Reader Request: Style Evolution and Transition

cowboy boots

Fabulous reader Rebecca sent me this question:

I’ve been thinking a lot about my personal style. I’ve always adored vintage styles, and as a country musician, I’ve totally been able to pull off my signature style of vintage dresses and cowboy boots. Lately, though, I’ve been pulled in a more streamlined, sophisticated direction. I feel strange looking in my closet and seeing these clothes that I LOVE but just don’t feel like wearing. I feel almost costumed in my signature style! I also hate to give it up…

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. Realizing that your style has shifted so drastically that your former signature pieces feel stale or wrong can prompt minor mourning. You loved those things once and you loved the version of you who wore them. But you’re someone else now, or on your way there.

As always, there is no single cut-and-dried way to tackle this challenge. But I’ll share a few of my suggestions and ideas, in hopes that it might help anyone currently struggling to realign how she looks with who she is.

Sort and purge

Spend some time sorting through your current wardrobe. Depending on your storage capacity, consider just stashing things that you feel you’ve outgrown. When you’re in transition, you can’t be sure 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 likely form your foundation. If they fit and flatter, keep ‘em. You’ll find a way to use them even if your signature style has shifted.


Most of our dressing decisions take place during the 10-minute window between showering and leaving the house. And if your style is shifting, you may feel even more Morning Wardrobe Panic than usual since your clothing options will feel simultaneously confusing and limited. So set aside some time to experiment. Give yourself a few uninterrupted hours to just create outfits from what you already have. 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.

Don’t shop

And here’s the reason it will be worth your while to devote some precious free-time to experimentation (and even hire a sitter): The temptation to buy new stuff can be very strong when your style is in flux. If mainstay pieces no longer feel like “you” when you wear them, you may decide that you just don’t have enough available, reliable options and need to get more items into the mix. This can work. It can also backfire spectacularly. Try to do the experimentation first and really evaluate your resources. Many items that seem utterly not-you in a quick visual sweep of the closet may prove useful on more careful consideration. Experiment, live with your current wardrobe for a couple of weeks, and see if specific holes in your wardrobe emerge.

Add new pieces, mindfully

Make a prioritized wish list based on your financial situation and stylistic needs, and whittle it down gradually. Once you’ve really determined how workable your current wardrobe is, start bringing in new pieces that will complete the puzzle of your new personal style. And if, like Rebecca, you don’t want to completely let go of your previous style, try to buy new pieces that will work well with your new looks but also potentially complement your old looks. Balancing contrasting styles can be tricky, but it can be done.

Be patient

This transition 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 and bum purchases. If you have the time and energy, snap photos of your outfits as often as you can. Look back at them every couple of weeks and note what’s working and what’s not. Keeping a visual journal like this is incredibly helpful in transition because it allows us to analyze in retrospect and really process our decisions and preferences.

Related posts

Are you in a period of stylistic transition? Have you gone through one in the past? How did you cope? What were the greatest challenges? Does this multi-step plan sound helpful to you? Any other tips for navigating a drastic change in personal style? Or one that descended unexpectedly?

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Originally posted 2014-11-03 06:27:40.

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