The Best Personal Style Has Breathing Room

Why the best supporting actors deserve a little more credit.

Not every item in a singular outfit can be precious. And I don’t mean this negatively, but to let those ‘once in a lifetime’ purchases shine. It’s why I warn clients against mixing logoed shoes and bags. You can’t wear all of your special pieces at once, to put it bluntly. A great wardrobe has fantastic everyday items in addition to the flair. And a great OUTFIT layers these items seamlessly, giving you, in turn, a more distinct and personal personal style.

Today’s newsletter is a partnership with Madewell, a brand I’ve followed since their launch when I was a wee junior editor. I know I’m not alone is thinking this (since I’ve talked to a few of you about it) but it seems like they are just waking up from a bit of a nap. The fits are feeling right (we will get into this later), the colors on point and they are pleasantly leaving the ruffles to Loveshack Fancy.

Madewell, and brands like it, act as a very specific piece in the outfit puzzle (an important corner piece, without which putting the rest of it together becomes a challenge.) They offer the breathing room. Or the glue. I could keep going with metaphors, but when they do it well, these brands become the solid foundation pieces that make putting on your personal archive a doable morning task. Without the right t-shirt, the right button down, etc. that sequin pencil skirt will probably just sit in the back of your closet because it’s too hard to figure out the styling. This is what Madewell does and has been doing especially well of late (which is why I thought now a good time to partner.) And pleasantly for all of us, at a price that leaves enough left over to urgently click to buy when your dream Prada SS20 Jacket in an IT40 surfaces on Resee.

Below, five things that make all the other things work.

A Cherry Red Cardigan

So happy! Finally fall and can wear a cardigan again! Paired with a vintage Prada gingham circle skirt, gold Manolo ballerinas and a CDLP t-shirt.

I’m sure you’ve already noticed by now that bright red knits are inescapable this fall. I would like to think we had something to do with it…remember when I professed my love to them last December? :) But I digress. This cardigan is such a good red. No undertones of burgundy here! Just pure pop.

And on another note that we must discuss first, I tried on almost the entire fall Madewell collection to research this newsletter and throughout it all, the proportions leaned cool! I usually size up when when buying classics to achieve a more thrown on look, but I didn’t need to for any of the pieces we will talk about today. Nice work fit team! This is a size small.

Red + grey = yay! Layering a cardigan with a suit is always a fun way to add personal style to very traditional shapes. This would also be cute with sneaks, don’t you think? Maria McManus blazer and pants in a size 4. Madewell cardigan. CDLP T-shirt. Chanel Ballerinas. Which, if you’re in the market, great. If not, these are so comfy and lovely.

Red works well with wild patterns. Imagine this outfit with a grey cardigan. It would look like something you just threw on because you were cold. In red, it looks like an intentional part of the outfit. When really, it’s the same cardigan. See what red does!? Rentrayage dress (which is an amalgamation of two vintage dresses brilliantly upcycled by Erin Beatty if you haven’t heard of this before. I love it!) Hereu Mary Jane loafers.

It’s a scarf! It’s a belt! It’s a SUPER SWEATER!!! JK JK but how much fun is it with a simple outfit like denim on denim? Into this oversized Madewell shirt jacket too (great jean jacket alternative for all you fellow j.j. haters out there.) Which brings me to these slim black jeans, to be continued below...

Black Stovepipe Jeans

For a cocktail party! Or a luncheon when you don’t know the dress code and don’t know anyone else going well enough to text and ask. Vintage YSL jacket. Madewell jeans. Prada heeled loafers procured from TRR at the height of Covid when I wasn’t sure I would ever wear a heel again!

Denim trends come and denim comes go. The one jean I always have in my arsenal, is a black skinny. Sometimes you don’t want your jean to be a part of the fashion statement. Sometimes a black jean is just the blank canvas your day needs. The thing about black skinnies (or stovepipes, aka that delicate middle between legging and straight leg) is that they just kind of always look stylish. Blame French girl style. I don’t know why, they just work! They’re failsafe for a weeknight cocktail event where you want to wear your “fun jacket”, essential for a kid’s bday party where you need a little stretch to squat down to break up a fight over the last mixed berry juice box, and chic with a vintage-esque blouse - a uniform idea we talked about during workwear month. You just kind of need to have ‘em. Even if you are a die-hard rigid, indigo dyed, made in Japan denim snob. I say this lovingly…because I’m also kind of that. Wearing my standard size 26.

APC vintage-leaning blouse. Madewell Jeans. M.Gemi boots from last week. Dorsey riviere.

See what I mean, I can get all the way down to the ground (and back up!) in these. Lisa Yang sweater. Madewell jeans. Madewell socks (these are so good I almost made them one of the 5!) New Balance sneakers.

Old blazer from Italian brand The Gigi. Blazé makes an elegant alt. Caron Callahan crocheted lace top. Madewell jeans.

A T-shirt with Long (Short) Sleeves

Madewell t-shirt. Caron Callahan pants. Emme Parsons belt. Celine ballerinas (but you should get these.) 

Sometimes the shapes shift in fashion and you don’t realize it’s happening until all of a sudden you wake up and all of your t-shirt sleeves are too short! I kid, sort of. This summer, I found myself looking for t-shirts that hit almost at the elbow. I can’t even tell you when or how this craving hit. But I can tell you why it feels so right for right now. By the end of summer, when I’d been living in t-shirts for months, I started to feel lazy when pairing plain tees with shorts, skirts, khakis, etc. It just didn’t feel done enough. I was looking for something that felt like it had a little direction, something to make my outfit feel finished, without giving up the idea of just putting on a t-shirt and running out the door. The longer sleeve does this for me. It makes me feel totally dressed and makes all my other pieces look current, even when they’re old old old. Once again, I’m wearing a size small and it fits exactly how I want it too, no need to size up (OR DOWN!)

