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@heymrssolomon · Jul 21, 2026

wear what you already have in a new way

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Hey Mrs. Solomon on Style · @heymrssolomon

[Just a note: Paid subs, please scroll all the way down for a tryon of my new Tibi pieces and more. And if you’re looking for Sunday Night Outfit Planning, it’s at the end of this post along with The Package Room.]

On my path to getting better and better at styling (yes, you can get better and better! You’re not just “born with it” — we do not throw up our hands!), one of the things I’ve realized is that … I’m a little afraid of the clothes. Like I have this reverence for great designers and great pieces. I will look at how it or a similar piece was worn on a runway and sometimes think that’s how I should wear it. Or I’ll worry about (you’re going to laugh) embarrassing the clothes? (Yes, it’s true I sometimes ascribe human qualities to clothes, like I feel sorry for something on the Real Real at 70% off. I feel it’s … lonely and misunderstood? And buy it, obvs. Because I am a nice person.) And one thing I feel often is that a certain detail is the whole gestalt of a piece, and I can’t HIDE that! Like the top of the dress is beautiful; I can’t put a sweater over that, duh.

But here’s the thing: These are OUR clothes.

We bought them. We own them. As close as we may feel to Miuccia or Amy or Olympia, they are not directing how we wear our Prada or Tibi or J.Crew.

Wearing the sh*t out of everything you own is the BEST feeling. You get your money’s worth. Or closer to it. You get a rush of virtuousness if you’re anything like me (wearing something out is a status symbol in my family). You get to feel creative. (And improve your style chops by even trying new ways to wear.) You solve problems. And as familiarity replaces cool reverence or rote repetition, these pieces become like friends.

Last week’s challenge: Every day, wear a piece in a new way.

Here’s how the whole thing went, and what I learned.

… ok, the Takeaways this week:

  1. Rip the bandaid off by any means necessary. Wear your clothes as soon as possible. If that means wearing a skirt as a dress, or throwing a sweatshirt and flip-flops on with a dress, just do it. The more quickly you get to know your pieces, the better chance they’ll come to feel like you and become valuable tools.

  2. When taking a risk, seek security. Whenever I try something a little “out there,” I layer on my Security Blanket items, things that make me feel comfortable and always work. I love using my mom’s hand me down bags and my go-to crewneck.

  3. Necklaces make great props. When you use a skirt as a dress or turn a shirt into a dress, etc., necklaces help. Somehow having this piece in the usual place makes it all feel right.

  4. Bridge colors make great Security Blankets. I notice that having a reliable piece that is also a bridge color is so valuable. Weird, murky, comfy sweaters (like this + this) do double duty as comfort and problem solver.

  5. Sometimes more is more convincing — two shirts, two necklaces, two tees. Try it.

  6. Don’t save holiday pieces for holiday. One of my favorite thinsg was wearing my silver skirt in summer. I’ve worn holiday-released sequins in summer too.

MONDAY

dinner with mom and dad (marinated in workout wear all day)

the flip: wore my silver skirt as a dress

Lofted Settledness? Yes! The perfect thing for eating outdoors; I felt so fresh. The weird red of the necklace gave me the right “wrong” with the pinks.

TUESDAY

happy hour with a new friend, and friend of HMS! (marinated in workout wear all day … again)

the flip: Using this dress as a maxi skirt

Lofted Settledness? Almost. I used a boyshort under the dress and I didn’t like the demarcation. I would do a nude thong instead. Also it’s too much “slim” - would prefer the gestalt of a bigger shirt, maybe a mock neck. And I tied the dress to keep it off the ground. I would just let it trail! It’s much cooler. I was literally heading to the bar next door.

WEDNESDAY

WFH, went into Back Bay for errands + research

the flip: Used two oversized shirts, making it into a skirt and a shirt

Lofted Settledness? Yes!

WFH + The Package Room

Lofted Settledness? Yes!

THURSDAY

flying to MIA

the flip: Took my polo dress and wore it as a shirt

Lofted Settledness? Yes. Once again - bridging jarring contrast colors with a weird color like this sweater helps; it’s why I chose it. Also a thin sock with the shoe made it feel better!

FRIDAY

WFH, MIA errands, hair appts

the flip: used my dress as a shirt AND slip/coverage for the open-back skirt

Lofted Settledness? Yes.

SATURDAY

in PJs until date night!

Lofted Settledness? Yes.

SUNDAY

brunch and shopping with Christian Botefuhr and Sunday Night Outfit Planning.

Lofted Settledness? Yes!

OUTFIT PLANNING + THE PACKAGE ROOM

INCYMI watch the most recent Sunday Night Outfit Planning below.

This week: Ditching your style crutch. By request.

Next week: Picking a color story. Lots of us pack this way. Let’s see if we get bored (and how to get un-bored) over the course of a week.

The Package Room — midweek special

Clothes

Accessories

Home + wellness

The Package Room, Monday July 20

Let’s get dressed.

p.s. I would appreciate it so much if you’d like or share this post so others can find me and I can make a living doing what I love. I am grateful!

For access to my weekly finds and cravings, follow HMS here on ShopMy

Now for the paid folks, the try-ons are here.

Read the original on heymrss.substack.com ↗

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