Radical proposal: Never buy anything "for an event" again

It's always a mistake. Like, 100% of the time.

OK, so you may have noticed I buy a lot of things. But one thing I never ever buy is an outfit for an event.

I suppose that to an outside observer, my spending and purchasing habits look cray. But in truth, I’m actually really thoughtful about the stuff I choose. Shopping for an event fails 100% of the time. (And I haven’t done it since my wedding, for which I bought a $69 Vera Wang Lavender Label sundress on Rue La La that I later sold.)

Here’s why:

• Cost per wear. You vow to wear it again. You think of all the ways you can make it look different. And then you don’t because it was too specific to that event, it carries the stamp and memory of that event, you kinda want something new for the next event, etc.

• But it’s a classic! Ok see above. But you’re smarter than that, you say? You’ll be the exception because you “invest” in a “timeless” piece. Nothing is really timeless in fashion, is it? And if there’s one thing that’s gonna collect dust, and that you will NOT be excited to wear with a bunch of friends for a big event, it’s that ole “timeless” dress. It’s the (slow) train to dowdy-town.

• Pressurized shopping. The event’s coming, the pressure mounts, it feels like there’s a lot riding on this, and in the heat of the moment you inevitably get confused and pick (or get pushed into) something that’s not aligned with your DNA. Or something that costs too much in relation to how much you’ll wear it.

• Wardrobe bifurcation. It’s something they talk about in Tibi Style Class, this idea of separate wardrobes for separate parts of your life (work/play, for example). Event dressing is bifurcation to the extreme, reserving space for something that’s like .0002% of your use cases. When the most interesting and useful way to shop and dress is to use clothes across all occasions.

• Dresses. Dresses are a problem if you love fashion. Because unlike separates, they’re harder to manipulate and make your own. Actually, I’m writing a piece on this now. Remind me to tell you the story of the perfect red Jil Sander dress I never wore.

• Your DNA. Maybe it deserves its own little section. In part because of the pressure, in part because of the event “rules” and in part because of “the dress thing” — event items often don’t feel like you. It’s hard to shop in this way and end up with something that hits all elements of your style DNA. As a result, at the event you considered important you feel the least like yourself.

Ok, I think you get the problem. And you’re probably like thanks, Rach, WTF do I do about it?

Try this:

• Start with how you want to feel. Picture yourself at the event. Having the best time imaginable and feeling just right in your clothing and in your skin.

• Now go shopping. In your closet. Imagine it’s a store, and you’re shopping for this feeling. It’s going to feel forced and annoying at first, but force yourself!

• Build a rack. If you have a rack, great. If you don’t you can use a device you stick over the door and take down when you’re done. Hang anything that fits the feeling you want to feel on the rack.

• Consider as a base something you love, even if it’s generally part of your casual wardrobe. a slip dress you usually wear with flip flops. A silky shirt you love with jeans.

• Play! As my friend Christian of @wastenotwantnotstyle says. As you play, quiet any thoughts of “But I just wore this” or “I worked out in this!” etc. Just play. From time to time, let yourself think: This might work if I had …. Then check in your closet for the closest thing to what’s “missing.”

• Don’t forget to accessorize. It can do a lot to achieve a feeling of newness. As you get closer to things that have potential, try

  • lots and lots of gold necklaces or a dramatic earring

  • a tuxedo-ish blazer over your shoulders

  • a shoe that laces up the leg and doesn’t “match” at all

  • a scarf on your wrist

  • a ribbon or barrette in your hair

  • a pin or pins on your shoulder(s), or the v point of a neckline

  • a visible lacy something

• Take pictures of all your looks.

• Take a break. Ideally until the next day.

• Then go to your phone and assess with a fresh perspective. You’ll be surprised, I think.

Just to put it to the test, I asked you (via IG) for some of your summer events. Then I tried to come up with something for each using what’s already in my own closet:

You’re going to … “8th grade graduation.”

I’m using: Tibi ivory top (bought used somewhere) + featherweight skirt. The Row Vera bag (Bergdorf sale, but this is a nice option), white Prada shoes (also used somewhere), my Hanna You ear cuff.

Why: All tones/shades of one color says “special day” and makes me think less of the routine ways I’ve used these pieces.

Takeaways: (1) It’s a nice idea to build out shades you like so all one color family looks are a possibility. Creamy colors (see, e.g.) are especially festive and chic. (2) I find a day-to-night clutch a very relied on item if you see them in your sales/consignment travels. (3) A Hanna You Works ear cuff is a great investment - it instantly gives “not dowdy” to something that is punching harder on the “heritage/classic” notes.

