7 Designer Investments that Were Worth Every Penny

Over the years, I have been lucky enough to accumulate a small collection of designer pieces. Prior to each purchase, I make sure to think long-term because the last thing I want to do is fork over a ton of money for something I barely use. Granted, I have found there are quite a few designer investments that I have gravitated to infinitely more than others. From the style of the item to the quality and durability, there are definitely some pieces that immediately stick out in my mind. Perhaps the biggest commonality between all of the below are the fact that each is relatively timeless in nature – pieces that I can wear 1 year from now, 5 years from now, 10 years from now and beyond (and perhaps even pass down one day). After all, this reliable longevity is the main reason I purchase designer. Whether splurging on luxury labels is new to you or you happen to be a seasoned buyer, I wanted to add my two cents on the 7 designer investments I have no regrets purchasing.

fashion blogger kaye bassey wearing a green tie dye cardigan, black satin slip skirt, cream knee-high boots and Chanel classic flab in beige - designer investments

7 Designer Investments that Were Worth Every Penny

Chanel Classic Flap

Hands down, the Chanel Classic Flap handbag has been one of my prized positions. Although undoubtedly a hefty price tag, it has definitely been one of the designer investments I do not regret at all. It is a handbag that is timeless in design. Everything from the quilted body to the chain straps and Chanel clasp logo is perfection. I have both the black and beige, both of which I have worn a numerous amount of times. Best of all? Chanel bags tend to appreciate year-over-year.

Chanel Classic Flap Measurements:

  • Chanel Classic Mini Flap Bag – 6.7″ W x 5.2″ H x 3.1″
  • Chanel Classic Flap Bag – Mini Rectangular: 7.9″ W x 4.9 H x 2.8″ D
  • Chanel Classic Flap Bag – Small: 9.3″ W x 5.7″ H x 2.6″ D
  • Chanel Classic Flap Bag – Medium: 10″ W x 6.3″ H x 3″ D
  • Chanel Classic Flap Bag – Jumbo: 11.8″ W x 7.7″ H x 3.9″ D
  • Chanel Classic Flap Bag – Maxi: 13″ W x 9.1″ H x 3.9″ D

New Chanel Classic Flap:



Dior Saddle Bag

Next up on my designer investments is the Dior Saddle Bag. My favorite iteration being the logo jacquard print because I think it adds such a statement to whatever outfit you decide to pair with it. First of all, the shape of the bag itself is absolutely iconic. It is unique while still being able to stand the test of time. This is a luxury handbag that is such a fun accessory to get secondhand because there are so many incredibly iterations of it from the past. It was originally designed in 1999 so that means there are a ton of chic vintage options on the market.


  • Dimensions: 25.5 x 20 x 6.5 cm / 10 x 8 x 3 inches
  • Strap length: 84 – 102 cm / 33 – 40 inches

New Dior Saddle Bag:



Gucci Jackie 1961 Hobo Bag

This beauty was reintroduced in Gucci’s FW 2020 collection and is one of my most versatile designer handbags. As you might have surmised, the bag itself is indeed named after Jackie Kennedy who was famously photographed with the bag in the 70s and became an instant hit. The sleek leather and curved design is enough to make anybody swoon. Plus, it is a handbag that can seriously do it all. Dress it up or dress it down – the possibilities are endless.

Gucci Jackie Sizes:

  • Medium size – 14″W x 9.8″H x 1.8″D
  • Small size – 10.8″W x 7.5″H x 1.6″D
  • Mini size – 7.5″W x 5.1″H x 1.2″D

New Gucci Jackie Bags:



Bottega Padded Cassette Bag

If you are looking for a bag that is polished, yet trend right, I have to direct you to the Bottega Padded Cassette Bag. This is an accessory that I am constantly getting compliments on every time I wear it out and about. Plus, it happens to come in a plethora of colors. Go classic and get the black or amp it up with the Bottega green or turquoise.


  • Height: 18 cm | 7.1″
  • Width: 26 cm | 10.2″
  • Depth: 8 cm | 3.1″
  • Strap drop: 50 cm | 19.7″

New Bottega Cassette Bags:



Saint Laurent Rive Gauche Tote Bag

Out of the above designer investments, the Saint Laurent Rive Gauche was the newest to my collection. It is the epitome of the perfect summer handbag, ideal for everyday use, vacations, and more. There are quite a few fabrications and sizes to choose from. Personally, I have the linen/leather tote in the large size but all of the variations are just as chic!


  • Large Tote – 48 X 36 X 16 CM / 18.8 X 14.1 X 6.2 INCHES
  • Small Tote – 39 X 31 X 18 CM / 15.4 X 12.2 X 7.1 INCHES
  • Shopping Bag – 38 X 39 X 17 CM / 14.9 X 15.3 X 6.6 INCHES

New Saint Laurent Rive Gauche Tote Bags:



La Mer Skincare

Although it is the most expensive skincare I purchase, La Mer is totally worth the hype in my honest opinion. Not only does it feel like a treat with each use but it really is a miracle worker for your skin. The Créme de la Mer Moisturizer is Holy Grail status. But when you couple it with the Treatment Lotion? Heaven on earth. Keep your eye out this holiday season for promotions!


Cartier Watch

Nothing says luxury quite like a Cartier watch. Trust me, I never really considered myself a watch type of person but once I tried this one on, I was completely sold. Again, this is an accessory that will never go out of style and certainly a timepiece that you can pass down from generation to generation.

What are your thoughts? Let me know what designer investments you don’t regret purchasing!
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