
Scan from a vintage Lord & Taylor catalog (courtesy of yours truly).
Confession: I am a self-proclaimed lover of all things fashion. I studied fashion (textiles and clothing, to be exact) in college, I devour collections every season, fork out far too much dough on international editions of Vogue and have had a subscription to WWD since the age of 19. I’m as interested in polymer science as I am hemlines and I can usually tell you which retailers are performing well in any given week. The majority of my non-fiction library is dedicated to books about fashion and dress; covering topics from African American clothing in the pre-war South to Diana Vreeland’s life story.
Yet, despite this voracious sartorial appetite, I sometimes struggle to define my style.
Personal style is a complicated business. Fashion is not style, after all, and a love of the former does not necessarily equate to success with the latter. And then, of course, there’s the question of whether one’s style needs to be defined at all. Is it relevant or important?
Everyone adorns themselves and makes active choices around what they wear, even if said choices are a conscious rejection of fashion. No one can escape the communicative nature of dress, but that’s a large part of what makes it so interesting and important. What we wear speaks to those around us before we open our mouths. As Lord Chesterfield said, “style is the dress of thoughts.” Our style evolves from the way in which we dress, and the way we dress is largely influenced by how we wish to interact with and be seen by those around us.
Style is relevant, whether we choose to speak to it or not.
In the past I’ve written about my (many) philosophies around style, but in the case of developing one’s personal style, I will narrow the list down to five key elements:
- Proportion is everything.
- Find what works and stick with it.
- Don’t force trends or silhouettes that don’t work for you.
- Style icons are not a bad thing.
- When all else fails, keep it simple.
Get To Know Your Body
I say this often, but it bears repeating: dressing for your body type is simply an awareness of what proportions and silhouettes work best for you. There is no difference between dressing a “plus-size” and “average-size” woman; it’s her body’s proportions that are relevant. The length of the bottom half of the body compared to the torso, a waist-to-hip ratio, the rise measurement, chest/cup size and shoulder width can all greatly impact how apparel looks on a body. Sometimes these dimensions require troubleshooting, whether the woman is 110 or 250 pounds, a petite size 2 or size 18 with a 34 inch inseam.
Getting a feel for proportion in dressing is kind of like understanding proportion in design; it’s challenging. Nailing the right proportions will trick and train the eye, and is simply a method of minimizing what you’d like hidden and amplifying what you’d like to highlight.

A top from the 2010 H&M Garden Collection, worn by Stéphanie (PC: Le Blog de Big Beauty), Natasha Poly (PC: H&M), and myself at 24 weeks pregnant.
Play With Your Clothes
The best way to get to know your body is to play with your clothing. Apparel, like most mediums, is malleable. It’s very easy to fall into the trap of wearing the same things in the same ways, which is why it’s always fun (and enlightening) to experiment with your clothing.
Put on some music, position yourself in front of a mirror and play around with your apparel and accessories. This is how you discover that you can pull up a skirt, belt it, and wear it as a dress. How you learn that your cardigans look better worn backward. A scarf as a top, a belt cinched over a blazer, your favorite necklace refashioned as a bracelet–try and let things happen a bit organically.

Tall leather boots slouched and twisted (PC: Jak & Jil), Kate Moss wears a jumpsuit from her new Topshop collection backward (PC: Zimbio) and I refashion a favorite mid-calf skirt as a top.
Wear What Makes You Feel Good
Ever have those days when you put on an outfit and you just look damn good, but you’re not entirely sure why? You’ve likely climbed into a outfit that 1) works well with your proportions and 2) you feel comfortable wearing. If you don’t have a firm sense of what works well on your body, these moments may happen sporadically, and when they do occur you may find yourself confused as to why. Always take note when you’re feeling confident and throw some observations in your bonnet. It could be anything; the way you’ve tucked in a shirt to reveal a flattering top-to-pant proportion, a color, the length of your necklace or the hem of a new skirt. Remember the times you’ve felt great in your clothing, think critically about why, and attempt to replicate.
And, by all means, when you find something that works, stick with it!

First Lady Michelle Obama adheres firmly to some personal style “rules” and clearly feels great in her choices. From left: highlighting a feature (arms), repeating a proportion that works for her body (pencil or full, pleated skirts paired with wide belts, shift dresses, mid-height heels) and stocking up on one of her favorites, the cardigan. PC: TFS
Seek Out Inspiration
It may be easy point out the “unoriginality” of those who reference Audrey Hepburn’s cigarette pants in Funny Face or Faye Dunaway’s beret in Bonnie & Clyde as style inspiration, but there’s a reason some women and characters are considered icons of style. As with anything creative, we’re influenced by the people, places and things we see around us. Fashion is cyclical and personal style is always inspired.

Inspiration abounds in Blogland. Blogger Gabi (of Young, Fat & Fabulous) proves that seasonal trends are not just for those with a model physique.
Keep It Simple
It’s hard to not feel fashionably inadequate or unadventurous when fashion magazines are constantly reminding us that we need to update our wardrobes or while reading through personal style blogs like the aforementioned Young, Fat & Fabulous and What I Wore. However, as much as I admire these bloggers, it’s important to remember that style is not always borne of a constantly changing wardrobe and some of the most stylish women keep their wardrobes fairly simple.

Sessilee Lopez, Brana Wolf, Nina Garcia (all shot by The Sartorialist) and blogger Sakina (of Saks in the City) keep it simple and classic.
I’ll be covering these five main points (proportion & understanding your body, experiementing with clothing & not resisting the urge to force trends, wearing what feels good & sticking with what works, seeking out inspiration and keeing it simple) in greater detail within the coming weeks.









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This is really interesting. Thanks! I’ve gained a little weight lately, which I plan to lose. I’m struggling with some of the clothes I own not fitting well, but not wanting to buy up a size and end up spending money on clothes I don’t think will fit later. Therefore the ‘get to know your body’ part is what I’m having issues with right now. I’m pretty much living in wrap dresses and leggings (dressed up) these days.
This post is amazing, Penny! You are a great writer and I look forward to working on my personal style with your tips. I am short and petite and I feel like a lot of popular styles of tops and dresses look like oversized bags on me. I also have dark skin, so I’m trying to work in more color in my wardrobe because I love the way Michelle Obama does. I also usually dress business professional for work so balancing my everyday and work wardrobe is a bit challenging.
Hey – this is a great post and thanks so much for including plus size inspiration!