How to Break Your Style Rules Like a Pro


Know the rules like a pro so you can break them like an artist
Learn the rules like a pro so you can break them like an artist

The other day there was a conversation over on the 7 Steps for Style private Facebook forum about breaking style rules and I loved this quote supplied by one of the members.  There was a question about how many rules can you break and how far you can push them.

How far can you go breaking your rules? Well there are a few things to consider.

1. Your Personality

Who are you?  Do you like to have a set of rules to live by?  Are you a more classic personality style?  Do you love to know what is right and wrong and are happy to live by these rules?  Or, do you push boundaries? Do you love to be more creative or rebellious?  Do you hate being the same as everyone else?  Do you love change?  The answers to these will tell you a little about whether or not you should break rules.

The reality is, some of us a natural rule breakers and others like to stick to the rules as it makes us feel safe and secure.  Neither is right or wrong, they just are.  So if your personality pushes you to breaking your style rules (which are guidelines anyway, not hard and fast rules) then of course break them!

2. Your Values

What do you enjoy wearing?  Some of us have styles that veer off the straight and narrow.  Others like a more conservative style of clothing, so tend to break fewer rules.  But that said, our style and our body are closely intertwined.  For example if you have a large bust, which will be minimised with a lower neckline (not super low, but not a high neckline) but one of your clothing values is modesty and covering up  your body, you may find that your modesty value trumps the flattery of a lower neckline, and you’ll choose to wear higher necklines, knowing that this is making your bust appear larger, but you just feel more comfortable covered up.

You may have a sensory value, where you like your clothing to feel comfortable, and this is one of your highest drivers. If it’s not comfortable you won’t wear it.  But maybe your workplace is more conservative and it’s more ideal to wear the dress code of more structured clothing and because you find them binding and uncomfortable you’ll break that dress code rule by wearing garments that have stretch in them, such a knit top rather than a collared cotton shirt.

If you are highly social and being like your friends and how they dress is important to you, then you may prefer to wear the latest fashion whether or not it suits you, whether it’s a trend colour or shape that isn’t enhancing to your unique body.  Do it with the knowledge and you can make the decisions just how far you’re willing to go to break your rules.

3. Your Body and Your Body Image

What shape is your body? What are your proportions? What are your body variations?  And most importantly, how do you feel about that body?  The more we have (in the words of Tim Gunn) figure ‘challenges’ that we wish to mitigate, the more likely we are to stick with rules as they help to achieve this.  Particularly if we don’t have a really amazing body image.  If we have a great body image, we are more likely if personality dictates it, to break our rules, knowing that it make make us look taller, thinner, fatter, shorter etc. but we don’t care, as we are expressing our personality and we know that we are breaking and why we’re doing it.

It’s a choice you make with the knowledge you have, and this is why having that knowledge, as Picasso says ‘learning the rules like a  pro’ allows us to decide how to break our rules without necessarily creating an outfit that makes us look like a disaster and plays up everything we may wish to downplay.  I break my rules all the time as far as what suits my body shape.  This is an expression of my creative personality.

One of the things I’ve discovered is that if you’re wearing colours well outside of your colour palette, if you wear them in the right contrast levels, it won’t be as unflattering as it could be!

4. Your Lifestyle

How do you spend your time?  There is no point having outfits that don’t suit your lifestyle, even if they fit all the style rules.  In the olden days (yep when I was growing up all those decades ago) we were told that every wardrobe needed a particular list of clothing.  That everyone needed a crisp white shirt, and everyone needed a little black dress etc.  But if you’re a mum at home and have no need for these items, nowhere to wear them, and they are not part of your personality style, then there is no reason to own or wear these garments.  There are no rules anymore as far as what you must have in your closet.  Your wardrobe needs to reflect your current lifestyle (not what it was last week or even last year!).


5. Your Existing Wardrobe

Unless you have an unlimited budget (and lucky you if you do), then you need to work with your existing wardrobe, even if it’s not great, until you can gradually find fabulous pieces that represent who you are today and your current lifestyle.  Yes black may not be your best colour and you may have a ton of it in there that you just can’t afford to throw out.  So learn how you can work what you have into outfits that you like that make best use of these pieces.  Then over time you can replace, but until then, don’t throw everything away until you have something better!


In my opinion it’s completely fine to break your style rules.  Just learn your rules and take everything into consideration first so you can break them like an artist and still look fabulous!

So what I want to know is how willing are you to break your style rules?  And when you do break them, in what ways do you break them?



I'm not sure if it's for you but how would you feel if you learned all about the colours and styles of clothing that suit your individual personality, shape and style? Just imagine what it would be like when you can open your wardrobe and pull together fabulous outfits that make you look and feel amazing every day? If you'd like to stop wasting money on the wrong clothes and accessories plus join an amazing bunch of very special women also on their style journey - then my 7 Steps to Style program is right for you. Find out more here.

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  • I like to put together colours that don’t belong. If my outfit looks great I need to add something unexpected and left of centre to it.

  • Ah rules. I like to break rules that hold me back. I stick to them closely when it comes to the fir of my clothes because nothing bugs me more than I’ll fitting clothes, but I break them when it comes to color and contrast. I love bright colors and especially love purples and turquoise/teals. So if find something that fits well in a color I like I don’t hesitate. My neutrals are supposed to be on the warmer side but those frequently don’t look as nice with my preferred colors so I usually end up with black, grey and navy and only an occasional piece in olive. But since everything fits nicely I’m pretty happy with how it all looks.

