What to wear now, during the 5th season

18 outfit ideas for late spring, which is not summer, but is also not not summer

Spring has two seasons: the end of winter and the beginning of summer. In the end of winter portion of spring, the sweaters feel too heavy and dark, like they’re wrapped up too tightly in the turmoil of winter while you’re ready to begin what my friend Jenn has referred to as the process of unfolding.

In the beginning of summer portion of Spring, it is technically hot enough to indulge in the whims of your summer persona (e.g. villa owner from Como), but the practical qualities of your current circumstance — that is, the fact that you are still traversing cement sidewalks/shuttling kids to school as opposed to like, drinking grapefruit juice while overlooking the sea from a lush landscape — makes it harder to meet up with where you are mentally.

Not to mention the days range 20 degree-discrepancies. You wake up and it’s chilly, but by 1 p.m., you could conceivably be tanning topless on the back of a boat with a Jenner.

If you’re committed to finding a bridge though — one that facilitates dressing for your mood and for the practical requirements of your days (or at a minimum, if you just want some inspiration as far as what to wear in the in-between), l have a number of outfit ideas for you, starting with:

Exhibit A: Show skin, but maintain discretion.

Frank & Eileen shirt (the white buttons are key), Courreges skirt, Jamie Haller ballet flats (I like that they’re not structured, but if you prefer something more rigid, these from Mansur Gavriel are good)

In my experience, legs can handle cold better than an upper body can. So if you have to leave home early in the AM, know it’s going to get hot, and want to show skin, try a button-down shirt with a mini skirt or shorts. The choice in color (or lack thereof) is deliberate to the extent that in spite of the skin exposure, you can still fly under the radar if that is your wish.

And if you don’t wish? B:

A’Court top, Saks Potts skirt, Gabriela Hearst sandals (these are like the seasonal update from the same brand)

Hello! Welcome to my subway car. I wore this outfit 2x last week — it’s a good way to conceal a larger portion of your limbs while also being clear that you are present — as in here. Alternatively:

This is a dress I bought from Shereen Muhmmad who was selling her clothes on a rack next to mine at a sale that Magasin and Passerby hosted in April. The pants are Paul and Joe (love these), the sandals are Gabriela Hearst

You can layer a sweater (not pictured) over a get-up like the above, which will serve you well until the sun reaches peak point and you reach peak hot. Then you disrobe from the top, keeping your bottom concealed.

If it’s a weekend morning, C:

Polo Ralph Lauren shirt, Live the Process shorts, Toteme sandals

Every time I have seen a woman dressed in bike shorts and a button-down shirt lately, I have thought: that is an easy outfit that looks great. As of last week, I’ve adopted it as my own weekend uniform with the add of an elegant (but big enough for kid snacks) clutch and personality sunglasses (Delarge).

If you run cold and don’t feel like wearing sandals:

Leorosa cardigan, Raey denim shorts, Shiloh Heritage boots

I walked into a gallery in the neighborhood of St. Germain de Pres in Paris last week and the shopkeeper there was wearing long-line denim shorts with a crew neck sweater and cowboy boots. I’ve tried the combination before but something about how she carried it read more refined and mature than my prior youthful passes had registered, which is why the cardigan and the lack of jewelry — no need for fanfare with this kind of look. I also brushed my hair.

Exhibit E:

Ven store sweater, Prada shorts (how about these from Marni for $190?), La Double J wedges

What to wear for a night out. It’s warm enough by sunset to go sleeveless, and I don’t expect that you’ll necessarily want to wear knit jacquard underwear but use this as a reference for pairing prints — keep the top as simple as possible and then mix a pair of personality shoes with another, different-kind-of-personality bottom.

I’ll also say while we’re here that these shoes are very comfortable — think it’s the ankle strap that keeps me in but also, the heel’s not that high. The fact that they’re metallic also makes them way more seasonally versatile to the extent that they’re great summer shoes but might actually even be better as winter heels with a dress and thick knit socks or basic tights. Let’s go dancing with the stars!

If heels are not your thing and actually, overall, you’d rather keep it simpler, F:

Dries scarf thing and shorts, Khaite t-shirt, The Row sandals

Plain Jane Bermuda shorts (alternatively called “walking shorts”), a dependable white t-shirt (mine’s Khaite, I love it, it’s boxy and cropped. This one from Everlane is a good shape reference), flat sandals (or shoes) that keep the majority of your out in the foot open (good for the look of your overall legs), and one element of whimsy. It’s the choker scarf thing for me — I love this one from Damernes Magasin too.

And doh! The bag. Another classic, helpful fancy.

Alternative bag solution is from Loeffler Randall, $325 and this choker from Damernes Magasin costs the American equivalent of $35, in case there is any confusion

One more for a night out that features a dress styled as a skirt:

Bode top (seems to be sold out, have enjoyed looking at this one and, unrelated, this one lately) and a negligee thing I bought on The Outnet like 8 years ago (same vibe right this way, but you will need to hem!). The loafers are from The Row (also pretty old — you can find a bunch by searching “the row suede slippers” on TRR), and the socks are Wolford

The other great thing about Spring: you can push the limits of how you think about layering without having to factor in too many weather constraints. This look makes sense for exactly 4 weeks a year when it’s not too hot to wear socks and suede loafers with a beaded vest styled over your dress, nor is it too cold to be, basically, naked…but not.

