Developing Personal Style – Wardrobe Upgrades

{A recent wardrobe upgrade}

This post is thanks to a great comment from Judy on this post that got me thinking…

Here’s a question for you: as you started defining your [menswear-inspired] style, did you get rid of your old clothes that didn’t fit into that look? I think I’ve finally found a style that will really work for me and my current stage in life, and I’m tempted to skinny down my closet because there are just too many things, but I have a hard time letting go of old favorites. (Or being guilty of keeping something around just in case I might change my mind a few years from now.)

The people we were five years ago* isn’t necessarily the people we are today. We grow older, our bodies change, our interests change, and our experiences mold us in different ways. Running parallel to our own personal changes are developments that occur in the world around us, like the general change in taste of what’s considered stylish and on trend. Often times, it just takes time to zero-in on who we are and what makes us tick, which can also be said of defining our personal style.

So it should come as no surprise that some items in our wardrobes we loved five years ago, may no longer be in line with our current personal style, tastes, or place in life. One thing to do with these items is to purge them from our closets through donating or reselling, making room for new favorites to take their place. But like Judy said, what to do about those things that we just can’t seem to let go of? Those items that aren’t really “our thing” anymore.

The process I’ve been taking with these items is what I call “wardrobe upgrades”. It is quite simply:

• Identifying what it is about an item that makes it hard to let go.
• Finding that characteristic in an item that’s more “you”.

I want to state here that “upgrade” merely means replacing with an item that better fits into your current personal style. That item does not necessarily need to be more expensive in any way. Just better suited for who you are today.

{Ann Taylor shell (old) & Banana Republic dress shirt (color may still be in stores)}

The case of the lavender shell (left photo) is a great example. It’s been well-loved for several years, but recently, I’ve largely ignored it in my closet. Despite a lack of wear, I just couldn’t let it go. It took some time and thought, but I finally realized why. I love the color!

The style isn’t quite me anymore, and the fabric is worse for wear (a bit pilled), but I realized I loved how the color looked against some of my favorites like navy, grey tweed, and even seersucker. Once I realized this, it was time to figure out how to incorporate that color into my wardrobe again, but in a way that’s more in line with my current style. My answer…a dress shirt (worn here).

Another way I’ve been thinking about upgrading items is as little sisters and big sisters. Some items, as you own them long enough, start to look a little too youthful. I call these “little sisters”. I catch myself wanting to replace these little sisters with something similar, but a little more sophisticated. I call these “big sisters”. A great example is below:

{Cole Haan Carma pumps (old) & Kate Spade Licorice pumps (also at Saks & Zappos) (similar from J.Crew)}

I’ve had the grey suede Cole Haan pumps (top photo) in my closet for almost five years now. As you can see, they’ve taken a beating and were very well loved, but I’ve only worn them once in the last year. Why? Because recently, when I put them on, they feel a little too “innocent” compared to the direction my style has taken. They just don’t feel right anymore, and I pass them over for other shoes. A mental note to replace these has crossed my mind more than once.

Metallic silver pumps have been on my radar but I wasn’t really interested until recently. Jean piqued my interest, Wendy sealed the deal, and I was soon really curious if there was room in my closet for a pair. When they arrived (bottom photo), I had an epiphany. The silver metallic pumps are what happens when the grey suede pumps “grow up”. They’re the sophisticated “older sister”.

While the grey suede is a bit sweet and safe, the silver metallic pump is daring and demands attention. The colors are similar ideas, and it’s likely that any occasion I could find to wear the grey, the metallic could easily step in, and turn up the volume while it’s at it.

Voilà…wardrobe upgrade.

Questions to ask yourself:

Why aren’t you wearing this item?

My answers:

Lavender shell: In this case, the design didn’t represent how I like to dress anymore, and the fabric was looking a little pilled after so many years of wear. These reasons made me pass it over in lieu of other items.

Grey suede pumps: I still liked the idea of grey suede pumps, but something about the style of these wasn’t working for me any longer. At this point in my personal style, I want my pumps to “pop”, and these were a snore-fest.

Why are you still hanging onto this item?

Lavender shell: In this case, it was really the color. I loved how the color looked when worn under lots of items from my seersucker blazer, to navy cardigans. I kept it around because I thought I may want to wear that beautiful color again.

Grey suede pumps: With so many of my shoes dark in color, I though the light neutral grey would be nice to have around.

What item would you wear, if it had the characteristics described above (the reason you’re still holding on)?

Lavender shell: When I realized it was the color of this shell that I really loved, it was an easy connection for me to make that I needed to look for this color in another style of top that would fit into my current personal style and taste. For me, a lavender dress shirt was the answer.

Grey suede pumps: At first, I thought grey suede point-toe pumps would be a nice replacement, but when my eye started to get distracted by silver metallic pumps, I realized those were going to do a similar (and more stylish) job.

Read More Developing Personal Style »

* I chose “five years” as an example in this post because this blog is coming up on it’s five year anniversary. In that time, I’ve seen a distinct shift in myself and my own personal style, so it felt appropriate.