get a detail shot… sorry).

This outfit was fantastic.  I felt so me in it, which was nice.  I also felt really chic, though a little out of place walking around The Abbey’s harbor, but that’s ok.  I’d rather feel like myself than be dressed in such a way that has me looking well-placed, but feeling out of sorts.

September 29: POW!

On the 29th, hubs and I drove into the city to pick up a TV that we bought from friends of ours.  After meeting up with them, hubs and I went to bopNgrill (a Diners Drive-Ins & Dives place) for a delicious lunch and then decided to walk down to the beach to burn off some of the calories.  For the adventure, I wore my teal fleece lined leggings, my new OTK boots, a POW shirt from Kohl’s, a striped asymmetrical zip up sweatshirt (that’s so not like a sweatshirt that I can get away with it at work–another great Plato’s Closet find).  I added a few fun necklaces–a crystal drop, my chevron, and a fox that made me think of Trixie–my midi ring, and my fringed bag.

You can always tell when hubs takes my pics for me… no doubt he gets me making some kind of silly face.

 This was the perfect outfit for all of our random adventures, from moving a TV (ok, hubs did that) to eating a huge lunch, to walking it off on the beach and through the city.  Ok, so maybe the boots weren’t perfect for the beach, but the sand was hard enough that they were ok.  Overall, I was a big fan of this fun look.

September 30: I Love This Skirt

I wore my Je’Taime skirt again on the 30th, but this time paired it with the jeweled Princes by Vera Wang shirt I got at Kohls’.  What a perfect match!  I added sheer black tights and my black OTK boots (I wore other shoes in September, honest!) and only accessorized with my Michael Kors watch. With everything going on, between the top and the skirt, keeping it simple was key.

I drank my lunch that day… nothing wrong with that, right?

I really liked the way this looked.  Someone at work thought it was a dress, even, that’s how well this worked together.  It’s definitely something I’d put together again.  This skirt is proving to be a little more versatile than I anticipated… maybe because it’s just black and white?  I dunno, but I like it!  Good purchase, for sure.

October 9: The Stanley Cup!

If you follow me on Instagram, you already saw some pics from this glorious day, but if not, prepare yourself for my up close and personal time with the Stanley Cup.  The husband of a friend of mine is part of the Blackhawks organization, and it was his day with the cup, so they invited friends and family over to check it out, take pics, and have lunch.  It was a pretty good time, and so cool to get to see it.

Because I had to work, I wanted to be presentable, but also comfortable.  I took a risk and wore shorts and tights (these shorts are the very same shorts Old Job told me were too short), again with my OTK boots, but this time with some sock peeking out.  I added a chunky sweater and a black scarf, and that was it.

I really liked this outfit, and didn’t have any issues with it at work.  I haven’t worn shorts since–I figure I’ll wear them very sparingly so that there aren’t any issues–but it’s nice to know no one complained about them.  With tights underneath, I think they’re fine.

October 10: Lovin’ My Yellow Ombre

I went in to see Jacqueline at Bii Hair Salon at the beginning of October for some color, and went with yellow ombre.  I loved it (it’s pretty faded now), and wanted it to really pop the first week or so I had it.  Since I didn’t really do that on the 9th, I wore a black turtleneck on the 10th.  I tucked the top into my American Apparel chiffon skirt and added floral tights and my cut out ankle booties, along with my cute fox necklace.

Hubs wasn’t a fan of this look (he doesn’t particularly like the length of the skirt on me), but that’s ok.  I liked it for its comfort, but also because it was so very fall.  The colors were just perfect, and really worked nice with my hair.  This skirt is definitely great for spring and fall wear, because it’s light, but a deep color.  It’s nice for those warmer days.

October 12: Mecum Auto Auctions

On Saturday, October 12 hubs and I went to check out the Mecum Auto Auctions, as they were in Schaumburg.  There was some pretty cool stuff there (which you can see on my Instagram, along with this video of the auctioneer doing his thing).  I knew I wanted a pic with something, but this car wasn’t my first choice.  It started to rain (which you can see in the pic), so we snapped quick and moved on under the tents and inside.

For this casual event, I wore a black tank with a burgundy high-low tee over it.  I wore my tribal print jeans, my floral embroidered knee high boots, and my black fringe bag.  I threw my hair in a quick braid and tossed a hat on, since hubs and I rolled out of bed and headed over there.

Be sure to check out my Instagram for some pics of really cool cars!

I liked this look, actually.  It wasn’t full of layers of necklaces or anything, like I usually do, but it was easy, comfortable, and worked together nicely.  I could easily add accessories too, if I wanted to recreate this look later on.  And this hat?  Fantastic!  I found it in the Target clearance section and am so glad I did.  Perfect for those days where you just wanna throw something on your head and not worry about it.  It will be great for the summer too.

