A dose of whimsy could make a plain outfit better

Crowns, hats, necklaces, belts: the flashlight amid your dark neutrals

The easiest way to add character to an outfit is by incorporating an accessory that disrupts the flow of the rest of the look. This disruption is a good thing, it creates new compounds that are often forged by the coming together of different elements.

When dealing with cool-weather clothes in fabrics like wool, flannel, corduroy, heavy denim, or leather, the opposing elements that work best can often be classified as accents of whimsy. This whimsy is like the dose of levity that technically uplifts the fabrics’ heaviness — and psychically, too, infuses it with a sense of humor, or at least one reason smile in a day that might boast none.

The best way to nail the proportions of heavy to light is to focus on building straightforward outfits around whimsical accessories — hats, jewelry, crowns (!) you name it. Some examples of what I mean are below.

The hat

Pardo Hats hat, By Malene Birger jacket, here is a great solid crew neck (my opinion is biased because it’s from a collab), Dice Kayek denim shorts (these seem like cool ones to play with), The Row lug sole boots (also here in green. If you’re a 7, get these…there’s a lot of good stuff here)

You can try to establish your ratio of plain to whimsy in one of two ways — by starting with the accent of whimsy or topping the look with it. In the above instance, I started with the whimsy and worked my way down with a fluted Barbour-style jacket, plain cashmere crew neck sweater (and the sliver of white peeking out of my collar is intentional), and simple denim shorts (the boots were chosen to balance the shorts and serve as a tie-in to the English countryside vibe of the jacket).

An example of outfit-first, accent second:

Jenny Walton hat, Veronica de Piante jacket, Max Mara pants (really like the khaki too, and uh, what are your thoughts on Spanx?), sheer socks and Gabriela Hearst sandals (here at $210 for the 7.5 among us)

I put this one on last week to meet someone for lunch (have been reaching for black way more often lately) and felt like I both needed something to break up the monochrome and also correlate to the wood-sole sandals. Jenny Walton’s woven raffia hat delivered.

The necklace

Marisa Klass necklace, St. Agni white t-neck, &Daughter sweater, Dice Kayek skirt (another one here with a bow accent, and this is more performance and here’s !Khaite!, then this vegan leather looks good), The Row boots — thoughts on these?

This whimsy accent is similar to the raffia hat in the photo above it because it’s a delicate shell necklace (summer materials) styled over an outfit (t-neck, sweater, mini, boots) for the winter. That necessarily injects into it some playfulness, but the other element to pay attention to is the length of the necklace. We’ve mostly been wearing collarbone-length strands of stones or straight-up chains but we are no doubt entering a new curve in the jewelry trend cycle where the necklaces will graze our navels again.

This is a great knit to counter a delicate necklace because the weave is cotton/wool blend as opposed to just wool.

Before we move on, here’s a collage of long necklaces scraped from around the web.

From left: Loewe gold balloon necklace ($1350, comes in silver and red too), black cord and pearl combo strand ($29.50 from Etsy), Jennifer Behr multi-size pearl strand ($525), Aligheri fish pendant on red threat ($162), Mixed glass, multi-shape beads ($200 from Etsy), Sophie Buhai shoelace string ($395)

The rosette

Damernes Magasin rosette, Dice Kayek jacket (this from Toteme as an alt is brown, but how about it?) and shorts (another alt, also brown, here), Stefania Vaidani shirt, Falke socks, Bally boat shoes (best comp for now)

Not sure how many notes one needs more on the red rosette I have basically turned into an outfit tattoo by now but the one thing I’ll mention is that there’s something about how it interacts with the combination of this “mid-wash” shade of grey and blue shirt. They both bring to mind renderings of such a corporate outfit while the rosette carries a big corsage energy. Think prom or black tie party lapel pin. The balance just, idk, makes me laugh.

A closer look at the interior shirt, which is decorated by crystal stripes — she’s cute too.

The sock-shoe combo

Vintage leather coat, Loulou Studios sweater (this isn’t the actual one, I can’t find it, but here is a good comp from J. Crew too, Veronica de Piante skirt (also good), Swedish Stockings tights, Manolo Blahnik flats

Implicit in all of this, apparently, is the fact that there’s never been a better time to get a good white crew-neck. It turns out they soften the blow of any winter outfit that features a knit crew or button down overlayer, in particular when you’re dressed in monochrome. But this is about the acid-gold flats that provide a burst of surprise and, depending on the style of the shoe, some femininity too.

