How To Choose Investment Pieces Wisely

Oct 17, 2016

yellow shirt dress


Dress: Marshalls (similar) | Boots: Stuart WeitzmanBag: Cuyana (c/o) | Lip: MAC


I was so excited to open up my boot box and pull out these Stuart Weitzman Lowland boots last week. There is finally a chill in the air, and one of my favorite combinations for fall is dresses and boots.  People have asked a lot about how and when I decide to invest in certain pieces, whether it be these boots or a handbag

My wardrobe is a good mix of affordable pieces with a luxury bag or shoe thrown in every now and then. That idea is really how this blog was born! I don’t really believe in spending a ton on clothes that will go in and out of style quickly, but when it comes to handbags and shoes I will occasionally spend a wee bit more.

Whenever you are deciding if you think a certain piece is worth the splurge or not, consider these things: 


How often will you use it? Make sure no matter how expensive something may be, you will actually use it. A pretty handbag that is easy to scratch or a shoe that can easily get damaged probably won’t be something you will reach for all that often. It you won’t use the piece consistently, don’t do it.


Is it trendy or classic? Although I’m a sucker for some of the trendy bags or shoes I see, I refrain from investing in those. Classic shoes and handbags never go out of style and you can guarantee they will always have a place in your wardrobe. A classic Chanel bag, nude pumps or these over the knee boots will never be trendy or out of style. 


Is it higher quality or just a designer label? I’ve found some ‘designer’ items are really no better than a more affordable version. Make sure you try them on in person, investigate the materials they are made from, and you see that the comfort and quality is there. I was sold on these boots once I tried them on! The quality and fit is nothing I’ve ever found and they are the only boots I’ve ever come across that fit my legs. 


I also try to plan well in advance for a big purchase so I don’t feel as stressed or guilted as if it were an impulse buy. Do your research – online reviews, check resale values in case you ever want to get rid of it, and take time to make sure you really love it and it’s not just a knee jerk reaction. 

I paired my boots with these adorable yellow dress I picked up at Marshalls last week and my new Cuyana bag! I shared this bag on Instagram stories and got so many questions about it. It’s tiny size is perfect for my phone, wallet and Chapstick and I love the grey leather and suede combination. 

Hope you guys had a wonderful weekend and here’s to a short Monday! 

cuyana saddle bag

stuart weitzman lowland boots

cuyana saddle bag

chicago fashion blogger

stuart weitzman boots

chicago style blogger

yellow tunic dress asos

chicago style blogger

fall fashion


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  1. Love the bag and boots! Those boots are worth the splurge!

  2. Tanvi says:

    Love the color combination here. One of my favorite. The boots are definitely worth it.


  3. Kayleigh says:

    Love that dress such a gorgeous color on you!

  4. Life in ATX says:

    This is a great post! I often have that internal dialog when I’m shopping something that’s more of an investment piece. Love this!


    Lee Anne

  5. FashionFriesX FashionFriesX says:

    Such a great post! Love the boots – they seem like the best investment piece!!!

  6. Great thoughts about investing. I just bought my first pair of SW and they are the only real investment piece I have. So far I am obsessed! Love this outfit combo.

    Amy Ann
    Straight A Style

  7. These are so cute and I love mine too. Worth every penny!!

  8. I shop the exact same way! Lots of high end bags and “low end” clothes. These boots definitely seem worth the investment!

    How 2 Wear It []

  9. OMG WAIT. It’s so weird that we were JUST talking about this this morning — I had no idea you’d posted about this! You’ve taught me so much about the importance of investment pieces… and I totally agree that they make life easier in the long-run! 🙂 LOVE THIS!

    Kelly | Kelly in the City

  10. Alex Carreno says:

    Such great tips, I love this post. I am still wanting these boots, but have a pair of Stuart Weitzman 50/50s that I wear all the time when it gets cooler so thinking I don’t need both.

  11. Maggie says:

    I absolutely love this post and totally agree with everything!! It’s like you read my mind! 🙂

  12. Nina says:

    Such good tips and I’m loving those boots!

    Xo, Nina

    Law of Fashion Blog

  13. Karen R says:

    These are such great tips!! Your bag is adorable, love the color!


  14. Sarah Louise Zerbe says:

    That yellow color is amazing on you! Also love the OTN boots.

  15. Brittany Boone says:

    Wow I love this together! Such a refreshing look

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