What if you flipped the switch?

If you're a masc dresser, try femme stuff. If you're a femme dresser, play in trad masc territory. Shake it up; it's only clothes.

[Just a note: paid subs, please scroll ALL the way down for a video walk though of Tibi Fundamentals — and shoe sleuthing. Also, if you haven’t already, be sure and peek at our paid sub chat where I also tried out Victoria Beckham jeans + tee to see if they’re really “all that” — ]

So if you’ve been here a minute you know my dad is my biggest style muse, and I’ve long been drawn to clothes traditional given the “masc” label. (We all know anyone gets to wear whatever and nothing you wear makes your more of a man, woman or person, obvs. Masc/femme for purposes of discussion.)

This started with a reader observing that when I theme a week around a muse, the muses are always male! Ok not always, there was Mrs. Prada. But mostly. And when I started thinking about a week as a woman, I have to admit, it made me uncomfortable. A good reason to try it.

Look, it’s really easy to get in a rut. Like I ADORE big huge pants. And big men’s t-shirts. Great. But I want to keep mixing it up and trying even things that scare me a little, maybe even because they scare me a little. I want choices and above all I don’t want to get stuck. More than anything, I don’t want to get stuck.

… ok, the Takeaways this week:

1. Lots of pastel > a little pastel. Pastels are one of those things that feel “girlie” to me, someone who leans more into traditionally masc pieces. But when I layer multiple pastels together, it feels more fun, playful, ironic, at ease to me. It works in other areas too. If you feel too prep, try adding MORE prep, which can end up feeling like a wink at prep.

2. If you’re trying new colors, seek out familiar shapes, and vice versa. When experimenting with newness, it really helps to It helps to keep something in the picture that’s familiar so you don’t feel so untethered. When wearing “pretty” colors, and lingerie details I still brought ins oem of the heritage items that make me feel like me, a button-up, a crew neck sweater.

3. When you’re considering getting rid of something, wear it until you know for sure. I almost got rid of my Miu Miu skirt; wearing it a couple weeks in a row made me have second thoughts, and I’ll keep going until I have real clarity.

4. If your outfit is feeling too “lady” for you (which also night feel like - too precious, too pretty, too little girlie), try these: a menswear style belt, keeping it all to dark colors, adding leather and or hardware, a sweatshirt or a bomber jacket.

5. Love your “basics”: A reminder, because I know I’ve said it before. But nothing in your closet should be a throw away. That’s what lets you experiment like this and still feel like you; because so much “you” has gone into your individual pieces. Even my navy t-shirt is particular.

MONDAY

working, The Package Room

• Tibi Gabe shirt - Pink and perfect. Classic on sale.

• Tibi lavender cotton sweater (past season; Tibi’s update is on sale and there are a range of sizes left! - J.Crew adapted their rollneck in a summer version that I think works well in this kind of role too)

• Aflalo lingerie shorts (past season - this is close and beautiful). I mean, the exciting thing is those teeny lingerie shorts the young turks have been wearing have now been elongated for the dimpled and dappled (aka human) among us. (take your true size. I tried sizing up thinking they might run small and it was way too much.)

• Miu Miu ballet flats — As $$$ as they are, I’ve had these forever and they continue to be useful. If you are a Black or Brown person, I think the brown silk are the better investment. I think what’s useful is that the pinky color is relatively close to my skin tone. M.Gemi’s Una (it’s been a huge success for them and they recently did a slingback version) is beautiful and holds up to endless steps.

• Celine smile bag — I love this pouch version, which is a lot less. And how about this - different, stunning, on sale.

Lofted Settledness? Yes.

TUESDAY

working at home all day, writing, shooting, organizing, etc. Put this on after my workout + never changed.

• Tibi lightweight Winslows

• Loewe script tee, old - here’s the current one … and this sale one makes me smile… but maybe this is what you stand for? (I do) … for $39 this one (in black too) is likely coming to my house soon. Friends of Bill may prefer this iconic Big moment.

• crazy long toe Mellitta Baumesiter flip flops (on sale in a few sizes), but the idea is just a flip flop that’s cool and unexpected. Like this for under $50.

Lofted Settledness? Yes.

WEDNESDAY

hair appt, working, lunch with friends, research in Bal Harbor

• Tibi crinkle slip skirt (past season … pre-order this one! the color goes with everything - easier than black; you’ll be surprised)

• men’s Canali t-shirt but this is perfect; I alternate

• croc belt from dad, like so

• Phoebe Philo flower - we all know this is right up Etsy’s alley

• secondhand (old) Marni multi-pocket tote … one left of this Sacai men’s! Very cute + great price; don’t know the brand. Ok not super related but Paul Smith bags are the best under-the-radar value.

Lofted Settledness? Yes.

THURSDAY

working, met Kelly Klein for matcha, doctor’s appt

• past season Miu Miu skirt (same shape … and want to see the current version?) … the most reasonable good alt is Marimekko! Ofc!

• Miu Miu sleeveless bomber worn as a top… great deal; get your dry cleaner to cut the sleeves, but not at the seam, keep overhang.

• secondhand Marni multipocket bag (as above) - but OMG just noticed the Tory Burch version I fell in love with IRL is on sale now…

• past season Tibi Wilder flat (size 7, here). Cute alt, on sale too. Also, this!

Lofted Settledness? Yes.

FRIDAY

• Rachel Comey Billie distressed short sleeve sweatshirt

• Old Prada skirt I bought new in 2019 (size 36, leather version in XS, size 6 - where are the sizes grrr … but we could do this. And more dramatically, this.

• Past season Margiela flip flops - size 37, 38. Then there’s this MM6 anatomic one. Here too. (More images + sizes.)

• Secondhand Chanel necklace, the thing is it’s LONG. Really long. This Chanel is five feet when not doubled. Mine is around six.

Lofted Settledness? Yes.

SATURDAY

brunch w/my hub - forgot to get a still; these are from my reel

• Past season Marc Jacobs “the” tee (also the newer JOY. ed here and here)

• Torisheju partial skirt

• Secondhand Rick Owen x Champion athletic shorts

• Margiela tabi mary janes … I think if you want a Mary Jane with some modern oomph, La Monde Beryl is a good brand, especially on sale … like here + here. Oh and these are fantastic; their shoes are good + comfortable.

• Secondhand vintage Hermes Constance (the patina on THIS)

Lofted Settledness? Yes.

SUNDAY

brunching and reading Substacks, running an errand in the Design District

• Loewe floral dress (sale here in a different print) good floral I like, like this brand for dresses

• Past season Tibi raffia flat (as above)

• Past season Tibi transparent “tee” they do all sorts of versions like this and this - new to sale! But if we want an alt, this would do it.

Lofted Settledness? Yes. I liked the layering of the sparkle tee and it allowed me to keep my arms covered in the sun.

OUTFIT PLANNING

INCYMI watch the most recent here:

This week: Domino Dressing. Each day, start with one item you wore the day before. (Alt approach if you like, only change one piece! Kind of a “reverse domino”)

Next week: Simplify. How pared down can you get and still feel like you? What happens when you rely less on additions and color clashes? Let’s find out.

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, here’s a walk through of Tibi Fundamentals (about to drop as I write), with a special look at THE SHOES. And… who among us has STILL been fixated on this moment of Victoria Beckham in her Netflix doc?

Miami got a VB popup, and I got the goods … see a “real person” try-on in our paid sub group chat now!