In Fashion, is There Hope for the Hopeless?

Last night after work, I decided to treat myself to a little shopping excursion. With a Visa gift card from my parents (a birthday present) burning a hole in my pocket, and a definite dearth in weather-appropriate garments in my wardrobe, I was feeling optimistic. And then I arrived at the store.

I don’t know when exactly I lost all confidence in my ability to dress myself in a way that could be considered even remotely fashionable. Indeed, I’m not sure I ever had that confidence to begin with; maybe the real problem is that in recent years I’ve just become painfully aware of how hopeless I am when it comes to finding clothes that look good on me and fit together to find a coherent collection and, ultimately, personal style.

Of course I understand that “personal style” is not the end-all, be-all goal when it comes to fashion. But that doesn’t stop me from wishing that I had one. It would just make life so much easier, to have a sense of what kind of things I have in my closet, how they go together, and what to do when they need replacing or upgrading or accessorizing. Instead of having this sense, though, I find myself going to stores in the hope that I’ll have some sort of revelation–maybe I’ll see something I can’t live without, and things will build themselves up from there. You may be surprised to learn that such a scenario has yet to occur.

Last night’s excursion consisted of me wandering around a bit aimlessly, trying to figure out what it was I should be looking for, and having an overwhelming sense of being in over my head. I can put an outfit together, but only for my mind’s narrow conception of the most ideal body type: tall, willowy, etc. When I try on the clothes that would suit that sort of body, I inevitably realize that my form is more solid and athletic than my choices are allowing for. Yesterday’s experience re-confirmed my lack of awareness of the point of intersection between the different factors that make an outfit work: body type, clothing style, and clothing fit. And as I move further and further into adulthood, I find myself having a harder and harder time accepting that this is something I might continue struggling with.

And so, dear reader, rather than offer you any sage advice regarding the finer points of style, I find myself in the position of having to implore you to offer some. Do you feel that this wardrobe-building quandary is something you’ve mastered? How did you develop a sense of how to dress your body? Is my only hope to go back to episodes of What Not to Wear, and hope that I can somehow win my own shopping trip with Stacy and Clinton?

Help me, reader. You’re my only hope.

By Emilie

Runner, yogini, knitter, Manhattanite in spite of myself. Also blogging at

15 replies on “In Fashion, is There Hope for the Hopeless?”

I finally smarted up and started shopping for pants at stores that have different styles for different body types. And ZOMG, when I wear pants that FIT, they make me look so much better, and I feel better about what I’m wearing. It’s expensive at Banana Republic, but…. Also, I’ve made peace with the fact that I have a big chest – and so I never, ever, ever buy button up shirts.


So I guess in summary – know thine body type, and dress to it’s specifications!

I have no interest for fashion at all, and I’d usually rather buy books than clothes.So for the sake of looking at least presentable, i’ve decided to go with a uniform fow summer, and one for winter. It’s not very thrilling, but I always have something to wear, all my pieces go together , and an item needs replacing, I can replace it within 5 minutes. In summer, I like a t-shirt and a a-line skirt (with flat sandals), and in winter I do jeans (or dark pants), a camisole and a cardigan. I’m a stay at home mom, so obviously I do not dress very glamourously, but I can dress up my outfit with a fancier top, or with accessories. Hope this helps !

What’s worked for me is to first decide what image I want to portray to the world, then take that and add my personality.  For example, I decided that I wanted to look basic professional so that I could easily transition from day to night, and that when going out to the store, I didn’t have to worry about what I looked like when I ran into a boss / customer.

I’m also a not-so-secret old goth and adore the batcave look.

So, button down shirts in black/gray/white with either jeans, a basic pencil skirt, or pants depending on where I’m going.  Always looks put together, and if I want to throw in something outrageous, I still have the rest of the basics put together.

That’s a tough one.

I myself have the feeling that I know what’s good for me, but still squander on the comfortable and cute. It’s like picking a cheeseburger over carrots.

I kind of grew into a style though. I watch which colours work with my skin (and I like. People want me in brown because I’m a ginger but no ffing way that I’m going to wear brown) and always want the less favorite bits covered.

Interesting article! What strikes me is that you seem to approach clothes shopping from a perspective of what’s fashionable, then feeling bad about things not looking good on you. In my opinion, it is important to first build a wardrobe that fits you, THEN accessorize with items that are “in-fashion” right now.