Alternatively:

LMND button-down shirt (in toffee), Vince skirt (here is the plain leather version…I like this knit skirt from Lisa Yang as an alt), Swedish Stockings socks, Arteana shoes (unrelated, but related)

You can try a knit sock with a satin sandal. The trick, if you’re doing this with a backless shoe, is to make sure the sock is thick/rigid enough that it creates a sort of friction against the sole of your shoe and that your sandal’s heel is low enough that you have good balance while in them. I’ve realized that the socks slide less when you can walk more easily.

Camp socks like this could work too, against a shoe that’s more like this. I have my eye on these right now which seem like they’d be great with grey socks or stockings too

One more add on the topic of socks and shoes because we went hard and deep with red tights last season and they are still totally relevant in this micro-era of red accents, so if your inclination is to use them as your accent of whimsy, you are right on the nose.

& Daughter polo sweater (for reference, I’m wearing a size small), Amotea brown shorts, Beaufille belt, Swedish Stockings “sharp” red tights, Bottega Veneta purple wedges

My only added comment would be: do you have colored shoes? Green, blue, yellow, purple. Could be one quirky way to play around an outfit of otherwise neutrals.

The bag

Bally jacket (maybe this is the closest alt? But if it’s a different jkt, I’d rather recommend a shape like this) and boat shoes, Bode t-shirt, Doen shorts (similar here from Etro or here from a brand called Amen), these are the same Swedish Stockings tights

A dose of whimsy in the form of a fabric bag — color can really be any to the extent that it defends on your outfit. Here I’m wearing a rigid leather blazer with velvet shorts, sheer tights, leather boat shoes and a cheeky t-shirt that correlates nicely back to the bag, but the real elements it is playing with are the jacket and shorts, the bread bookends of the look.

While the bag is sold out, I have high hopes for the future of this slimy, charmeuse-ish green, so here is a selection of 1, 2, 3 alternatives sourced based on the merit of their hue.

Alternatively:

Tory Burch coat, The Garment dress, Prada heels (alt), The Row two-in-one satin pouch

A more mature interpretation of the above look, something you could wear under more formal or serious circumstances that won’t undermine your sense of creative freedom. It employs the same shade of green for bag, which reflects nicely off the coat. Lately, I have also liked playing with differing hem-lengths across coat and skirt/dress, reversing the order of which one should be longer in the skirts and dresses’ favor. Adding a solo shot of this dress so you can see it, rosette and all:

The rosette is part of the dress, and when I wear it solo I like it with wide-shaft boots like these or these. (Or these, which are the ones I’m wearing, by Toteme.)

The unlikely belt, or peplum (or straight-up skirt) over your pants

The Garment jacket, Bally t-shirt (this is a good color ref), Chanel necklace (I’m telling you, though, I’m feeling these), Lisa Yang knit top which I’m wearing as a skirt styled over Maria McManus pants, which seem to be entirely sold out but here are these on final sale from The Row for $323 and these from Toteme and then…hi.

There are several ways you can interpret this call-to-action to wear a mutable belt — you can go the way of an actually festive belt (with one like this from Sable for example), or you can fashion an a-line micro mini skirt into a peplum belt as I’ve done in the past with a crochet mini, or you can take a proper skirt, maybe one that exudes a lot of personality a la this and lift it over your pants (this technique works especially well with jacquard pants or jeans). The key is to make sure the over piece doesn’t actually feel so much like a skirt over your pants as it does a styling technique to redefine your pants.

Per my last point up there, the knit top-as-skirt works over the wool pants because the two fabrics are not strangers — we wear knit uppers with wool pants all the time. To reimagine that upper as a skirt gives the pants a new device to play with that is still familiar.

And the last but most important whimsy is: The crown

Bode crown; this one is darling too, Bobkova black suit (here is another good jacket), The Row tennis shoes (I like the rusty sole, but they are great in this neutral too)

The piece that ignited the creation of this send was Bode’s bullion starlet crown, inspired by a conversation I had earlier this month with Jalil Johnson. When I asked him what he was excited to wear this fall he said a tiara and when he did, it was like particles were settling into their right place in my mind: Ah yes, that’s the right element to offset the heaviness (knitwear and trousers) and the seriousness (plain neutrals), to add enough levity that it might even incline you to let open your heart for one small moment.

I love making this newsletter. Thank you again so much for being here. I’m signing off yours,

Leandra