Already Prettypoll: Dressing Our Imaginary Selves

Closet orphans can come from many sources, but many of them are purchased for our imaginary selves. These versions of ourselves can wear four-inch heels without tripping, can make use of a gorgeous down coat even though it never gets below 50 degrees, and can safely wear shoulder-duster earrings without risking having them tugged out by a wee one. We see things that we adore in theory, and buy them before admitting that they’re never gonna work in practice. It’s a behavior that can be eradicated if carefully monitored, but even those of us who are mindful occasionally slip up. (Says the woman who lives in a city with six months of brutal winter yet still can’t resist mid-weight jackets. Which get about 47 seconds of wear PER YEAR, if I’m being honest.)

Do you shop for your imaginary self? What do you buy for her? Are the things you wish you could wear for seasons or occasions you just never experience? Or are they due to a lifestyle shift? How does your imaginary self dress?

  • phira

    My imaginary self wears really short dresses and adorable 3-inch heels. And then I wonder why I don’t like the majority of dresses I own, or why I never have a pair of comfortable formal shoes!

  • ModernSauce

    Uh oh… I’m a BIG shopper for imaginary me! It started as a shoe issue – too tall, hurt, but look so darn good I NEEDED to have them in my life even if I just wear them to do the dishes sometimes. Then I noticed I bought a lot of clothes for imaginary me too – mostly items that I felt were too flamboyant or too edgy or not “me” even if they really spoke to me. Is it the most practical thing? Probably not. But I realized having those items in my closet actually gave me a bit more confidence to experiment and maybe even wear them out in public sometimes. I need a little fantasy/escape in my life even if it is just sartorial! ; )

  • Cynthia

    It could go the other way though. Last year, I started buying clothes exclusively for my imaginary self, who is becoming an artistic witchy woman type in her middle age, hoping to end on the “distinguished” end of that trope, and, for the moment, it’s working out swimmingly.

  • ako

    my imaginary self wears funky striped leggings and cute skirts effortlessly. I however, can’t seem to get that look together.

  • Annie Mouse

    Imaginary me wears a lot of dresses – especially sheaths! Because that’s how you look polished and grown up!

    Reality me passes over those dresses 98.7% of the time, because they never quite fit right in the bust AND the waist AND the hips (even after altering, which Reality Me also has a tough time getting around to) and because it’s just… not me. I always end up feeling awkward and overdressed. Reality Me wears separates, because when you have the torso of someone who’s 6’3″ and the inseam of someone who’s 5’2″ (I’m not exaggerating), it just makes more sense.

    • Annabeth

      I’m in the same boat – I’m 5’8″ and wear petite pants, which means I have this incredibly long torso. And I, too, love dresses, but have regretfully realized that separates are more likely to provide a good fit.

      That said, I can find some dresses that work, and I actually love casual dresses and will wear them as often as possible! I just wish so many dresses these days weren’t made for women with even shorter torsos than the norm. (Seriously, some of these dresses – I can’t imagine that the waist line wouldn’t hit the boobs on most women!)

  • walkercreative

    My imaginary self wears clean crisp white year round, lots of silks and stiletto shoes. My real self has three kids (and has destroyed many silks and white suits) is clumsy (spills any food with a deep color and works off of a gravel road) and has fussy feet (that can’t walk two steps in stilettos). Once I designed my wardrobe around my REAL self, things were much easier. Perhaps I’ll get to lounge in silk whites during retirement on a beach somewhere! :)

  • LinB

    Imaginary Self is about five inches taller, fifty pounds lighter, and twenty years younger than Real Self. I’m doing much better lately about dressing Real Self, by buying and trying items from local thrift stores. It takes a longer wearing than merely trying on things in a dressing room at the store to get a real feel for what works in real life, I’ve found. At less than $5 per item, I don’t feel cheated if something ends up NOT working for me. It just goes either right back to the store, or into my sewing pile to scavenge its fasteners for another use. I’ve found that some colors and styles I would never have considered in the past are actually quite useful in my wardrobe. Still have problems letting go of things I spent many hours sewing for myself, even if they are horrible to look at and feel nasty when I wear them. sigh.

