Has anyone ever asked you to define your “style”? I don’t like that question, nor can I answer it. I do, however, have opinions about dressing, which I’ve outlined below in no particular order. These are, by no means, rules. They are simply the philosophies around style that I’ve stuck to for a number of years.
As always, I would love to hear about yours as well. For now, here are mine:
Proportion is everything.

I can’t stress this enough, and it’s directly related to highlighting your best features and what is normally referred to as “dressing for your body type” (I hate that phrase). The thing is, getting a feel for proportion in dressing is kind of like understanding proportion in design; it ain’t easy. Nor is it simple to explain.
Some of my favorite proportions are the ones that work best for my body type: a long blazer paired with a short dress/cut-off shorts, cropped, billowy tops paired with skinny jeans, long cardigans with fitted ankle-length pants and heels, loads of light layers and low slung, wide-legged pants. I dislike anything cropped, with the exception of cropped jackets layered over longer tops. Because I am proportionally long on the bottom half of my body, I like longer tops to even things out a bit. Proportion in dressing is simply an extension of covering up what you want hidden and playing with shapes, lengths, heel heights, accessories and add-on layers.
Shoes: Keep them high or flat.

This is a rule that I would never impose on others; because, really, mid-heel shoes are probably the most flattering for the majority of women. However, I can’t stand anything under 3.5″ that is not flat. Which means, of course, that I am totally fucking up my feet.
After putting on your jewelry, remove one item.

This is a variation of some advice I picked up from Cynthia Rowley’s book “Swell” years ago.
“Before you walk out the door, take one thing off. When you look in the mirror, pick your point of focus. If it’s the silver shoes, let them shine. Meaning no competition from rhinestone hair baubles or a couple of cocktail rings.”
I nearly always prune one item of jewelry before walking out the door. Which means I sometimes end up wearing no jewelry at all.
Do not underestimate the value of a good tailor.

I hear a lot of people complain about not being able to find clothing that works for their bodies — “No one makes anything short/long/wide/narrow/slim/full enough for my figure!”
They usually do not want to hear this, but a tailor is their answer. Expecting clothing manufacturers and designers to produce clothing which molds perfectly to your body is plain ridiculous. Sure, sometimes you luck out. And certain items of clothing (say, a denim jacket or stretchy cropped jeans) have more allowance for fit than others (blazers and classic trousers).
Carolina and Diane would tell you to find a good tailor. And stop your bitching.
Find what works and stick with it.

No reason to veer from what works if you rock it, right?
Style icons are not a bad thing.
![]()
Don’t let anyone make you feel bad for thinking Kate Moss has great style (because she does). As with anything creative, we’re influenced by those around us, be it a stranger on the street or a film icon like Katherine Hepburn. But, I warn you, looking at too many photographs of Francoise Hardy will make you want to take scissors to your hair.
Play with your clothes.

This is how you discover that you can pull up a skirt, belt it, and wear it as a dress. How you determine that your cardigans look better worn backwards. 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. Stand in front of the mirror and play around with your clothes.
Perfect an easy hairstyle.

Everyone’s hair is different, but this rule is essential for all women who hit the snooze button at least ten times in the morning, only to discover they have 15 minutes to get out the door. In addition, the EH is great when you’re sick, tired or just feeling lazy.
My EH goes something like this: pile dirty hair on top of head and twist with a hair tie, pulling out bits and pieces here and there, and add a headband (growing out bangs is a bitch). Or, a twist, which I have perfected, using bobby pins. Either way, people compliment me on my hair far more when I’ve pulled out an EH, and I have to bite my tongue to prevent myself from blabbing about how I haven’t washed my hair in three days.
Never pair dark eyes with dark lips.

An oldie but a goodie. A makeup artist may be able to make it work on a model, but there’s a 99.8% chance that it won’t work on you. When approaching the eyes and lips, keep it ying and yang, folks.
Scarves make every outfit better.

Scarves are, by far, my favorite accessory. From oversized shawls to whisper-thin silk squares, I love them all. I am usually toting at least one around. I like to wear them messy, let them flop out of my purse and tie them onto my bags. They’re an often cheap and simple way to elevate an outfit.
Don’t force trends or silhouettes that don’t work for you.

I would love to wear belts but they will never work with my body type. I would love to buy a jumpsuit but they don’t look all that great on someone under 5’9″ who’s not south of 100 pounds. And trying the unaccommodating item in different fabrications, colors and styles won’t change the fact that it doesn’t work for you. Don’t waste your time.
A pop of color in an outfit is great; two will work; three is pushing it.

Think of it this way, would you paint your bedroom with three shades of vivid color? Okay, maybe you would, but I wouldn’t.
Show off your best feature.

