Fashion Friday: Trying Things On

When you’re shopping for clothes… where do you start?

As regular readers of Fashion Friday know, I’m a fan of the fashion makeover show, “What Not to Wear.” I have some issues with it, but on the whole, I find it entertaining, informative, often oddly touching, and loaded with both specific tips and broad philosophical insights about fashion and style. (Not to mention insights into human psychology.)

It’s fascinating to watch the mental processes and emotional rollercoasters the show’s participants go through when their entire wardrobe is decimated, and they have to start from scratch. And one of the most common reactions the participants have to shopping for a new wardrobe is paralysis. They walk into a clothing store in New York with $5,000 of someone else’s money… and they have no idea where to start. They try on a couple of things that don’t look right… and they get frustrated, or they feel like failures, or in some cases they have a complete emotional meltdown.

I actually understand this, and have sympathy with it. I’ve only been seriously into fashion and style for a relatively short time, and when I was beginning to explore this hobby in a more conscious and thoughtful way, I often felt overwhelmed by all the options, and had no concept of what to even try on.

So I developed three rules for myself for trying things on — actually, they’re more guidelines than rules — and I thought other people might find them useful. Or at least entertaining.

Rule #1: If it catches my eye, I have to try it on.

I cannot tell you how many times I’ve picked up a piece of clothing in a store; thought, “Nah, this probably won’t work”; thought, “Well, what the hell, I’m going in the dressing room anyway, I’ll give it a shot”; tried it on — and fell head over heels in love.

You can’t always tell what something’s going to look like on your body, just from what it looks like on the hanger. I’ve thought, “Nah, that dress is too shapeless” — and on my body it looked simple and elegant. I’ve thought, “Nah, that jacket is too professorial” — and on my body it made me go, “You know, I can kind of rock the professorial look.” I’ve thought, “Nah, that cut is too severe” — and on my body it made me look like a Fortune 500 CEO who moonlights as a $1,000 an hour dominatrix. (And yes, that’s a good thing.) I’ve thought, “Nah, that print is too garish” — and on my body it made me look like I was radiating pure, exuberant joy.

So if it catches my eye — I have to try it on.

There are some exceptions to this. Again, it’s more of a guideline than a rule. If I’m in a big hurry and am really in the store to just try one thing, I don’t pick up everything else that catches my eye. If a piece is way outside my price range, I’m not going to try it on. I don’t want to fall in astonished love with something I can’t afford. (I’ve done that before, and it did not end well.) And if a piece is too much like something I already own, I usually don’t bother.

But in general, if I’m looking at an item on the hanger, and I’m on the fence about whether to try it on — the default is Yes. If it catches my eye — no matter how far outside my comfort zone it seems, no matter how wacky or boring it looks on the hanger — I have to try it on.

Rule #1 leads directly to Rule #2:

I have to try on a LOT of things.

Here’s the thing. Once I’m in the dressing room and am down to my skivvies, it takes thirty seconds to try on a piece. Maybe a minute, if it’s complicated to get on and off. I don’t make my final decision in thirty seconds — but I can do my first round of culling very quickly. “No. No. No. Maybe. No. Hmm… strong maybe. No. OH MY SWEET FICTIONAL JESUS, YES. No. No. Maybe. No.” Doing the final cull from my Maybe pile takes a bit longer… but I can figure out pretty darned fast if a piece has any chance at all of working.

There are lots of good reasons to try on lots of things. It gets me outside my comfort zone, and into a wider range of possibilities. (See Rule #1 above.) When I was anxious about shopping and about trying on clothes, it made the experience seem more normal and familiar. And of course, it just gets the law of averages on my side. The more stuff I try on, the more likely I am to find pieces that fit, and that rock.

Again, there are exceptions to this rule. If my time is tight, and I only came into the store because one piece in the window caught my eye — I don’t try on a zillion things. If I’m on a tighter budget than usual, and I’m really only looking for a very specific item — I don’t try on a zillion things. But on a regular free-form shopping trip, or even on a somewhat more focused “I’m keeping an eye out for long-sleeved blouses and dresses” trip, I generally go into the dressing room with an armful.

And Rule #2 leads directly to Rule #3:

If something doesn’t work — blame the clothes, not myself.

When I was fat, I used to get very down on myself when clothes didn’t work on me. I’d try a bunch of things on, and only a couple would look good on me, and I’d feel like a loser. (When I wasn’t getting furious at size-ist designers, that is.)

