Transitional You

How to change your style

Beautiful Beckydropped me this note:

Although I’m in my 30s, I recently made some major life changes: I moved cross-country, took a new job teaching a different age group, and am renting my first house. I made the move back to my native Midwest, and so far, it’s been a WONDERFUL change … but even good change, I think, can be very disorienting. This disorientation is showing up in my clothes.

Old standby outfits that used to make me feel fabulous now often feel wrong. My hair and my makeup no longer seem to fit my new routines. Most of my shoes are sandals … now I’m facing boots and sweaters and long underwear for the first time in forever, and I feel so lost!

But mostly, I think I’m just “thrown” by not being able to rely on my closet for my usual dose of self-confidence and self-definition. Who I am is not currently in sync with what I wear. The disparity both reflects my disorientation and contributes to it.

So do I just go out and buy some new stuff? Wait until I’m more settled? Or … what?

Here is a conundrum that so many have faced, often without the added bonus of moving to a completely new climate. How many of you have suddenly found yourself in a new phase of life, facing a closet full of clothes that suit your previous personality? I know I’ve been there. And it’s overwhelming and disheartening, and makes you wonder who the hell you really are; The person you feel like, or the person you look like.

As always, there is no single cut-and-dried way to tackle this challenge. Since what Becky is describing is, essentially, a sudden and drastic shift in personal style, that means that navigating the shift is going to be a highly personal experience. But I’ll share with you what I shared with Becky, in hopes that it might help anyone currently struggling to realign how she looks with who she is.


Think of this as a tremendous opportunity. You are in a place in your life where completely transforming your style is not only acceptable, it’s well-nigh mandatory. Take some time to think long and hard about what you want to look like. And I don’t mean set aside an hour on Saturday, I mean set aside a WEEKEND. Make no plans, talk to no one, just hole up with your notebook and some catalogs and magazines and brainstorm.

Don’t let any mental roadblocks slow you down. Dream big. You’re creating a whole new you, so why limit yourself?


Make lists of adjectives that describe your aspirational style. Make lists of key pieces – clothing, shoes, and accessories. Make collages from catalogs and mags and take notes on what you love and hate, want to embrace and hope to avoid.

Then go through your current wardrobe. Depending on your storage capacity, consider just stashing things that you think you’ve outgrown. When you’re in transition, you don’t know where you’ll end up … and a giant purge may just leave you full of regret once you’ve evolved a bit more. Those items that feel wrong now may just be wrong because you haven’t figured out how the new you is going to WEAR them. So, if you can, hang onto them.

Be sure, especially, to hang onto basics. If you’ve moved climates, you may have to embrace layering, or adjust which items fall into heavy rotation. Tees, sweaters, pants, and skirts in solid colors and classic styles will form your foundation. If they fit and flatter, keep ’em. You’ll find a way to use them.


Now, just spend time playing. Give yourself at least a half-day to just create outfits from what you already have. Remember, clothes are tools. Only items that are decidedly singular in purpose – ornately embellished, daytime-activity inappropriate, etc. – are truly confining. If you’re struggling to love a wardrobe that once worked, you may be thinking of your pieces as only “going” with certain other pieces. Mix and match, experiment, play. See what you can come up with.


Only after you’ve done ALL of this should you consider a shopping trip. And only after doing some serious thinking about what you truly need to make your new look work. Make a prioritized wish list based on your financial situation and stylistic needs, and whittle it down gradually. Once you’ve determined how workable your current wardrobe really is, start bringing in new pieces that will complete the puzzle of your new personal style.


Finally, be patient. This could take a year, or two, or three. Personal style takes time to cultivate, so don’t get frustrated if you have some false starts. If you’ve changed climates, your body may also change, so prepare for that, and embrace it as part of the process.

Originally posted 2009-09-25 06:02:00.

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22 Responses to “Transitional You”

  1. Meli22

    I love this- and I wish I had seen this post last year at around this time!

    I was a regular college student (holey jeans, hoodies, tank tops anyone?) and worked a regular factory job (can I say, nice clothing not needed?). I turn 21, and suddenly feel like I am still dressing/looking like a teen, and start to feel unhappy about my wardrobe. Suddenly, I am promoted into the office world, and have to wear NICE professional clothing. AAAAAhh! It was the worst, most terrible transition you can imagine. I literally had NOTHING to wear, and NO personal style. I bought some things (thinking it was what I needed) that I never wore and ended up hating. Around the same time, personal issues hit. It has been a hard transition, but I found the BLOG world, and have since been learning alot and developing a style of my own.

