Sally McGraw, a Minneapolis-based fashion blogger that I follow, recently wrote this piece on transitioning your personal style to a reader (cis-woman) that was changing her lifestyle. Her thoughts are equally apropos to our community as we transition from male to female whether for shorter or longer periods and try to decide what personal style best suits our personality.
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. I have a personal “Lookbook” of outfits I love taken from retail websites, blogger looks, and Pinterest and they range from everyday wear to glam to just pure sexy. Here is where you dream.
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.
And consider not only where you live now but where you are likely to travel. I live in the tropics so 90% of my wardrobe is summer related, but if I visit friends or relatives in NYC in January, I’m going to need a few warm pieces and some longer skirts and dresses.
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.
If you have a female friend. enlist her help. My wife was marvelous at teaching me how to create different outfits from what I had
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. Here are some tricks to creating a capsule wardrobe.
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.