I AM PROBABLY not the only person to have suffered a minor, first-world breakdown at Madame Paulette, a Manhattan dry cleaner that bills itself as “the world’s leading cleaning and restoration specialist.” Not New York—the world. I’d gone there in an attempt to salvage a flared black wool Azzedine Alaïa skirt purchased in Paris years before. Bought on a deep discount, yet still expensive for me, the skirt was pivotal: I’d worn it at least once a week for over 10 years. It was, unequivocally, my best fashion investment ever, and due to an encounter with a savage dryer setting it appeared to be ruined.
With the help of one of Madame Paulette’s elves, I managed to resurrect the skirt, and its near loss made me even more conscious of how important our investment fashion pieces are. These are the precious—usually expensive but not always—garments that we wear faithfully year after year. Although pulling the trigger on a perfectly cut camel-hair coat or a handmade pebbled-leather handbag can be painful, with time the expense can be worth it. That’s why sources ranging from penny-pinching blogs to your Aunt Sue encourage you to think about an item’s CPW: its Cost Per Wear over time. But can fashion ever really be a good “investment”?
The behavioral economist Cass Sunstein explained to me that there are two ways to think of investment. The first, he said, “is that you have it, and you enjoy it, and you use it for a long, long time.” Like a solid family car, or a good suit. The second kind is a more typical investment scenario: putting money into “stocks or comic books or art” in the hopes of reselling it later at a profit. Although fashion investments have historically fallen into the former category, they’re now entering the latter too.
Fashion speculators have long hawked rare Supreme hoodies and Hermès Birkin bags on the secondary market, but consignment websites like The RealReal and Rebag are making it easier for laypeople to resell. Of the pieces that fall into the investment category, Charles Gorra, the founder and CEO of Rebag, said, “It’s rare that they are pure financial investments, but what we see most is a hybrid rationale,” a combination of a “fashion-oriented decision” and a “rational financial mind-set.” Buy it today because you love it and want to wear it, but be comforted by the idea that your wardrobe has value. (Those who have read “The Devil Wears Prada” will remember that its lead character buys her independence from a particularly demeaning 9-to-5 job by selling her designer clothing.)
Investment shopping needn’t be dryly analytical, however. I interviewed 10 stylish women about their best fashion buy ever, and their passionate, idiosyncratic answers run the gamut from a lavender flowered skirt to bondage-inspired harness boots.
Lucia Pica’s Red Puffer
Chanel’s global creative makeup and color director on the unexpected chic of a $790 North Face down jacket.
The Piece I went on this Ayurvedic retreat in New Mexico and I wanted to be warm and comfortable. I saw this puffer jacket and it was the best red I’ve ever seen.
Why It’s Endured I’m wearing this warm thing but I don’t feel dressed down because of the color; it’s like wearing a lipstick that brightens up your face. It’s hard to hide with a bright red jacket. And funnily the color red seems to go with everything. I wear it with jeans and a Chanel bag and red lipstick. I feel quite empowered by the color.
Estimated Cost Per Wear $.89 per wear if worn every winter day for 10 years.
Yasmin Sewell’s Elongated Biker Jacket
The Farfetch VP of style and creative on a $2,750 tweaked classic by designer Magda Butrym.
The Piece I can’t recall any moment from when I was a child until now that a biker jacket wasn’t in fashion. Normally I don’t suit the shape of a biker because they’re a bit short. But when I saw this one in the Magda Butrym lookbook, I thought, ”That’s the most beautiful biker I’ve ever seen.” Because it’s longer, it’s not an obvious shape.
Why It’s Endured With something you can wear for 50 years, you might as well buy the best quality and get the most bang for your buck.
Estimated Cost Per Wear $10.57 per wear if worn once a week every spring and fall for 10 years.
Angela Dimayuga’s Thigh-High Garter Boots
The creative director for food and culture at Standard Hotels considers the fun-per-wear of $800 Helmut Lang boots.
The Piece I feel good about spending my money at a place like Opening Ceremony because my friends run it, and that’s where I got these boots. They were definitely a splurge.
Why It’s Endured With the garter that’s on them, it ends up making sense that you want to show off the garter or the harness by wearing it with a skirt or shorts. They’re a pretty strong look and I dress very much like a New Yorker where you have to go from day to night often or just wear something that’s super comfortable or ideally both. I know that they’re kind of edgy-looking but they feel timeless. I bust them out when I want to have a fun night out.
Estimated Cost Per Wear $3.33 per wear if worn twice a month for 10 years.
Lisa Eisner’s Rose-Colored Glasses
The Los Angeles jewelry designer on the allure of $500 vintage Cartier gold sunglasses.