But now I’m about a size 8 or 10 (in most pieces). And I still try a bunch of things on, and only a couple look good on me. And it’s finally dawning on me: Oh. It’s not me. It’s the clothes.

Not everything in the store is going to look good on me. There is no woman on earth who everything in the store is going to look good on. Things that look good on tall women often won’t look good on short women. Things that look good on angular women often won’t look good on busty women. Things that look good on 25-year-olds often won’t look good on 50-year-olds. Hell, Ingrid and I are almost exactly the same height and weight and general build… and things that look awesome on her often look weird and lumpy on me, and vice versa. (My theory is that it’s because she’s long-legged and short-waisted, and I’m long-waisted and short-legged.) There is literally no way to make a piece of clothing that will look good on everybody. Human bodies are just too different.

(It’s also true that there’s plenty of size-ism in clothing design: designers don’t make enough nearly options for fat women, and the ones they do make are often sad to the point of being insulting. But that’s a rant for another day.)

So if something doesn’t look right on me, I’m careful about my language. I don’t say, “I don’t look good in this.” I say, “This doesn’t look good on me.”

It is not a personal failing that yellow makes me look jaundiced. It is not a personal failing that the dress in that gorgeous pansy print sat on my torso like a nightgown. It is not a personal failing that the skirt I wanted to try on was out of stock in size 10. It is not a personal failing that ankle boots make my legs look stumpy unless they’re cut at an angle. (The boots, not my legs.)

It’s not me. It’s the clothes. Some clothes look good on me; some don’t. Some clothes make me look like my best real self; some don’t. It’s not about whether I fit into the clothes. It’s about whether the clothes fit me.

And with this rule, there are no exceptions.

Fashion Friday: Trying Things On
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25 thoughts on “Fashion Friday: Trying Things On

  1. 1

    Little harder for me to try on clothes that I think are super cute… I could imagine “excuse me, sir, where are you going with that dress” and yea, I don’t want that. I just buy something that looks cute and try it on at home and if it works, yay, if not, I return it.

  2. 2

    I’m with you. When I was younger, I felt shitty every time I looked in the mirror and saw that the ensemble looked shitty on me. Also felt bad when something wouldn’t button or zip. But watching What Not To Wear showed me that the woman on screen might look great in one outfit and a lot less than great in another. I did the math and realized that she was the constant and the clothes were the variable.

    I agree with your conclusion and I, too, try to try on larger armfuls of clothes, including clothes that I think are probably wrong, but I want to see just to find out. I also try to try on a more diverse range of clothes, not just the stuff in my, um safety rut.

  3. 3

    This article made me tear up (maybe because I seem to be pre-menopausal and I’m randomly crying at everything – it’s like being on my period for 3 solid months so far).

    But something hit me about this. I’m 47, happily married for 22 years, have 2 teen girls, I’m a special ed preschool teacher – and I’m starting to wonder, is this it? Is this me? Is this as good as it gets? I go for practical, comfortable, durable clothes – I get my girls whatever they need but my whole wardrobe is from thrift stores. If I do see something awesome, I think, “I don’t have anywhere to where that, anyway.” Something about the clothes is connected to the dissatisfaction I’m feeling about my great life. I’ll be looking and thinking about this some more.

  4. 4

    Katherine Lorraine, I used to work in a retail store and I remember getting really very cross when my manager wouldn’t let a transgender woman use the fitting rooms. Your comment just reminded me of that. In the end (obviously out of earshot of the lady in question as I didn’t want to make her any more uncomfortable than she’d already been made to feel) I persuaded my manager to let her try on in the old fitting rooms which weren’t in use any more. They were bigger so she could take her partner in with her for opinions and guidance etc, and she’s now a regular customer. I went in last week after having not worked there for a few years and saw her coming out of the old fitting rooms again with an armful of pretty dresses.

    And how is it different from the fact that I prefer men’s jeans to women’s? I get funny looks all the time when I take men’s jeans into the female fitting room. Look, it’s my body, it’s my choice what clothes I put on it so stop judging me you judgy little people…


  5. meg

    One of the things I’m better at sorting out is the difference between a cool concept and the reality of the garment. I used to buy stuff because I loved the idea of it, not how it actually looked. I am all for getting something you love, even if you don’t have someplace to wear it. Wear it Saturday morning while drinking coffee in good china. I do try to adhere to a sort of ‘one in, one out’ rule for my closet; it helps me prioritize.

  6. 7

    @1 Katherine – I have a similar problem, but I get around it occasionally by only grabbing one or two femme things, then fake-shopping in the men’s section. Jeans are good for this because they can cover up what you’re carrying really well.

