Breaking the Cardinal Rule

I love rules. Without them, life can seem quite overwhelming to me. I’ve never gotten a speeding ticket, I floss every night, and I don’t litter. I’m a rule-follower by my very nature.

As you’ve no doubt noticed – since I’ve shared many of them with you awesome people – I create and follow an inordinate number of rules about style. Avoid crewnecks, no white pants in the fall, mind your skirt-to-leg-to-shoe ratio, and on and on. But my cardinal rule of style is a very common-sensical one: Wear only styles that flatter your figure. Learning your go-to styles is an ongoing endeavor, as different garment types fall into and out of favor, and new cuts and color combinations are introduced. But avoiding shapes, colors, and silhouettes that work against your fabulous natural assets is a relatively easy and extremely important practice.


Occasionally, you’re going to desperately want to buy things that DON’T flatter you. And that is completely fine. In my experience, there are two main reasons to purchase an unflattering garment:

1. Comfort
A giant, boxy cowlneck sweater or fleecy college sweatshirt is going to mask anything womanly about you. A pair of thick-knit sweater pants is going to cling to your butt and show any and all wiggle-age. Cushy Keen high top sneakers look a bit like clown shoes. And OH FREAKIN’ WELL. Sometimes comfort is needed, wanted, and deserved. Although the majority of comfort clothes in your wardrobe should be both flattering AND cozy, splurging on the occasional cozy-only item is not only acceptable, it’s important.

2. Experimentation
I bought these slightly weird shorts over the weekend.

I’ve been curious to try something in the paperbag-waist family, especially after reading recently that, with my proportions, I would be unlikely to pull it off without looking short and misshapen and generally foolish. And although the cinched, high waist emphasizes my smallish middle and adds some oomph to my mini-rack, I look pretty grandma-like from the side. My spare tire tum juts out weirdly beneath the skinny belt and the extreme volume of the legs is just confounding.

But these are INTERESTING. They’re unusual and envelope-pushing in a wardrobe as tame as mine, and yet they’re not so outlandish that I’ll never wear them. They make me feel brave and fashion-y and fun. Oh, and it helps a lot that they’re so comfy I pretty much want to live in them until it’s 40 below zero.

Occasionally opting for a piece that is less flattering and more fascinating is well-advised, especially if you feel like your wardrobe is all basics and no spice. Be careful not to buy something just because it’s pretty or trendy or downright bizarre: Think carefully about HOW you’ll wear it. If it can fit into your existing wardrobe with relative ease, it’s worth considering. Also be sure that your item of choice still allows you to showcase something awesome about yourself. If it obscures your glorious boobs, pair it with a tight skirt to show off your bootay. If it hides your sculpted legs, be sure to wear something with a fitted bodice on top. My weirdy shorts may hide much of my lower half, but you’ll see that I can still show off my waist and bust by wearing a slim-fitting tank.

Picking up an experimental piece can be a great way to stir up some dormant energy in your closet! Be ye not afraid of the occasional unflattering garment.

For those interested in how I came to purchase these unusual shorts, Husband Mike and I took a field trip to Intoto this Saturday, a stunning high-end boutique in Uptown that neither of us had ever visited. You have to be buzzed in, and with good reason. $1,000 Marni dresses, silky Thakoon skirts, Dries Van Noten batwing sweaters, and perfectly tailored Paul Smith slacks line the racks, quiet and stately and breathtakingly expensive. At least, by my standards.

But peeking out from the picked-over sale rack were these adorable shorts. And I tried them on and was deeply smitten. And I cannot refrain from telling you that they are $300 3.1 Phillip Lim shorts that I landed for $39. And although I certainly don’t aspire to shop at that level, I have long adored Lim’s work and it made me deeply happy to encounter such good shopping fortune. See below for proof.

I guess breaking the rules can feel pretty fabulous. Even to a goody two shoes like me.

  • miss cavendish

    Breaking rules can be a breath of fresh air. I clicked over to your neckline cage fight and really enjoyed it. You didn’t note collars though (a neckline I abhor for myself). Do you do collars?

  • Middle Aged Woman

    Am pricing tickets to Minneapolis…desperately need wardrobe help! And I’m only half-joking!

  • Budget Babe

    you read my mind! i’ve been fascinated with the paper-bag-waist since Angie talked about this style on youlookfab. i googled the term and found those Phillip Lim shorts on net-a-porter but the were still full price. i can’t believe you scored them for $39. i’m so jealous. hehe. anyways i think they work for all the reasons you outlined. great post, and expect me to copy you in the near future :)

  • K.Line

    The paper bag waist really is a leap of experimentation (I know from experience). It does do wonders for the waist but it makes my not negligble rack seem rather epic :-) Nonetheless, a girl needs to branch out so I’m working it.

    May I suggest that these great shorts would look fantastic, going into fall, with a crisp white collared shirt (Gap or BR?), a fitted cardi, a great scarf tied jauntily around the neck and a chunky heel? What a score, btw!

  • enc

    I really like the way you look in these shorts. The color works is perfect on you. The waistline is super-flattering, and they fit you well.

    All the mags would tell us to run away from these shorts, which makes trying them all the more appealing, because it feels like an act of rebellion.

    I love rebellion. Rave on!

  • Christina Lee

    Great Post! In love with the necklace!

  • Sharon Rose

    Yay-an excellent designer find, very well done!! I also felt like you when I got my faded wide legged levis jeans last week in eastbourne-you just get drawn to things for no good explanation!! Its great when you can work these items into your wardrobe though, well done!

  • yiqin;

    Excellent post!!! I have been looking for paperbag shorts/pants FOREVER! Where'd get yours?! & ys rles are meant to be broken! If not how will new ideas come about.

  • Kris

    Rules were made to be broken!

    And I love those shorts; anything with a high, cinched in waist I am absolutely besotted with!


  • Hammie

    I go along with K-line, but can I suggest opaque tights. It has been a strong feature of our wintery spring and barely summer over this side of the pond. And it works.
    Check with Imelda if you don’t believe me.

  • E

    I could have sworn I saw your pretty behind on my way into work this morning! That was quite a Two Worlds Collide moment for me until I got a little closer :) Weird, though!

    I love your rules. And that necklace!! Yum!

  • Anonymous

    Rules are meant to be broken and you look smashing in those fabulous shorts!!

  • Sal

    You ladies are da best.

    Miss C: You know, I don’t really wear collars that often myself. But it makes total sense to do them as a follow-up to the necklines. I’ll stash that in my idea box!

    MAW: I’ll pick you up at the airport.

    BB: I’d lend you mine anytime, but they would literally fall off your slender frame! Hope you find a gorgeous, tiny pair somewhere soon.

    K.Line: I’ma write that down. I want to keep these in rotation until fall, and those are great suggestions.

    enc: You’re a born rebel, my dear, and I hope to learn from you.

    SR: Thanks, lady.

    Yiqin: These came from a Mpls shop called Intoto. A link is in the post.

    Kris: Too right, you.

    Hammie: Ooooh, for surely. I really need to begin the tights-shopping soon … my current selection is positively woeful.

    E: Someday soon, we’re totally hanging out. Like in a planned way.

  • ambika

    You know, I really like the paperbag waist on you. & honestly, if it feels adventurous and you're enjoying it, nevermind the rest.

    Also, love that necklace and you really have a fabulous smile.

  • Skye

    I think you could roll the bottoms of those shorts for a sort of double paper bag effect (that’s what I do with mine). Experimentation is the best (closely followed by awesome bargains)!