Also, we must mention the color. The washed black gives everything a bit of a laid back vibe. It blends brown and black well and makes everything else you wear look SHARP. Madewell t-shirt and necklace. Tod’s skirt. Grenson fishermans.

Not sure why I’m standing like a ballerina here, but it’s a perfect match for my chambray pleated Miu Miu midi which I just scored on TRR. See what I mean about fashion + not so basic basic? The balance is right. Madewell t-shirt. Grenson fishermans.

A Khaki Button Down

This outfit defies all dress codes, no? Cocktail. Office. Dinner.High Holiday services? (Happy new year to those celebrating!) Madewell button down. Kallmeyer silk pants. Mizuki pearl earrings. Sophie Buhai necklace. Manolo Blahnik ballerinas.

I’ve actually been searching high and low for the right khaki poplin button down ever since I posted this newsletter and everyone asked me about it (even though we were meant to be talking about the earrings, and mine was an old Tod’s mens shirt!) I love a big khaki shirt for so many reasons. Buttoned halfway and tucked reads so feminine to me. Unbuttoned, it’s a nice jacket for days when it’s 60 in the morning and 77 by the time you get home. This one is also thin enough that you could put it under a sweater in the coming months without much bulk even though it’s oversized. Once again, wearing a size small.

Go the glorified pajama twin-set direction. I can see myself in a Nancy Meyers movie now! Madewell shirt. Skall Studio pants. Worishofer shoes. And yes, I’m joyfully leaning into the wrinkles here.

Or as a shirt jacket. Madewell shirt. Kallmeyer t-shirt. Old Alaia skirt. The Row shoes.

Or with jeans and mary janes for everyday. Looks great sticking out of a leather jacket. This one makes me want to say “Huzzah 20 pounds for the king!” …yet I love her? by Malene Birger jacket. Madewell shirt. B Sides Jeans. The Row mary janes.

With your statement pants! Madewell shirt. Prada pants found on Yoox (thank you friend of 5 Things Lily S. for the tip!) M.Gemi boots.

Which brings me to our final item, the black dress below. I’m super into these paper doll style picture stories that have happened by accident the last two weeks. Maybe we should make this a thing?! Madewell cardigan, shirt, t-shirt, dress (which we will discuss next!). Birkenstock clogs.

A Micro-Pleated Slipdress

Great on its own! I’d like to bring this dress on vacation to Italy, eat all the pasta and still feel and look great. :) Probably could have just said it’s roomy. Madewell dress. Sophie Buhai necklace. Emme Parsons sandals. Here is the current version of them.

This comes in a skirt and a dress, but I intentionally went the dress route here because you can really wear this both ways. That said, the skirt is great, too. If you want to go that route, I won’t be offended. But sometimes, you (I) just don’t want something touching your waist. In relation to that, this would be an INCREDIBLE maternity dress for those of you out there who are pregnant or are considering. I honestly think this could take you to full term! For the rest of us, it’s just a fantastic LBD (long black dress :) ). The micro pleating almost acts as a lengthening tool, creating a linear look to your silhouette and at the same time doesn’t cling to your body the way a bias cut, silk slipdress would. The end result is very forgiving. Very flattering. Very no fuss. I am wearing a size 0. You don’t need to size up for stretch! I tried the 2 and it was big!!

See what I mean here about how it can also just be the skirt if you are more in a skirt mood? Layered with a Matteau long sleeve t-shirt (with a cinched hem making it great for creating a waistline over a dress). The Row Mary Janes. Loewe bag.

**Editors note*** In not the best news, the black is almost completely sold out online in a last minute, unexpected twist. This literally happened last night, without time for me to order, shoot and show you the dress in another color. The good news is, the three other colors (my favorite being the “teapot blue” which really appears more like a soft grey) are still fully stocked AND 40% off. So I’m going to offer you some additional ideas here, in words only, unfortunately:

• check your local store, maybe they still have some sizing!

• Thank you to reader and friend of 5 Things Anne Hjortshøj for finding the black version at Nordstrom. LINKED HERE.

• the mini version of this dress is also still available. You know I love a mini so would highly consider this. I would probably wear it in the following ways:

  • Alone, with sandals wrapped up the ankle (or sheer tights and pumps come November.)

  • Layered over jeans and under a blazer.

  • Layered over dressy leggings (without a blazer but maybe with a casual trench-esque jacket.)

  • IF you are pregnant (since I mentioned this would be an awesome maternity solution) these are hands down the best maternity leggings. IDK what they are made from. Genuine magic? But they’re really all you need.

• Consider an actual silver lining: the greyish blue version will pair so well with all of your black separates in a way that would read pretty flat with the black dress.

• I happen to have an extra black dress in a size 2 at my apartment and and will mail it to the first person who says they want it in the comments. :) So please make a note below and we will offline for your address.

Make it romantic! Cashmere in Love tie front cardigan. Madewell dress and necklace. Gigi Burris hair bow. Maryam Nassir Zadeh pumps.

And last but certainly not least, dress under silk shirt, belted at the waist. When I attempt this styling method, I like to leave the shirt mostly unbuttoned - just two or three buttons closest the waist. It makes everything fall a bit more elegantly. By using the dress instead of the skirt version of this, I don’t have to hunt down the right camisole, lest I bare it all when I sit or lean forward. Just to get really specific. Hashtag Old Celine heavy silk shirt (purchased three sizes too big to create this effect), but so many gems second hand. Madewell dress. Brunello Cucinelli men’s belt to finish it off.

Lots of outfits. Five wardrobe helpers that let it all sing! Until next week.

Yours TRULY,

Becky

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