I love a good dress + moto jacket mix. It’s (again) the happiest blend of masculine + feminine in an outfit.
About a year and a half ago, I wouldn’t have even considered wearing a black leather jacket. Now I can’t imagine NOT wearing one. Isn’t it funny how that goes?
I know I mentioned this yesterday, but I’ve gotten so much joy lately from this idea that clothes are fun twice — once when you wear them and feel cool, and once when you look back on them and laugh about it. I used to get all indignant + embarrassed about outfits I wore 6 years ago, but I mean — life’s too short.
Past outfits are just another reason to laugh.
And — best part — they just keep getting funnier.
So tell me … what’s something you used to wear that makes you laugh now?
For me it was wearing leg warmers and flip flops … WITH camouflage print cargo shorts from the men’s department of Target. Hello college Caroline. My, aren’t you stylish. I just know you’re going to have a blog about style one of these days.
Your turn! :)
Jacket: Zara (similar)
Scarf: Nordstrom (similar)
Dress: J.Crew Factory (similar for 60% off!)
Shoes: Kenneth Cole (similar)
Bag: Marc Jacobs
Rings: Moulton (discounted for Unfancy readers)
Bracelets: Moulton (discounted for Unfancy readers)
Do overalls count?? I know they’re making a major comeback but I still look at pictures and laugh. Especially when I tied a flannel around my waist. Also, over-tweezed eyebrows! Why was I allowed to have tweezers???
Are those like workmans dungarees? We wore them in denim with one strap unbuckled!!
OMG I wore overalls (brown corduroy with Pooh on the front pocket) in college – they should NEVER. EVER. come back in fashion for anyone over the age of 5.
Ha! Agreed. In high school and college I had a denim pair and a tan corduroy pair. They were comfy if nothing else!
I’m pretty sure I had that exact same pair of Pooh corduroy overalls.
Michele R. says
I LOVE this outfit!! I laugh at all of the years I spend wearing weekend capris and t-shirt and my “good” office job capris and t-shirt! Really? Pretty much everything I wore before finding your blog, scanning other blogs, and seriously taking a look at my wardrobe and PLANNING purchases. You’re the bomb!!
Speaking of overalls; picture khaki overalls-flared (we’re talking wide flares here, if you’re going to wear flares you have to make them count)-worn WAY too often
I used to laugh at the skinny jeans trend when they were first were coming into fashion. I remember buying my first pair because they were in style, and putting them on and feeling so weird! I had, of course, been wearing flare and boot cut jeans throughout high school, and the tightness of skinny jeans were just so foreign. Now, I laugh at the fact I wore flare and boot cut jeans and think they’re awful! I live in skinny jeans now!!
The flares, oh gosh. Or wearing an oversized t-shirt and feeling really cool. Top it off with skateboarder trainers…. No, I think it’s definitely the flared jeans that I laugh at the most – and they’re making a comeback! It’s too soon, way too soon!
Steph M says
I wore overalls into Grade 9, so…1996? And I am just not getting on that wagon this time. I jumped on to flare jeans after that and never looked back. At the time, I thought tapered and straight leg jeans were the worst. (Skinny jeans weren’t even a thing!) Now I have a nice pair of flare jeans but I don’t know what to wear them with anymore! Skinnies are my jeans life, suit my body well and show off my cute shoes (!) and I am so nervous that flare is coming back in style because I don’t know what I’m going to do about that. My hope is that all jean cuts can coexist peacefully.
The other one is second-hand baseball t-shirts. I wore them like it was going out of style back in my university days. I had one karate dojo shirt that I would kill to have in my drawer again, though. I wore it to shreds.
But I feel like I’ve never gotten too trendy and a lot of the clothes I wore ten years ago I would still wear today.
LOL @ hoping jean cuts can coexist peacefully! Cant stop laughing and totally agree :)
Tania [girlwithanakita] says
Oh man. I was reviewing old photos the other day – and I fell to the white eyeliner trend. Sometimes I pair it with black lip liner and stick straight hair. It’s quite a stunning combination.
Does anyone remember the striped shirt trend? I was in high school and it was ‘on’ for a full two years, I think. They always hit at the waist, fitted, with a white collar and half button down, and it’s usually thick unflattering stripes.