You’re going to … “my daughter’s high school graduation, but I prefer pants.”

I’m using: Same as above, but to make the pants feel respectfully dressy I went with gold shoes (old, used Tibi - here’s a silver pair) and added a giant (used) Marni bracelet.

Why: See above, and also at the HS graduation the white/cream is a nice contrast to all the black robes.

Takeaways: (1) Pants are fine in many event situations, but I often think out of respect for the person being celebrated it’s nice to then take it up a notch with accessories. (2) I didn’t buy the Marni cuff for an event, I bought it used because massive cuffs are my thing. It’s nice to have something you love wearing to instantly feel “you” at an event. This is a shot of my “Miami” DNA pillar.

You’re going to … “Backyard party for a recently married couple. Basically a super casual wedding reception.”

I’m using: The Row black taffeta kinda feeling skirt with pockets (bought used at Castanet; you could also pre-order this one rec’d by Becky Malinsky in her recent newsletter) + Tibi top (it has a back cutout - discounted here in a couple sizes) + Raf Simons “lunch sack bag” (used) + Margiela shoes.

Why: The full skirt/texture, cutout/shape of top + shoe interest says “party.” The calmed palette + flatness of the shoe says “I know I’m in a backyard.”

Takeaways: (1) It’s wise to have a flat shoe with some impact. (Not mad at this!) Sometimes a party heel is too much/impractical. (2) Full skirts are just a treat in summer, as Beck said. And look at this reference for a Van Sono skirt I just bought. Great any day, with a tee and flip flops. and also really event-friendly.

You’re going to … “a young relative’s wedding”

I’m using: The Row skirt (above) + an old Balmain belt hunted down after seeing it on Trinny Woodall, and a Tibi semi gauzy tank + (used) Tibi nude sandals. Would bring the blazer.

Why: You can totally do black for a wedding, especially a young one. Worn together, these useful pieces look like a cool dress. The belt means I can go without jewelry. I am not trying to look young like the young couple, I want to look like a cool aunt! (or whatever).

Takeaways: (1) It’s good to start by thinking, “who am I at this thing” and “what do I want to convey”? Like: I am not the star of this show. (2) A black tuxedo blazer is always a good idea. Good with denim. Good on occasions like this. I confess: I have more than one.

You’re going to … “a black tie wedding by the beach.” (!) How is this a thing, but ok ok, trying not to judge…

I’m using: Tibi sporty nylon (alternatively called “Italian taffeta “ — which makes me feel better in this case). Ear cuff I bought at a Stitch Lab Miami, an incredible marketplace featuring Latinx sellers. Egg-shaped Simone Roucha bag from Dora Maar. You could also indulge in this mini version, on sale.

Why: I get nervous when I see “black tie” because some people equate it with “full length.” So I went to this full length set. I’ve worn this just out to dinner on a Saturday night, and also as separates. But the fact that it’s long and all one color makes it feel dressy if you want. I also picked dressy accessories. (I started with a rhinestone necklace and tuxedo jacket but they were too weird by the beach.)

Takeaways: (1) When you see an “out there” bag or piece of jewelry that speaks to you and is a really good value, scoop it up. These are the add-ons that make things work across multiple occasions. (2) Sets are a great way to dress up. It’s why I often go for an accompanying piece.

— oh and I almost forgot: an afternoon yacht birthday party!

(I gave you two options because the fact that I have a “boat shirt” felt like cheating.)

If you still crave newness after all this, first ask if you could borrow or rent. And if that’s still not cutting it, rather than shopping for an outfit, shop for a piece, a piece that you can use for lots of special events to come that will work with many things you own, taking them up a notch. For example:

• a single very large bracelet, or 2 medium sized matching cuffs (what you want is a serious statement)

• a necklace that functions like a collar or even like a shirt

• a blazer with tuxedo details (generally oversized or cropped is best)

• a wearable piece made of pearls or sparkly beads

• a dramatic “third piece” with structure

• a blingy shoe or a satin one

• A transparent or tuxedo shirt

• one or more tennis-style necklaces

For me, the hunt for these kinds of game changing items is ongoing, because they’re serendipitous, not about anything upcoming.

Of course, I’ve forgotten my favorite tip of all: Go to fewer events. It’s ok to prioritize the ones that mean something to you, including the ones that mean something to you because they mean something to someone who means something to you. But the rest? Decline the committee/invitation and make a donation. Decline the event and send a gift and a note. Honestly as long as you’re warm, respectful, thoughtful and generous, people generally feel good and celebrated. And that’s the point.