How to know if you “Have to Have”

Sale time is here so let’s nail this.

If you follow Tibi, its Style Classes and its CD Amy Smilovic, you know that she breaks pieces in a wardrobe into 3 categories: fundamental/without fails (or “WOFs” — those 4 season, always work pieces), in and outs (you crave them, wear a lot, then put on pause), and the aptly named have-to-haves (HTHs). And if you follow me, you know my struggle. Have-to-have overload. (Sigh. #leoproblems)

Drama! Sparkle! Neon! Sculptural shapes! Fringe! Harness! Emotional person + love of fashion = a closet that veers very close to Aladdin’s cave territory. Like style icon Trinny Woodall, although I have more minimalist moments, my “Miami” modifier (style DNA: eased, modern, heritage, Miami) means extreme pieces can often feel very core to my style, versus more subtle, no-fail moments, although there is a balance in my wardrobe these days. In the past, I was working with a Saks stylist and she did an intervention. I walked in, all, “Can’t wait to see that sale skirt with the crazy eggplant pattern.” And she was like, “Yeah. I thought we’d spend today making sure you have the basics. To go with all those fun things you love.”

Ouch.

Now I try to, you know self-regulate. Stop laughing. With varying degrees of success. It’s why I recently had to cull black blazers, black pants, jeans, and white shirts. I try to tell myself to get those just-right WOFs and then I overdo those too. (Insert facepalm emoji.)

And now …. here we are. Sale time.

It is the best of times. It is the worst of times. On the one hand, I’ve picked up some of my favorite pieces at sale time. Restrained, high end pieces I buy because the deal is irresistible — that turn out to be WOFs (I call these “sleeper WOFs” — more on that to come). And HTHs I’ve dreamed about and wishlisted but couldn’t rationalize … until now. But also “serendipity HTHs” — things I didn’t consider before and then get some sort of strange animal instinct about in the moment.

This year, instead of sort of shooting myself into sale like a drunken arrow, I thought I’d try to go in with a touch of thoughtfulness. And I’m sharing these thoughts here, in case any of you are as wonderfully open to the universe (okay, weak and susceptible) as I am.

And I promise this is all fun and worthwhile in the end, not (totally) ridiculous. Because sale can be about pushing and learning about your style. And that is ultimately a stand-in for learning — and evolving (evolving, the key to forever ageless) who you are.

First, some basic guidelines.

1. Re-evaluate the HTHs you’ve had on your wish list. Just because you’ve thought of them as HTHs and they’ve been on your list all year doesn’t make pulling the trigger a forgone conclusion. Ask yourself if your heart still pounds. Or are you over it?
2. Have a “no” list. Yes, you’re going to flex for serendipity. And the very notion of a have-to-have conflicts with list making. But if you have a glut of something, chances are that’s an area of weakness, and confronted with big discounts, you might get weak. On my no list: No white shirts that aren’t machine washable. No mules. No Teva-type shoes. No heavy wool sweaters. No boots.
3. Say yes to the “sleeper WOF.” Beyond thinking of sales as a time to pick up a game changing HTH or two, don’t overlook your next WOF. Not the obvious one on your list but the kind that turns out to be a sleeper hit you can’t remember living without. These are a little tricky to identify, and they’re quieter, especially amidst all the noise of the HTHs. But they’re a true prize. Start with an eye for unbasic-basics. Things that have a heritage or classic sensibility at their heart but the quality is something special. Things your sale-magpie eye might overlook. A simple tank top shape. A menswear belt. An unadorned turtleneck in a neutral you don’t usually look at. A crew neck sweater with an interesting stitch. And then force yourself to evaluate them while looking critically at your rules (“I never wear brown” “I’ve never liked or bought X designer.” “I don’t like fitted.”).

Here’s Trinny Woodall in a coat I’d call a “Sleeper WOF” and great sale buy — this is worth a watch.

4. Check in often and ask if you’re having fun. You know how you’ll be listening to a Grateful Dead song and then ten minutes later you’re like “what is this shit in the background” and you kind of tuned out but they’re still playing the same song and they’re off on some ambling, annoying riff? Sale shopping itself is not a “have to” anything. If at any point it feels overwhelming and/or a chore, if you pick your head up and wonder what you’re doing here anyway, drop the shopping and resume if/when you want to. Nothing about this is necessary. Stay attuned to how you feel. Sometimes I’m knee deep in some list of sale items that I’ve refined with only designers I love, and I’m mindlessly scrolling in it with some weird urgency and suddenly I’m like “I’d rather listen to a podcast.” Don’t keep going.

