4 styling tips to make getting dressed more fun this winter

One thing I remember about what made last winter kind of depressing is how easy it was to not get dressed. I would wake up, change out of my pajamas into the workout clothes slung over my bathtub, take my kids to school, and then because I’m anchored at home as opposed to an office or someplace else, many days, I wouldn’t change (or leave home) at all.

And by the end of the day, I’d have all this pent-up energy and wouldn’t know how to expend it so I’d usually drink a glass of wine in my crusty, stained leggings and then feel too lazy to shower or wash my face and the wine would keep me up longer than my body probably wanted to stay awake and the whole cycle would repeat itself the next day. I think it was the lingering after-effect of the lockdown, a sort of comedown from the year of Letting Myself Go.

I feel pretty committed to not letting that happen again this year or in other words, like the utility of that behavior is no longer useful but I can already feel how easy it is to slip back into a pattern of malaise — to let go and call it “being gentle with myself,” when really its just escape. One other intention I set for the year is to make meaningful limits, cut off the melancholy when its getting indulgent and I think I’m near rounding second base. Maybe this is because it been a pretty grey start to a new year, or (related!) a result of the general lethargy that often sets in when daylight is limited, but one easy commitment I always return to in the bland calm of too much alone time is the ritual of getting dressed.

This probably shocks the hell out of you because I never talk about getting dressed and in fact find fashion and style deeply superficial and hollow, yet here we are.

For the season, I’m thinking styling tricks more than actual garments and what I’ve come up with so far is:

Styling an anklet over your tights

Calzedonia grey tights, The Row derbies, Dorka S. necklace wrapped around ankle twice

I’m noticing this thing lately where I feel like I’m dressed too plainly if there’s no hardware/embellishment on the look — if I’m styled into an amalgam of “soft garments” (that is, no explicit buttons/snaps/shiny buckles). One easy way to counter this is with a belt. Another is by wearing a pair of shoes in an attention-seeking material (like satin or patent leather), or by wearing shoes that have hardware — something like this. These are really the platonic ideal of the moment but if you don’t have a pair like it, as I don’t, and don’t really wear heels (even if they’re block/kitten) during the day, affixing something to your ankle, in partic when it’s over your tights or socks achieves the same effect a buckle would. Go ham on your other appendages too.

Wolford turtleneck — I can’t believe how much use I’ve been getting of it this season. Would recommend investing in a white t-neck, here are a few at different price points. Venstore sweater (I like Everlane’s alpaca one too), Maria McManus skirt

Captured while walking home yesterday with a homemade anklet featuring extravagant charms

The key reason I like it — in particular with masculine shoes — is because it adds an unexpected feminine kick that can be very subtle depending on how you do it.

Wearing less conventional tights

Do you have Christmas tights? Now might be the time to show those motherfuckers who decides what is what.

That is — what is Christmas and what is real life. This, I tell you, is real life.

Maria McManus black and white striped shirt — here is a similar option, Courreges skirt, Calzedonia tights, Roger Vivier slingbacks

This style tip is also a great way to (1) eschew color in an outfit without actually eliminating it altogether (2) recontextualize any shoes (colorful or otherwise — maybe brown) you haven’t worn in a while.

Venstore sweater, Another Tomorrow skirt, Prada platforms I got on Yoox when I still lived on 1st and Bowery, which means at least 7 years ago

The reason it works is because the tights give the outfit a bit of an electric feel, emphasizing your ZEST for GETTING DREST without having to pull you too far out of your comfort zone because you’re still wearing all the clothes you usually do, just with different tights (you can wear them as socks too — will get to that, but first):

Is also a good way to make friends:

And here’s how easy it is with pants:

(I’m wearing a By Malene Birger top here and jeans from a brand that no longer exists called Blk Dmn. The shoes are old Gucci.)

Meanwhile, the other option:

I think this one works because the pearl buttons catch the white tights/shoes but a more plain navy blue blazer (or, idk, try black, try grey, try brown!) like this would work paired with a strand of pearls like these. The sweater’s from Uniqlo, the jean shorts and slingbacks are Khaite (if you’re looking for a kitten heel and have a bit of budget, I’d actually get a pair in black patent to produce the same or possibly a better effect with white tights) and per the tights, these are Calzedonia too (they had a very good sale going on last month).

White tights are feeling pretty fresh to me these days. This might be the extremely insular perspective of a woman who has spent every morning for the past 2 years getting her two young daughters dressed for school, but something still seems right about them. Not pictured here is how they look styled with patent leather slingbacks (per the caption) and a mini skirt or tapered black trousers (preferably velvet/corduroy/some fancy silkish taffeta), but I did do this too, which I loved:

Mansur Gavriel jacket (the shape on this one from Sandro looks nice, and this one from Max Mara is on sale) with Maryam Nassir Zadeh mens vest under, jeans from aforementioned 2015-heyday brand called Blk Dnm (these are the closest comp I could find, but you can also do a slit leg like these) and old Celine sandals (they can be found sometimes meandering about The Real Real; these from Emme Parsons could be good too)

Reminds me of a Gucci look from a Fall 2016 show that I loved:

The other thing I’ll say about tights, and why I keep recommending pants for under them is that they’re potentially more useful than socks because they can be both socks and tights. Will keep your legs warmer too, but your feet might suffer. On to tip 3:

Chunky socks with ballet flats

New Arrivals jacket (I think a sequined sweater could accomplish the same effect), Tibi jeans, Comme Si socks, Savette clutch

I originally saw this pairing approximated on Chloe from the Instagram account louloudesaison

and it set off a lightbulb that helped me reorient how I think about when to wear a more structured ballet flat. The Miu Miu/actual ballerina way (above) employs chunky knit socks to wear with the supple flats a la:

But there is something about a more structured flat, and what a pair of chunky socks adds to it — a solid combination of disheveled (c/o socks) and prim (perfectly symmetrical tights that look very put together with, say, straight-leg pants) to convey a rough edge.

And as you know from that disproportionately long story I once wrote about socks and shoes, when the bottom part of your look is produced so thoughtfully, its easy — even preferred! — to wear your most reliable/boring garments if it pleases you on top.

A durable boot matched with a fancy outfit

Bobkova suit, Shiloh Heritage boots

Like a black suit, for example. A pants look is my preference because the shoes are most likely going to be boots, and overall, they’re simply easier to style with pants, but this means that the top half of the look should evoke some sense of delicateness or preciousness.

Which is the primary reason I’m not wearing anything under the blazer, and why I added a strand of pearls (love this one from Sophie Buhai), a “tennis” necklace (not real — Daphine) and navy blue opals (very fancy! By Arielle Ratner), plus some gold chains that dangle up and down my wrist when I move (important because it calls attention to your bare limbs, which is unexpected in the cold when we are so covered up), and a couple of rings. The green jade ring is actually more of a nod to the boots — and per the boots:

I went with a pair of holy cow!boy boots, but your durable shoe can be any: hiking boots, snow boots, Uggs, not Uggs, a practical rubber sole that bleeds efficiency! There is also something about this mid-calf length on a flat boot that does something interesting to an outfit, either by its creating a seductive ballooning effect on the tapered trousers, or cutting off an assumption that could be made about what kind of look you’re going for — taking it to another, unexpected place. I really like these ones from Soeur too, and Toteme’s fur-lined creatures. If you have more budget, these from The Row are on sale.

And that concludes this episode of Life After Fall. If you are interested, btw, in reading an interview that Abie and I did for the Substack of an acquaintance we both admire, here it is — we mostly talk family values and writing for the internet.

Signing off yours,

Leandra