Bowie, Moss, Cumming: How to dress like a tomboy with boobs?

“In a time when it seems absurd that my gender, my sexuality or my nationality should dictate what I do, I am certainly not going to let my body type let me dictate how I express myself sartorially! “


Looking at my heroes and fashion “icons”, I realized an unfortunate thing recently – none of them are even close to being full-chested. Most of them aren’t even female. That makes fashion inspiration a little tricky.

What they share is a certain androgynous edge and a common appreciation for Berlin cabaret from the 1920’s. David Bowie. Amanda Palmer. Alan Cumming. Kate Moss. To be honest I have no idea whether Kate Moss likes the cabaret. Still.

While there are many admirable blogs offering inspiration on how to tailor your style according to your body shape, I realized there are few to suggest how to dress your assets according to your personal taste.

This will be my quest. 

I have big boobs yet I have spent most of my life being really a tomboy. I may enjoy the occasional dip into vintage but really, A-cut dresses are not my style.


I like dressing like a man and I like my men dressing well. In fact, my favourite look on a man is also the one I like best on myself

In a time when it seems absurd that my gender, my sexuality or my nationality should dictate what I do (even though in my case in particular, all of these are as mainstream as you can get really), I am certainly not going to let my body type let me dictate how I express myself sartorially!

In the words of an absurdist playwright Vaclav Havel – “We refuse to be bullied by facts!

How to pull Kate Moss and not Lena Dunham?

I love Lena and I like her character Hannah on Girls. I have fierce respect and admiration for this incredibly accomplished young artist. However I do give a fuck about being attractive to the rest of the world (guilty there! caught in the conventional beauty paradigm still). I want to look fabulous pulling a Kate Moss look without looking bulky and pregnant. Hannah’s love for cuts and jumpsuits which accentuate her worst assets is legendary and cute… and also a little warning to me. So how to pull off what is – let’s face it – “heroin chic” when I am not skinny and flat chested?!

To start with, I put together “the rules for a full bust” versus my preferences:

Accentuate your waist

  • I really like low waist of the 20’s or at least at hips.

Show a bit of your cleavage

  • Most time when I flash some boobs I feel like a hooker – can’t help it. Prefer to keep it all covered up with some wide shallow neckline. Somehow others are significantly more successful at achieving tasteful cleavage. Worth analysing and a separate post for sure!

bp-pt362bst-largeThis Pepperberry dress is really nice but so not me!

Fitting, fitting, fitting

  • I like baggy band T-shirts, I like the festival look and despise anything elastic!

Embrace your femininity

  • I prefer trousers to skirts, boyfriend cut jeans to leggings, button up to any cleavage and, as the title suggests, male fashion icons to female ones.

So basically I’ve got it all wrong. Solution?

First I believe as long as you feel comfortable and your look has a clear idea, you are already on the right path.


For me this idea is slightly androgynous “underground chic” (to avoid the horrible drug term and replace it with some nice Velvet Underground reference). The challenge is to accentuate the fact my waist/hips are on the more petit side without accentuating the very feminine hourglass trope.

Rules to try:

Tying tops at the hips (so from the side it is clear you are slim). I prefer when at least one of the garments is feminine/on the skinny-fitting ish side (can be a tailored masculine item too – shirt, vest etc.). If I am wearing a tighter top, I can go for boyfriend cut jeans. While I don’t really do waist belts, I try to make sure around my hips something will be fitting.

1. IMG_1874

Accentuating the vertical lines – The length in shift dresses or oversized tops will highlight the vertical line, achieving a slimmer look and level out the boobs.

Lighter fabrics – when not perfectly tailored (to me) I often choose lighter fabrics that will align with my figure (without being too elastic!). Much too often, harder fabrics will just create a tent down from my boobs – especially if they are not long enough. That way, my boobs are also still visible in silhouette, just not on display.


Legs over cleavage – if I can, I try to up sexiness with a shorter bottom item over a deep cleavage so a short skirt and a baggy T-shirt tied at the waist is a popular choice for a night out! 

Tailored shirts – my personal favourite is a crisp white shirt with denim!

I tailor my white shirts myself (as I still haven’t had the courage to just get one significantly overpriced online, but I am getting there, promise!) and tuck them in my jeans.

1. shirt susp. best

Yes, suspenders are a crazy thing to wear with big boobs, but I got more compliments on them than anything else!

And finally a longer black jacket – this one will not accentuate your waist the same way a leather jacket would (and often it is worth trying which one of the two suits the outfit better). And yes: if you are pulling an underground rock chic style, you will eventually need both! The longer jacket rather highlights the vertical line again, giving you that tall, skinny look.

Shoes and accessories

Accessories are pretty crucial and as I like to keep my looks simple, the accessories are bold but never tacky or too shiny. Shoes are the most important – they elevate or crush a look easily. My personal favourite are oxford shoes in all colours (always genuine leather), Converse (mostly black) or some seriously elegant black heels. Also never underestimate socks. They can be a source of endless fun!


With these basic looks such as a white shirt, sometimes a little playfulness can divert attention from your bust – such as a colourful bowtie or suspenders. They are one statement piece and give a simple look a lot of attitude.


While I am sure these are not the ideal solutions, they work for me to keep my personal tomboyish style, with a bit of punk or hipster thrown in now and there. Not surprisingly, the looks are closely linked to the lingerie underneath – my preferences go against moulded bras because they make me look wider. Instead I prefer full cup underwired bras with a teeny weeny pointy shape, just enough to make appearance under clothes and yet to be natural. My favourite everydays are Fauve Emmanuelle for dark (have it in three colourways) and Fauve Coco in dusky pink for anything white. They are all full cups; the lace hopefully levelling out the amount of coverage in terms of sexiness. Sue me; I am 23-year-old girl who likes to get laid at times!

Overall I do not find it impossible to find clothes in high-street – even though at my size, I am definitely in the curvier spectrum of even the full bust brands such as Pepperberry and Urkye. However their fashion just doesn’t speak to me at all so I try to pair together edgier outfits myself.


The key is a clear idea of what vibe/look you are going for. Combining fitted and baggier items and clean, vertical lines will make you look slender and stylishly messy instead of frumpy. Too messy can be dangerous too – which is where good shoes or statement watches can do wonders. And of course, it all comes down to a well-fitted bra – no amount of style can handle lack of uplift or worse a quadboob!

Do you struggle pulling androgynous look with bigger boobs? What are your “rules” and suggestions? And most importantly any advice on how to look like David Bowie?