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.

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:

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.

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.

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

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.

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:

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.

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.

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.

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.

Alternatively:

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:

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.

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