The Good Ick #17: To Bye or Buy
The Good Ick #17: To Bye or Buy

Getting to the point of knowing your personal style is a process. Not as simple as a Vogue headline touting “3 key items loved by Kendall.” I mean, that’s all fine, but don’t conflate that with style. Personal style. If you follow me here, there’s a strong shot that your personal style vacillates between the urge to be highly creative and the knowledge that anything that lacks pragmatism, utility, will end up barely worn. You see why I refer to myself, our team of individuals here at Tibi, as “Creative Pragmatists.” How we show up in the world, our team, and I can say the majority of you I correspond with regularly through DM’s, is with a sense of ease. Genuine appreciation and comfort with those around us. And, if not always an ability to stop and observe, there is at least an intense desire to be able to do just that. There’s a need to push ourselves and be fully present and in the moment, curious and seeking what is new and modern. Underlying all this is a longing for grounding and familiarity. Not so strictly defined as to hold us back, but rather as an acknowledgment of the craftsmanship and beauty that artisans passionate about their craft can create.

One would certainly think that as an owner of a designer brand for 26 years now, I would have had this nailed from the beginning. I was not only simply curious as to why this was so, but I knew if I could unpack this it would be better for business. What I didn’t realize was how much better it would make me feel. Personally. It was a process for me to step back and look at the things I knew about myself and distill them to a few adjectives. Chill, Modern and Classic (pages 35-38 in The Creative Pragmatist Book). Words that were so central to my core that when I looked back at old photos, remembering moments in my life, I knew I felt very centered when my visuals matched these adjectives. And conversely, I often felt uneasy when they did not. Unease that showed up as a lack of confidence, unsure of myself and not able to be fully present and in the moment.

Amy Smilovic

This picture was from the late 90’s. It was the first time I had ever traveled overseas and I was in Greve, in the Chianti region of Italy. I remember having splurged on a blazer from Calvin Klein. And when I say splurged, I mean it. It was $900. That was a huge chunk of my paycheck from my marketing job at American Express. I wanted to make sure I got my wear out of this piece, I didn’t want it limited to just the office. Here I’m wearing it with a tee, old levis, and my Adidas Stan Smith‘s (yes, to any of you, these sneakers pre-dated street style). This was great. The problem was, I didn’t know how to codify what it was that made me feel so great. It wasn’t as easy as saying, oh - ok, I am a blazer/denim sneaker person.

And here’s why.

If I had reduced the “success” of this outfit to “nouns” - a blazer, tee and trainer - then it would stand to reason that a fitted, princess seamed blazer, scoop neck tee, fitted jeans and designer sneakers would be the next purchases after the aforementioned. And this is where it all unravels for many. Because it wasn’t the nouns I should have been chasing, but the adjectives. The feelings these items exuded. On a side note, this is where designers often go off the rails. I speak from experience. Merchandisers and sales determine “blazers” sell. “Let’s make them shrunken, fitted, sexified” they declare. But many fail to realize that it wasn't that “blazers sell great”. What was selling was the feeling - eased yet put together, current, and possessing a sense of familiarity. In other words, chill, modern and classic.

You see my point here…..right?

Two women, one has text saying

The same items. Totally different mindsets.

Super clear, right? And if through this, you realized the outfit on the left is your thing, then you may even realize your style is more classic, sexy, trendy. And there are still words of wisdom you may glean from this discussion. But for the Creative Pragmatists, this will be a very solid starting point to help you get your closet in order.

Before we jump in, take a step back and read your chapters on the closet construct - the idea of Without Fails, In & Outs and Had to Haves (pages 65-89 in The Creative Pragmatist Book). I’ll be referring to these concepts quite a bit, so it’s good to familiarize yourself in advance.


“If you haven’t worn it in 6 months let it go.” Honestly, this advice just pisses me off. It has no depth and you’ll often end up tossing out items you invested in that stood a good chance of making the cut. The key is to understand why you haven’t worn something. Here are some questions to ask yourself:

Q: “What role do I want from this item? Should it be the item I count on to make me feel myself - a WOF? Or am I content that I love it and I’ll wear it when I’m in the mood and maybe not forever - an In & Out. Or is it so emotional for me that I just can’t let it go - an HtH - Had to Have.” If it’s none of the above, start setting aside that purge pile now.