    Good luck Becky- I know how you feel/felt! It's a long, hard road, but it is worth it in the end.

  2. Wendy

    Imogen over at Inside Out Style is doing a series on finding your own style that meshes well with Sally's advice, and it has a lot of good exercises in it that Becky would probably find useful.

    See especially her posts titled "Who You Are" (9/16) "What do You Do" (9/17) "How to Find the Holes in Your Wardrobe (9/8) "6 Simple Rules for Cleaning out your Closet" (9/7) "What's Your Style" (9/21) and Kristophene's guest post "A Scientists View of Style" (9/18).

    re: Sally's advice to spend an afternoon playing with your clothes…I did that recently, and took pictures of each outfit with my iMac's Web cam and it really helped me come up with new ways to style older items and incorporate my new fall purchases. Being able to study the photos also helped me evaluate which shoes and accessories worked best with an outfit, whether a top looked better tucked or untucked w/ a belt, which outfits created the proportions I wanted, etc.

    Since I was just playing at home, I was also a lot more daring and creative w/ my color combinations and layering, and now I can go back and look at the photos to evaluate the combination more objectively before I leave the house in it.

    I plan to print out pictures or a contact sheet showing many of the outfits to use for inspiration in the morning, when I'm too sleepy to be creative.

  3. fröken lila

    this is great – i know i'm going to be in some kind of transition period in a few months as i will be done with university in about two months time. then i will not only move together with my boyfriend who lives in a much colder country (norway), but i will also be looking for a job, and while i already think a little about what might be smart to have (say, a great blazer and nice tops/blouses) i can't really start shopping now because a) the big move is still in the future (and i don't want to take too much stuff with me, as it will be expensive), and b) it will be good to know what kind of a job i will have (and that could be anything from a corporate office job to a project in the independent film industries or, to cover the months in between, a job at h&m's or any other store just to make some money) before i start buying stuff. i know that my personal style is constantly changing a little, so i am actually very much looking forward to this period, at least when it comes to questions of style and what to wear. on the other hand i am facing a lot of insecurity right now as i have no idea how and what and where. it's scary and exciting at the same time. i just wish i knew already what i will end up with, it would make things so much easier…

  4. Haller Family G

    This is quite timely as I also feel that my previous style is no longer working for me. As a SAHM I have quite a bit of freedom to dress as creatively as I want, but sometimes I just need something stylish yet practical to get my work done in the day, run errands, etc. Living in the Canadian prairies means plenty of cold and snow, so often cute jersey dresses and knee length skirts don't cut it, but I can only wear pants so much. Just last night I was thinking that I need more interesting tops and sweaters to go with my jeans and pants, because I used to rely on interesting skirts to be that pop of style for me. I will definitely be using your suggestions. Thanks to Becky for asking this question.


    Great post Sal!
    I'd say my style will continue to evolve… It's good to finally realize that I don't look good in certain colors & still timid to wear loud-BIG-bold prints somehow… This year I have the courage to have more fun experimentation with classic wear which in the past made me look older than my age…perhaps I'm finally all grown up now! Above all still in love with fashion…

  6. Maegan

    you have really great posts …I bet you inspire and help a lot of women 🙂

  7. K.Line

    Such smart advice for everyone! We're all in transition most of the time – even if not so pronounced. My fave A is the acquisition 🙂

  8. positively present

    I was completely inspired by this post. LOVE it. Thanks so much for writing it and for sharing so much of yourself with your readers. You rock!

  9. Anu

    Wonderful post!

    I went through a transitional period (and in some sense I am still going through it) when I moved from South India (hot pretty much through the year, with one or two months of extremely heavy rainfall) to Ithaca, NY (really cold, snowy winters, with rain showers sprinkled throughout the year). Add to that the necessary changes in style I had to make to account for American tastes (as opposed to Indian ones) and I floundered for quite a while. I feel like I finally have a handle on things now (I know not to buy horrible acrylic sweaters from Target, for example), but there's still a long way to go before I feel as comfortable in my skin as I did back home in India.