    • catherine

      Lin, knitters have the same problem. You can knit ugly, ill-fitting monstrosities that sit on your shelf for years, because you while you won’t wear them, you worked too long on them to get rid of them.

      • Anne

        I have half a dozen of these hand knit sweaters staring at me every day! Someday the Real Me is going to donate them.

  • Tutti

    My imaginary self loves pencil skirts!

  • Kim

    My imaginary self wears pointy toed suede heels and other assorted high heels. My real self ends up wearing these shoes around the house only and wearing moderate heels around town. Love those shoes though! Maybe someday my imaginary self and real life self will merge.

  • Emily

    Imaginary me is a super funky artist and wears boyfriend jeans with tunic dresses and layered sweaters and sequined t-shirts and really cool boots. Until I saw a picture of myself and realized that with my figure and height and age (extremely hourglass, very tall and over 40) that what looked fantastic in my head made me look a bit like a bag lady. I am not “cute,” so why was I dressing that way?
    Over the past year I have been cleaning out my wardrobe (I gave away or sold more than 50 percent of my wardrobe) and starting fresh as my real self: a 44 year old mom to teenaged boys who is also a writer and part-time university prof and hates anything tight, has sore feet and looks best in streamlined clothes. With cool boots. I’ve slipped up occasionally, but it’s been a lot easier to get dressed.
    Imaginary me: sequinned tops and sweaters, vintage dresses, cute cardigans, 40s looking shoes with heels.
    Real me: slim jeans, wool blazers, washable dresses and sweaters that have a little edge. Nothing that gets caught on my knitting needles, please!

  • Becky

    My imaginary self swims, hikes, and goes to the gym a lot more than I do!

  • K Hoffman

    My imaginary self loves to buy dresses—especially cocktail dresses. I have several in the closet that still have tags on them. But if I’m ever invited last minute to a fancy soiree I will be ready.

  • Heather

    wish I’d bought more for my imaginary self this winter, when it got COLD and I didn’t have enough warm clothes to wear. Sinc e everyone else in my family has moved north, I now have an excuse to buy these, too.
    Outside of that, I love my wardrobe, and I’ve spent years planning it as I’ve had to rebuild it due to weight loss.

  • Jessica

    I buy fancy cocktail dresses for my imaginary self, despite having nowhere to wear them.

  • Connie

    I do find myself looking at things that are now inappropriate for my life and my figure. I used to have an hourglass, which has filled in over the years, I don’t know how to dress myself in this new shape. I find myself looking at things appropriate for office jobs when I no longer have one. I do a lot of thrift store shopping and lately bought the cutest dress but it is a size 20 and I don’t think I will be able to resize it to fit me. Oh well.I guess it could make it into a skirt.

  • bubu

    You have really hit on something here. Imaginary me love high heeled pumps and dresses – real me is always freezing and walks a lot, so wears a lot of low heeled boots and pants or tights with skirts. I have had a lot more luck controlling imaginary me since I developed a shopping list that lives on my phone – items I identify as needing when I’m actually trying to get dressed day to day. I went shopping a few months ago, and tried on about a dozen heels, marveling at how fab they looked, but forced myself to by the low-heeled boots I’d been wanting and needing for two years – and now wear all the time.

  • Annabeth

    I would say that this is the #1 thing I’ve gotten better at in the past five years, fashion-wise — I used to shop almost exclusively for imaginary me, the version with the long, swanlike neck, long legs, and an average bust. By paying a lot closer attention to my body, my proportions, and how different types of garments actually fit on me, I’ve been able to shop for real me much more productively.

