Estate Sailing

By Jenny Kimball Brown


I love matching my outfits to rooms for Instagram, I found this pretty floral dress at an estate sale in the spring. It worked perfectly in my in-law’s sun room in Michigan

Last fall, I was about to jump on my bike and head home with my oldest son from flag football at Montrose Harbor when I checked my phone and saw there was an estate sale in Lincoln Park, a quick detour on our trip home.  I feigned innocence as I mentioned this to Pierce, knowing he would resist being dragged to yet another estate sale, but he conceded and off we went.

I had driven past the building hundreds of times, in fact, a large design project I had been working on for three years was right next door.  A modernist relic of the ’50s or ’60s, this tower did not possess the prominence of its more classical neighbors and, when we got off the elevator and walked down a bland beige hallway, I assured Pierce that we would be in and out in five minutes. Okay, maybe ten.

When we entered the modest apartment, I knew immediately we had a collector: the walls were covered with paintings and mirrors and small shelving units filled with various trinkets and figurines.  We walked down a hall, and I poked my head into a closet that was overflowing with table linens and floral bedding.  While I have yet to buy secondhand sheets, I had an inkling right then that I liked this woman’s style. We entered a room at the back of the apartment where I came across a few framed shadow boxes of small dried plants that reminded me of another pair I had picked up along the Dixie Highway the year before. I knew right then that I was not going to be leaving empty-handed and looked at Pierce who was already getting restless.  We passed quickly through the other back rooms, thumbing through drawers of handkerchiefs and kid gloves and scanning dresser tops scattered with porcelain dishes and boxes when I walked into a closet and saw a huge stack of vintage Ferragamo shoe boxes in my size.  At this point I handed Pierce my phone and started going through the boxes, discovering six unworn pairs that I couldn’t pass up.  Okay, now I was on a roll.

I always turn plates over to see where they are from and am especially tempted when they say “Italy”

As I entered into the main rooms of the apartments, I discovered a large set of Canton Rose Medallion place settings and another complete set of dishes that matched the partial collection of one of my clients, tucked away in the kitchen cupboards.  I wasn’t sure about the first set of Canton Rose Medallion place settings but knew I couldn’t pass up the second.  It was clear at this point that I was not going to be carrying these things home on my bike, so I made my way to the register to confirm the items I was committing to.  As I spoke to the women behind the desk, I perused the jewelry only to discover half a dozen Italian micro-mosaic brooches and earrings, similar to the small collection I have been amassing since my semester abroad in Rome. Giddy with the thrill of my newfound treasures, I paid for the purchases then peddled home with Pierce to get the car so I could return to retrieve everything before the end of the sale an hour later.  When I returned I did one more quick sweep throwing in two sterling silver salt cellars, a small evening bag, and a vintage rose quartz necklace from Friedman’s in Alabama, and was offered a price I couldn’t pass up for the Canton Rose Medallion place settings.

They made me an offer I couldn’t refuse for these Canton Rose Medallion place settings

I love estate sales, a combination of antiquing and house touring, two of my favorite hobbies.  When I was little, I remember riding bikes with my brother around Lake Forest, stopping at every garage sale and open house we could find, roaming the houses as if we might actually buy them, and deciding who would get which room.  My love of shopping for vintage was further developed when I arrived at the boarding school, St. Georges, outside of Newport, Rhode Island.  While I donned my pleated, pegged Banana Republic khakis, it soon became clear that the height of fashion was vintage Levi corduroys, and the only place to procure them was the Salvation Army.  I distinctly remember returning home for October break and insisting my mother drive me to Waukegan, where she sat out front with the engine running and I ran inside to shop for pants.  During my free time in school I would walk to antique stores scattered throughout town and tour the various “cottages” lining the Cliff Walk. While I cannot recall a single thing I bought, I do remember the feeling of excitement and wonder perusing these elegant objects and uninhabited homes. I have always taken comfort being surrounded by old things.

Estate sailing in the time of Corona Virus

These days, “estate sailing” has become a favorite pastime, and I am delighted to share my own rules and strategies for shopping these sales like a pro. Unlike a garage or yard sale, when you arrive at an estate sale, you often walk into what feels like the entire contents of a house, as if the family just picked up and left.  While some higher ticket items may have been sent to auction or kept for posterity, you are likely to find everything from ball gowns to barbells, sofas to sterling, transferware to Tupperware. This is surely one of the things I find so exciting about estate sales in general: you never know what you might discover.

Every room in this house on the North Shore had a colorful patterned wallpaper with curtains in the coordinating fabric, reinforcing a favorite design mantra to “pick a pattern, put it everywhere”


This North Shore sale was worth it for the retro interiors alon

For me, it is about the thrill of the hunt. While occasionally I will spot something perusing the pre-sale photos listed on, I rarely go to a sale planning to buy and am just as happy to leave empty-handed.   Which leads me to Rule #1: You must never feel pressure to buy. You win if you find something, you win if you don’t.

Now I know there is a school of thought that, if you go early, you will get the best stuff, and I’m sure in some instances that is the case. As I am only buying for myself and not, say, a store, I am just as happy to arrive at the last hour of the last day of the sale when the sellers are willing to make the best deals. Which leads me to Rule #2: Don’t worry about being first in line. While I actually prefer going on the last day, at this point, I just go to the sales when it works and don’t stress about the timing. Also keep in mind that there are serious buyers out there, so if you do go at the opening, you might find yourself waiting in a long line to get in behind the early birds. No thank you.

Collectors gotta collect

Rule #3: Resist, resist, resist. It may be tempting to scoop up a set of cereal bowls at $1 each, but you must ask yourself if you would like them as much at, say, $10. Or $20. Do you like the cut of their curve? Do you need cereal bowls? The more you shop, the better you hone your taste and can easily recognize pieces you cannot pass up (but I would rather you enjoy your cheerios out of a coffee mug than find yourself with aesthetically inferior wares that clutter your cabinets and lives).