I am really a fan of the loose, drapey thing happening right now. Phew!
OHMYGOODNESS! The collared unflatteringly-wide striped shirts! I had some of those. I think I wore them with a dozen tiny butterfly clips in my hair too.
Omg butterfly clips! Forgot all about them! Haha I definitely rocked those as well.
Rugby shirts! Oh my, I had tons of those! We looked like we were wearing boys clothes!
Caroline, is your dress black and white or navy and white?
Cute either way, just wondering.
Hi Wanda! It’s black + white. :) xo Caroline
I adore this outfit!! It’s interesting but simple. And what I laugh about now is my oversized sweatshirt phase. The sweatshirt dress if you will. I pretty much wore a shapeless blanket to school but hey, at least I was comfortable! Haha
Picture it: 1998, 6th Grade. Bad hair, bad eyesight, bad fashion sense. It was right when 70’s fashion thought it had gotten its groove back. It hadn’t. These days I laugh about my worst outfit of all time which was a lavender, baby blue, and mint polyester, tie-dyed, short-sleeved, button-up OVER (yes, over) lavender corduroy overalls WITH embossed, white platform sneakers. To top it off, I had a long perm.
Oh yes. I was cool.
OMG! This. Trumps. all.
When I was in high school I had this pair of genuine vintage GIANT flare Levi’s bell bottoms. I LOVED them! I wore them with clompy platform sandals and glittery blue and green nail polish. I’m actually not embarrassed about it, though. I enjoy wearing skinny jeans and leggings now, but I do miss bell bottoms (actually I still have a pair or two stashed ’cause I love them so). I AM slightly embarrassed about the big, puffy, lacy, floral print dresses…
Oh, also with the bell bottoms? Toe rings. Lots of them.
Toe rings! Ah! I had so many. *shakes head* :) xo Caroline
I look back on the early stages of my blog and am totally embarrassed by some of the outfits, it I think a lot of it is an evolution of style….streamlining, trying, tweaking…..it all has helped me figure out what I really like now, as well as what flatters my shape. I love this outfit and adore black tights and boots, I could pair them with a out everything.
I hear ya, Ginny. Totally feel like I’ll look back on the early days of my blog and just shake my head. On the other hand … growth — in any form — always deserves celebration, so it’s cool to be able to look back and see it. :) xo Caroline
I laughed the other day because when looking through photos with my husband, I noticed I wore my Arizona Birkenstocks 24/7 on the few days a year that I didn’t wear a school uniform or dance leotard. Now they are “back” in style.
Can we talk about style? Back in my day…high waisted jeans AND shoulder pads in everything was the style…UGH…
In college I was into the rave scene and everyone wore jncos – GIANT pants. I had pants where the cuffs were as big as the waistband!! Not to mention copious facial piercings, hot pink hair and cropped shirts.
I’m a professor now, and my students would loose it if they saw me when I was 18!
ME TOO!!! JNCO jeans with huge legs. HUGE. You could smuggle a family of 5 anywhere in those things. I think i even had a pair with a secret crotch pocket where you could REALLY smuggle something illicit!!! I found them in an old box in the closet the other day…AHHHHHH the memories. So glad smartphones & FB didn’t exist back then…..muahahahahhahahaha!
Can’t say I didn’t rock the JNCOs. Although I don’t really regret them. I just remember feeling so comfortable and relaxed when I wore them. Like, no one will make fun of me if I wear these to school (I was in 8th grade so I had very little self esteem and cared what people thought of my clothes). But man I’d rock those jeans again….just to see if they’re still fit me. Ha!
Oh and the blue high-lights did match the jeans so well.
Great outfit! I love that birks are back in style – so comfy! However, this time I am wearing them sans wool socks!
Can anyone recommend a good real leather jacket? I’ve been eyeing a madewell one and one from aritzia. It would be a major purchase for me so I’m hoping for feedback.
In junior high one of my go to outfits was a pair of mens boxers as shorts, saltwater sandals, and knee high tube socks. why…..
Aaah! I wore the boxers as shorts, too. Why??