    Every once in a while imaginary me still gets a new item of clothing – like this amazing peacock-blue shantung silk evening coat I found on sale for about $40 in a thrift store. But when that happens, I make it a personal challenge to wear that item. (And I might wear that coat tonight, actually!) Sometimes the gap between imaginary me and real me can be closed, at least for a night.

  • Annette

    I am getting better at curbing my imaginary self, but she keeps coming out to play. Her favorite thing is increase my fabric stash and/or pattern stash. Thankfully the real me can use most of those items. I have started letting imaginary self play with my stash and then the real me takes over and edits the results into something the real me will wear. A good example is some real nice rayon challis that imaginary self wanted to make a one shoulder long dress suitable for resort wear. Real me is making a very nice long skirt with enough left to make a summer top. Both pieces I can wear a lot more than the dress. Imaginary self is good at picking fabric so I let her.

  • Lisa

    My imaginary self wears vertiginous heels and vests. In reality, I hate it when my arms get cold and I need flats or walkable heels as I don’t drive.

  • Lisa

    I used to do this, but that’s one good thing age gets you. No more imaginary self dressing. My real body doesn’t like it.

  • Lisa

    P.S. Love the new look of your site, Sal! So fresh and clean.

  • Michelle…

    My imaginary self works in an office and wears beautifully cut suits with silk shells and 4 inch heels (Louboutin of course dahling).

    Reality me works in a soil lab and wears jeans and a t-shirt (practical and no “floof” to get in the way) under my labcoat plus flats cos I’m on my feet all day.

    I really struggle when I shop. Practical is boring. I try to think of ways to jazz it up but always come back to the tried and true.

    • Yolanda

      I work in a soil lab too and have the same problem! I love buying cute clothes but never wear them to work because they’ll just get soil and/or plant material on them by the end of the day. Thus, I have way too many “weekend”/going out clothes… Even then they don’t get worn that much because I am ALWAYS cold and for whatever reason my definition of “cute” is generally too flimsy to keep me warm.

      Answering the general question, fantasy me wears only skirts and dresses with really funky tights and/or thigh-high socks and/or basic tights with cool legwarmers. Too bad I need to wear pants in the lab….oops.

  • NeenaJ

    i just pre-ordered a pair of Vince harem pants for my imaginary self. Luckily, Nordstrom has an excellent return policy in case my real self hates them!

  • Tara

    My imaginary self is more conservative than my reality self! As a consequence, I have more brown clothing than I ever feel like wearing …

  • Cari

    Imaginary self imagines she is actually going to get around to making up all those patterns she’s stashed with all that fabric she’s stashed. That said, I do a way better job of making things I love to wear than I do buying them. Apparently my real self loves to dress a little quirky, and it is hard to find quirky Ready-to-wear that feels like me. Shoes are still my downfall. I could easily collect a closet of 4 inch heels I can’t walk around in, just because they are cute. Imaginary me never has foot/knee/back pain and really never sprained an ankle when she was 21 by falling off a pair of stilettos when she sat down with her legs crossed for too long and her foot fell asleep.

  • Shawna

    Yes, and I am beginning to explore this issue on my blog. My imaginary self is a sylph and my real self is tall with a soft hourglass figure that can look blocky without enough definition. Problem: I like flowing, loose clothes. So my personal taste in clothes doesn’t fit with the actual body I have. I’m all boho when I should be bombshell.

  • Patti @ NotDeadYet Style

    I buy clothes as if I were a New Yorker and it makes me happy! I am working towards being one and the clothing puts me in the mood. xox

  • Allison

    My imaginary self apparently doesn’t exist below the waist. I’m short and hourglassy and have a hard time finding pants I like, so I don’t look and I don’t buy. As a result, I have, right now, three pairs I can wear. My real self does have legs and really needs some pants.

  • Beth

    Imaginary me spends a lot more time in the boardroom and at fancy dinners than real me. At least i do virtually all of my shopping for imaginary me at thrift shops!

  • Cornelia

    Thankfully no more of that. It was a long and winding road, but now all this money is spent on the real me. And now, if that t-shirt costs some serious money, I do not feel a bit of guilt either. Win-win.

