I’ve probably had some version of a Chelsea boot in my wardrobe since I was 17 years old, and I’m not sure I can say that about anything else, except obviously jeans. As a teenager, I liked them because they felt British and rock and roll to me (if Elvis Costello didn’t wear them, then I imagined he did) and in my hipster 20s I duly wore the clunky Doc Martens versions to a thousand indie rock shows. But after that I began to understand Chelsea boots as classics, and went for iterations that felt more refined. Now I have it both ways: my clunky Blundstones for days when I’m going to be walking all over creation, and my more grown-up Church’s brogue boots for when I’m looking to come off more polished. The appeal never really subsides. They’re a little tomboyish, just the teensiest bit edgy. And comfortable, always. This particular pair is shearling-lined, which just sounds like heaven.
A stacked heel gives this one a feminine feel.
Oh, I am just nuts for the grey suede and old school crepe sole here.
Your beloved Doc Martens, but slightly de-clunkified.
I’m a big fan of the brogue detailing on this splurgetastic pair.
Your handy under $100 option.
And I like this pointy option, with its substantial Cuban heel.
The wood-grain sole on this one makes a kind of cool statement.
Let’s start with the one I am dying for the absolute hardest: this suede and leather beauty, from Jane Mayle, who has resurrected her beloved-by-many clothing and accessories line from the 90s/early 00’s.
This is just Madewell’s simple Transport Tote, but in the best blue.
I find the black-on-black stripes here to be quite elegant.
OK, in addition to the Mayle bag I am also very much dying for this splurgetastic Jerome Dreyfuss option, with the excellent chain detail.
I love the elongated shape of Baggu’s Basic Tote.
The genius of this one is that you can adjust the handle depending on whether you want to carry it or wear it on your shoulder.
This one from APC is not the most convenient option—it has only the one set of straps, with no shoulder option—but it is so damned elegant I could die.
I am including this navy floral by Sea even though it is already sold out in some sizes because it is just SO lovely—I am always pleased when designers keep the shape of a floral dress clean and simple instead of getting all floofy with it. UPDATE: I’ve put in a new link to Nordstrom, where the dress is available in all sizes.
The styling here is rather austere, what with the buttoned-to-the-collar business, but I feel like this dress—which is by DKNY, where a new design team has been installed—would become a serious everyday favorite. And I love the low-slung waist.
The dark-on-dark stripes on this flatteringly-cut shirtdress are a nice touch.
That gathered detail at the waist and the bold windowpane check are what I’m liking here. Also, you’d definitely need to wear it with the sleeves scrunched up.
Your zero-effort-looks-like-a-million-bucks option.
Another flattering take on the shirtdress, and a nice, subtle plaid for those of us who are intrigued by plaid but maybe a little scared of it too.
A good black silk blouse is an excellent lazy girl’s styling tool: it says I made an effort even on days when you totally didn’t, and always looks together and elegant. It’s also very adaptable in a dress-it-up-dress-it-down kind of a way: it makes jeans less casual, and strikes the exactly right note with a pencil skirt or skinny pants for work. First up: I own a cotton version of this Nili Lotan tuxedo blouse, but in silk it’s like another piece entirely—so sophisticated and sharp.
There is something rather understatedly sexy about a black silk button-down.
I love the kimono sleeves and overall slouchiness of this option.
This top has a nice soft, feminine feel but at the same time a quite clean silhouette.
A silk tee always looks so cool, and I like that this one has blouse-like cuffs.
Is it bad to want to buy this blazer just for the lining?
In the spirit of me being in no way ready for crisp white shirt season to be over, I bought this excellent specimen from Everlane. Perfect half-tucked into army pants for a slouchy-all-around effect.
Reader, I splurged big-time on this army jacket from Nili Lotan, and I’m justifying it to myself on the grounds that most army jackets, no matter what their pedigree, skew sloppy. They hang unflatteringly, add heft. But the fit here is absolutely fantastic—more like a blazer than anything—and I’m pretty sure it’ll make anything I throw it on with look more polished and together. That’s what I’m telling myself.
A reader—I wish I remembered who—sent me the link to this simple, devastatingly chic little sphere necklace, which I think looks way more fancy than it is. And it’s from Madewell, where they do a good job making cheap jewelry that feels sturdy, not dinky.