how to approach the hard to style pieces in your wardrobe

wearing:  Levi’s Trucker Jacket {men’s large}  |  Everlane Authentic Stretch High Rise Skinny Button Fly   |   Everlane Pima Micro Rib Scoop Neck |  Jeffrey Campbell booties |  Cuyana leather tote

The oversized denim jacket is a versatile piece yet it can be challenging to style!  Although that seems like a contradiction, it is my true story.  For the longest time, I had my eye on this Levi’s Trucker Jacket and then when I finally got it in my closet…I hardly wore it for a while.  Not because I didn’t love it!  I absolutely love it. Truth be told, this is one of those pieces that, for me, required some…work.  I used the process I outlined in my ideal wardrobe series to figure out how to love this cool jacket on me.  First, I perused Pinterest in a quest to remind myself of the vibe I’m drawn to in terms of styling an oversized denim jacket and to identify what I don’t care for.  This helped me understand why  this super cool jacket was on my radar in the first place, and more importantly, how to make it fit into my personal style aesthetic.  The insight I gathered made all the difference because now I’m wearing mine regularly!  This process works!  Trust me…

Sharing my style roadblocks with you is something I value so much.  These real life examples of pushing through style sticking points and identifying what really works is what Diari Di Cuore is all about.

Have you ever struggled to style a piece you love?  Each time you put it on it doesn’t feel right and you wonder what you’re missing?  I understand how incredibly frustrating this can be, and the spiral of negative thoughts it can kick off. My Levi’s denim trucker jacket is a perfect piece to map out my process for working through such situations. I’m going to share how to approach a hard to style piece that you love. 

Tried & True Steps for dealing with hard to style pieces

  1. Don’t Panic! Also, I suggest not forcing yourself to wear it while you are still not satisfied because this will intensify negative association with the item.  
  2. Set the piece aside and do your research!  I always begin this process with Pinterest as it is the perfect platform to search for a particular piece of clothing styled in different ways.  You can create a board to save the looks you like and then determine the commonalities.  The idea here is to identify a certain aesthetic or vibe that you are drawn to which will help make your love for the piece less abstract.  You will start to understand what initially called your attention to the item, and how you can recreate this same affinity when you style it on yourself!
  3. Pay attention to details.  Sometimes it is something small that makes all the difference.  For example, I struggled with what to do with the sleeves on my oversized denim jacket.  A popular way to style this item is to roll the sleeves up above the wrist or even just below the elbow.  I just don’t like this on me at all.  I tried leaving the sleeves all the way down with the cuff buttoned, and with the cuff unbuttoned.  None of it felt quite right, and that always leads to fidgeting.  Then finally, I tried buttoning the cuff and rolling the sleeve once. Bingo! Perfect sleeves for me.  
  4. If you have come to the conclusion that you still love the item but may need to refresh your wardrobe a bit in order to style it to your liking…this is not necessarily a bad thing.  Just make sure the items you choose to purchase mix in well with other items in your wardrobe too.  You don’t want to go purchase several items just to make one piece work.   Approach this with intention.  Set aside your hard to style item and take your time in selecting the right pieces to add to your wardrobe.  Also, spend some time trying your hard to style item on with different pieces you already own and pay attention to what you like best, and what is missing.
  5. Finally, if you’ve done all this work and you are still not happy with how your hard to style item looks on you it may be time to let it go.  Sometimes this happens and, if you have learned from it, it is not a failure.  It is far better to donate or sell the item, let go of the frustration and take the lesson into your subsequent shopping experiences.

Styling The oversized denim jacket

In addition to the sleeve situation I mentioned above, there were other aspects of assimilating this item into my working wardrobe that were challenging.  One of the biggest obstacles, for me, was pairing it with other denim pieces.  As you know, I am a lover of jeans so the majority of my bottoms are denim.  I wanted to be able to wear my denim jacket with jeans, and I can but I had to pinpoint how I could do this and be happy with the look. I prefer styling a denim jacket with a significantly different shade of denim but it can look very current with a pair of light wash vintage-ish 5o1s or something in a similar shade as your jacket.  Also, the silhouette is crucial for me.  My jacket is very oversized so I need to balance it properly by pairing it with sleeker pieces such as classic black trousers, skinny or fitted denim, fitted scoop neck tops, and feminine knits (not too over sized). Having several bulky layers on top with this piece does not work for me even though I’ve seen it look cool on others.  

Here are a few of my favorite oversized denim jacket looks: Leia Sfez Style denim on denim ,  Andi Csinger ,  Les filles en Rouge,  British Vogue ,  Jeanne Damas ,  Jeanne Damas again

Last time I styled this jacket with black trousers and a fabulous pink knit here.

I hope this was helpful.  Please shoot me an email or leave me a comment below telling me what items you’ve had a tough time styling and how you resolved it.   Or any other questions or comments are welcome as well!

For now, here are a few of my favorite oversized denim jacket options!   The Levi’s Denim Trucker Jacket is currently 30% off, use code FRIENDS.

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Some of the links in this post are affiliate links. If you go through them to make a purchase, I may earn a commission.  Please know that I  link these brands and their products because I wear them, use them and believe in them. Not because of the commission I receive from your purchases.  If you do decide to make a purchase, I hope you love it as much as I do and thank you for supporting Diari Di Cuore

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