personal style vs. fashion rut

Hi Stephanie, I’m a big fan of your books, blog and style! Here’s my question in a nutshell: What is the difference between having a "personal style" and being "in a style rut?" I’m a 32, pretty tall, size 10 mom of a toddler, and I’m a teacher. I don’t want to look like my high school students, but I don’t want to look like their parents, either. I like clean lines and am somewhat classic/preppy (Banana Republic, J. Crew, Cole Haan, and Tod’s when feeling flush). Jeans are a good example: I am a boot cut/long length with heels, but I am seeing all these skinny jeans/boyfriend jeans/tapered pants now. I’ve watched enough What Not to Wear (BBC, not TLC!) to know that tapered pants make women look like upside-down triangles. I’m not feeling it! I also can’t picture the the rolled, slouchy jean look on me. Do "real women" really wear this now? If I only wear what I think "works for my shape," will I look like I am stuck in a time warp forever? How do you balance the two?

straight up advice

I balance the two with two secret weapons: alcohol & accessories. Okay, so not always alcohol, but at least the confidence that comes with the loss of inhibitions. Allow me to digress, just a wee bit.

Ever notice the way films, books, and after school specials about popular girls feature some dorkstick of a teen sighing just before she says, "Why do they get to be so popular? What is it about them, exactly, that makes everyone think they’re so special?" And the answer is always "Because they believe they are." That, or they look like the twins from Sweet Valley High. They treat each other as if they’re more entitled, more knowledgeable, more experienced, more worthy. And people respond to it. It’s all about owning it.

stephanie klein cheapo

True, some fashion-paralyzed peeps heave out of their shirts, and yank on their camel toe, walking around as if they’ve just discovered their best look, ever. But most of us don’t always feel as secure, despite the fact that we look more comely. And that’s when I rely on accessories to keep me current.

I stick with what I know works with my shape (v-necks, boot cuts, a-line, you know the story), but from time to time I will branch out realizing, Okay, so this isn’t my most flattering look, but I feel good in it because it’s current. No, that does not mean I’ll wear skinny jeans. Ever. But I will roll up a more narrow cut jean and rock ’em with cute boat shoes… definitely a day look. Quite frankly, I’m all about JCrew, especially for accessories, but the key there is you can’t fall into the trap of buying everything from JCrew. You have to mix it up, pair that darling cardigan and chandelier necklace with some bleached-stained jeans and you’re good to go. I always try to mix in a little dirty with all the prim and proper prep. And sometimes the inexpensive (target) alternative really does give you the same overall look as the pricier splurge.

go ahead, ask


If you have questions or need advice on anything from where to eat to how to get over the bastard, just email your question to my advice email address. I’m no doctor, not a therapist, but since people are asking me anyway, I promise to give you my opinion, straight up.




  1. I’m running to Target now for Halloween supplies, and now for a necklace too. Thanks Klein.

  2. Do you have a favorite brand of jean?

    BTW, I love these advice posts you’ve been doing lately. Keep ’em up.

  3. Those two necklaces don’t really look at all alike. Though I guess you could get the same effect if you buy two of the target ones. I’m not sure, though I have looked at those target necklaces lately, and they are cute. Thanks for telling everyone.

  4. This might sound a bit stalker of me, but I recently saw you in TN. You were walking the street near my store, and I was out running for coffee. I couldn’t believe it. There you were, my morning cup of coffee with my coffee. Even in the rain, you looked great. So please do share, what are your favorite brand of jeans? I have your same body type. Thanks.

  5. One thing that helps when I want to change my look but I’m not sure how, is to go out somewhere (maybe the mall, or a park) and sit and look at what other women are wearing. Which outfits immediately draw your eye? What details could you add from them to your own outfits? I think you can get a lot more real-life ideas this way than from magazines or stores, because if I see a picture of a model in a dress and boots I might think I’d be really self-conscious in that in real life, but to see someone wearing it can make it seem more accessible.

  6. Great post! I like the way you spun it to create an even more in depth response to personal style and image making.

  7. I get a lot of jewelry from Target. $4.99 for a pair of earrings or $7.99 for 3 different size hoop earrings – you bet! Your comparison of the Target necklace to the JCrew one reminded me of the tv show on Style or E! years ago called “The Look for Less”. Matched w/ a stylist to find an outfit w/accessories that looked like a much more expensive version of that outfit but for only $150. That’s what I try to do. I also agree w/ Kat and people watch to get an idea of what I like, what I think I might like and what I know I don’t and go from there. I also have a good friend w/ a sense of style and bring her shopping w/ me a lot. She has helped me get out of a rut and “find my inner hottie”. If I shop alone and get things I’m iffy about I let her see the items first on me before I cut off the tags and wear. She’s brutally honest and sometimes the truth hurts, but sometimes the truth also gets you a better wardrobe.

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