018. Stress-free styling [Part Two]
What makes a wardrobe work? And how do you integrate trends into your current wardrobe?
“Growing up, I was always a tomboy.”
I hear this sentence about 50% of the time I talk to women about their style.
Usually, it signals me to categorize their look into the Gamine and/or Natural style type. A little rough around the edges, rebellious to style rules, and comfortable in its own skin, these types are relaxed and nonchalant, with the potential to be elevated or dressed way down depending on the wearer.
Conversly, I’ve also heard the phrase, “When I was younger I hated pink… now I love it,” repeatedly.
Personally, I identify with this phrase more than the first. And looking at my style now — in its balanced blend of edgy Gamine elements, punchy-yet-polished Drama, and just a wink of Classic cuts — I can see the influence of this belief as I’ve grown through different ways of dressing through the years.



My take is that the first sentence openly, comfortably conveys a message of complete disinterest in anything remotely “girly.” Whereas the second secretly speaks a longing to embrace feminine dressing, with an unknown block preventing that freedom.
I talk about the identity behind style psychology in more depth, here.
In those days of figuring out my style — and subsequently, myself — I wish I’d had someone to coach me through it to 1) decode my thoughts, beliefs, and functions into garments, and 2) save me a ton of money while doing it.
Years later, on the other side of learning the language of style, I’ve become the coach.
Have your pie and eat it, too
Contrary to what you may have thought, fashion is not the biggest metric for the success of any given wardrobe. This is good news! News I hope lowers your blood-pressure.
A “successful wardrobe” is one that works for your body and your lifestyle; its comprised of clothes that make you feel good about yourself exactly as you are, not silently shaming you to be someone you think you should be.
A winning wardrobe is the catalyst to presenting yourself as the expert you are, for the sake of serving others well.
If you’ve been here for a while, you’ll know that I’m a numbers person. So when I learned a capsule wardrobe creation method called the Lifestyle Function Analysis, I was very excited.
The premise is teaching you how to break down your lifestyle into the different activities (functions) you do on a regular basis and how many hours a week you’re engaged in them. From these numbers, I determine how many items you need per capsule (yes, there are multiple) so you have as many options as possible without actually owning a lot (unless you want to).
Break up with having “nothing to wear” ever again. This is Fashion Math that works.
Want to learn more?
How do you know if a trend reflects your ideal wardrobe?
Back in January I wrote about how to tell the difference between liking a style for ourselves vs simply appreciating one.
🗝️ The takeaway was to pay attention to general elements (or details) of life that you love and be on alert for garments that present those elements through different trends or styles.
Take the humble baseball cap:



I love this look because of my love for athleticism. I think they’re practical as a sunblocker and I just think they look really effortless, cool girl chic. Apparently, WhoWhatWear has caught onto the same feelings.



A second example comes from my learning about the car coat — “a silhouette that dates back to the early 1900s, car coats are often about knee-length, a feature designed to make it easier to sit in a car.”


Turns out I’ve been wearing these for a few years because I like the look and the practicality (as mentioned above), but WhoWhatWear only just now labeled them on-trend, quite possibly because Kendall was spotted sporting one.


A big part of getting comfortable with your closet is in accepting that pretty much everything you own will fall in and out of ✨trending fashion✨ at some point in time.
🗝️ My advice is if you can afford a storage tote or two and have the space to do so, pack away “off trend” clothes for a later time so you don’t have to reinvest in the same items 2-3 years later when the style comes back.
And here I go quoting
again, but really, she said it best:As I’ve gotten to know myself and my style, I find there are some core garments I reach for over and over again regardless of the trend cycle. But there are other garments (namely denim, skirts, and shoes) that I always keep an eye out for fresh takes on. Jackets too, I’m always looking for something cool.
My thoughts are that if you really love a specific type of garment (ie a leather jacket), maybe it is worth it for you to get 2 or 3 different styles. But it’s not an obligation, despite the media making you feel like it is. It’s just a variety offering.
Two tips for trend integration
Tip #1 when it comes to unearthing your personal style and deciding to take the deep dive into curing your closet woes:
⚠️ Don’t do a total “wardrobe wipe” without first having a plan to shop for new garments.⚠️
Otherwise, you’ve just gotten rid of everything for the sake of getting rid of everything, without considering how some pieces you already owned could’ve been worked into your new closet. In this scenario, you truly would be left with nothing to wear.
Tip #2: Don’t get rid of things you love, just because they’re “not trendy.” Or because don’t know how to wear them.
As you go through the process, you may realize that the item you love is something you only appreciated the style of and would never really wear1… but sometimes the garment is something you love and want to wear more of, you just don’t have the support pieces you need to make it work.
🗝️ My recommendation is to be patient with yourself on this new journey, and not get rid of anything until you’re at least halfway over the bridge to your true style.
As a Stylist, I like to start by taking my client through a Lifestyle Function Analysis because it helps her understand the why behind needing clothes (something I mentioned in Part One of this series).
Once you understand the why, you can relax and focus your energy on understanding your personality as expressed in clothing.
That’s when a Complete Wardrobe Restoration and/or Personal Shopping Sessions will become even more fruitful.
Cleaning out your closet and shopping for clothes becomes a purposeful event, not a dreaded chore.
Grace strategies
If you’re really interested in trying a trend, but not fully convinced you’ll love it enough to wear it enough (think cost per wear #girlmath), try alternatives to retail like shopping secondhand at thrift stores, consignment shops, or clothing rental services.
Above all, learn the art of hanging onto your receipts and tags!
I can’t stress this enough. I keep a small box on a shelf in my bedroom with all my clothing receipts and tags until I am absolutely sure I want to keep an item. Honestly, reselling on Facebook Marketplace just isn’t as reliable as it used to be.
Until next week.
💌, Tess
In which case, the softer breakup may be passing the item down to a friend or loved one, instead of sending it straight to the thrift.






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