Q: How do you emulate iconic style comfortably?
A: You do you. Everything I wore this week. Inspired by Diane Keaton.
This week feels longggg (more on why later). But it had its moments.
First up, homage-ing Diane Keaton again. And she deserves endless homages. But I really wanted to do it differently, and to learn something along the way. The first time I was miserable! I love the swaggery sensibility BUT I did it too literally and I hated the emphasis on the waist - so not me.
This week I found a new approach to “inspired by” dressing - because I do think it’s such a good creative push when done differently.
Let’s start there.
How to Do Better Inspired-By Dressing
Begin with this reminder: It’s not Halloween. The point is to push yourself, play, and spark new ideas. Not to be recognizable as “on theme.”
Make a Selective Mood Board. The key word here is “selective.” Pick and choose ONLY looks that actually speak to you. You’re not a documentarian. Just getting dressed.
It’s ok to start with copies in theory, but move beyond them. Last time I was inspired by Diane Keaton, I was really literal. Everything I planned had that defined waist she does so well. But I actually don’t like the feeling of enclosure like that. I needed to feel that and adjust.
After you look at your mood board, stop looking at it. Get a gist and feel your way forward. That will help you with 2, above, being less literal.
If all you want to take is a sliver, that’s fine! If your one Diane Keaton thing is styling with a tie, or belting something, or wearing shades of white from Something’s Gotta Give, that’s fine. Feeling good is more important.
Once you have a look on your body, make it as good as it can be. You never see Diane Keaton in a skirt, and I didn’t plan to wear one. But I knew a shirt I’d planned would feel best for me with a slouchy easy skirt. So I made that switch in outfit planning. The comfort I felt in it made me feel more “Diane” anyway. She always looked comfortable with herself.
Just because you own it doesn’t mean you have to wear it. I say this in other contexts too, like just because you have a matching bag doesn’t mean that’s the automatic choice. Here, just because I own a big belt or white turtleneck doesn’t mean I’m locked into it. Struggle less, feel more. Know what I mean?
MONDAY
day
What:
Tibi featherweight pleated pull on skirt (sold out in pearl white but more colors and fabrications available - here are other options too)
old Celine white mock neck - more good white shirts w/ interest
Why: I was thinking of Diane’s white on white street style look with sneakers. This shirt is one I “like too much” to wear - so it was a great push to enjoy it! But you lose the detail with pants; it sits much better with a skirt. I liked the brogues which continue the white but don’t look too precious.
Outcome: Lofted Settledness.
TUESDAY
Morning
What:
Left on Friday brown leggings, cut shorter
Tibi macrame skirt (sold out) more open styles
Why: Pre workout work. Just loved the colors and love wearing my clothes functionally. And ripped the band-aid off on my new tote.
Outcome: Lofted Settledness.
Afternoon
What:
The Frankie Shop shirt dress, I recently had the sleeves shortened (shirt dresses I like)
ATM muscle slub tee from our white tank edit (find it at the bottom of this story)
secondhand old Partow carrot shaped pants - more interesting khakis
Tibi Herbert loafer and here is a good selection of loafers I like
Celine flat tote as above
Why: Busy work day getting lots done before surgery. I was thinking about Something’s Gotta Give, the casual whites of different textures and the khakis. I actually loved that the slub tee offers a different texture without being a sweater. I shortened the sleeve on the shirt dress, which I only wver wore with the sleeves rolled. I liked that acting like more of a shirt. And normally I would not pick a black shoe, but I wasa surprsied to like it when I planned the outfit - it made it less sweet.
Outcome: Lofted Settledness.
[Note from Rachel: On Wednesday I had my “beauty treatment.” Obviously sharing more with the smaller paid community. But I am not going to rate these as Lofted Settled or not - I mean can you be lofted or settled when your ears are numb, etc? I will say, though, that trying a little bit DOES make you feel better. It just does.]
WEDNESDAY
What:
Comme des garçons Tokyo sweatpant - more playful ones I like
Hub’s Kith brand shirt (can’t find secondhand) here's a selection of ones I like
Brave Pudding Varsity Strolls (Walking to our parking garage, hub said: “Cool shoes.”)
Heidi Merrick sweater — a/k/a my Security Blanket sweater
Why: Going to have surgery.
