Style + Fantastic Finds

Reviving the ‘It’ Bags of Yesteryear

Every year or two, there is a new must-have handbag that explodes onto the pages of fashion magazines and takes over your social media feeds. (Right now, my Instagram is awash in Senreve, but Naghedi is closing in.) But what happens to the fashion-forward bags of yesteryear when they’re no longer the currency of cool?

I’m talking about the brands that dominated the handbag conversation for a season or two and then went away — Reed Krakoff’s belted totes, the Mulberry Alexa and Bayswater bags, the Chloe Paddington bag, etc..  The handbags that every ‘cool girl’ carried to show that she was in the know.  The bags we ooh’ed and ahh’ed over when a friend showed up to brunch with one (even if she had to rent it). Where did those must-have bags go?

Last week, I spotted an ad for The Real Real that featured an ostrich Reed Krakoff Boxer Bag that I melted for when it was released in 2010.  The bag cost $7,600 when it was new — that was roughly three-months of my post-tax Capitol Hill salary– so I felt poorer just looking at it in the pages of Vogue, but I never forgot about it.  And there, like a beacon from the past, there it was, shining like a National Guitar from a Google sidebar ad for…wait, what?  $350?!?!? The bag was 95% off?  Were they serious?

I thought about the bag for three days. Couldn’t stop. That tote was living rent free in my head like an ex-boyfriend who gets therapy, takes up TRX and marries a girl who looks just like you.  There was no escape; so I decided to buy it.

You know, to make sure it wasn’t a scam.  When the bag gets here next week, I may host a party to celebrate.  Just a small soiree — 2022 me (pregnant with a good job), the ghost of 2010 me (size 2 waist who works weekends at a tanning salon to be able to pay bills), the Krakoff bag we both love, and a glass of Dom Perignon…nothing fancy.

Purchasing the ostrich tote made me wonder what other chic bags were available on The Real Real.  After all, most of us don’t live in a place where someone will see our handbag and think “My God, Becky, look at that bag! So 2010.”  And even if you happen to live in a city where women really care about fashion, how many of them will remember a bag from five, seven or ten years ago?  Further, where else can you get a well-made, real leather bag in a fab style for less than $300?

$150 will usually buy you a bag from Nordstrom Rack that’s covered in mall-brand logos. $295 might buy you a decent quality tote or satchel, but rarely one worth writing home about.  A fashion-forward bag, a cool bag, a bag you’re excited to carry is typically $495 at minimum.  And frankly, most of the bags your favorite influencers carry cost $795 to $3,500 without batting a perfectly lifted and tinted eyelash.

In a climate like that, wouldn’t it make sense to revive a cool style from a few years back?  To snap up a bag that you lusted after when you were young and underemployed at a great price, instead of spending the same money on a bag that’s just okay?  So here are a few bags that you may remember from the fashion magazines of your 20s, but that are just as chic today as they were then, just at 80% off or better.

This completely functional, very cool belted Reed Krakoff bowling bag comes in at an easy $140.  (This similar bag in red is $110.)

This slouchy tote, also from Krakoff, is non-descript and impossibly cool for $125.

This Meli-Melo bag was when it came out.  It’s still a unique tote for work or plane travel, and it won’t make your wallet cry.

I remember thinking the pebbled leather and blackout hardware on this Loeffler Randal satchel was to die for, now it costs the same as a canvas beach bag.

This Valentino Rose Bag is iconic, a piece of fashion history.  At this price, put it in a dust bag and wait for Mr. Valentino to pass from this Earth before reselling.

Who remembers when this Alexander Wang handle bag was the obsession of every NYC cool girl?  It’s now under-$250.

Whatever style catches your eye, there are so many stylish bags for under-$300.  Bags you would have killed for then, and that you will still love now (even if they’re gently used).  Plus, shopping for resale items is more sustainable and better for the planet.  At least that’s what I’ll be telling myself as I tote around my Boxer bag.

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  1. evie says:

    Meli-Melo! That was the former name of DeMellier. I have the Milan when it was still Meli-Melo from 2014 and it still looks new!

    June 3, 2022/Reply
  2. KC says:

    Good reminder that buying second hand goods is a great way to make your wardrobe budget stretch further. I’ve been known to stalk items I missed out on (or frankly, were not in my budget at the time) years later on eBay/Poshmark. While some items are obviously trendy, leather bags can definitely pass for more timeless if you pick the right one. Enjoy your new bag!

