What to wear right now? How about a pair of overalls

The ideal bridge all-in-one between two seasons, when you're checked out of summer but not quite yet at fall

I recently partnered with the travel app Amigo, which is like if Yelp and Instagram were one thing, and have mainly been using it to keep track of who sells what at my favorite grocery stores in and around NYC but I did also just update it with a list of some good beaches (for water sports, private hikes, plain old hanging out), restaurants, activities and places to shop in Ibiza. If you want to check it out, sign up here using the code LMCGO.

Would you believe me if I told you that I woke up one morning earlier this month, still in Spain where it exceeded 90 degrees (Fahrenheit) before 10am nearly every day, which made so few clothes necessary for my trip that I managed to fit myself into a carry-on for a 25-day sojourn, and I thought: I need a pair of dark wash overalls.

Call it divine prophecy, the kind of download you get first thing in the day with no context or reason, just enough conviction from the gut instinct that powers it.

And you bet your bottom tarot card that from my house in the middle of northern Ibiza, dressed in a yellow swimsuit and nothing else, I typed Carhartt into the search tab on SSENSE and lo and behold:

Carhartt blue nash overalls, $165

A dead ringer.

Though no rationale underpinned the yearn-towards, when I got home to New York and the overalls were here, it occurred to me that when you’re sick of not getting dressed but aren’t ready to get too dressed — when you haven’t put in much effort but don’t want to go full throttle Dries gold coat quite yet, when it’s been a while since you’ve last thought in an outfit, and you crave that pathway but don’t want to lose so much of the rest of what intrigues your neural interests just yet, overalls are a great bridge piece.

They’re like the connector between two bodies of waistline and a dependable, flexible, completely unresentful companion — or maybe more like a therapist, present to support you through whatever mood strikes.

5 way to wear them now as demonstrated below:

Wardrobe.nyc t-shirt, Carhartt overalls, Emme Parsons loafers, and a medley of handbags

The ingredients are straightforward: grey t-shirt, sleek loafers (not usually one for a pair without the classic penny cross strap, but the cut on these from Emme Parsons hits the top of the foot in a really good place for matters of making your ankles look good) and overalls. The red lipstick is optional, but it adds something festive and the real bang that gives it some character is the pair of bags layered over each other.

I really like this one from Savette too, or this, coming soon from Soeur. You could layer both with something like this. Some other good bag pairings include this and this, or this with this. Here, I’ll collage it for you:

You need not use this framework as anything but gleaning material for inspo to recreate with the contents of your closet

I doubled up the chain strap of the red bag (which is slight and dainty), halting its length, then looped it over the strap of the white and blue bag and let it hang down from behind. I like creating the contrast of different fabrics (in this instance canvas and leather, but could be leather and satin, suede and jacquard, etc) to add a new complication to the overall look, and as far as practical logic goes, mine is such that you can use the smaller one for things like your lipstick and phone, and the bigger one for, idk, snacks? Legal documents? A journal? The book you’re reading? Let’s go to the next look.

Yali hat, Tory Burch coat (looks like there is one left in a size 0, but this green satin one is alive, well, and 40% off), Falke socks (I’m going to get orange too; feels right with a navy pairing), Adidas/Wales Bonner sneakers

Here’s an errand runner that factors in dirty hair (baseball cap), comfortability (sneakers) and creative independence (gold coat). The trick of a STATEMENT PIECE like a gold leather coat is you want to wear it within contexts that make it feel like a given — so less like it’s a precious piece to wear only on special occasions when you want to stand out, more like the sun you bring with you when clouds are out and there is dry cleaning to retrieve, or whatever.

I feel down a Tory Burch rabbit hole just now and need also to share this sale top with you, this polo, this belt and this could be the jean jacket that makes getting a new one worth it.

A good choice for a day hang with kids too because 7 pockets. Next look:

Maryam Nassir Zadeh shoes (here they are in a shade of caramel), Damernes Magasin floral choker (keep in mind the prices are in danish krone — they amount to about $50 USD)

Here’s the baby you wear on girls’ night. Like when you wanna feel hot but also like you’re dressed for the ladies with a twinge of before these boobs breastfed my kids I used them for other things.

One more note on the rosette and its versatility: it comes with a pin and a clip hooked into the rosette so you can wear it on the lapel of a jacket or clip it into your hair

It’s less provocative from the front, you see.

You can achieve the same effect of the overall outfit with a flimsy white tank under the overalls, or just a bra (who makes your favorite bra? I’d like to start wearing one!).

The other dynamics to consider are (1) how high you raise the straps on your overalls. I like them high enough to meet me mid-chest, creating a square neckline not far from my collarbones, and (2) whether you’ll roll them up.

Because the shoes are pretty naked, I choose to show at least the top of my foot — that bone that protrudes from the middle of it, so I rolled up the overalls x2.

In the previous look, they were rolled up x3, so you could catch more of the red sock. As far as color pairing goes here (it’s a thing!): yellow and red (warm colors) to offset the denim’s coolness.