I love this sentiment! I was thinking something similar last week about how much I feel my style has evolved in just the past year. And how I still feel ridiculous posting style advice on my blog. Me? Fashionable. Surrrrre… But life really is too short to get indignant about “fashion faux pas” — or anything really. Hm… for me I think one I’ve let myself off the hook for was wearing camo pants (like legit army surplus ones) to EVERY high school football game. *Sigh* Oo oo! Or fake hair that imitated a fancy pretty bun? Yikes.
Crop tops! Or really, in my case, shirts that were too short for my torso, so they didn’t reach all the way to my pants.
In high school I had a seriously hard time with clothes, and one of my least favorite parts of the day was in the morning when my mom would tell me “Your stomach is showing, you need to go change.” I resented her so much because hello! (said 16 year old me) They don’t make shirts that long, duh, this is all I have!
When I got to college I proudly wore all my too short shirts and thought I looked super sexy and that my mom was, as always, wrong.
Now I look back at those pictures and I know that my mom was, as always, right. I didn’t look sexy. I just looked like my clothes didn’t fit.
ha! for me it was probably dresses over jeans, but before there were skinny jeans on the scene. And the dresses really weren’t short enough for this look, the jeans were straight leg and not flattering. yep, just seems really bad.
Lol!! Ah yes. Many. I have many moments to look back and laugh about. Hmmm…hard to pick just one, but perhaps walking around in a navy blue skirt for several months thinking it was black. Thanks to my roommates for the fashion help they attempted to give. But, of course I was too proud to listen. :P
Victoria B says
In 6th grade I wore plaid shorts with a solid color t-shirt from the boy’s department. Every day. I had a large range of colors/patterns. Haha!
High School- I wore super baggy sweatpants with basketball shorts underneath, a hoodie, a (very) messy bun….and giant dangly earrings. Every single day. And I was SOOOO happy about it.
I will say I *think* I just may have started the dangly earring trend though
I LOVE this outfit! I really want a dress like that. I bought a striped one from New Look but it’s bodycon fitting. I want something looser for a more casual look
The year was 1993. 7th grade me slipped into a pair if HUGE bell bottom jeans as my mother looked on in disbelief. I marched confidently right into my middle school, certain this was going to be the beginning of a new/old trend. I rocked those jokers like there was no tomorrow. However, the trend didn’t seem to catch on ’round these parts. Not sure what the rest of the world was doing as there were no fashion blogs for guidance. Eventually I settled into a decade + of flared and boot cut jeans. I still have one pair of boot cuts stored away, after all, skinnies won’t be around forever! ;)
PS – Caroline, I accidentally posted today’s comment on yesterday’s … sorry!
I went to high school in the early 90s in Portland. We wore Doc Martins, tights under men’s boxer shorts & plaid shirts. It was all about the angst. Or babydoll dresses (hello Courtney Love) with tights & Docs. Then I went to college in the mid-late 90s & we were all about overalls, JNCO jeans (HUGE LEGS), platform shoes and glitter. SO. MUCH. GLITTER. Remember the Delia’s catalogue? That was us. Little plastic hair clips, candy necklaces…..and don’t forget the glitter!
I have some particularly incriminating photos of myself rocking butterfly clips like there was no tomorrow. They COVERED my head…why? :) :) And, you know something funny? Back when Doc Martens were cool, my sweet parents wouldn’t spend that much money on a pair of shoes that I was going to grow out of in a few months, so I always felt “uncool” with my fake Doc Martens. I’m ALMOST tempted to get a crazy pair now, just to fulfill that dream of being cool. Hah! :) xo Caroline
doc martens are not the same now, unfortunately. they used to be so well made. the pairs i had lasted forever. now they’re cheaply made – don’t waste your money :(
I bought a pair of Doc Martens in 2001 and have been continually wearing them ever since. I wore them to work in a bakery daily for two years in there even. They are still going strong. As you can probably tell from this story, fashion is not my strong point. But I was still excited when I saw that they were back in style!
In 6th grade I had 2 pairs of sparkly jeans (royal blue and black) that literally had glitter ALL over them…courtesy of limited too! I loved them so much though, so I can’t be too embarrassed by them. I seriously got glitter everywhere! Oops :) xx…love this outfit by the way!
