My stylist friend Teresa Brink (now a buyer for an upscale European multibrand) once told me never to buy a second of something. She said you’ll always like one more than another and that’s the one you’ll end up wearing. As I wrote here I agree. In my case, I reason: “You rarely need a second one of whatever, no matter how much you love it. Fashion moves, and by the time you wear it out (a badge of honor!), you will actually want something different. Especially the case with jeans and shoes and especially sneakers. They change the fastest.” And I still agree with this statement. Add to this that the only thing worse than reckoning with a mistake is reckoning with two of them.
But.
As with everything, there’s always a time to break the rules. I’m typing this while sitting in the fumes of my own rule breaking (Skims made me do it - more below.) So while it’s fresh, I thought I’d share the why of doubling down, how to do it without regrets. Through the lens of 7 repeat purchases I’d make again today. And one I wouldn’t.
The tip: If you have something classic in appearance whose lifetime is inherently finite, i.e. a tee won’t last forever, and you find yourself thinking on more than one occasion: “Thank G I have this” (or praying that it’s clean), you’ve got a contender.
The story: I stumbled into this tank by accident, looking for white muscle tees (and it only comes in “marble” not true white). It feels like a tank more than a muscle tee. Here it is in action.
The why: It ends up solving so many things. It’s got great length. Enough coverage to make leggings “city ready” for me, and it works so well under a cropped “third piece” when you want a line of color poking out (and coverage!). It can be dressed up but still looks workout appropriate. And the neckline is high and doesn’t look sloppy. It’s not 100% cotton but it’s got high cotton content and feels light and breathable. I love the deep armhole, it’s ready for a peek of colorful sports bra, bandeau, etc.
The repeat: I’ve been craving gray and brown tees and tanks lately. Now I have them.
The tip: If it’s something where comfort is crucial, you’re using it a lot, you won’t outgrow it, a different color has a different impact, and it’s an independent artist you admire (you’re supporting something that means something and feels good), consider a second.
The story: I first bought a Hannah Yoo earcuff in red on Tibi when she was its design director. I love earcuffs as a premise, because they add instant modernity to a look. But too often, I find them functionally deficient; they’re too tight and hurt or too loose and fall off.
The why: This one was simply perfect. Perfect in both beauty and function. When Yoo went out on her own, I knew I’d become a repeat customer (she radiates goodness on top of everything else).
The repeat: Often I found I wanted to add my earcuff to a look but the red was too much with the other pieces, so I asked her to create custom creamy bejeweled design, which I can wear almost daily if I like. I predict I’ll go for a third in another color. I feel instant edge and palpable joy whenever I put these cuffs on.
The tip: If it’s a classic item, the fit won’t change, and you’re using it 4 seasons, dressy and casual … it’s one to think about.
The story: I knew this was coming and couldn’t decide if I wanted a go-with-everything neutral or a color pop. So I bought gray and yellow at once. I was trying to decide, testing them out and already using them so much I decided to keep them both.
The why: I use the hell out of these and they often are what makes an outfit work for me. I put them around my neck, waist, over a tank. when I’ll be out all day from sun to A/C they save me. They don’t take up much space in my closet, either.
The repeat: The yellow and gray are really different. I go to both a lot. When an older version turned up in green on a resale site for $60, I went for that too.
Alo Yoga High Waist Iconic 90s Capri Leggings.
The tip: If it’s something where comfort is crucial, you’re using it a lot, you won’t outgrow it, a different color has a different impact, and it’s an independent artist you admire (you’re supporting something that means something and feels good), consider a second.
The story: I don’t like shorts. At all. Workout or otherwise. I think some people consider these pants but for me they are the perfect length shorts. I used to love a kneecap legging by All Access but stopped being able to find them. Then I stumbled on these.
The why: I don’t like the logo. But I love everything else — so flattering, just the right coverage and tightness, and this really smooth almost sueded feel but so light. I like wearing these both to work out and as part of a regular look and they fit the bill perfectly.
The repeat: I didn’t get black, because I already had black ones, so I started with gray. Then I got this sheer skirt and picked up mint and red to play with under it and serve double time as workout wear.