The Piece I got them at a flea market. I had been looking for them. It was sort of a fetishistic thing, like, “I have to find those Cartier sunglasses.” I still wear them all the time, and nobody has them so that’s the greatest thing ever.
Why It’s Endured There’s something perfect about the lens color. It’s not too dark, it’s not too light, it’s just right. It’s almost like rose-colored glasses. And the gold, the geezer look of it, and that little bit of burgundy lacquer, that really drove me crazy.
Estimated Cost Per Wear $.27 per wear if worn half the year for 10 years.
Tata Harper’s Flirtatious Trench Dress
The natural-beauty entrepreneur on a $1,300 Khaite trench dress with a surprising back.
The Piece It is serious and timeless in the front, it looks like a trench. And then in the back it has a little cape and an open back, so it has just a touch of sexiness.
Why It’s Endured The fabric is really nice and heavy. When I wear it I feel very feminine. When I have it on, people always mention it. They want to know the brand.
Estimated Cost Per Wear $10.83 per wear if worn once a month for 10 years.
Kai Avent-deLeon’s Perfect Slip Dress
The owner of Brooklyn store Sincerely, Tommy on the ease of a $245 John Patrick Organic slip dress.
The Piece It’s one of my go-to pieces that I can throw on really easily, and now that I’m pregnant and my belly is growing, it allows for extra room. The fabric feels good against my skin. I’ve always loved slip dresses and usually I’ll go the vintage route but it’s hard to find vintage bias-cut slip dresses.
Why It’s Endured Because I can just mix and match it, it’s really simple. I appreciate that, for someone who’s on the go a lot, and now being pregnant, just not having to make a huge fuss.
Estimated Cost Per Wear $1.02 per wear if worn twice a month for 10 years.
Olivia Kim’s Navy Men’s Watch
The Nordstrom’s VP of creative projects on the pleasure of buying a $23,550 Rolex for herself—at the airport.
The Piece Growing up, my mom, my aunt, my family, they all wore Rolexes. To me that was always a watch that you strive for. When this series of men’s watches came out in Basel I was obsessed, and then they came out with navy, one of my all-time favorite colors. But you don’t just go out and buy a Rolex every day. The funny thing is that I bought it at the airport, which is my absolute favorite place to buy watches because the selection is really good. It’s also a sense of accomplishment where it’s like, I worked really hard, I can afford a watch.
Why It’s Endured It makes you feel dressed up even when you’re not. Half the time it’s covered by your sleeve, but there’s something elegant about having something that is so beautiful and functional, and is not this big showy piece. It’s the way that women feel about lingerie—it’s completely for yourself.
Estimated Cost Per Wear $6.47 per wear if worn every day for 10 years.
Elizabeth Stribling’s Red Couture Pantsuit
The chairman of Stribling & Associates shops for serious pieces on vacation, and this $4,500 Christian Lacroix outfit is no exception.
The Piece Since I work hard in the real-estate world in New York, I do my shopping when I’m on holiday, and when I’m on holiday, I’m in France. So I bought this suit at the Christian Lacroix boutique in Cannes. He cut clothes in a way that fits my size and he also loved color. I’m a woman who was born in the South and we wear lots of color in the South.
Why It’s Endured Red is a powerful color, and it makes a statement. It is a real power suit, and very feminine.
Estimated Cost Per Wear $37.50 per wear if worn once a month for 10 years.
Rachel Cope’s Lavender Printed Skirt
The co-founder and creative director of Cope Wallpaper on the $450 special piece from Rachel Comey that helped her break out of her shell.
The Piece I bought it for a photo shoot for a collaborative exhibition that we put on for Salone de Mobile. I love Rachel Comey and I typically go to her store if I have a special occasion. I really respect her as an artist, as a mother, as a business owner.
Why It’s Endured The color stands out from my wardrobe. Everything I have is black and it’s this beautiful light lavender burst of purple. It improves my mood. It’s symbolic that I’m feeling more confident being a female designer and I don’t have to be afraid to be seen.
Estimated Cost Per Wear $1.88 per wear if worn twice a month for 10 years.
Taryn Toomey’s Uplifting Boots
The creator of exercise empire The Class on the $680 Isabel Marant suede boots that dress up her everyday leotard.
The Piece Even though they’re suede and something that you would wear for the colder seasons, I wore them all summer, because they have a hidden heel. I’m still wearing them every day and I bought a second pair.
Why It’s Endured I’m often going from the studio to the street, so for me to be able to throw a boot on that has a little bit of a lift in it is key so I don’t look like I just left the gym. I always put some sort of footwear on that’s not sneakers. It just makes you feel a little bit more elegant.
Estimated Cost Per Wear $.65 per wear if worn twice a week for 10 years.