I’ve written several times and at great length about my fears of androgynous dressing, but I believe I’ve made great strides in the past few years. In fact, my entire style has shifted toward more tomboyish, androgynous looks in some ways, though there are still links to my old style which relied on heels and full skirts. Making the switch from one style to the other pushed me pretty far outside my sartorial comfort zone for a long time.
Some people are perfectly happy to locate their zone, create a wardrobe that works within that zone, and dress impeccably within its parameters. Not a thing wrong with that … until you get bored, or feel stagnant, or just want to explore. It’s all down to your preferences and choices. So if you’re currently feeling a bit stylistically restless but unsure how to reach beyond your established looks into more challenging ones, here are a few ways to test the waters:
Make a plan
If you know it’s time to shake things up a bit but you don’t know how you want them shaken, take some time to think. What about your current style feels stale? Is it the colors? The proportions? The overall aesthetic? What looks are you feeling drawn to that are different from your own? Are they more romantic? Minimalist? Rocker? All of the above? Or is there a specific person whose style you wish you could emulate, but with your own flourishes? Consider making an inspiration board – on paper, in a folder on your laptop, or maybe in Pinterest – to give yourself focus. Otherwise you won’t know what to change and what to keep the same.
Start with accessories
Once you’ve determined your new direction, a great way to begin mixing up your looks is to incorporate accessories that align with your aspirational aesthetic. Clothes are the foundation of any look. Shoes and accessories add depth and character, but often feel like less of a commitment so they’re fabulous tools for easing out of your comfort zone and into a new realm. If you’re headed in a romantic direction, consider some chandelier earrings, soft scarves, or patterned tights. Minimalists can do sleek necklaces and sculptural shoes. Rockers try studded belts, combat boots, and cuff bracelets. Consider thrifting any experimental accessories, since you’re still in the process of honing and may not want to spend big just yet. See if you can work these items into outfits built from your existing wardrobe.
Consider taking self-portraits
Since venturing outside your sartorial comfort zone can feel daunting, and since it can be difficult to gauge your progress, consider snapping some quick self-portraits in the mirror. Give yourself a day or two to get some distance, and then take a peek at them. What do you love? What would you change? Do you feel like you’re headed in the right direction? If not, consult that inspiration board and see what folks who nailed it are doing.
Don’t force it
Experimental dressing is a marvelous way to expand your horizons, but it should never feel like a chore. Don’t feel like you’ve got to start dressing in a new way and never fall back on your tried-and-true outfits. Let any changes unfold as slowly and organically as you need.
Identify a few key garments to purchase
Once you feel like you’re on a roll, you may want to make a short list of garments that will help you continue to build new looks. It’s important to keep the list short, and I’ll tell you why: You lived in your comfort zone because it worked for you, and the items and looks that reside in that zone should still be a part of your dressing life. Completely transforming your look is an entirely different project. If you just want to add some new and different touches to your current style, make sure that the clothes you were wearing before stay in rotation.
Now, this is a long-term, meticulously planned way of shaking up your style. It’ll work best if you have one or two main looks you’d like to incorporate into your daily dressing patterns, and also if you feel ready to commit to making some real changes. If you just want to create some mini dressing challenges within the context of your current wardrobe, here are a few great ways to keep yourself sartorially alert and engaged:
- No black for two weeks
- No neutrals for three days
- All pants-based outfits for a week
- All dress-based outfits for a week
- Craft outfits around the same pair of shoes, skirt, belt, or other item and wear them for seven days straight
- Limit yourself to 15 items for two weeks
- Pick out your top five favorite-but-underutilized items. Craft two outfits around each one.
- Mix patterns. (Here’s a great guide.)
These are just examples, of course. Cook up any challenge that strikes your fancy, stick to it, and see what happens. I suggest taking both notes and photos so you’ll be sure to remember the experience, and can apply new knowledge moving forward!