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 interestWendy 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.

Join the Conversation


  1. says: E.

    This is a really fantastic, smart post, and another example of why you stand out in a style blogging world where (increasingly) everything looks the same.

  2. says: Cee

    Great post, Kelly! Love both examples you used and the logical reasons behind each upgrade. Sometimes I find myself keeping items for sentimental reasons when I shouldn’t be looking at them from an emotional point of view. Or, I’ll let the obvious sway me into holding onto an item, rather than dig deeper to figure out the true reason. In your first example, I’d see the rosettes and think, “ooh, unique! keep” and not “it’s really the color I love.” Over time through experience, these “roadblocks” are easier and quicker to spot.

    1. Thank you Cee! My recent move was a big help in picking out the pieces I wasn’t wearing, and still felt the urge to bring with me. There was a reluctance to put them in my nice new closet, so it was a challenge to figure out why I needed to bring it along, yet still didn’t want to wear it. Nothing quite like a closet purge and/or re-org to make you re-think old choices!

      I really like the direction your style has taken. =)

  3. Thanks for this! I’m in my early 20s, and I’m trying to upgrade my wardrobe so that I no longer look like a college student. This guide is super helpful and will help me evaluate why I’m holding onto clothes I no longer wear. I’m also trying to move towards a more menswear inspired/minimalist aesthetic, but I have a lot of “girly” clothing in my closet. I’ll definitely keep this in mind for when I look through my clothes.

  4. says: Judy

    Cool, you decided to do this post! I had a feeling that lavender top was the one you were referring to – you featured it in your “go to outfit” post way back when, but I can’t picture you wearing it now. It’s really interesting to see how your style – and many other bloggers’ styles – have changed over the past several years since you all started! (BTW, five years of blogging, that’s incredible!)

    I agree with you on your approach of upgrading and embracing the sophisticated “older sister” look. I’m so guilty of hanging onto items of clothing even when they’re literally worn out – I’m going to have to take your advice on “upgrading” these items.

    Thanks for posting this!!

  5. says: Carrie

    Thank you, Kelly! This is EXACTLY the followup post I was hoping you’d do. The little-sister vs. big-sister idea is a great one and will help me evaluate my closet so I can move forward with my style and shop more wisely. :)

  6. says: michelle

    over the last year i have spent a lot of time and money to upgrade my wardrobe. i realized i really only wear a few colors and shapes. and the things in the colors i like weren’t shapes i like and the shapes i like weren’t in colors i like. i finally have a closet i am happy with but still need a few more items. and being as OCD as i am, i have a very specific list of things that i need.

  7. says: Amanda Shelton

    You are brilliant. Thank you for this post. I read a handful of blogs and have been reading the same ones for several years now…yours since early 2010. You are by far the one I most connect with—even though I do not share the same distinct taste in style, or walk in life(SAHM), or even age…. I do share your frame size and love of fashion. You are FULL of wonderful, insightful, Helpful, fresh ideas than what other blogs focus on (at least the ones I’m reading…) I love your blog. Never stop blogging. I will read for life. :) Though at some point as we both age…i would love insight into your take on skin care. :)

  8. says: alice

    I really love how you gave concrete examples and pictures because it’s so helpful. Thanks for another awesome post!

  9. says: Ana

    I love this post. I think I just recently figured out what my personal style is and am finally feeling comfortable in my clothes. I feel and look confident. Now I need to start figuring out how to replace the “little sisters” with some of my own “big sisters”….. Love those metallic shoes.

  10. Thank you Rachelle! You are so right…it’s a very gradual process! I have a section in the back of the my closet where I send those items that I’m pretty sure are on their way out, but can’t quite let go of. Every few months I visit that side of the closet and see if I’m brave enough to toss anything. =)

  11. says: Katherine

    This was such a great post Kelly! I really liked how you framed the “little sis/big sis” example and there are a lot of “lil sisters” in my closet that probably need a grown up sibling. Do you always keep them once you “upgrade” to the big sister version?

  12. says: TheLizzyIzzi

    I really enjoyed this. The idea of big sisters/little sisters is great. I definitely see myself employing this idea to my own wardrobe in the future.

    As for the original question: I too have been paring down my closet quite a bit in the last years. I’m amazed at the amount of stuff I can get rid of and not even notice. But there are always items I’m on the fence about. It keep or to donate, that is the question. I’ve realized that it takes sorting through your wardrobe every four to six months and getting rid of stuff over and over again. Because you’ll probably always have a sweater or a shirt or something in there that’s not really you anymore.

  13. says: Mai

    Thank you so much for this! I am recently venturing to find and build a nicer wardrobe but after donating some items….I barely left a dent in my closet! I am having a tough time letting go but this post will make it much easier for me to make up my mind. Love your blog and your tips.

  14. says: suz

    You hit the nail on the head! I love your blog and have for five years, being a super petite myself, although I am old enough to be your Mom or Grandmom…..Need more hints on where to get size 4.5 shoes though. All I have been able to find are vanelis for the past 20 years! Kissy to you and your very smart blog!

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