THURSDAY
What:
Secondhand Acne button up shirt and other good ones
Secondhand Tibi Stella pants, Tibi selection here and more white cotton and nylon pants I like
Vintage Cartier scarf - our scarf boutique here
Why: Trying to channel DK while recovering.
FRIDAY
What:
past season Oak sleeveless hoodie with neck tie (I haven’t tried this brand but I really like the look of this) The best hoodies generally IMHO are in the TRR men’s section. And look at this Marni one - the back!
Secondhand Alan Bilzerian soft sweatshirt-material blazer - lightweight tweed jackets I like **THIS may be the perfect option; I would size up at least one size and/or go for tall if you want it to cover your butt.
Why: Recovering and trying to feel decent! On this day I had a doctor’s appointment. This jacket is mens and looks like herringbone but it’s just a print. My dad has the same one. It’s such a good piece because I could feel more pulled together. I think a soft blazer or two is really helpful in that way.
SATURDAY
What:
Past season Fe Noel shirt (not the same but similar). This is cropped in the front with a longer back - other shirts I like with interest.
Gucci cotton scarf (alt here) and a boutique for you here (mine was actually a pareo. Good use case!)
Secondhand Alan Bilzerian soft sweatshirt-material blazer - lightweight tweed jackets I like
Why: Still home recovering, got to shower and just keeping it comfy but craving some dignity (LOL)
SUNDAY
What:
Day pajamas, John Elliot — the Donni Pop set is the most like it; I am also loving the Chan Luu PJs if we believe in one size fits all; these and more here and unrelatedly now I can’t stop thinking about this.
Red printed Comme des Garcons socks (heroes! - they add fun especially when you may not be in shoes at all) one purple pair and lots of colorful sock options here
Same blazer, scarf
Why: My friends came over for breakfast and mood lifting. And it was so perfect. Christian suggested we all stay in PJs. Solidarity!
OUTFIT PLANNING
This week: Comfort formulas. Flexible, comfortable combinations that always work. Dress them up and take them back down.
Next week: 1 formula, 5 ways. Take a go to basic combination right now — and try mixing it up a little differently all week.
Let’s get dressed. And if you like this post, I’d be grateful if you hit the heart so they show my work to more people.
XOXO,
Rachel
And if you want to ask me anything about this beauty treatment, join me n the paid subs where I’m answering friends in the DMs.
Notes:
I am using affiliate links. In fact here’s a whole post on it. And another. Thank you for using these links to shop. Every little bit helps!
Our Market editor Wendy and I are in limited, special, and really particular ways working with a select group of partners and accepting gifts in order to inform you better, especially around attainably priced brands and pieces. Here’s something on that.
We are also starting to get promo codes from brands, and here’s an updated list; be sure and check weekly before purchasing. I grew up shopping Filenes Basement. Your girl loves a discount:
TREATS
HAPPI: 25% off first purchase with code RACHEL25
CLOTHES
FRAME: 15% off with code HMS15
CALLAS MILANO : 15% off with code HMS15
HEIDI MERRICK: 10% off with code HEYMRSSOLOMON10
LEFT ON FRIDAY: 10% off with code HMS10
SANCTUARY: 15% off with code RS15
LUISAVIAROMA: 30% off full price items with this link and code LOVEX30 (excluding Adidas & Salomon)
ASHER: 15% off with code RACHEL15
SANI: 20% off with code HMS20
SHOES
NOMASEI: 15% off with code HMS15
BEEK: 10% off with code HMS10
SCAROSSO: 20% off with code HMS20
JEWELRY
ATPRESENT: 15% off with code HEYMRSSOLOMON15
KOZAKH: 20% off with code HMS20
ACCESSORIES
SARDINE: (sunglasses) 15% off with code HMS15
BEAUTY + WELLNESS
LAKE & SKYE: 15% off with code HMS15
URSA MAJOR: 20% off with code HEYMRSSOLOMON20
FRE SKINCARE: 45% off with code MRSSOLOMON
ST. ROSE: 20% off with code HMS20
UBEAUTY: 20% off your first purchase with code HMS20 through ShopMy link
WELLECO: 15% off with code HMS15













Love these looks and your advice of ‘struggle less, feel more’ 💖
Those CDG sweatpants!! 🤤