  • I would love a post expanding on this idea of how to work with black for a while until you afford to change it out for more complimentary colors. Addressing the affordability aspect more when your closet is full of black (and shouldn’t be).

  • I am an H shape with square horizontal shoulders, and so boatneck tops are verboten for me, but I choose to wear them because they fit my style and I LOVE them! Emphasizing my shoulders with a thin knit top is much different than emphasizing them with shoulder pads or a coat with epaulettes.

    Black is not my best color, but I choose to wear it because it is classy and practical. I don’t wear it head-to-toe though. I treat it as an accent almost (if your shirt color can be an accent).

    Another rule I break (and I should say I am very much a rule follower, so I have had to have long talks with myself over these 3 things, to tell myself it’s okay!) is the length of sleeves. I am thin and tall. Either I fit my arms or my chest/waist. The fit around my body is more important to me, so my long sleeve items always have sleeves that are a bit too short.

  • I am short and I love being short. I’m never going to be 5’11” and willowy and I don’t think there’s anything wrong with that, so why should I have to fake being taller with my clothing all the time?

    Snub flats or contrasting shoes may shorten my legline but they also show off my tiny feet.
    The rules say large accessories may overwhelm me, I say they can accent my delicate frame!

  • I’m definitely a rule breaker in every single aspects, but the most dominant ones are personality and lifestyle.

    Although coming from Sweden, we don’t have any specific dress codes and lifestyle attires and haven’t been since the 50’s (there are some clothing etiquettes) , but I’ve never believed in “your clothes should be tailored to you lifestyles and suited to your personality” rules because how I dress will *never* match Who-I-Am.
    I’m lazy, clumsy, down to earth and honest with an occasional personality swings which many might associate with the Natural/Relaxed Sporty generic styles, I do value comfort, but doesn’t always a equal a sporty-casual jeans or flip-flops look. I dress after what I feel comfortable in and what fancy me, not dressing after “aha, you must be THAT kind of person!” type of first impressions. Like I often getting the impression of being shallow and attention seeker (mostly online) because I love dressing up and wearing bold feminine clothes & colors. My motto: Treat people the way you want to be treated, not after the color/hemline of their skirt or cut on pants!
    When I was a teen people mistook me for a BF stealer because I dressed up,but in reality I only did it for my own sake. Clothing and Makeup can also be a form if art, not only expressing yourself or looking for one or several mates. 😉 It Took me years to learn my values a d stopped listening to stereotyped prejudices and I can admit during a time Period I was literally scared of wearing bold red clothing to my internship because of these stereotypes. There IS differences between personal and professional advice. I wish I learned that a couple years ago. >_<;;

    With Colors and Body types: I Adapt to and Alter them, not always breaking them. 😉 I'm pale and softly warm pink muted, but my personal preference to clear, dark & cool always wins. The overall look is more important to me. I love harmony but not the extent where you force yourself for the sake of clothing. I've broad square shoulders but feel more comfortable in formfitted bottoms. With necklines, ionly avoid the worst options.

    And sorry for long comment. 😉 it's a topic I love reading and comment on!

  • I am not a rule breaker, I have great difficulty driving through parking spots in carparks and NEVER cross against the lights. Having said that I have definitely been breaking style rules all my life because a) I didn’t really know there were rules, and b) I have always had a low self worth and did not think I was worth spending a great deal of time or money on. Now that I am learning some style rules about what will suit me and what doesn’t, I think I will be very happy to sit with the rules for a while and start feeling a little more worthwhile.

  • Imogen, here is a way for individuals to visualize their body shapes, (silhouettes) & proportions fairly easily. Graph paper & a yardstick. I myself, am amazed to see it. Take the shoulder width (outside), the narrowest part of waist, the hip bone, and hipbone to crotch, with various widths at hip, going down, if they vary. Then the verticals, as top of shoulder to narrowest part of waist, shoulder or waist to hipbone, crotch to floor. Convert all onto graph paper. and there you are. I could see from your site info that my bottom half was figure 8, as high hipbones/long legs, and with wide shoulders/narrow waist & hip, with hip straight down from hipbones. My stylist told me before that I was Hourglass top, Figure 8 bottom. But thanks to your more precise info, I can now see how that should be dressed. And I can take my graphed outline and overlay different clothing silhouettes on it to see how they look as well.

    Many thanks for all you do & publish for us. And best wishes for great happiness in your new marriage! Gigi

  • I’m not a rule breaker (still have a hard time wearing black and blue together!), but I’m also that modesty person you were talking about. If it’s low enough to show cleavege, I know I’ll be uncomfortable wearing it. Aside from the current trend of low V-necks, petite manufacturers frequently miss the mark and cut proportionally lower necklines on their petite lines than on their regular lines. This is all in contrast with my body; while I’ve recently lost some weight, I’m used to having a large bust for my frame. Deep V necks look flattering on me.

    I’ve found that I can usually reconcile the conflict with a camisole, shell, t-shirt, or something similar. As long as there’s some contrast in the colors or value, the impression of a deep V is still there, just without all of the skin showing and making me uncomfortable.

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