    At places like Macy’s, there isn’t much checking done as to what you’re bringing into the changing room, and I haven’t had any trouble getting a dress or top in.

    No one has ever challenged me, but I always have an excuse in my head if someone did. I’d say something along the lines of, “This is for my wife, I just don’t want to set it down and lose it.”

    Now, department stores may cost too much, but if you find brands and sizes that fit, it’ll make shopping at a Ross much easier. You won’t have to try it on there, since the fit should be the same.

    Also, both Macy’s and JCPenny have policies in place such that individuals can use which ever changing room they are comfortable with. If you’re presenting female, passing or not, you are allowed to use the women’s changing area. Same if you’re presenting male.

  7. 8

    Cut matters with clothes. I am average height with tall-gal proportions and quite small overall. I learned back in the ’80s that the big and baggy stuff made me look like a small child dressing out of her mother’s closet, even if it was in vogue. I had a lot of difficulty with sleeve and inseam lengths (and still do).

    I was in a theatre program in university and between performing in shows and constume design classes learned that it was the cuts that were to blame. Bespoke dresses for the stage looked freaking fabulous on me, I didn’t look like a stick figure at all. So I learned what to look for and how to alter something that was not too far out – but alterations are either expensive or time consuming, and as a student and then later, didn’t always have time or money for it.

    And still, even knowing all that, it took me years to figure out that it’s not a bargain if it doesn’t fit. I have friends who tease me about being a label hound, but the fact is, some brands feature cuts that work and lengths that aren’t too short and others do not. I’d rather spend a little more on something that won’t make me feel gangly and ungainly or frumpy because it doesn’t sit right. And it’s nice to find a line of clothes that won’t cost me alteration fees on top of it – again, that’s no bargain. Unless, of course, it’s something really amazing.

  8. 9

    🙂 My version of #1 goes more like this: if I like the look and feel of something, I try it on. Further requirements are that the garment in question must be in my price range and a type of clothing I’ll wear. (For example, I have a medical condition that makes staying cool very important, so I never look at sweaters when shopping for myself. Any long-sleeve item of any but the thinnest material must be easy to alter.) And I do at least hold the item up to myself to get a feel for the size before trying it on.
    Honestly, texture is more important to me than look. I have bought things because I loved their feel even though I wasn’t much more than ok with their look. I never buy things if I don’t like the texture no matter how much I like the look. No use getting an item I can’t bear to wear.

    Ooo, I have a corollary to rule #1: the same applies to shoes and accessories (that can be tried on). I make my own cooling neck band (well, inserts and sleeves), so most every time I’m at the craft store, I browse the bin of scrap fabric. If it’s (mostly) cotton, thin enough, cheap, and I love it, I’m grabbing it. I go by the same rule for hats (where brim size and opacity are the important bits), which accounts for my blossoming collection. Also for shoes. I have balance issues, presenting another issue shoes must suit. But I recently tried on a pair of strappy black sandals that I was almost sure wouldn’t work for me… and they were perfect.

  9. 10

    One of the things that What Not to Wear taught me about was alteration is not only for hems. I like elbow length sleeves more than shorter ones. When I find a long-sleeved shirt for warm weather that I want, I take it to the tailor and have those sleeves shortened. I’ve also had too-long shirts made shorter.

    Yes, that does add to the cost of the garments, but I would rather have fewer things that fit me really well than lots of just okay stuff.

  10. 11

    Ulla Popken, with a few things from Silhouettes and one or two from Junonia. I have serious issues: notably, since this is after all Arizona, NO SYNTHETIC FIBERS. Cotton and cotton only. And I get irritated when I click on a picture in an online catalog, thinking I’ve found a nice cotton shirt in a print I like, and find that it’s “embellished” with gorp like beadwork or sequins. I need to be able to wash my clothes. I need to be able to machine wash them, and I need to be able to wash them frequently. Hence, no gorp.

  11. 12

    #5: “It’s practically legal to beat the shit out of trans*persons.”
    Oh, that pisses me off! This is America, god-damn it! You can wear whatever the fuck you want to! The founding fathers (in their wigs and tights…fabulous!) made that very clear.
    You come to New Jersey, Katherine. We know how to treat a lady.