There is a theory that every decade of the 20th century favored a different body style. What you should find is a decade which favored a body type that resembles yours. Take a look at how the clothes were cut, how the proportions worked and then go find something that would match this today.

It is also important to have a good look at your body and think about what you like about yourself, hence what would you like to accentuate?

For example: I am small, very curvy, with a petite upper body and slim midsection. My decades would be the 40s and 50s – fitted tops, knee-length (A-line) skirts… you get the picture. And I can rock the hell out of a nice skirt or fitted dress!

In comparison, the current look – 80s style voluminous tops and leggings is NOT a good look for me. I look short and frumpy if I hide my waist and accentuate the widest part of my body – my hips.

Hope that helps a bit!

Good point: I am sort of stuck on the idea of what’s fashionable *now*, and stuck because it’s not really something that works for me. I’m more of an athletic body type- broad shoulders, muscular legs, a waist and hips that are defined, but sort of proportionate to each other…I like the idea of looking at different decades and seeing what can be appropriated.

Is there a celeb whose body yours resembles?  A google image search and fashion bloggers’ reviews of outfits can give you good starting points for what does and doesn’t work on a person who looks like you.  And when in doubt, opt for modesty and minimalism.  I’ve seen way too many girls who clearly fancied themselves fashionistas wearing the most garish combinations of revealing items accompanied by delusions of edginess.

I had many of the same difficulties for years. I’ve started to conquer them through reading. I do not think the Good Lord Above blessed me with a natural sense of style or proportion. It took me measuring my body and finding out my shape, and then reading style manuals ABOUT my shape, to figure out what sorts of clothing I should seek and how to make use of the clothing I have.

I’m a classic hourglass and a tad tall, so my big rules are “Avoid Frumpy Shirts, Especially If They Cover Cover Your Ass” and “Always Check Out Your Ass in the Jeans Before Leaving With Them.” Curvy bodies can look great from the front and side but be disasters in the back.

I’ve had to refine my shopping habits, too. I used to just buy whatever looked good, fit my budget, and seemed to hang well on the clothing model/mannequin. That’s no way to dress yourself, though!

So it is not possible to win the trip? Because this article resonates deeply with me; I could have written it myself (except probably not so well). The only advice I can offer is from my husband’s stepmom’s Woman’s Day magazine. Hang everything in your closet backward. As you wear and return it to the closet, flip it around. That way, after six months the articles that are still backward should be ditched. That’s the only fashion advice I’ve come across lately that I can actually work with and that I have the budget for and so far it hasn’t helped me a damned bit, either.


When I shopped with the “something perfect will jump out at me” mentality, it was terrible.

I actually found that one of the BEST tools for getting me to develop my personal style was to set a minimum. Say I had a $100 gift card, I’d tell myself that I HAD to spend at least $30. That way, I’d find something I liked, get it, and not feel guilty that there was something perfect out there I was missing out on.

If I’m shopping anywhere besides Target, Old Navy, and H&M, I HAVE to do this, or I get overwhelmed and confused by all the many many choices and kind of just give up.  Last time I went to Macy’s – a really big one in the Chicago loop -  with a gift card looking for something nice to wear, I ended up buying a pots & pans set (which, I’ll be honest, I use more) because I had no idea where to even START with clothes shopping there.

I started with two points, and tried to find a place where they met in the middle. Those points were: what type of style made me FEEL best, conceptually. And, what cuts of clothing LOOKED best – to me – on my body?

For me, I’m a little taller than medium height, and curvy enough to qualify as plump. I adore my body but my fashion tastes included a lot of flimsy, gauzy gowns and straight, angular urban-officewear looks. Not great looks for a round, rosy gal. You look a bit like a sausage stuffed into very chic casings in these garments.

So then I thought, well, what really appeals to me about those looks is their simplicity and elegance and maybe just a little bit of tricking myself into believing that they’re luxurious (soft fabric and pretty rich colors do the trick just fine for me!), and I started finding sweaters that had slimmer, more elegant cuts, and skirts that were straight but had a little give for my hips and thighs, and pants that fit properly. Voila! It takes longer. I can’t just walk into any store and pick up anything that looks pretty to me and feel good in it. But I’m starting to develop an eye for the things that DO work for me.

I really like that–thinking more about what it is you like about the articles that you’re drawn to, and then finding ways to translate those qualities into something that works for you. It seems so simple, but I never would have thought to do it! I am definitely going to adopt that technique.

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