Jenny’s Style Makeover: From Vision to Reality

This is the first in a series of posts dedicated to analyzing the vision boards that our readers submitted for the Make It Real! style makeover challenge. I’m still accepting submissions through this coming Sunday, September 16th.

For those who don’t know, the Make It Real! makeover challenge was all about helping our readers create a vision for their authentic style, and then translate that vision into realistic, practical recommendations. Today, the subject of our style makeover post is my co-author on this blog, Jenny. Jenny has been chronicling her experiences throughout the challenge on this blog; in her latest post, she shared her own assessment of her vision board.

Let’s get started!


Jenny is a writer and editor who is currently launching a new career as an ESL teacher. Jenny is cerebral, creative, and complex; she also craves simplicity. This is a paradox that she wants to solve, and express, through style.


(click to enlarge)


I find this board to be an excellent representation of Jenny herself. It’s streamlined, sharp, creative, deceptively simple, with an avant-garde influence. There is a feeling of substance and quality to it; a touch of sleekness and a dark, futuristic feel; and a subtle sense of humor. It’s feminine, but in an unexpected way. I keep waiting for a smiling black cat to stroll out of the corner of this vision board.

I find the use of color very interesting here. Jenny opts for blacks and blues. These colors convey depth, calm, intelligence, coolness; in feng shui, these are Water colors – the colors of philosophers, writers, thinkers. Jenny is most definitely all three. If you’ve read Jenny’s own comments, you know that she is drawn to both complexity and simplicity in equal measure. She doesn’t think that her style is cohesive. She also thinks that her style comes across as boring. She is drawn to good quality, status items. This is not easy to reconcile with her inherent creativity and independent spirit.


Jenny’s board fascinates me for one simple reason: how successfully it refutes the misconceptions that Jenny holds about herself and her style.  Specifically:

  • “My style is disjointed; I can’t reconcile my creativity with my desire for high quality and simplicity”
  • “My style is boring”
  • “My style doesn’t have drama”

This is where objectivity is such an invaluable tool. For those of you doing this at home: try to be objective when looking at your vision boards. It’s difficult, but try. Imagine that you are looking at something created by a stranger. Divorce yourself from your expectations, just for a few minutes, and look at your vision board with fresh eyes. Because if you do, you’ll be able to see what I saw: the truth.  Let’s play style myth busters, shall we?

  • Jenny’s vision board is incredibly cohesive, both in form and in spirit. The big picture influences I outlined above are present in every item. The level of consistency here is enviable. No matter what Jenny’s internal struggle, the result is smooth, sleek, flowing. It makes perfect sense.
  • Jenny’s style is anything BUT boring. A woman who wants to wear tuxedo-inspired black manicure and those sleek, color-blocked dresses? Who doesn’t want to know this woman? She is like Nikita from the TV series of the same name: a volcano under a calm, competent facade. Look at her vision board more closely. Note how every single item looks deceptively simple. Simplicity comes in many forms and has many expressions. Jenny’s mistake was to think that in her case, simplicity meant boring, when in fact it means smooth and uniform on the surface, but unexpectedly interesting when you look a bit more closely. It reminds me of a Monet painting: you don’t see the incredible details until you start paying attention. Every single item has something in it that elevates it from mundane simplicity to understated complexity. The items in monochrome colors have something to distinguish them: cut, shape, fabric sheen, or texture. The accessories have weight, presence, and unique details. The feel you get is that of something streamlined, yet totally unexpected. Even a seemingly trivial pair of moccasins look both interesting and expensive because of their material (suede) and color  (an unexpected shade of blue).
  • Jenny’s style IS dramatic. Every single piece. It’s in the dark colors; the sleek, architectural, geometric lines; the high level of contrast. Now, between you, me, and the Internet, Jenny hates red (she even had doubts about the block of maroon color on one her dresses above). Red is the obvious drama creator, the color of passion and extraversion. But if we’ve learned anything about Jenny, it’s that she is never obvious. Color isn’t the only way to convey drama, and consciously or not, she found a different, subtler way of conveying it. Here we have Jenny, the “I am so boring” Jenny,  using snake skin print, fur, polished metals and sleek silhouettes to express her unique sense of sensuality. This is the key to understanding Jenny’s style: the dramatic statement is not absent, it just isn’t blatantly obvious. It’s covert, almost challenging you to discover it. Like the archetypal black cat, she refuses to try too hard, yet manages to captivate your attention completely. And like the black cat, Jenny will never make it easy for anyone to solve her inherent mystery. Therein lies her distinctive appeal.