Saks round neck cashmere sweaters
The tip: When a store or brand keeps re-making something it’s because there’s demand. If there’s demand, it’s probably reliable in fit and trend-indifferent. A house brand like this recutting something over and over means something. Probably not a big risk. Classic. 4 season (think: summer nights in Maine). Always in style.
The story: My Saks stylist recommended it over more expensive options and it was on sale at the time. I sized up for the easy fit I wanted.
The why: Your whole life you’ll want a crewneck in these neutrals. The cashmere is delicious, they wear well, and there are 2 subtle details: a line design in the knit in the back that’s very Row-esque and small vents to make partial tucks easier without looking over designed.
The repeat: I got black, navy and gray at once. No regrets. Look at the picture below or (via fashionista.com) and tell me you don’t need the gray.
The tip: If you have a tough area (and please be kind to yourself as you evaluate, I mean functionally tough, like in my case bunion on foot or elongated earring hole), something that solves a wardrobe issue while meeting this functional need makes repeating — within reason — seem smart.
The story: Truly a discovery at the apex of my Amy Smilovic obsession. For a while there she was sporting them almost exclusively. In the past, I avoided anything that would over expose the bun-buns (ok bunions) but they made things look so — right. Maybe that little bit of fabric in front would cover the bun-buns.
The why: These shoes are high maintenance. They aren’t that comfy. They are completely flat. They unwrap spontaneously. But they make EVERYTHING work. Maybe it’s because they’re so naked and that contrasts with the big pants and skirts I’m drawn to. Maybe because the lacing up feature makes them a flat that won’t ever be dowdy or because I can use it to wrap a too-long pant.
The repeat: I got my favorite color, the bright blue Amy has on above. But I found myself going to them over and over, frequently turning up as the only shoe that worked. I worried about wearing them out since there’s not much to them. So when they went even more on sale, I added the red and the green to my repertoire.
7. Tibi pull-on pleated skirts.
The tip: It’s the perfect go-with-everything non-statement piece that might be worth replicating. The perfectly executed basic that suits you. You won’t get sick of it. And there are more ways to use it. It’s a tool, not an end in itself.
The story: A navy Tibi featherweight pull-on pleated skirt was one of my first Tibi purchases. And it was suddenly all I wanted to wear. But I was wary of making a doubling up mistake! So I held off. And then right before Italy, I looked at my old Zara white pleated skirt and bought the white Tibi one.
The why: Even if nothing’s working, these work. I was meeting a client for a drink and grabbed this with a camp shirt and sandals. It’s a get-out-of-fashion-panic-free-card. I like a pull-on. Easy. Sometimes I’m too tired to fasten into something.
The repeat: After the navy. And the white. I got 2 other Tibi pleated skirts. A red one, used. And this toffee maxi.
8. And, the Fail: Balenciaga Hour Glass Blazer
The thought: If something makes you feel you, all by itself in any situation, maybe it’s worth repeating?
The tip: Maybe not. We evolve, we change, we’re curious. And it’s not 1 thing that defines your “you” it’s probably more like how you put it together. Live and learn.
The story: I saw this on IG at a time when blazers were my uniform. It stopped me in my tracks.
The why: I’ve said “sculptural” about a jacket before, but when I saw this, I thought I hadn’t even known from sculptural. I found mine used. Wore it a ton. My “in a rush” answer became this jacket and denim. I love the length in addition to the shape. It can be a blazer or act as fall/spring outerwear. It seemed like the most me of the most me items in the world!
The repeat: I first found the brown plaid. Then a black and white herringbone. And then black! Brushed gold buttons. All 3 used. But still. I am going to keep the herringbone, which is the lightest, and I will wear over a tee or tank in Miami at night or toss on for a Zoom. I’ll sell the others. I’m too hot for them. In the having hot flashes kind of way.
interesting point about jeans and i’m sad that it’s true because jeans are such investment pieces for me. b sides and r13, i’m looking at you!
shoes too but they get worn out more quickly (i walk a ton) whereas jeans could last so many years if we didn’t tire of the silhouettes.
I missed out on the featherweight pleated skirt and still dream about the adventures we could be having.