Ok, so now you’re in the right frame of mind. And you’ve got a potential WOF or 2 in cart. How do you know when you’ve stumbled on a HTH?

1. It’s been on your wishlist and you still feel just as in love as when you put it there. You can’t believe it’s here, at this price, in your size. You are not over it, hardly. It wasn’t a passing thing. You have an emotional reaction still.
2. You try it on and feel palpable joy. There’s a reason Marie Kondo has clients touch everything. Honing in on an HTH is easiest in person. When you put on a HTH, you have a strong, physical, visceral reaction. My friend/biz partner Susanne always says “Oh no, she’s dancing.” HTH’s make me want to dance around. If that’s not you, maybe you may feel a sped up heart rate. You just know. If ordering online, and you suspect it’s a HTH, and it’s returnable, wait and see what you feel, physically, when it arrives. (But look carefully b/c anything 50% and over generally isn’t returnable.)

This recent skirt is 100% HTH. It’s CRAZY. It’s not flattering. (This is a nice pic.) It looks like a cake. I don’t want more black. I find black challenging. And I couldn’t go home without it. There was a lot of dancing.

3. You want to wear it immediately. When you get something you feel you have to have and then don’t want to wear it right away, it’s possible that you were just crossing it off a mental list — you thought it was urgent and it wasn’t. It may end up being a joy to have, or it may end up being a dud (as a friend of a friend one said “If it’s not a hit, it’s shit.”) but that’s not an HTH IMO.

This skirt somehow felt like a HTH and yet I haven’t wanted to wear it yet. There’s no ease. I do like it styled with my WOF striped shirt though. We will see!

4. Your rules fall away. You never wear logos, and it has one — or lots!, but it’s got this … charm! It’s not flattering at all but somehow it just feels so … fresh. Linen is completely impractical, but the practical part of you has left. the. building. Amy says “taken out of context, these items would surprise someone that you bought it.”

5. Or, it’s like you on acid. You, broken free of the constraints of practicality. Like you love a full skirt — this one looks like a cake someone could jump out of.

A love a 3rd piece. But bows are not me. I don’t need more black. This looks like a monk collar. HTH.

6. You don’t mentally say the words: “I know how I’ll make this work.” You probably can make lots of things work at this point. That doesn’t mean it’s a HTH. That means you found something you like or that’s interesting to you and the price is great. (And for a WOF, the feeling you’ll have will be more like — “this will make so many things work.”)

7. You know that you’ll be able to wear it with a WOF and feel like you. (Again, paraphrasing Amy, below.) This means that even if it’s you on acid or a you no one knows, it’s not “not you.” Ok this is tricky so I’ll explain. The brand Chloe is not me, not ever. Beautiful brand. Just not any facet of me. I bought and returned a Chloe chunky raffia sandal recently. If I put that with WOFs like any of my easiest to wear blazers, it still wouldn’t work. If I am seeing a Chloe something and thinking it’s a HTH it’s a sign that I may have been swept up in seeing it look great on someone and thinking I want it versus actually wanting it.

8. It pushes you. See Amy’s note below. “It pushes the boundaries of your style.” A great HTH — even if it sits in your closet — actually pushes, teaches and inspires. It makes you ask questions. It makes you less inclined to settle for blah in things. It forces you to re-evaluate proportion. Look, it’s really easy to get stuck. In makeup world, Trinny Woodall did these youtube makeover specials and often found that people get stuck in the makeup from a time they felt the best. The same can be true in clothes. We get in a rut that’s hard to even be aware of, let alone shake. Sometimes the role of an HTH isn’t to wear a lot but to shake us out of the rut. There’s a lot of value in that. Here’s an example of Trinny Woodall in something that pushed her, these pants, and you can see how much she took away from it. I still have my first Old Celine piece — a blue unlined oversized wool coat with slits, bought in the throes of a long affair with print and 50s fit and flare silhouettes. It introduced me to minimalism and sparked a style evolution. And with it came a certain maturity in my career goals and approach. I don’t wear it often, but I still love it.

Happy hunting, friends. May you find just what you didn’t know you really, really needed.