It is fun to see what people collect and always keep in mind when adding to my own collections that they may be sitting for sale on a card table one day too

Now don’t get me wrong, I still have a pang of regret when I remember the Tiffany tea set they were giving away at $100 I passed on at the last hour of the last day of a Coy Krupp sale but can rest well knowing that I have not consumed, let alone served, a single spot of tea since that sale so many moons ago. The regret of not buying something is far less painful than the burden of storing or stashing useless dishes, let alone furniture, sports gear, toys or tools. This leads me to my next point . . .

Rule #4: If it has no value to you, it is not worth anything. Will I be tempted to buy a set of Baccarat crystal wine glasses? Sure, but what you realize quickly is the fleeting value of things. Surely these glasses were cherished and brought out for only the most special occasions. Or, worse, perhaps they have spent their existence on display for fear of being broken. Yet here they are being sold for mere pennies on the dollar some 30 years later. This is not to say that they were not a worthy investment but just a stark reminder that the value of your possessions is measured by their worth to you. This goes for everything from appliances to sports memorabilia. Unless you are truly in the business of flipping or reselling items, resist the temptation to snatch up something you have no use for because of its perceived value and keep in mind that the sale is being run by professionals who have usually done at least a little legwork to make sure the prices reflect the market value, even at a deep discount. Remember, friends, you are not buying for your own estate sale, and if you ever get the sense that you have gone overboard with things you have no place for and aren’t just wild about, put them down and run out the door. I do it all the time.

Loved this pretty set of glassware bit would not want to deal with packing it up and bringing it home from Michigan

So what should you buy at an estate sale, you ask? Well, nothing—you should go into an estate sale planning to buy nothing, then anything you do find is truly something you want. That being said, I always peruse the books for subjects that interest me, like art and design, and books on military history for my boys. Again, it is easy to get sucked into leaving with a mini-library, so use your discretion.

Furniture: Small side tables and chairs are easy to transport and you can usually find a place for them. I always make sure to turn them over to make sure they are not damaged and look for a maker’s mark.

Brown wood is back, and this handsome desk would be beautiful behind a sofa

Never neglect the basement!  This set of dining chairs were far more elegant (and less expensive) than their modern replacements for sale upstairs

Lighting: I love vintage lighting and if I like the shape or style of a table or floor lamp and have a place for it, I will buy it without much hesitation. I have purchased ceiling fixtures and sconces and have them all collecting dust in storage to prove it. Resist purchases that require professional installation unless you have a specific place for them in mind.

Clothes: I don’t ever spend much time in dusty closets, just a quick glance to see if anything bright and colorful jumps out at me, like the pastel pink silk shantung bejeweled dress I found that felt like it was waiting for me at a Highland Park sale and fit like a glove. I knew when I saw it, it was meant to be.

The dress!

Art: Now you can hardly call yourself a collector if you don’t have a few paintings stacked against the wall in some room of your house, but again, make sure you have a place for it or really like it and remember hidden costs of reframing, if necessary.

Upholstery and Rugs: While I have found rugs and chairs at estate sales, they usually go directly to my upholsterer and/or cleaner, so proceed with caution before purchasing any soft furnishings.

It was probably a good thing that this chaise had sold for $20 right before I arrived, I am a sucker for bamboo and rattan and with new cushions this would be a stunner.

Holiday Ornaments, Kitchen Appliances, Serving Pieces, and Linens: Take a peak but again, only purchase if completely compelled to do so.

I love beautiful linens but am also realistic about the fact I rarely use them so I only buy if they really speak to me and are in pristine condition

Jewelry: They usually keep the jewelry near the checkout, and I always give it a once-over. I have amassed a spectacular collection of vintage jewelry over the years and again, I only buy if I really think I will wear it.  The same goes for handbags. I am a sucker for anything wicker or made in Italy, just make sure they can fit your phone!

I collect box purses and was thrilled to find this Iconic LOVE box purse by Enid Collins

I found this beauty at the tail end of a sale for $7

I have also had great luck in the garden department and will pick up metal plant stands to have powder coated later. Same goes for cachepots and vases, filled with flowers these make wonderful hostess gifts, just make sure to turn them over and scrutinize the quality, no need to pay for something left over from a long-forgotten flower arrangement.

Cachepots make great hostess gifts and I use them all the time around my own house.  I passed on these but wish I hadn’t.

I had this pretty plant stand powder coated in dark green to match the other vintage furniture in my garden

In the world of fast fashion and furniture, I am always happy to buy vintage and going to estate sales is a fun way to find it. I love to see the houses, the way people lived and decorated, and the things they amassed over their lifetimes. There was one house on the lake I went through with a sweeping staircase covered in wall-to-wall shag carpet. Last fall I visited a David Adler estate built for an Armour in the ’30s that was a mashup of architectural genius and ’90s remodeled horror. Sifting through a houseful of items is a gentle reminder that you can’t take it with you, so do not bring anything into your house that does not serve a purpose or bring you joy.

I resisted buying these plates but wish I hadn’t!

Birdcages are great to display in front of windows as they won’t block the light.  I bought three of the at this sale.

I have a certain reverence toward these sales and the passing of belongings from one person to another.  At that sale I mentioned earlier, as I was walking to the car with a cart brimming with shoes and jewels and plates, the doorman commented on my success, and I asked if he had known the previous owner. “Oh she was the most elegant lady,” he said with a smile and then with a wink added, “You two would get along.”

Be sure to follow along with Jenny on her estate sailing adventures @jennybrowndesigns