Jenny is a fantastic example of a woman who has been long searching for something she already had all along. Thousands of women all over the world try to emulate the kind of cool, offhand, mysterious appeal that Jenny conveys without trying (some French blood there? I wouldn’t be surprised!). And the funny thing is, she doesn’t even realize it. This is it, right here, the most important secret: your true style is what you are when you stop trying so hard to be something you are not. You’ll know it when you  start listening to yourself. You’ll discover that you’ve had the answer all along.


Let’s summarize the common themes we observed on Jenny’s vision board in more detailed, practical terms.

  • Colors: deep, cool, high contrast. Color blocking, or monochromatic. Dark neutrals. Energetically, they are serene and intense at the same time.
  • Shapes: sleek, geometric, architectural, dramatic. Lines, small squares, ovals.
  • Textures: mixed. Mostly smooth, but with judicious use of high-texture materials to alleviate simple colors. Some sheen. Fabrics have weight. Fabrics with less weight are layered.
  • Lines and prints: a mix of straight and slightly curved. Elongated. Slender and sharp, yet somewhat rounded. Uncluttered. Snake skin prints in neutral colors.
  • Details: dramatic, but not loud. Sleek geometry; polished (but not bright) metallics. Strong, concentrated statements on plain background (jewel detail on flats; futuristic embellishments on watches). Some unusual touches (the use of Edgar Allan Poe’s words on the green bracelet, a great example of a writer conveying both her love of words, and her sense of humor, through her accessories).
  • Every item has presence, yet nothing feels heavy or weighed down. This is because there is a clear sense of balance: heavier textures are combined with sleeker lines; lighter weights are layered; squared shapes are kept small and combined with sleek, elongated geometrics.

Now, let’s see how these practical elements can be combined with Jenny’s physical characteristics. Can she wear her ideal vision easily?  [OH NO, JENNY DELETED THE PICTURE OF HERSELF WEARING ALMOST NO CLOTHES – SORRY KIDS, YOU’LL HAVE TO IMAGINE IT]

It really helps to see a woman’s body while discussing her style vision, because this is where you can see whether her ideal style translates effortlessly, or requires some extra tweaks. In this case, we are very lucky indeed. Read the description above and you will see how perfectly it applies to Jenny’s physical characteristics: her body shape; her face and body geometry; her coloring, contrast and texture levels; and even her energy. In fact, again, I am astounded by Jenny’s astuteness here. She intuitively picked items that work incredibly well with her physicality. She can easily wear every single item on her board, no tweaks necessary. Again, we have the kind of discernment that most people would sell their left pinky for (but don’t expect her to make a big deal out of it!).

I do have a few recommendations:

  • Be careful not to use items that are too weighty or chunky. If you pick bolder items like big masculine watches or cuff bracelets, make sure that they do not overpower your slender bone structure. If they are on the big side, make sure that their detail and / or texture are kept sleek and / or minimal.
  • Be discerning when spending your money. Categorize and prioritize. Many of the more basic items that Jenny likes (trousers, shirts) can be bought in regular stores and don’t require a special investment. However, shoes and outerwear in particular need to be selected judiciously. This is where it’s worth spending some time online; store websites often carry much bigger selections, and it pays to shop around a bit to find the more special items. The great thing about jackets and footwear is that they can be combined with simpler items in numerous ways. If you go for signature items in your footwear and outerwear, you’ll be able to create consistent personality in your wardrobe through endless combinations with other, easier to find, basic items.
  • In terms of jewelry and accessories, I also suggest categorizing. Choose where you’ll invest in quality, and where you’ll express your creativity. This way you don’t have to compromise on either. Accessories are a great way of expressing flair. To alleviate the pressure on your wallet, choose one high-quality item to invest in, and decide which items you prefer to change more frequently (and thus spend less on, individually). For example, buy one absolutely perfect watch if you don’t like to change watches often, and make it your investment item. At the same time, don’t invest in expensive earrings if you like to change them up every day: instead, go for things that will highlight  your face and express your creative streak. Also, don’t forget that makeup and hair are accessories, also. The right kind of hairstyle or lipstick can create a feel of effortless drama.
  • For shopping, check out Kenneth Cole, Armani Exchange, Zara, French Connection, Donna Karan, and Mango. For creative items, try Etsy (think steampunk!), second-hand stores and boutiques.
  • Honor your body and its need for long, narrow, sleek lines, gentle curves and occasional small, sharp geometrics (learn more about body geometry here). Avoid clutter at all costs, but respect the balance. If you’re going for texture, keep the lines simple; if you go for one color, play up the geometric details and unexpected cuts.
  • Don’t be afraid to explore. Experiment with prints, details and textures (but always judiciously).
  • Remember that in your case, simplicity doesn’t mean lack of visual interest; it means complexity hiding in plain sight . To achieve this effect, make sure that every item you select has something in it that elevates it from being pedestrian, but in a subtle way: a simple blouse in a bold shade of your favorite color; a geometric necklace with slightly futuristic lines; a narrowly tailored blazer with sharp, sleek edges; a simple sheath dress with a bold cutout on the back. Whenever you find yourself doubting whether something is “boring”, ask yourself: does it have that subtle detail that elevates it (color, neckline, print, etc)? If the answer is yes, this is an item to consider.