  12. 13

    Goddamn. The nonsense trans women (and presumably trans men) have to go through to shop is appalling. I used to work in a local designer’s shop, and she had a strict “no men or trans people trying on my stuff” poicy. Not ’cause she had a problem, you see, but the *other customers*. What if they’re made uncomfortable? It used to really piss me off, and I broke the rules whenever I was in the shop by myself. How dare she ask her staff to make someone feel unwelcome in the store? Was it really part of my job description to be mean? raaaaaaaage. She had a similar attitude towards fat people. I have since found myself a much better establishment to work in.

    One that offers a tailoring service! Seriously, folks, I know it’s an added expense, but it is beyond worth it. I can’t tell you how good it feels to make people go from looking ok to looking awesome with a few well-placed pins. Pin someone up and they’re usully instantly sold on alterations. I have come to see RTW items as simply “blanks”- generically-sized items waiting to be customized for the person who will take it home. RTW almost never fits anybody-like Greta said, it’s not YOUR fault something doesn’t fit, it’s the CLOTHES.

  13. 15


    See here and pay attention to the Hate Crime Laws part as well as the Discrimination Protection. I can be kicked out of my apartment for being in a relationship with a man (since I’m non-transitioned) as well as for being trans and I’d have no recourse.

    Hate crimes do not address gender identity or sexual orientation, and trans panic defense is accepted in matters of assault and murder.

    Lovely state we got here.


    See, fortunately for me, I’m built like clothes are designed for – tall and skinny – and women’s clothes fit me a hell of a lot better than men’s clothes.


  14. 16

    @ Katherine Lorraine:

    Sickening. Barbaric. Dog allmighty, sometimes I hate this country. So smugly proud of what it is, so far from what it should be.
    Some might ask me why someone in my demographic (hetero, white male, top of the pecking order) cares about trans peoples rights. Simple; I don’t. I don’t care about the rights of gays, women, blacks or immigrants either. I care about MY rights.
    If your rights can be assaulted, my rights can be assaulted. If the law doesn’t protect you, it doesn’t protect me. If you are not free, I cannot be free. We’re all in this together; hang together or hang seperatly, remember?
    Anyway… hang in there, Miss Lorraine. There are many, many people on your side. (Even shaggy, bearded knuckle-draggers like me.) And our numbers are growing.
    And meanwhile… there’s always New Jersey.

  15. 17

    @Katherine Lorraine, hope sense comes to your legislators soon 🙁

    @scramble, that shop – are you serious? “oh, the other customers might be *offended*”? does the owner chase out the overweight, elderly, disabled, and anyone else that’s not in model form?

    @Greta Christina, you are so right. It’s hard to silence the inner esthetic police, but you have to ignore them and try on all the things, take chances, etc. otherwise we’d all end up in burlap sacks. It can be hard to keep confidence up when

    I’ve got to the point where I ceased going to stores at all, other than Marshall’s/Goodwill. Those can be excellent sources for fashion one would never have considered in a “regular” store. And they are inexpensive, so it’s low-stakes for experimenting with a new look. Also good for giving fashion the finger and wearing whatever amuses you…luckily, I can get away with going to work looking like the love child of Mrs Frizzle and an early Dr. Who, so that may not be workable to all. But with some patience, thrift stores can yield up really nice goods. Just have to try on *everything*!

  16. 18

    Is anyone else noticing a huge shift in the way clothes are cut and sized? What I’m finding is this: even in the “better” stores, things are just not made the way they used to be. I can walk into a store wearing a shirt of theirs from several years ago, size medium, and be completely unable to button a medium over my bust. By the time I get a size to fit the bust, I’m up to a 2X and everything else is freakishly out of proportion. I used to blame myself, but I’ve got a closet full of clothes in “my” size that still fit like the day I bought them.

    Additionally, designers seem to have decided that the only type of shirt a woman can own is extremely cheap, see-through fabric. I’m in a career field; I can’t go to work in see-through clothes so the only option would be to layer seven layers of shirts over each other. Since today is slated to be 106 degrees, multiple layers simply will not work (plus there’s the cost of so many layers when one layer used to do).

  17. 19

    Tracy: “plus there’s the cost of so many layers when one layer used to do” – Yep, that’s it. Mass produce one or two cuts that fit a reallly tiny portion of the population, and ensure the clothing is so thin/poorly made that you not only have to replace it more often, but you have to buy redundant garments just to be dressed.

  18. 20

    @lizdamnit: Yes, I am. She was a bitch. With delusions that her shop was somehow an ‘exclusive boutique’. But in reality she was stuggling to pay the bills. And chasing away customers. I actually suggested once that she watch “Gordon Ramsay’s Kitchen Nightmares” and consider some of the things he had to say about attracting/not repelling customers. I was looking for another job not too long after. Just as well.