  • Pretty pink

    This is just what I needed to read now! Ordered a gorgeous red purse I loved it- it is for my imaginary self who attends high end parties 😉 and goes on fancy dates with the hubby. Good thing is – sometimes I can buy more of such items from online shops that offer free return shipping. I can stare and look hard at the item of desire for a few days till it sinks in how it is not in sync with my every day real life and then it can get returned..

  • Chris

    My imaginary self wears period clothing of famous warrior women, both real and imaginary. Think Elizabeth I fighting with her soldiers, Boudica, the Trung Sisters (Viet Nam, 1st century AD), Xena from the TV show, Tarna from the animated film Heavy Metal.

  • julie

    My imaginary self and real self blended mostly a few years ago. The real self was a mostly stay-at-home mom who wore jeans, t-shirts and awful practical shoes that could be used for pulling toddlers out of mud puddles etc. The imaginary self wore expensive heeled boots and shoes and carried a briefcase and wore make-up.
    My real self does all those things now, and lucky I had some items in my closet that I could wear when I went back to work outside the home, but the imaginary self now accessories beautifully, is always wearing a scarf and necklace and great earrings, while the real self is trying to tame her hair and running out the door without the great scarf and necklace. My sweetheart solved my earring dilemma by gifting me with some beautiful new diamond studs on Valentines Day, so now I wear them day and night.
    My imaginary self lives on a tropical island part of the time though judging from the bins of summery maxi dresses that I own for someone who lives where is literally winter for half of the year. sigh

  • Jen

    I buy for a job I don’t have, but hope to someday. Meaning, I teach one-year-olds, but I love dresses, skirts, nice blouses, slacks, etc. I have found I can wear certain “casual” skirts or dresses at work, although even then I’ll get comments asking why I’m so dressed up. They do get some wear at church or out on the weekend. But jeez, most of my work clothes look like they’ve been through a war zone while my “nice” clothes are hardly worn. I’m applying for more management type jobs, though, so maybe they’ll get to come out and play soon.

  • Angela

    Imaginary me loves blazers and pencil skirts with kitten heels. Real me prefers drape cardigans knit tops and trousers. With wedge heels lol

  • Texas Aggie Mom

    Love this thread – it’s reassuring to know I’m not the only one who’s Imaginary self is much better dressed than my Reality self! Even when I was struggling to leave a bad marriage, and later as a single mom, I would buy clothes for Imaginary Me and stash them at my best friend’s house. As she wisely said, “You don’t want those clothes. You want a new life that requires those clothes.” Twenty years later, I still have most of those clothes, most of which are party wear for the imaginary parties Reality Me has never attended. Over the years, I have gotten better about finding clothes that Reality Me loves and can actually wear, but the fancy pieces, most of which still have tags, are waiting just in case someone invites me to something fabulous. You never know…

  • Veronica

    My imaginary self loves fancy dresses and heels, real me rarely wears the dresses and heels. I have kids to chase after and do not wish to break anything.:) If I get any chance to though, I will wear them.

  • Distracted Frog

    Imaginary me loves the look of leggings and used to own four pairs.
    Real me never wore them because they make her sweat (even in the dead of the Canadian winter).
    Imaginary me loves sparkly tops/dresses.
    Real me doesn’t wear them because they make her itch.
    Imaginary me loves the look of corsets (pretty ones with embroidery), forties-style underpinnings, and lacy bras.
    Real me can’t tolerate any foundation garments except cotton undies and a natural-fabric slip due to sweating/itching.
    Imaginary me thinks dry-clean-only garments are gorgeous.
    Real me stashes bags of clothes-to-take-to-cleaners in random places and forgets about them for years.
    Imaginary me is controlled and impeccably accessorized with not a hair out of place.
    Real me has things falling off, hair in all directions, and mayo on her skirt.
    Imaginary me is Betty Draper.
    Real me is a lot closer to Betty Suarez.