I’m losing track of where I’m at in the alphabet museum, welcome to exhibit…G?:

LMND shirt, Emi Mess trousers, Rene Caovilla sandals

G! What to wear to work. A combination of classic Italian suiting of a more masculine ilk — a blue shirt and tailored charcoal grey trousers — and details you might find on the sciuri of the town.

The credits are right below this caption

With tiny gold hoops (Lucy Delius), a pair of giant gold chain bracelets (Paco Rabanne, Paola Sighinolfi), another delicate charm bracelet and a set of necklaces — one gold and one “diamond.”

My necklace is Jenna Blake, but I like the Laura Lombardi necklace pictured above ($95) for this combo. Next to it you’ll find a Dorsey lab-grown diamond necklace for $550

The shoes are a key component too. They catch the jewelry and tie the full look together. You can accomplish this vibe with a pair of classic gold or silver sandals — like these or these. But if suit pants are not your thing, maybe khakis can be? Welcome to Exhibit H:

Sessei top, The Row khakis (a great sample sale find) and mesh slippers; the sunglasses are from Blanca Miro’s brand, Delarge

Featuring a late spring, unsung hero of the ages in the form of a pair of red flat shoes! Mesh shoes seem to be all the rAgE right now, which I credit to The Row, who has been making these shoes that look like hosiery/aquatic shoes for the last like, 4 years. There’s a twinge of Pearl River Mart slipper about them too. It makes them all the more alluring.

The shirt I’m wearing is from a French brand called Sessei. It’s a good contender for this season’s best button-down — but more on that later.

I:

Skall Studios trench coat and Soeur sandals — I can’t remember the make of this skirt but here is a fun one and two, they’re all iterations of the one Prada made for Spring 2017; the bag is Dior

Here’s what you wear when you are going to be out all day and want to feel spectacular. You can sneak a pair of knee-cap leggings or shorts on under the skirt and go to a yoga class in the morning, then trot on with your day. To make the look more youthful, just:

Thanks again, Cereal Aisle member Chrissy Westerman for finding this original Bottega hutton clutch for me! The hat is from my friend Pia’s brand, Yali.

Add a hat and change your bag. Like don’t use your arm as a rest, use it as you would if you were a quarterback — clutching that ball for dear life.

J:

Soeur scarf and pants, Emi Mess vest, The Row mesh slippers

One concept I’ve been thinking about a lot is neighborhood assimilation — like the extent to which one might want to dress to be in harmony with their environment. A condition I definitely experience regularly to the extent that I value harmony.

The goal is to not lose sight of your own character while accommodating the character of the place where you find yourself. The above is an example of Upper East Side assimilation with its overall vibe of looking put-together, influenced by a few days in Italy (the vest/scarf combo is inspired by a Brunello Cucinelli vest I saw in a shop window while in Milan), with a healthy dose of ~me~ mixed in through the weird shoes and the combining of two masculine shapes on my woman.

The other key piece of it is weather. Here’s another look I wore last Wednesday, it was 54 degrees when I left home but by the time I got back, had climbed up to 75. Layers can be a key companion this time of year, so can be a long sleeve grey tee.

Jigsaw shirt, Khaite belt, Etro jeans and Delarge sunglasses

Another outfit I wore on Thursday:

Rodebjer sweater, Soeur pants, Havaianas flip flops

I’m into big, but straight pants right now. They pair well with loose hem/peplum style tops, creating the right ratio of a-line to straight line.

As far as weather conditions: This sweater in particular is good because it’s breathable and you don’t have to wear much underneath — maybe just a bra you can fashion into a top if you get really hot.

Back on jeans: if you do just want to wear regular jeans, which maybe you do, it’s actually easier to have a point of view in them this time of year. Exhibit K:

Flore Flore boat neck shirt, Giuliva Heritage pants, Marni sandals and here is a cool comp for belt

Why? Because you can wear them with sandals and very easily get away with no jacket. I chose a boatneck t-shirt with three-quarter length sleeves and a personality belt to pair with my jeans (Giuliva Heritage), and some great Marni sandals I bought from TRR last winter.

To this point, another great feature of the season is that if you have any garments that don’t make sense with coats but do look great with sweaters, it’s a nice time to let them shine.

High Sport polo, Rosie Assoulin pants, Marni sandals

Granted, this is not a sweater, but do you get the point? Here’s what I mean about a garment that makes no sense with a coat:

Ass bow! Now what are your thoughts on underwear as pants?

I actually do think you can get away with this one (using any white poplin boxers you have/like — they don’t have to be irreparably short) pretty seamlessly because of the contrasting materials — how the velvet counters on the jacket (La Veste) communicates with the cotton shorts, then the fisherman shoes tie them together by acting like a mediator. The bag (leather) is a reminder that you’re still in reality as opposed to the seaside.

And finally, the most tried and true, best-feeling-look I’ve come into this bridge season is the concluding look for this edition of What to Wear.

We end on the letter L. L for luscious, for lustrous, for lago and loquacious. L for the la dolce far niente and luxurious! For Leandra and, of c, for le very Last Look:

The key to getting the vest right is pairing it with something wider than it, be that trousers or an a-line skirt. Sometimes it really is as simple as two garments in two tones of the same color and a pair of fisherman shoes — Tory Burch skirt, Attersee vest (like this one from Co too), Grenson sandals

That concludes this edish. Have a great week!

Love, 👇🏻