I’m loving that jacket! Oh man… I have so many laugh/cringe-worthy outfits of the past… super baggy jeans and slip on sandals with socks! :(
I was in HS in the 80’s so feathered hair, bell bottoms, dolphin shorts, Dittos…all that. I just had this conversation with my 10 & 13 year old DD’s this morning. The youngest made a comment about how she could not believe she used to wear some of the things she did 2 years ago and how stupid she looked. I made the point that styles and taste evolve and that you never look stupid – especially since the others were wearing the same thing. I made them promise to never say that again – about looking stupid. We all evolve and trying out trends.. is what being young is all about.
Haha funny! I hate looking back on pictures from the past, my hair is ugly or I did some weird thing with my eyebrows… Lol! But you’re right, life’s too short.
Ohhh man, our college-selves were unfortunately dressed twins. I was allllll about leg warmers and men’s cargo shorts (*always* from Target) in ~2004. yikes!
Haha no way, Erica! Ah, SO glad I wasn’t alone! Twinsies! xo Caroline
Chopsticks in the hair, sarongs as skirts, massive chunky platform shoes (oh wait, those came back in style).
Suffice it to say, there were a few looks back then that aren’t in the current rotation.
Chopsticks in hair — YES! :) xo Caroline
I LOVE that outfit. love love love love. The multiple blacks & whites & golds work so well!
I remember the outfit I wore to hear my college boyfriend’s band play for the first time… embellished jeans, a neon green vintage polyester top, and VERY ugly clogs from J. Crew. I thought I was so chic and now it’s too funny.
All of these comments have been so fun to read.
Caroline, when you breaking out the colorblocked sweater? We haven’t seen that one yet!
Hi Laura! I know right! I’m having a blast. :) It’s just now getting cold enough now, so it’ll come out soon. :) xo Caroline
Teenage me had a tie-dyed dress with a fairy painted on it. I am no style guru now but I know I at least make better decisions than that!
Caroline—I love your humbleness and ability to laugh at yourself. I use to wear polo shirts with popped collars and pearls. Oh my. The 2000s. What a great time for style. Laughing.
Thank you for providing endless inspiration!!
I forgot about my camo shorts phase until you mentioned it. With a black studded belt…woof. So bad! Loved the podcast, especially the portion about the negative mind chatter. Gotta remember media is not the norm, it’s just another product that is sold. You definitely keep inspiring me. Love your blog!!
I love this outfit!!!! Also, I completely agree with and love your double-fun philosophy. I think we can take more risks with our clothing when we view it as fun and changeable. I kind of feel like all the stuff I want to laugh at in my past is coming back in style in a new form, so I don’t know what to say….I did wear the multiple watches on one arm, but I still think that was really fun and I’d probably do it again if it came back…or I could BRING IT BACK!!! ;0)
Steph M says
Steph M says
I…also just remembered that I once had a bodysuit. Yep, with crotch snaps.
Kathy Mader says
In college we wore blouses with great big bows tied at the collar…yep, we were pretty little packages waiting to be untied. UGH. Preppy was really in, which wasn’t too horrible as it is somewhat a classic look. Being a teenager in the 70’s though, it doesn’t get any worse than that style-wise. Hip huggers, bell bottoms and, to top it off, long stringy hair parted in the middle and covering most of your face. Mr. IT comes to mind.
Hi Caroline, I recently discovered your blog and I think it’s awesome. I’m a college student and I’ve always been really interested in fashion / building my personal style and although I think I’ve always been a minimalist at heart, I never really knew how to define it or how big of a following minimalism had. Anyways, I really admire your lifestyle and I have a question for you. The holidays are coming up, and something that really stresses me out every year is purchasing / making presents for all my loved ones. Do you have any advice for a minimalist approach to holiday gifts? I absolutely love giving presents but I don’t like contributing to the American habit of excessive consumerism and I don’t like the idea of giving people gifts that they will never use.