  • Charlene

    My imaginary self lives in London or Paris where I browse the museums, go to theater openings, etc., etc. My real self lives in a little Texas town where I teach school and where jeans and tees are the norm. But I actually shop and dress for my imaginary life, with the dresses, skirts, scarves, jewelry, heels, and yes, even hats. But it’s all good. I love my look and get many compliments. I think maybe because I’m comfortable and confident with what I wear, I find acceptance and even approval from others.

    • TexasAggieMom

      I applaud your courage and your convictions! I am typically considered overdressed, even in a much larger Texas city (Fort Worth – large, but laid back to a fault.) Do you have any standard comebacks for those who question your choices? Or maybe you are so supremely confident that you are applauded, instead? Either way, I have to remind myself that if you can do this in a small town, I can surely get better at it in the ! Wish you could post photos of some of your favorite outfits. Do you have a blog or are you on Pinterest, by any chance?

  • Dianne

    My imaginary me is somewhat boho/cowgirl/English equestrienne/hard-edge rocker chick. I love the floaty-small-floral print-under-jean-or-moto-jacket look, but I find it difficult to find pieces that fit my 60-yr.-old body. So I make do with skinny, dark-wash jeans, t-shirts or tanks under cropped, fitted jackets (that won’t button, if they fit my shoulders). Boots (tall and ankle height) are a staple, but stacked, not stiletto heels; some are cowboy boots, others flat-heeled riding boots, some have 2-3″ stacked, blocky heels. Jewellery is a mix of chains/pendants/ glass beads re-purposed from thrift-store finds. I don’t have a lot of closet orphans, but on the other hand, I don’t have much to wear to a funeral. My hardest season is winter; we have had a couple of months of -35 or more wind-chills, and it is difficult to be stylish. I guess I am fairly happy with my current wardrobe/style, but am a bit bored, and would like to expand it a bit.

  • Andrea

    I shop for real me but love to sew for imaginary me. Last year I forced myself to focus on sewing for real me since I have less time to sew than I used to and honestly … boring. This year I’m embracing the full-skirted 50s dresses imaginary me loves … because I don’t have that much time to sew anyhow, so what the heck. Maybe when I get tired of looking at all those unworn dresses in my closet I’ll sell them on eBay.

  • Sue

    My imaginary self goes to a lot of fancy events calling for cocktail dresses and pretty jewelry.

    My real self mostly goes out for burritos.

    • 33

      haha i did the same, could not say not to a pretty formal dress or any item that sparkles. in reality i never go to one black tie event and haven’t been to any wedding in decades.

  • Maya

    Imaginery me loves skirts! Real me hates skirts and prefers to keep my legs nicely covered in pants. It was tough to clean out my closet recently and realise I had about 20 pairs of skirts, most of which I’ve only worn once or twice at most. In the end I only kept 2 and am trying to get real me to wear these every now and then.

  • SEC

    I am in the process of weeding out my wardrobe in preparation for a move back to the US after 11 years overseas. Items getting tossed include a gorgeous red silk trench (never worn in 10+ years), graphic Ts, colorful rewsort style sundresses, and all sorts of colorful cute ballet flats. My imaginary self is still in her 20s in NYC, funky and going out to clubs. The real me wears has three kids and a demanding job, so in reality I adopted a uniform of a black or gray cardigan sweater with black or blue pants or skirts every day to work. On weekends I mix it up with slim cut jeans and maybe a pullover sweater. But I am holding onto my bright yellow knit blazer, my bright purple dress and a few other colorful items — because maybe the real me will become more colorful if I try harder…

  • Melanie

    I love your new blog design. But then, I loved the other one too…
    My imaginary self, she’s demanding, by golly, high power executive wearing only pinstripe pencil skirts, ties, and impossibly high heels, and feminine, chiffony, floaty, ethereal. The meeting ground? Grrr. Still figuring it out.