  10. Tea Lady

    Interesting post. I moved country 3 years ago. Although there wasn't a big change climate wise… there were some pretty big changes in my life. I got married, moved country, made new friends – massive changes. Those changes helped me to find myself and discover myself more, including my style.

    Over time I have built up my wardrobe to reflect the new "me". I've learnt a lot about my style, my likes and dislikes. Of course, that could have something to do with being 26 when I moved to America… and being 29 now.

    I would suggest investing in nice pieces over time. Over time you realise what clothing/style you really love – and you will be able to make sure it reflects your new life.

    You might need some basics at first of course. Consignment/thrift stores are wonderful for this… until you have the time and head space to really figure out where you're at "style wise".

  11. Sharon Rose

    Hi there-what a very informative post with excellent advice! Have a great weekend my dear!

  12. Caitlin

    This is great! I went through a small transition this summer…moving from Orlando (little sundresses and sandals every single day) to back home in Nashville (requires a bit more layering). I'm also transitioning from carefree theater kid to grown-up married lady…and that will definitely require a transition! I'm going to bookmark this page while I sort through my wardrobe!

  13. Mar

    Good luck Becky! I know sort of how you feel. I haven't had to deal with the major climatic shift so much, but I had a big shift in my mental state over the summer, and now I'm completely restructuring the way I dress. I'm so excited to finally have a personal style (jeans and t shirts do not count if that's all you wear — and that's what I used to wear 365 days a year)! I've bought a few key things — a pair of shoes, a few jackets — but mostly I've been restyling everything in my wardrobe that I actually like. New outfits plus a few interesting accessories that I picked up over the summer or have owned for years but never worn have yielded pretty awesome results so far! It's so exciting to overhaul your 'look'. Have a blast!

  14. Becky

    Thank you, all, and thank you HUGELY Sal for the wonderful advice. I am following all of it, and have actually already bought a couple new pieces of clothing. Using the new stuff, I was able to put together two outfits this week that made me feel fabulous and confident and like the "new me." Yay!

    The most helpful piece of this advice, imho, has been to try to see the change as a style opportunity rather than a burden. It's not often in life that we get to completely reinvent ourselves. I am trying to be patient with the transition, recognize that (as Sal says) it's going to take time, and to enjoy the journey as much as the eventual destination.

    Good luck to the rest of you in your own transitions!

  15. lisa

    What a great post full of sensible tips for how to dress yourself during transitional stages. I love how you advocate thinking about what works and what doesn't, assessing what one already owns, before encouraging someone to shop.

  16. The Raisin Girl

    Since I'm only 20 (but only for seven more days!), the biggest lifestyle change I've had was the transition from home to college. In high school, I worried a lot about the way I looked. And not in a healthy way. In a "what group does this put me in" way. I wore a lot of "punk" and "goth" clothing, went through a distinct hippie stage, and even did the ultra-bright retro-nerd thing. You know, the people who get obsessed with random 80s television shows and wear bright clashing colors and put "x-core" on the end of everything?

    So basically, my style wasn't personal, it was an exercise in collectivism.

    When I moved to college, I got a little less genred. And I had–have–no idea what to wear. Occasionally I find things that I like, but they're short-lived usually. And I've gone through that transitional closet cleanout more than once, only to regret my large Goodwill donations later, when I realized I could really have used all the stuff I got rid of.

    And the change from a yearly school shopping trip to "buy-it-when-you-can-on-minimum-wage-part-time" budgetting really changed the way I think about clothes in general. They're not just something in my closet anymore, they're a big treat. When I have the extra money to buy something to wear, I'm SOOOOO selective and sometimes I get so frustrated that I just don't buy anything.

    I wish I'd had this blog a couple of years ago, basically. 😛

  17. enc

    I don't know why I didn't think of this. I could really benefit from going through this process myself. I think I've been holding onto an old idea of myself.

  18. Anonymous

    Boy oh boy have I been going through a transition for about 5 yrs after retirement. Thankyou for blogging about it because I didn't think of everyone going through the same thing as a normal part of life. We all just do go through transitions, and there probably will be more for me as time goes on. I am having so much fun with style now. I love tis blog and for great style advice and a wonderful community of helpers.

  19. Amber

    This is me right now!!! I am in transition bigtime, thank you so much for this article.