Like: Legs (relatively long), Shoulders (really a part of the body that is beautiful on everyone)
Dislike: Middle Area (short torso, stomach not as pancake flat as it once was), Hands (sad, sad nails and fingers nowhere near as long and slender as I’d like – I rarely wear rings)
My general feeling is that curvy girls look best in tailored, classic clothing, especially if they are lucky enough to have a slender waist. Wrap dresses are a universally flattering shape, unless you haven’t a hint of a waist and a short torso (like me…..damn). Slouchy clothing, tent dresses and painted-on jeans generally work best on slender girls. A perfectly constructed cropped tunic works wonders for busty women when paired with a slender pant. Showing the collarbone and décolletage works for just about anyone.
You only need one to two pairs of sunglasses. And make them classics.

Classic sunglasses make you look cooler, more glamorous, and mask/shield hungover eyes. I’m talking your classic Ray Ban styles (aviators, wayfares, etc.), simple black frames in a flattering shape and your typical oversized “Jackie O” glasses. I am not talking about glasses that are so large you look like a bug, any accessorized glasses or colored frames.
Black really is best.

It’s slimming, it’s never busy or distracting, it looks good on everyone and it’s classic. The only downside? It’s sometimes hard to launder and collects crazy amounts of lint. Easily remedied with a cold wash and lint roller.
An excellent jacket frames any outfit.

Seriously, jackets and coats are the shit. Everyone has their favorites — classic jean jacket, one-button blazer, military, wrap, trench, motorcycle, leather….the list goes on and on. And the great thing is, most styles work for most everyone. The wonderful thing about, say, a trench coat, is that while a very busty woman may be unable to wear it belted, it looks just as smashing open.
Mix high and low; be inventive.

I’m not just talking about mixing formal with casual, but textures/fabrications, seasonal items, weights, etc. A masculine blazer with a slip of a dress or cut-off denim shorts with a crisp, white button up, for example. Layer thrift camisoles, wear a once-piece bathing suit as a top and look for items in the kids department. Wear something a little glitzy with an otherwise dour outfit. Have fun.
Layers make everything better.

Piling on the layers, in moderation, is awesome — just make sure they are light! I have a habit of throwing on a blazer in the morning and tossing a cardigan in my purse just in case it gets too warm. I am lazy, I hate checking the weather.
When all else fails, keep it simple.

Note: Many photo credits attributed to The Sartorialist, Garance Doré and Jak & Jil.









