I distinctly remember my first Gucci bag. An aunt and uncle gave me large hobo with the signature Gucci logo print emblazoned all over it for my sixteenth birthday. I LOVED that bag. I promptly replaced my backpack and started carrying it around to school every day, until one day some weeks later, the metal clasp of handle completely broke.
And that my friends, was the day I learned that there is a difference between Gucci and “Gucci”.
Needless to say, I’ve had my fair share of designer loves and mishaps over the years. I waver somewhere in the middle between “designer goods are worth the investment” and “designer goods are a complete waste of money” so I don’t own that many pieces, but the ones I have were usually bought to commemorate some event. Although I don’t have a huge designer collection, here are the best and worst designer purchases I’ve made so far.

Best: Jimmy Choo Romy 85
My go to black pumps, these shoes are the most comfortable heels I own. The heel is just under 3.5 inches, which is high enough to elongate the legs but low enough that you’re not teetering about. I don’t feel bad whatsoever spending $600 on this pair of shoes because I know I can wear them well into my fifties.
Honorable mention: Tamara Mellon Frontline Platino Napa
I bought these to wear for my wedding, and although higher than my Jimmy Choos, these are extremely versatile and fairly comfortable evening sandals. Before starting her own line, Tamara Mellon cofounded Jimmy Choo, so no wonder I like both brands.

Worst: Prada Vitello Daino Shoulder Bag
I first saw this bag while in LA for my birthday two years ago, and it struck me as a very adult everyday bag. I loved the white leather and the slouchiness of it, so when I saw it on The Real Real for a fraction of the price a few months later, I jumped for joy. After carrying the bag for a few weeks, I got annoyed with having to keep the white clean while wearing denim, and I didn’t like the length of the handle because it was too bulky to wear comfortably on my shoulder. I was able to sell it back to The Real Real, but now I feel like a white bag is missing from my closet. If I were to try white again, I’d get a structured formal bag like this Prada one instead.

Best: Louis Vuitton Neverfull GM
I bought this bag on my trip to Paris last year, and it’s the perfect large tote for daily use or travel. It fits several outfits at a time, so I often carry it when I have a photoshoot. I debated between the Damier Azur (the light beige) and Damier Ebene and am glad I got it in the darker print, as it’s far more versatile and I easily carry it two-three times a month.

Worst: Christian Louboutin Decollete 554
Don’t get me wrong, these are probably the sexiest shoes in my possession. And red bottoms will likely never go out of style. But I can’t wear these for more than 30 minutes before my feet start crying out for help. I bought them in Paris, which was a phenomenal experience, but I think being in the boutique as opposed to a department store made me afraid to speak up, and I’m pretty sure I have them in a half size too small. But they are so pretty to look at!!

Best: Gucci GG Leather Belt
This was Jonathan’s birthday present to me last year, and it is my go to belt! So much so that my mom has complained that I wear it too often ? But it’s a $300 (well the price went up since I bought it, now it’s $450) belt, so I’m going to get as much wear out of it as I can! I have it in either 75 or 80cm, which can be worn around my waist or around my hips so it’s versatile. It did take a long time to get when I ordered it, but it was definitely worth the wait and worth the buy.

Another Best: Thrifted Gucci Blazer
I just got this blazer at the beginning of the year, and it’s already a favorite! Slightly oversized, trendy check pattern, and best part, it was MUCH cheaper than most Gucci items because I got it secondhand at thredUP! I’m a huge fan of buying designer items secondhand – many people take excellent care of their designer purchases, so you can find like new and excellent pieces for over 50% less than new prices.

Undecided: Gucci GG Marmont Shoulder Bag
This post was actually inspired by the Gucci bag I bought when I defended my PhD dissertation proposal – I was so proud of myself for reaching that milestone, and super excited to buy the bag. But now when I pick it up to wear it, I am confused to how I spent $1800 on it. I don’t know if it’s too trendy, too small, or something else, but I’ve thought about selling it because it no longer brings me joy, as Marie Kondo would say. However, it does represent a huge milestone, so I can’t decide if that’s enough of a reason to keep it!
My 2 absolute best designer purchases were my “Dirty Thirty” birthday presents to myself:
-Marc Jacob’s Spring 2010 Fringe bag https://pin.it/zebp2luo6qebjy
-Dolce and Gabbana tan brown leather bomber jacket. Both are in excellent condition after years of wear and they spark so much joy.
I feel like if I bought something that expensive, I would be too scared to wear them. My very expensive winter coat can attest to this lmao; I never ever wear it. But to celebrate finishing your dissertation chapter, buy the Givenchy!!! It has a bosslady vibe to it. Speaking of dissertation chapters, my proposal is kicking my ass and coupled with all the toxicity, I swear, I don’t know how you have continued for so long. I’m so exhausted Lol
I’m too much of a frugal person to buy designer, but I’ll take that blazer off you on poshmark. ?
It was nice to read this post. I’m not one for designer items – maybe because I can’t afford them (:p) or that I’d rather spend the money traveling and experiences. I appreciate the deisgners and luxury items from afar, but I’ve never felt compelled to buy anything.
I meant to say I haven’t taken the plunge yet.
I took the plunge yet to buy expensive high end bag yet. I do have several in mind this year to get. They can be of my own purchase or someone gifting it to me. I’m expecting big things this year because my Father doesn’t pay retail. ???