Erica M says
Someone else on here mentioned Living Light by Coco, check out her youtube channel, good stuff. If you feel comfortable enough with your loved ones you can ask not to exchange gifts. My husband and I are giving each other a gift but not our families, partially because we live across country so our gift is spending money on flights to be together, that is after all the most important part. They understood and agreed :) I do like gift giving like you and I am drawn to making and giving consumables/edibles. You could make apple butter, candies, baked goods etc and package them beautifully as a present. Or make a body scrub with salt/sugar, oil and essential oil and package it in a cute glass jar. Recently my mom got me a handmade bar of soap and delicious chai tea from her travels. I loved them and used them up! Plus no guilt from a present sitting around that you don’t like/use. Hope this helps :)
Oh man! There’s too many to count. I was a big fan of Juicy Couture track suits, I had a couple of them and loved wearing them to school. And it’s even worse because I think back and they were expensive, especially considering they were velour. Not the best look…
I used to feel “sexy” with my Levi’s 501.
Now, when I see photos from that age… OMG!! I had a Steve Urkel look like!!!
Sheila D. says
Ummm…skater jeans/parachute pants?!!!
Growing up religious= cheating that modest is hottest game. White short sleeve tees under tank tops and leggings under mini skirts. Accessorize with sequin scarf belt.
I’ve since learned how to stay covered and still look on trend:)
Hmm….so many mishaps – but let’s see which stick out. Velour sweat suits, bell bottoms with smiley face’s on the bell, leggings under mini skirts in College, oh my, I can’t, I’ll be here forever LOL.
Because I always went to private schools with uniforms and had gymnastics in the evenings and weekends, the majority of my fashion faux pas were either in summer or in the accessories department. Definitely guilty of tiny little cornrows, giant butterfly clips, and chopsticks in my hair. And I would wear anything from Limited Too or Mary-Kate and Ashley Olsen’s clothing line without asking.
I’d still wear anything from Mary-Kate and Ashley without asking.
Erica M says
Oh gosh in high school I wore shirts that were too short (partially because it was the style, partly because I was too tall for them!) and jeans/overalls that were too big. I thought it was the “artist” look somehow! ha!
Man! All the wonderful thoughts that went through my head just now, reading all of these!
I don’t think I regret any of my fashion decisions. There are one or two that I probably wouldn’t do again, given the choice. I remember my neon windbreaker and matching shorts. I remember my kangaroo shoes. I remember the crazy, knee-length, multicolour dress with beads and ribbon sewn all over it. I remember my giant purple sweater that I cut up so that it only had one sleeve and really wide neck. And the knee socks! Oh, and the hair cuts I gave myself… Well, those were special. Ha ha!
Way more things are fun rather than embarrassing to remember. :)
Oh, gosh, and those butterfly clips! The big plastic ones and the little springy ones!
High-waisted jeans. A/K/A “mom jeans.” And yes, I know they are once again “having a moment,” but seriously. Even when you look at pictures of models trying to rock them, it fails. They make MODELS look, well, larger. So what hope do the rest of us have?
I wore paper-bag-waisted jeans in the early 90’s and thought I was so beyond cool. And perms, of course. I also used Sun-In on my hair, which left it the delicate texture of a Brillo pad. Those were the days!
Does anyone remember hyper-color shirts? You know, the ones from the early 90’s that changed from one color to another with heat? They were *the* thing in junior high. I remember feeling so cool headed to the first day of 8th grade in my all new stone-washed jeans, hyper-color shirt, and denim jacket. Of course, since it was August, it was much too warm for the jacket. But it was new and I wanted to show it off (that being what the first day of school was all about), so I wore the jacket as long I could stand it. And when I couldn’t stand it anymore, my ridiculously ill-concieved shirt let everyone see exactly which parts of me were that most overheated in varying shades from blue to pink. Why did anyone ever think such shirts were a good idea?!
Sooo many… flare/bell bottoms (I had two pairs I especially loved – one in snakeskin print on jeans and one in leopard print on jeans), chopsticks in hair, springy butterfly clips, overalls (my friends and I would wear them with one strap unbuttoned and off the shoulder), roll on body glitter, baggy track pants with stripes up the side, shirts that changed color with heat… I recently found a ton of photos of me in middle school wearing baggy camo cargo pants with a black studded belt and a babydoll top…
I wear a very similar outfit constantly! It is my favorite! There are just too many old fashion favorites to even mention. I love looking back at photos and remembering how I felt so stylish and put together, but it’s just so painful now!