How to Step Outside Your Sartorial Comfort Zone

fashion comfort zone

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!

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  • Even though I don’t want to shake up my style too much (I’m in a happy place), I adore your mini-challenges. I’m going to play around with those; they help the idea factory to keep running.

  • Carrie

    What a timely post! Thank you for the clear, concise advise, as always. Been feeling extremely frumpy the last couple of years–dressed super-funky and cool in grad school, but somehow haven’t been able to make the transition to dressing as a professor. Been trying to isolate the root of the frumpiness (I think it has something to do with needing to wear very low/flat/comfy shoes due to walking and teaching on my feet a lot, which of course creates a domino effect in terms of cuts/lengths of pants and skirts that will look “right” with said shoes). Awesome post!

  • Love that sweater and the shoes. You look great!

  • Great tips! I especially like the one about photographing your outfits. Because I’ve been photographing my outfit 5 days a week for 4 years, I’ve learned so much about what works and what doesn’t for my personal tastes! Sometimes the mirror just isn’t enough!

  • Fab post! Really good tips and I am totally with you, life is much more interesting when you shake up your style every so often. Currently constrained to maternity wear, I absolutely cannot wait to wear all kinds of non-black, non-neutral outfits with all sorts of patterns. Maybe I’m in danger of becoming too experimental…! Great to find your blog x

    (Sorry, forgot my website first time round!)

  • That sweater might look awesome (or hilarious) with a skirt of mine (this one: http://fashionflirt.me/2012/01/18/the-skirt-that-made-me-feel-like-a-real-style-blogger/).

    I love (and hate) stepping outside of my sartorial comfort zone, mostly because it is never as bad as I think it is going to be. And then I can wear a ton of new things, and incorporate them into my wardrobe. Makes things much more interesting!

  • These are great times for deliberately pushing yourself to change up your style. I wear things these days that I wouldn’t have even considered 5 or 6 years ago, and there are things I wore 5 or 6 years ago that make me cringe today. But I feel like I’ve kind of been evolving all along, and at every stage of the process I’ve felt comfortable with whatever I was wearing.

  • Oops, by “times” I meant “tips.” Gah coffee hasn’t kicked in yet.

  • Great tips, particularly love making a list of items to work into your wardrobe. I think style is one of those comfort zones that once you find a stride, it’s harder to break out of. I’m all about experimentation and stepping outside of your box though, so kudos on arming us to do just that!

  • Thanks for the challenge! To perk up dull January, I’m going to wear all dresses and skirts for the nest week. It’s too easy to slip into some jeans every day in winter, so I need the fun motivation. I started with my red skirt today and a woman at the mall salon I visited today called it “kicky”. I loved it!

  • Katie

    Thanks for this Sal! I can’t emphasize enough how much Pinterest helped me pinpoint my personal style! Because of that site, I have narrowed down my aesthetic (which I initially thought was very schizophrenic)! That said, with regards to my comfort zone, I think I’ve lived the last 5 or 6 years experimenting with different styles. It used to be that belting wasn’t comfortable due to my wide waistline, but thanks to Imogen’s blog, I figured out a way to wear a belt! Basically the only “uncomfortable” means of dressing for me is going for unflattering garments or garments that press down on my belly. It’s both a comfort thing and aesthetic thing, and given that I’ve tried so many styles through the years, I really don’t feel the need to break out of a “rut” at all.

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  • Angela

    These are such great tips; thank you!

    One “challenge” that inspired me was the Summer of Dresses. ( http://www.summerofdresses.com/pages/about ) Some friends of mine participated in 2010, and I loved seeing everyone’s outfits, so I jumped on the bandwagon in 2011 by consciously making an effort to wear more skirts and dresses. I’m one of those people who is perpetually cold (even when it’s 70 degrees out, but especially in an air-conditioned office), but I decided that the occasional temperature-related discomfort was worth enduring in exchange for the mega awesome mood/confidence boost I got from dressing up and wearing pretty things.

    One of the trademarks of my personal style, I think, is to actively seek out novel and unique pieces or outfits. When I go shopping, I’ll grab a ton of things that may not look good on the hanger, and may or may not work for me, but some of the best fashion finds I’ve come across are from taking a chance and trying on something funky that I wasn’t sure would work. If I find two items that I like equally, but one of them is something that fewer people are likely to wear, I’ll go for the more unique piece. Harem pants, unusual silhouettes or textiles, men’s neckties, shoes with crazy architectural heels… they all inspire me to keep things fresh, try new combinations, and maybe start a conversation or two! (And one of the bonuses to this is that these kinds of things are more likely to be deeply discounted! Sure, a hundred people may have passed on an item for a reason, but assuming it fits and flatters me, I enjoy the challenge!)

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