Q: “Is the item fundamentally broken?” If it’s completely out of line with your adjectives, I strive to match all three and not just two (CMC), and you want this to be your everyday piece (WOF) , then you need to recognize it’s not working. And never will. Because it’s not fabulous enough to function as an In & Out, and it’s not emotionally special to qualify as an HtH. Bye.

Q: “Is it a great item but it lacks supporting players - like the right bottom or top?” You loved it right from the runway, you sought it out from your favorite store. But every time you wear it you feel like you're in costume. These turn into keepers if you can nail down the right fundamentals in your closet to let it thrive whilst still retaining your identity- your personal style. That amazing top from JW Anderson, coupled with 3 other runway items, will likely make you feel a little fashion victim. But paired with your favorite oversized pleated trouser, or cut out blazer, you’ll likely feel just like yourself. Anytime I shop for new directional pieces, I always wear my WOFS in the dressing room. It’s how I know if it will be a piece that I can slide into my life and work with what I have.

Q: “Is the piece something I love, fits my adjectives, but just haven’t been able to make it work?” If this item throws you because the proportions make you feel (short, tall) or the cut makes you feel (big, dull), then this requires some work on your part. By work I mean play, manipulate, take pictures worn in different ways, tie it up , safety pin it. I’m not generalizing here - a lot of people dm me expecting their jacket to just hop on to their back and make them fabulous. Clothing is like a partnership - it will often require love and attention from both sides. Demand a lot from your clothes, but there’s work for you to do too.


When you start the purge, it’s helpful to know what needs to be in your closet to make it all work. We’re all different, but we share a similar mindset - so I’ll show you my musts for my closet. The items that, without them, the ability for me to just simply and effortlessly get dressed and have my own personal style, would simply crumble.

My musts….

long sleeve top, black pants, green pants, grey blazer, blue button down, white t shirt, black tank top, blue jeans

a. The pant that gives a proportion statement. My pant purchase would be the fuller style, it’s what I wear most. Someone else may choose the skinnier trouser. It’s not an either or situation, but rather just deciding which comes first in the closet. I’m partial to the big pant because I can cinch it, let it sit loose, roll it up. It’s really multi-functional that way.

b.g.f. The tops that are simple enough to go back with everything from the easy denim to the most over the top pieces from the runway. They have a point of view but don’t overtake the message. They work as a layer when it’s cold out but are just fine on their own in warmer months. Their fabrication can be worn with all different textures and the finishes are refined enough to hold up to any office or dinner out whilst still chill enough for the most basic of every day activity.

c. Something in nylon. It gives texture to nearly every outfit. Texture gives depth - I wear a lot of neutral colors together and a range in touch (and even sound) makes everything more interesting.

d. The blazer in an eased style that is still fully tailored and refined. This functions as my evening wear item over my shoulders, it’s my sport jacket layered over my leggings for Barre class, it’s my airplane substitute for a cardigan. I wear this any place I'd wear a jean jacket, and of course, it’s my office suit.

e. The properly tailored shirt that has a strong point of direction or clever functionality. The high side slits on this one make it perfect for manipulating in many ways. TIP: if you buy an old vintage men’s shirt here, you can add high slits. All you need are scissors and a steady hand. It’s easy, ok?

h. The straight jean that’s not too wide and not too slim, not too high and not too low. If you are asking me which jean I’d buy first, it’s the Slouchy Carpenter Jean for this reason. This is my go to with any new piece I add to my closet that pushes boundaries. A new (or vintage) Margiela or Comme des Garcon piece feels infinitely more familiar with my Slouchy Carpenter Jeans. I’m passionate about style and being able to experiment with new styles but still feel like myself is really important. To me.

Here’s an analogy to think of when you are setting the foundation for your closet. Think of a house. These pieces above would be the equivalent of my floors, my walls, my roof. I plan on having them for a very long time, they set the tone for my vibe, and it’s nearly impossible to really choose the right couch or lamp if I’ve not decided first if the walls are plaster, mud or glass.

Pass It On

These are the things I invested in, and I can’t bear to have a reseller tell me I’ve earned 3 cents on the dollar. If you have a good friend who’d be thrilled for the item that once meant something to you (or worse, never did) then that’s a feel-good moment. And if you can get a good ROI through resale, go for it. I hope you do.

I obviously can’t cover everything here - the whole closet reconstruction has many layers of thoughts to it. But this should get you pointed in the right direction. Allowing you to be a little more thoughtful about what you purge, purchase and pass on. And that will probably feel good.

Explore Tibi.