October 13: Walk Around Lake Geneva

Did you know there’s a path that goes all the way around Lake Geneva, and it’s all public access?  Well there is, and it’s pretty cool.  Hubs and I walked a very small part of it on the 13th and are looking forward to exploring more of it together next summer.  Without really knowing what to expect, I wore layers in the form of my custom-designed tee, my favorite flannel, and my olive vest, all over black leggings, with black combat boots.  I added my hat, my Rachel necklace, my MK watch, and a new ring–a class ring that belonged to my biological grandmother.  I never met her, but recently found my biological family, and they decided that since I was the oldest granddaughter, I should have the ring.  It was a pretty incredible thing to get, and it will always remind me of where I came from.

I had hubs snap a detail shot of the stud I added to this vest for you.  Cute, no?

This outfit was perfect in pretty much every way.  I wasn’t too hot or too cold (ok, I added a jacket for the walk, but didn’t take pics in it), I felt like myself in it, and it was an excellent example of my style.  I’d wear this again in a heartbeat.

I’ll write about the story of finding my biological family at some point.  I’ve told it to quite  a few people, and everyone is amazed by it.  So it’s something I’ll share when I get some significant time to get it all down.

October 14: Floral Leggings

After all the walking over the weekend, all I wanted to wear were flats with my orthotics in them; my feet were killing me.  So I wore my combat boots again, but added burgundy over-the-knee socks, floral tights, a black cowl-neck dress, and a grey cardigan.  A nice, texture rich outfit.

Despite the texture in this look, I just wasn’t feeling it.  I think it was the boots that threw the whole thing off… with OTK boots this might have been cuter.  Or maybe a different top with a black cardigan?  Or maybe it was the total lack of jewelery (I was rather unmotivated in the morning).  I don’t know… but I wasn’t a huge fan.

October 19: The Great Pumpkin

On October 19th I hosted a pumpkin carving party, which started out at the local pumpkin farm where we all picked pumpkins to carve (or paint, or just leave alone, like I did haha).  Last year I ended up changing out of my outfit because I didn’t want to get it dirty, so this year I wore something that I wouldn’t mind getting dirty.  I layered up (though I should have added a jacket, since it was pretty brisk out), wearing a tank top under a cream henley, topping it with my asymmetrical sweatshirt and olive vest.  I wore leggings, a black cotton skirt, cream and brown socks, and my combat boots.  I put my hair in braided pigtails, because why not?

I liked this look, though the texture of the leggings were such that my skirt kept riding up.  They were completely opaque, but they were cheap, and I wanted to make sure I didn’t terrify any children with my butt showing through.  This is definitely a long top pair of leggings, that’s for sure.

October 22: Layers, Layers, Glorious Layers

It was freezing in our office on the 22, and I’ve never been so thankful I layered up.  The heat was broken, and just blowing constant cold air.  I had intended on just shedding layers as needed throughout the day, but spent the entire day bundled in my long sleeve tee, sweatshirt, and poncho.  To keep it looking a little nicer I wore my coated Rock & Republic jeans and my burgundy thrifted booties.

I adored this look!  It was comfy but chic at the same time.  A couple of my coworkers were envious of my poncho, which was kind of awesome.  I’d wear this whole outfit again for sure.

October 29: Kitteh

I actually wore these cat ears the day before, but left them at work… so they made it on my head again.  They were too fun not to, and the week of Halloween meant I could easily get away with it.  I wore black leggings with my black space tee under my black and white plaid top (dress really, since it’s more than long enough and has pockets).  I added a thin puffer vest and my OTK boots, the ears, and called it a day.

Oh, and what’s that? I got contacts again!

Aside from the ears, I’d totally wear this outfit again.  It all worked so nicely together, and it was pretty comfortable.  Ok, I’ll admit, I think the ears are stupid adorable and I’d totally wear them again, not just during Halloween week.  I found them last year at Five Below and snagged ‘em, because why not?  They’re subtle, so they work for my 30-something self nicely.  Would it be weird to wear them randomly?  Would anyone even notice?  Probably not.

October 31: Yar, it be Halloween!

I dressed up for work, shamelessly, as a pirate.  Here’s my costume, though I toned it down a little from how I’d normally go.  I used my poncho as a jacket, which worked nicely.  I was pretty much the only one in costume, though another coworker wore some Disney Halloween stuff, including some pretty cute Minnie Mouse ears.

I’m sure you recognize some of the necklaces, rings, and other things I have on.  I actually got rid of my boots that I usually wear with this, and could have kicked myself for doing so.  But they were donated, so hopefully they found a good home.  These boots worked nicely though, so yea.  Did you dress up for Halloween?

So that’s it for September and October’s Random Outfits.

Quite a mix, though I didn’t really wear all that many pairs of shoes.  My feet have been bugging me quite a bit, so yea, I’ve been a little limited.  Hopefully they get better soon.

What was your favorite look from the two months?  Anything stand out to you at all?  Let me know in the comments below… I love hearing from you!



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