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Fashion

A Start On Holiday Dressing

Taylor Reed
Last updated: November 1, 2026 3:12 pm
Taylor Reed
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I hope you all had a magical halloween and are pleasantly reaping the benefits of daylight savings (JK, I know you have kids! LOL!) Welcome to your Sunday morning sweet relief. I hope you have a cup of coffee and a locked door for the next 15 minutes. 😂.

A big plan to bring you a big guide to holiday dressing this week was quickly derailed by some stacked life lemons but I figure, half thoughts are better than NO thoughts! Especially since you earned your quiet time this morning. So today, you’re getting a haphazard letter that includes the two outfits I was able to shoot this week, a collage of teensy bags that are a true one-item-solve and a few open tabs of the things I would want to wear to a party in the next six weeks once this full moon gets the heck out of here. Next week we will get back on track with a think piece on American Sportswear (capital A, capital S) and how it relates to solving the whole “work holiday party outfit” conundrum.

Until then, some quick hits from my brain on velvet (its everywhere), teensy fun bags (really all you need?), dresses over pants (all I want to wear!) and the few tabs I have open for my holiday plans.

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A delicate, ornate, make everything a little more decadent, decorated evening pouch

If you do nothing else, get yourself a fun little pouch and just put on all black and make your way out the door. I’m telling you, you will feel fancy and fab and it’s as easy as that.

From left: Anna Sui, Sac Decoratif, Dries van Noten, OneOf, LeSundial, Sophie Buhai (not pictured but 1st runner up for Susan Alexandra. It would be hard to have a bad time using/wearing/carrying anything from this holiday princess.)

A billowing velvet top

Maria McManus velvet blouse (more sizes here!) which I struggled to shoot in a way that shows you the lovely texture that it is. So you will just have to see for yourself. I love how it just drapes and is not too long if you choose not to tuck. (The sack is the Prada in purple. It’s an addiction at this point.)

I ordered this Maria McManus blouse in early September and it has been biding its time in my closet. So good with my slew of skirts but also so elegant with my dinner jeans and a belt and a heel. Good tucked or untucked (ok maybe slightly bulky tucked but its fine.) Maria got the memo that we need TOPS for evening.

But really there is velvet everywhere. You don’t even have to look! The Row’s velvet trim is to die. Aflalo’s velvet pants are perfect. There is bright velvet (I love this Ulla Johnson top! The color! The drape!). Black velvet. Crushed velvet. Silky velvet. You get it. I was planning to make you a bunch of outfits with these, but instead, just remember – one piece of velvet, simplify the rest. A pump, a fun bag. And be on your way.

All I want to do is wear a dress over pants (or a long skirt)

Or a tunic, or whatever! This Toteme leather shoulder padded top makes me so happy when I put it on. And so flattering with the skinny pants of the season. But also, I imagine I’ll wear it over a flowing skirt, too. This Cos one is high on my list. And look it has a matching dress to layer over and get THE LOOK!

Or combine ideas with our velvet obsession above and try this Khaite mini dress, which I am insanely into (I think I had an almost identical one from Monkey Wear during my bat mitzvah era?!?!?!?! Only way to explain the infatuation.) to wear with sheer tights or the same slim pants below!? Or what about this sheer Paloma Wool dress? Perfect for trousers since well…it needs something underneath.

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Toteme leather top thingy (I’m wearing a size 36 to fit it over my hips :)) and pants, also in a 36. An Attersee velvet pouch and the Row Liisa. Mine have an ankle strap but the pump version is back in both high and low heel heights for holiday. Sweet relief for women everywhere, the world’s most comfortable plain black pump!

Celine Fall 2026, now and forever on the mood board

Or a dress over a skirt to create a long, interesting line like the Row Winter 2026

Some holiday dressing musings

  • Same, same but TOTALLY different. Is this the best skirt over pants contraption I’ve seen? I think so! How fabulous with a little grey sweater and Birkenstock Bostons for daytime. Or A pump and blazer for evening? So cool.

  • I keep coming back to this longer knit, pretty much daily. Should we try it? How good with a long corded necklace over it. We could put it over a slip dress or with a wide cropped pant. And a long lanyard necklace hanging down the center line. Seems like a perfect “I’m fabulous, but just threw this on” kind of vibe, no? Not to mention, comfy.

  • These pants (mentioned briefly above) are feeling like a very 2026 way to do velvet on the bottom. Not too thick, slouchy in shape. Will be good with a black evening jacket, or even a flannel shirt and heels and some pearls? Fun! I’m kind of into the white but I realize I’m more of a masochist than many of you. A great solve for Thanksgiving dressing – always tricky for dressing up but comfy when dining at home. With a lightweight knit so you don’t sweat pulling the turkey out of the oven?

  • Should we each just get a decadent black column dress and call it a day? I mean! The Row. Cos. CO. Kallmeyer! Very cocktail to black tie ambiguous. My favorite style of dress. Huge bow in the hair. Drop pearl earring. Go!

  • I feel confident there is only one brand that could make me want to wear a tube top and that is High Sport. I know everyone is gaga over her pants but I find myself in a gravitational force field being pulled toward her thoughtful tops season after season. And I love this with slim black pants or even a high waisted, wide leg variety. Under a suit even? Or with the matching pants if you are going to a dance party in someone’s home. Yes Marisa M, I’ll probably wear this to yours!

Ok, those are all the half thoughts all I have for you today. See you back here next week. And sending all my energy to those of you running the marathon!!!!! Best NYC day of the year. We are with you!

Yours TRULY,

Becky

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