{ 1 trackback }
{ 19 comments… read them below or add one }
AhHHHH! Great post. Can we Ask Aunt Penny some questions?
I am 5f10, with an insanely long torso and neck. I can’t find trousers that flatter me at all, except if I wear very high heels (not always great when already tall). Should I just give up and wear dresses?
Atalanta I am not nearly as tall as you but still tall, and long torsoed, with a chunky ass and thighs. Pants are hell. I actually don’t think I own one pair I really love; even suit pants are problematic, gapping at the waist. I wear almost exclusively dresses (belted, usually, to establish a normal center for my body) and skirts and if I wear pants tend to fuss them up with belts and scarves.
I know they are controversial but I have always been very comfortable in quite high waisted pants, since my first pair of seventh grade sailor pants from the army navy surplus. Low rise jeans make me look hideously deformed and stubby; I loathe them.
I actually think I could get away with some of the really weird slouchy pants out now but I just can’t be bothered to figure out where I would even try a pair on. If you are that tall I bet they would look good on you too.
Penny I know about that take away one accessory rule but I just reject it totally. For others, absolutely, you look chic and fabulous. But I just can’t give up on scarves, dangly earrings, big beads, belts, huge wooden bracelets…all at once. When I’m not all stacked up with jewels I feel totally naked and invisible and plain.
Oh also I would recommend bell bottoms; they usually come in higher waists and balance out the proportions of a tall body.
JD, so funny, my first thought to Atalanta was….”high waisted pants!”
Thanks, styling team…JD, thank you for the empathetic advice. And I agree on accessories. Since I’m tall, I feel more comfortable piling on the scarves and necklaces; maybe if I were short…
Penny, you have lovely legs and you look really tall in those shots, whereas I always look tiny because of my proportions. Heh!
First, I want to thank you for putting this post together. It must’ve taken quite a bit of time. I agree with all your tips. Do you have any advice on jeans? I’m 5’3″ and can’t figure out if bootcuts or flairs look better with my frame. Thanks!
I agree with so much of this post–proportion, proportion, proportion. I am barely 5’2″ with a pretty straight, but muscular figure (currently a runner (marathon training), always an athlete)–my friends refer to me as “compact.” Very short torso, not much difference between my waist and hips (mostly because my rib cage basically sits on my hip bones), flat-chested. I find that long/lean pants styles (like a fitted flare-Joe’s Rockers come to mind, as do most Rock & Republics) make me look taller and fit well. I can also rock the deep, deep v, because with no chest, it never looks obscene.
I cannot do big, blousy tops, as they swallow me and give me a roundness that I do not have. I have problems with skirts–because they tend to hit at the wrong point on my short legs, but just below the knee and high-waisted pencil shirts with a tucked in shell and belt always work (and, I work as an attorney and must always look professional).
I never miss a chance to wear big, dangling earrings, and when not at work, I am often falling back to jeans and a James Perse tank (with heels–the taller the better). One rule that I always consider is that fashion is about fun and taking risks–dress like a rocker when you’re going out (even if you’re a 31-year-old lawyer), wear something confusing and geometric, pair red stilettos and a leather skateboarding bracelet with your black suit. Life is too short to care if someone is judging your outfit (aside from situations regarding employment).
This is an AWESOME post! A lot of my rules are similar to yours. Proportion is really important. I am 5’10 (with hips, thighs and a butt) and I have a long torso and my legs are about the same length of my torso. So I am literally half torso half legs so my legs can look short if my tops are too long. But I need longer tops to cover my torso so I always check the proportion of my outfits and even play with it sometimes.
I am always on the search for the perfect pant. I have to always fit my booty thigh hip area first as it is the biggest part of my bottom half. But I also have a really small waist which means that pants can gap really easily. I have a pair of GAP skinny jeans that fit really well although I wish they were 2 inches longer. And Levis have been surprisingly good to me.
I have always been a stickler for the amount of jewelry I wear. I either something on the ears (chandeliers mostly), neck or wrists (stacks of bangles) never a combo. I recently purchased a necklace that is a bunch of plain layered gold chains at Forever21 that I have been wearing all the time. It is so simple and is one piece but it totally pulls my outfits together.
I am also all about simple hair. My normal hair is simple-wavy layers with side swept bangs. When I have dirty hair or hair that just looks like crap I either sweep it up or I will braid the front and pin it under. Braids in the hair have been my friend. They make dirty hair look more pulled together.
Ok to wrap up this really long comment…..I would say that my style is taking classic basic pieces and dressing them up with accessories. I love long cardigans with tank tops and a layered necklace. Or a slouchy v-neck tshirt with a fitted blazer and skinny jeans. I always try to add a little boho flair a la Nicole Richie. I am looking into adding to my wardrobe clothing with a bit more flair to it now that I have a bunch of basics
Jess, for what it’s worth, I am built like you and have found Express pants to be my safest bet for avoiding tons of tailoring costs. But vintage dresses and skirt suits fit me best of all, and I refuse to believe they are not work appropriate.
Love the post. You hit many of my own personal style rules. I stand at a paltry 5’3″ and I feel like I have to keep the lines of my outfits lean or I look way bulky. I am also a sucker for high heels and minimal jewelry, choosing either one statement piece for a simple outfit or toning the piece down when the clothes are more bold.
Robin, I love your ‘dress like a rocker’ philosophy. One more year until I hit the legal world, but I will refuse to let that turn my personal, non-work, wardrobe into a mundane mess.
Count me in as a member of the 5’3″ and under club. Do you ladies have any suggestions for jeans? Do you prefer bootcut or flare when it comes to an everyday jean? Thanks!
What a fantastic post! Your philosophies are similar to mine. I know you’re right about the importance of a tailor, but for some reason I balk if the item is inexpensive. As in, I feel silly taking something from Old Navy, for example, to a tailor, even if it would improve the fit and the look dramatically. Silly, I know.
Melissa, it really depends on your shape and what you’re comfortable wearing. I would say that a bootcut is more universally flattering, but flares run the gamut from subtle to whoaaaaa-70′s-redux.
Fantastic – I loved this post!
I hadn’t yet learned to embrace scarves until I studied abroad in London in college, and I was totally blown away by how chic the girls there looked, how a scarf could completely make an outfit 10-times more fabulous, and am still amazed at how much warmer you can stay just by wrapping a scarf around your neck! I have so many now, it’s borderline ridiculous.
…and my feet are a total mess because I also roll with the “Tall, Flat, or Nothin” philosophy when it comes to shoes :)
I love everything about this post. That is all.
One thing, I wish I had more money to afford some of these cool clothes.
Melissa – I rely on Joe’s Jeans in their provocateur fits for petites like you and me. I think that skinny jeans are tricky on short people, they can make your legs look stumpy unless your legs are rail thin, which mine are not. So, I tend to stick to straight or slightly bootcut to create a more lean and long silhouette. I avoid wide flares because I just don’t think my legs have the length to balance them out.
I know you posted this about a week ago, but wow! What a great post. It must have took some effort to collaborate all of the pictures to use as examples, but it turned out well. You give out great tips and advice and examples for everything! Love it.
You are so right about proportion being so key – it’s actually more important than ‘body shape’ even though so many are obsessed with this.
Proportion is the key that creates balance – and we tend to find balance so pleasing to the eye.
Great list!
This post is awesome, Penny! Since I read it a few days ago, you’ve inspired me to a) wear a button-up shirt with cutoff shorts and flip flops, and b) turn a necklace into a bracelet by wrapping it around my wrist three times. Thanks!