How to Dress: Now Taking Requests!


The series “How to Dress” has kind of taken on a life of its own, which makes me really, really happy. “How to Dress” started as a way to answer reader questions about fashion and my closet reorganizations.

Why the interest in fashion, you might be asking? Well, I was pretty down after my experiences with infertility and miscarriage and tried a number of things to get happy, including spending a year trying to live joyfully. Nothing really took, until I started re-engaging with a previous love of fashion. I cleaned out my closet, started planning outfits and began following fashion blogs like The Sartorialist, Garance Dore and Man Repeller.

To my amazement, these efforts started to pay off. When I looked cute and put together, I FELT good. And that small step parlayed into dividends. I think there’s an idea out there that once you’ve had children or move out of your twenties, you shouldn’t worry about how you dress any more. You can just wear a work “uniform” you don’t think much about. As a SAHM, I had resigned myself to a permanent uniform of yoga pants and exercise clothes. (Not only were these clothes drab, they also weren’t very flattering. I felt how I looked: frumpy and gray.)

Here’s the thing: we get dressed every day. We wear clothes every day. Why not wear clothes that make us happy?

Fashion can be perplexing and sometimes it seems like you have to be thin and perfect to wear great clothes. Which is totally untrue. There is a unique style out there for EVERYONE that will make you feel good. Yes, there are basic lessons (which I try to teach here) but fashion should be fun and a way to release your creativity and sense of self. Whether your inner fashionista is a 90s soul wearing Docs and punk rock T-shirts, a later day Audrey Hepburn with elegant capris and trenchcoats, a romantic drawn to lace and florals or a Sophie Loren bombshell favoring curve-hugging styles, you have one. Everyone does!

So I am taking requests for my “How to Dress” workshops. Here’s what I have so far:

From Palm Tree Mama:

“I could use some fashion advice for a sporty chic look this summer!” 🙂

From Miss OhKay (and seconded by Mandski):

“Not in season now, but I can’t figure out scarves. They look bunchy and stupid when I put them on but I like them on others.”

From MomPharmD:

“1. Work postpartum and 2. working in wide temps in a white coat please.”

What questions do you have for “How to Dress?”


Filed under personal style

12 responses to “How to Dress: Now Taking Requests!

  1. Great idea! I need shoe help with pants and also how to dress casually without looking like a slob. I usually wear jeans on Friday and since I spend most of my effort on work clothes, I don’t do a great job with casual clothes.

  2. KeAnne has the same idea I do.

    How to look chic this summer while being yoga-clothes comfy and not breaking the bank? (Is that even possible?)

  3. Ana

    I love that your are finding joy & confidence in fashion—I’ve recently rediscovered my interest in clothes/shoes/accessories as well. Since my body has changed so drastically, I had to buy new clothes anyways, so I figured I should experiment with new things! I still have trouble figuring out shoes—i.e. what shoes go with what. For years I basically wore the same shoes every day (sporty-ish flats in the summer, flat or very low-heel ankle boots or below-the-knee boots in the winter). I’m starting to buy different styles of shoes (and heels, I’ve actually found comfortable heels!) but then I feel like I have to develop an outfit around my shoes because I don’t have a natural sense for it. Also I third the scarf advice. I still haven’t taken that plunge.

  4. Why not wear clothes that make us happy – yes!!!!

  5. I will admit to having my schlepy (is that a word??) days, and I am prone to wearing yoga pants or shorts & T-shirts around the house — but when my outfit is well put together, I feel better about myself. 🙂

  6. I love this series!

    How about 5 or 10 key clothing items you think all women should have/own?

    What clothing, jewelry, hand bags/purses and shoes are worth splurging on and which do you recommend being more frugal about?

    What are you favorite low budget and splurge stores and websites?

    How about some kind of “what not to wear” post? I.e. You may think _______ is still in style, but trust me, it’s not…

    Okay, that’s a start! 🙂

  7. You always look fantastic, and if you have any ideas, I’d love a post on how to dress for varying weights. I’m back and forth on a number of medications + PCOS that are causing weight gain and bloating – and then within a few weeks of finishing, the water weight drops. How to transition between having a flat belly one week to a pretty serious one within a couple of weeks?

    I love to dress well, but this constant yo-yo of weight is severely frustrating and doing a number on my self-esteem.

    Also would like to second Kathy’s suggestions!

    I’ve really been enjoying all your “how to dress posts”. Looking forward to more in the future.

  8. I like this series! And I second KeAnne’s idea about how to dress casually without looking like a slob.

    I’m not sure I have a personal style, though. I think I am happiest when I can just throw something on without worrying about how I look. Today, for instance, I am dressed for work, and I’m worked my pants are too tight, my hair keeps coming out of its clip, my toenails aren’t painted… But if it were a weekend and I was wearing jeans & an old shirt, I wouldn’t think about any of that and I’d feel less stressed. Planning my outfits like you do would stress me out! Maybe that can be a topic somehow?

  9. I love this series! I’ve learned so much from these posts.

    Here’s my request. I tend to be fairly casual and would live in jeans and t-shirts if I could. In fact, I work at a university where jeans are okay as long as they’re paired with something funky and hip because that’s the prevailing aesthetic. My problem is that I cannot figure out how to be funky and hip. I sometimes *think* I’m putting together a cute and fairly hip outfit, but I get to work and look like I walked out of a Lands End catalog. I guess what I’m really asking is how I can avoid looking so conservative without looking ridiculous. What is funky and hip and where do I get it? I see women in the hallways at work looking adorable, but I can’t figure out where they get these cute things. I must be shopping in the wrong stores. Maybe that’s really my request: what stores/catalogs/online shops might be the best for a funky and hip, but casual, aesthetic? I’ve tried Boden, but it looks too little-girlish on me and the sizing is often not right for my body (I’m a 14/16). Other suggestions?

    Thanks again for the series!

  10. I see some others also asked about shoes – I have some specific issues, though – I live in a very rainy city and I walk to work, so suggestions for chic water-proof shoes/boots would be RAD, and also ideas about how to use color in shoes. I tend to buy only black shoes, but my husband tends to buy me very colorful shoes that don’t always match the colors in my wardrobe (yes, he buys me shoes – it’s kind of weird!) I don’t typically wear heels at all, or only a very low heel. I love Mary Janes but my husband hates them. I also feel like I have huge feet so shoes that make my feet look smaller are always good!

    Thanks 🙂 You give rad advice!

  11. I’d like to add belts to the list. Skinny, wide, colored, neutral. I’m not sure when to do what!

  12. I love that you’re talking about fashion. It (dressing cute) so hugely affects how I feel during the day, and I also feel like making an effort to look nice is one of the best things I can do for my marriage.
    I have a couple requests…maternity dressing (if you feel like going there at all…if not, I totally understand). And also, I recently moved into a house with SMALL closets, so I would love some advice on how to look great without having lots of stuff.

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