    June 3, 2022/Reply
    • Amy says:

      I do the same!

      June 4, 2022/Reply
  3. Lucy says:

    I’ve purchased items from TheRealReal 4 times, and 3 of those times they turned out to be knockoffs/inauthentic. So I would be careful about shopping there.

    June 3, 2022/Reply
    • Laura says:

      Also, on sites like Poshmark and ebay, ask to see pics of the real item, not just a stock photo! Every time I’ve bought something where the seller only posted stock photos, I’ve been burned (admittedly I’ve only made two such purchases. Once was a lipstick sold as new but clearly very used and the other was a winter wool coat when the seller posted a light waterproof trench).

      June 3, 2022/Reply
    • Ana says:

      Wow! How did you know? Was it that obvious or did you find out later? And did they refund you?

      June 3, 2022/Reply
  4. Sarah says:

    I still remember a Burberry all leather slouchy saddle type bag I saw on a girl at a party before Obama was President. Still. I wish I could find it, but I doubt it would be discounted!

    June 3, 2022/Reply
  5. Katel says:

    Agree with KC – the real real is great for finding discontinued styles – I snapped up a Longchamp style I never saw sold in US (not pliage) for a song on real real.

    June 3, 2022/Reply
  6. Jennifer says:

    The ex-boyfriend description was shockingly accurate so thank you for that perfect description.

    While I’ve purchased from TRR or Poshmark in the past I never thought about looking for my younger-me covet items… what a great idea! Definitely the perfect pick-me-up and a good reminder of how far I’ve come on a day I’m feeling like it’s been more backwards than forwards.

    June 3, 2022/Reply
  7. Nadine says:

    I just this week snatched up a Lo & Sons bag I have coveted for years but couldn’t justify paying for (I’m not even sure they ship to my country) on eBay and it made past me so happy!

    June 3, 2022/Reply
    • Genna says:

      Which lo and sons bag? I love the brand and have several!
      I think you raise another category aside from price and popularity – I Am drawn to
      Indie/ small business brand bags.

      June 4, 2022/Reply
  8. Laura says:

    I totally covet a Fendi peekaboo satchel but sadly they are still in the 4-digits on The Real Real. Maybe I’ll set a calendar reminder myself to check five years from now… Hmmmm

    June 3, 2022/Reply
  9. Dia says:

    Thank you for promoting consignment. It’s a huge staple of my style & so fun to hunt. The begs are gorgeous.

    June 3, 2022/Reply
  10. HBM says:

    The timing on this is almost spooky. Christmas of 2012 my dad bought me a Chloe Angie bag. Completely unsolicited, no input. Love it. It’s been in my closet for 8 years and last night I dug it out and took it in for conditioning. I also looked to see how much it’d fetch on poshmark. Maybe $300. I spent a good hour looking at older bags and resolved to look more often.

    June 4, 2022/Reply
  11. K says:

    Ha I remember splurging on a boxer tote (just regular leather, however) after getting a bonus a few years into working. How elated I was! I still have that bag and love it, though I haven’t worn it as much lately. It’s kind of back ‘in trend’ now with the popularity of structured totes + the belted look of Loewe’s Gate bag.

    For anyone into the Phoebe Philo era of Celine – there are great deals to be had on consignment sites. You can get an excellent condition Trapeze for <$600, a steal compared to their original price tag of $3k+.

    June 5, 2022/Reply
  12. Marisa says:

    I love this post and this topic! I love getting past IT bags – some definitely are classics! My favs are the Lim 3.1 Pashli (love it so much may find another on the RealReal) and the Sezane Farrow bucket bag I was obsesssssed with a few years ago. However, my best find ever was this weekend – I found an Anabel Ingall Isabella tote at goodwill for $7 dollars! I have one that is a few years old and love it – could not believe my luck.

    June 6, 2022/Reply
  13. Allyn says:

    This post inspired me to pick up the proenza schouler ps1 messenger I had my eye on about 10 years ago. Now a fraction of what it cost then

    June 6, 2022/Reply
  14. Orla says:

    Love this! A year ago I snagged a NWT Alexander Wang 2.5 Pashli satchel in large for $350!!!!!!!! Approx $1500 less the retail value. I think the larger size plus being 2/3 seasons off made it an outlier in the luxe market but it has proven to be THE BEST work satchel – I think Hope Hicks also carried one at the WH (this was pointed out to me by someone on the street one day!)

    June 7, 2022/Reply