  • Susan

    Sometimes imaginary me takes a bunch of stuff in the fitting room. Then real me laughs her ass off. Imaginary me pouts all the way home.

  • julie

    @TexasAggieMom – the real me is often “overdressed” due to the extremely casual nature of the small northern rural towns where I mostly work and live. At first, people kept asking me where I was going, or what the occasion was, and I always answered, “because it is Tuesday” or “the occasion is my life and I like to dress for it.” and now no one asks anymore, it is normal for me to be wearing a dress and heels when everyone else is in yoga pants, sweat pants or jeans.

  • Aya in Couturgatory

    It took me several years to figure out the reason I was always shivering violently was I kept buying light and midweight jackets when I lived in a place with 90+% humidity, 15 mph winds, and no sun most days.

    I still like the look of light and midweight jackets so much. >.> I just started putting big warm coats on top of them and long-sleeved layers under them.

  • Angela Moore

    Imaginary me is able to scale down her wardrobe to a tiny capsule and eliminate all excess. Minimalist to the point of owning one silver bangle and only one bag or purse. Ha! Imaginary me wears mostly dove grey and pale nude and pink, sometimes with black leather…even to breakfast on a Saturday morning. Imaginary me needs several cocktail dresses and business suits even though her current job is way more on the casual end of the continuum of business casual.

  • f.

    See, I just started making some concessions to imaginary me (Formal shorts, big cable-knit sweaters, form-fitting pencil skirts, heeled boots) and… turns out she was the real me all along!

  • Molly

    My imaginary self is myself back in high school, with slightly more education about figure flattery. I’ll be thrifting and find the perfect thing for myself in high school, which looks a bit too young for me now, and I’ll have a really hard time passing it by. Lots of bright, trippy patterned shirts made of polyester. I like my fabrics natural these days, and my clothing is a bit more adult, but it’s always tempting to stumble upon something my 16-year-old self would have loved.

  • 33

    I am guilty for buying coats. they never get good use in Los Angeles (the opposite of your dilemma).
    I am guilty for wanting to emulate “fill in the blank”. This resulting having a closet with 4, 5 different style directions. I feel bored if I had to choose ONE direction for the rest of my life.
    My biggest imaginary self is a tall and lanky model. She can pull off any garment and any combo. She’s fabulous in big boxy structured top and billlowy wide leg pants. She’s effortlessly chic rolling out of bed.
    The plus side is I am getting better at controlling my tendency these days. Being older sure does help. I realize that no matter how skinny I am, I will never be a model. I realize that not every style suits my body, life style, and personality. I now know what to invest, what to save, and what is priority. I wish I knew these when I was in my 20’s and 30’s but it is never too late to mature, isn’t it?

  • Leah

    Imaginary me is a minimalist with a paired down closet of expensive basics and only a few pairs of shoes and purses. Real me is not a minimalist (AT ALL) but is starting to get there by only holding onto pieces I really LOVE.

    Imaginary me loves to wear high heel shoes. Real me has super problematic feet and has to wear orthopedic shoes and/or comfort shoes.

    Imaginary me loves pea coats, field jackets and leather jackets. Real me lives in Florida and virtually NEVER gets to wear them!

  • Yipp ee

    I keep trying to buy delicate items that require dry cleaning, being really careful – that once I buy….I never wear…bc of those very reasons!

    Real me likes her dresses, cardigans, zip hoodies & yoga pants (& uggs).

  • shannon

    Oh gosh, this is a brilliant turn of phrase! I catch myself shopping for my “not-plus sized” self, my “doesn’t hate walking in heels” self, and my “loves wearing bright patterns” self every once in a while. I’ve gotten better about catching it before forking over my cash, though, so that’s something. Part of it is wishful thinking, I think, and part of it is historically inaccurate optimism (along the lines of “well, I used to be that size” or “I hated that last pair of heels I bought, but these are totally different and will be super comfy and they’re on sale!”)