  19. 21

    I’ve incorporated a rule that was really hard to adapt to: Don’t buy it if you don’t look good in it. I’m fat, and just finding things that fit at all is a chore and a hassle and likely to end in tears (at least it used to, I’m a little better about that now). That often meant I’d buy something for which I hated the color, or wasn’t thrilled about the cut, or was made of material that made my skin crawl a bit, just because it draped well enough to not look too terrible and I could move my arms in it without straining the seams. And I felt like crap when I looked through my closet, and I felt like crap when I wore almost anything, and it was awful.

    I got the idea directly from Lessons from the Fatosphere (buzz market!) that it’s way better for my psyche to have just a few things I feel good in than to have several that I feel like crap in. And it’s actually true! I feel good when I wear the clothes I have. And I can march out of a store being haughty and annoyed that they don’t carry anything I care to spend my money on rather than slinking off in guilt and disappointment that I’m not good enough for their clothes.

  20. 22

    Carlie: Yes, a thousand times yes. Like I said about trans people, it is appalling what fat people have to go through to shop. Fashion and style should be a source of fun, not a source of tears. It enrages me to know you’ve experienced this. I know I’m biased-tailoring is my profession-but just as alterations are worth paying for, so is custom work. To paraphrase you, better to have a few well-made, somewhat expensive alterations and custom pieces that make you feel awesome than a closet full of mass-produced crap that makes you feel like crap. As an added bonus, your clothes will be higher quality and more flattering than those of most of the population. My mom was fat, and just *adored* fashion. So, she spent the extra money on tailoring and custom work. Result? She wasn’t just the best-dressed fat person of her entire acquaintance, she was the best-dressed person, period. By a long shot. It’s been well over a decade since she died, and people still tell me how much they admired her beauty, elegance, sophistication, and her confidence. The woman remains a style legend in our community.

    Really, I’m not just promoting tailoring to drum up business for my fellow tailors. I’m passionate about this-I’ve seen the change in people when they see themselves in something that works on their body, the difference it makes in their lives. The RTW industry is poison-it’s past time we took fashion back!

  21. 23

    When I’m going shopping, I always try to wear and outfit I love and look good in. That way, if I put something on and think ‘OMG I’m a hideous whale!’ I can always say to myself ‘did you look like a hideous whale before you got undressed?’ and the answer will always be no. Makes it a lot easier to blame the cut of the clothes.

    (I’m 5’4″ and extremely busty, so there are a lot of clothes that make me look like a beachball. Luckily I have long legs relative to my height, so short tops and long pants are my friends.)

  22. 24

    Thanks for this Greta. I have an arthritis-like condition which makes shopping for and trying on clothes tiring and painful, so I only do it twice a year (and thank the internet for online shopping these days). But like you I get and try on almost everything that catches my eye, knowing I’ll likely send half of it back.

    And I’ve discovered I hate shopping in sales – they’re too crowded, the clothes are usually poorly dispalayed and trying to find my size is a nightmare. So I shop as soon as the new season lines come out in spring and autumn. Apart from the rejects I end up with 2 piles – the ‘fabulous – buy it now’ pile, and the ‘maybe’ pile. The stuff in the ‘maybe’ pile is usually things I’m not prepared to buy at that price. Then when the sales come around, if I can face them I’ll go and see if any of my ‘maybe’ pile is still available in my size at a price I’m willing to pay. The advantage is I’ve already done the hard work if trying on, and I know exactly what I’m looking for.

    PS – I love your Fashion Friday posts. One of the reasons I keep coming back here is the variety of stuff you talk about, so thank you for making this blog such an interesting and entertaining place to visit.

  23. 25

    One of the things I’ve noticed working retail- a lot more places train their staff to be able to wardrobe you than you’d think. I wouldn’t try it at Old Navy, but Ann Taylor (and the Loft) for example expect their salespeople to be able to dress you. If you’re in a place and the person who lets you into the fitting room gives you their name, don’t be afraid to go “oh So-&-so! This blouse doesn’t sit right on me. Do you have something similar in a cut that will?” They’re often not working commission, but their job is to make sure you leave happy and not frustrated.

    (and no, a medium is not a medium is not a medium. Three similar-looking blouses could have drastically different fits.)

    And if she gives you lip, tell her boss. Sometimes even salespeople have bad days, but as a manager getting that feedback lets me know who I can trust to create happy customers, and who gets relegated to the quiet/tasking shifts.

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