Make sure to keep the overall look balanced between extremes (creativity and sleek, dramatic simplicity). Don’t think of them as separate; embrace them equally; combine them in every look, and you will express your essence successfully.

I hope you enjoyed analyzing Jenny’s vision board as much as I did. If I were to summarize her style in two words, I’d call it understated complexity. Never obvious or loud, yet impossible to ignore, that is our Jenny: the elusive, mysterious black cat.


8 responses to “Jenny’s Style Makeover: From Vision to Reality

  1. Wow, what a great post Valeria! I can totally see what you are talking about in Jenny’s collage and I too find it fascinating how incredibly cohesive the whole thing is and how consistent it seems to be with Jenny’s energy and physical body. Very insightful post, can’t wait to see others in the series!

    Jenny, what a beautiful vision board you created! I sure hope in the coming months we get to enjoy glimpses of you putting this style into practice because it is PERFECT for you and very attainable with some careful shopping. I bet this will be a big help in your fall closet clean out!

    Oh, and on a funny note, those two snakeskin print cuffs nearly made an appearance in *my* vision board! They are gorgeous…

    • Tiara, I’m so glad you enjoyed this post. I feel like I discovered so much about Jenny from analyzing her board! I do hope that reading this helps her realize just how good she is at this… and also shows other women that they are so much better at knowing what works for them than they think they are!

  2. What a fantastic way to kick of this part of the challenge! I am also in awe of Jenny’s collage making skills – mine might have looked slightly better if I’d sprayed a sheet of paper with glue and just thrown the pictures at it. Oh well.

    I love the comments about the hidden complexity and sleekness too. I don’t know the show Nikita, but there’s something very…secret agent-ish about Jenny’s collage. Maybe a female James Bond? Jenny Bond? 😉 The ring/cuff with the blue stones could so easily conceal a fantastically space-age gadget, spikes could appear from the studs on those cute blue pumps, and the blue stone earrings could contain tiny bubbles of a sleeping draught or true serum).

    And lucky Jenny gets to wear pretty much all of her items without needing any tweaking. Oh well, brace yourselves for a *real* challenge, as I’m almost done with my board, and will be trying to get my photo taken later on. 😉

    • Kitty, you are so spot on! Nikita is, in fact, a female spy 🙂 You really zeroed in on the whole thing so perfectly!

      Please don’t worry about the “quality” of your collage. It honestly doesn’t matter as much as getting the items that express and appeal to your genuine self. I hope this example illustrates how much you can glean from a vision board like this, one that is made with next to no self criticism, and with a degree of openness.

      I’m actually looking forward to submissions where a woman’s physicality won’t always mesh perfectly with her selections. My goal, and really one of my main passions, is showing women that it absolutely IS possible to wear what you truly love. It may not be 100% as it appears on the collage, but there are ways of interpreting what you see that both honors an item’s essence, and your own needs.

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  5. I love this look, which is far from boring and suits Jenny so well. The interesting thing is, I totally identify with that paradox of being complex, cerebral and creative but loving simplicity – had never seen anyone else highlight this before. As an art lecturer and practitioner I have struggled to find the right look and only just cracking it this year. I love a creative look, but not a frilly, overblown or boho creative thing at all. Unlike Jenny, I love red but only in small dozes (and always denied myself even this) and black, black and more black! Having worked out I’m a soft dramatic type, I am moving towards the odd strong, chunky red necklace worn with black (I used to go for tiny, boho things, which realise now, looked weedy on my tall, hourglass figure. Obviously her body type differs from mine, but I think the neat fitted dresses shown would look great on Jenny as she has a very neat figure with strong shoulders and not too large hips. I see a sort of arty sleekness there in her body and personality which is mirrored in those choices. The strong, individual jewellery pieces highlight her creativity and suggest a clarity of thought as well. I love the edginess of the look, which says, “my complexity is on the inside” – this is strong, contemporary, architectural creativity and I love it; I feel its just right for Jenny and hope she enjoys growing into her own unique style.

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