Next:

Pucci top (not sure why this one is a little less expensive; for something solid, I really like this), denim shirt from a collab I did with Closed in 2020, Christopher Esber shoes (these are the more structured version perhaps?)

Here’s one way to give yourself a waist in overalls: tie a shirt around the center of the one-piece and make sure to squeeze yourself in there tight.

Here you’ll notice the legs aren’t rolled up: the shoes are more like a film of crystals over my bare feet (Christopher Esber’s box office hit of the summer!) and that calls for a baggier leg that can puddle slightly and instead of going the traditional route of cotton tee or button down for under the over(alls), I chose a slinky silk printed top with a simple neckline to keep it direct. Another great option is this seafoam pal from Vince.

Now here’s my favorite one of the bunch, I saved it for last:

1990s Chanel jacket, an auspicious purchase I made when I was pregnant with Madeline and Laura in 2018 from TRR (this set is not exactly the same but it is vaguely similar); Soeur white button-down shirt (more crisp and refined than the classic LMND — and while we’re here, I found your ideal bridge pants too), Wolford knee high schools (Hue’s are a reliable and less expensive option too), Emme Parsons Leandra t-straps.

Black tie overalls! Crisp white shirt styled under the overalls, with a black collarless jacket layered over, then sheer socks that play a central role on account of the steep double cuffs (I’ve been craving capris, they are inching back! But the shoppable evidence is still paltry so until then: this is a good DIY for straight-to-wide leg pants) paired with the patent leather LEANDRAS. I do have a wedding coming up in October, it’s black tie, do you think this worx?

Brought the socks down a bit so you can see the break up between the leg cuff and the socks and changed into these suede ballet flats from Doen

One more iteration with black suede flats too. I let the socks down a bit so you could see they’re not tights — think the vibe here is still cool and girly in that Chanel way but possibly one degree less playful than with the patent leather witch shoes. Could you wear this to a business meeting?

A few things to consider about the overalls, overall:

1. Color. Dark denim reads more formal than light wash varietals, and this works in your favor if you’re after a polished look (but comfort feeeeeel) in your overalls.

2. Sizing. I bought them a size bigger, anticipating they would fit a bit roomier which would make them a good foil to sweaters later down the line, but also give them that throw-on-over-clothes workwear effect.

3. Shoulder straps. I adjusted the shoulder straps to get as small as possible to raise the neckline up as high as I could on my chest without suffocating my arms. This made the length of the overalls a bit shorter (preferred), and also made them easier to style without any top under (boob).

4. Leg cuffs. You can really play around with how you cuff the bottoms — one time thick, one time thin, two times, three times…I’m 5’6 and a half (never omit the half!) and triple cuff them if I want to expose sufficient ankle (like in the event I’m wearing socks that I want to show, or a long/boxy/big coat that makes me want to break up all the fabric present with the unveiling of a real life limb.

   

   A real life limb covered in sock. You adjust your cuffs as you see fit — when I’m triple rolling I usually make the cuffs pretty short and keep them deliberately messy. Rest of the look is:

   

   This Skall Studios trench coat (this is a slightly longer version but forget that, see this), and a black button-down from Ines. After all that hoopla last Friday about exposed white buttons, I got the wrong shirt!

   I double cuff them to hit right at the bone on the top of my foot, which is good with open-foot shoes like the wedges above, or flip flops or any such sandals.

   This cuffing works well with loafers too. The pants length remains long enough to make your legs look tall, but short enough to be comfortable while you’re walking.

5. Styling. Another creative way to cinch the waist that doesn’t include a shirt (or a belt, which could look right but I have to think about how) is with a silk scarf tied like a sarong around the waist.

   

   This, too, was inspired by my friend Laura. The loafers I’m wearing are Jamie Haller and the shirt under the overalls is more like a vest, from a Shanghai-based brand called Märchen. (This dress must be really fun to play with too.)

   1. Single-breast jackets look most crisp over because they maintain the least fabric

      

      Jacket’s Bouguessa, shirt is Flore Flore and the shoes are Toteme from last yr (there’s a size 37, 40 or 41 on sale for $252 here or a 35, 36 or 37 here for $409.)

      but a swing shape could be cool too. You can get creative here because the overalls are so basic, so casual, even though they’re FANCY DENIM. Something like this or this or dare I once again show this.

   2. Simple crew necklines are my choice under layer — they’re the easiest to style around by adding a jacket or necklace or scarf or whatever. They don’t fuss or get in the way of the overall picture. Cotton works fine but fancy fabrics are an unexpected surprise.

   3. The best thing about a pair of overalls has got to be that you have free rein as far as shoes. I could see them working with boots, with sandals, flats or heels — the only thing I’d caution against is going too high with the heel (example) if you’re wearing a stiletto (if it’s a platform or wedge, by all means!), especially if you’re sizing up in the overalls. Sometimes the interaction between such skinny high heels and big pants creates an imbalance that’s hard to even out.

      I have plenty more thoughts on how the leg should interact with the shoe, but maybe it’s better for me to wait for any questions you have than to start laying out the hypothetical, so…

That’s it for today. Signing off yours,

Leandra