Last week’s post on dating led to a couple of requests for me to tell you what I wear when I go out, and while I don’t think I’ve even begun to get it down to a science, I’m more than happy to share. I subscribe to the philosophy that you should go for a look that is just slightly sexy on a date: I should probably go with tighter clothes, but I almost always wind up wearing a loose top and tighter pants, because that is what I own (I almost never wear dresses, at least on first dates, for no particular reason). On a recent first date that went very well, I wore a white, collarless cotton Isabel Marant button-down, half-tucked, of course. Nothing makes me feel more sexy and confident than a white button-down. This tuxedo shirt from Nili Lotan is a nice stand-in for the Marant—or on the less pricey end of the spectrum, this button-down from Everlane.

I paired the button-down with leather jeans, which can be a little too little forward for a first date if you’re wearing them with a risque top; the shirt subdues them, makes them come off as the (very sexy) classics that they are.

I had two dates over the long weekend, and on one of them, I wore this Ulla Johnson top.

I paired them with slightly cropped black jeans. The date went horribly—truly one for the books—but I looked all right.

It’s too cool outside in the evenings to go out without a jacket right now, but I hate when I carefully assemble a look and then my outerwear shlumpifies it. This Iro jacket, which I just acquired at the Net a Porter sale, keeps things snappy. I wore it on the date with the grey top and the black jeans.

On the second date of the weekend, I decided to go more casual,wore this Everlane button-down.

And these R13 grey jeans. That date was kind of fun.

This may look like a clunker of a shoe, but I promise that on it is really quite alluring—even my brother who hates my taste in footwear approved. They dress up jeans nicely.

I bought these heels recently to wear to my mom’s upcoming 80th birthday party, but find that they’re working well for when I’m feeling like dressing things up a little on dates, too. I never thought pumps could be sexy until I tried these on. It’s the ties that do it. Also, they are surprisingly walkable given the height of the heel.

I try to carry a smaller bag on dates; my everyday bag just feels too clunky and workaday. This one fits all the essentials and is pretty cute.

The only time I put on anything with a really high heel anymore is when I go on dates. The rest of the time, I crave comfort, and I know you do too, because this is a frequently-requested post. Lucky for us all, low heels are kind of a thing at the moment, and there are many quite suitable options to choose from. Maryam Nasser Zadeh makes tons of splurgy pairs, and I am especially enchanted by this red number.

Platforms aren’t technically low heels, but I’ve included a couple anyway because of their supreme walkability: this pair is pretty classic in a 70s way that I like.

A grey pump is a nice departure from black and a stylish touch this time of year.

And here’s another great pump, currently waitlisted at Everlane, but worth waiting for, to my mind.

Just a very simple, versatile mule.

This could not be much more adorable and is dirt cheap.

I love Kork-ease: there is no more comfortable platform—or if there is, I haven’t found it—and this pair is neutral enough to go with just about anything.

This strikes me as a good, solid work shoe.

A pointy toe pump in a really fun hue.

This silver sandal is appealingly retroish without looking costume-y.

A good one for kicking around on summer weekends.

This dress is a little tricky, but not intimidatingly so, and the lines are really sophisticated.

I am actually really tempted to go to Maje on Prince Street this afternoon to try this  floral  midi dress on, because they’ve got it in the window and it’s been tempting me for days.

A pleasingly simple shirtdress with a nice, subtle print.

Sexy, but also really easy-looking.

I think the ruching business at the shoulder is quite cool.

Lacing like this almost always looks cheesy to me for some reason, but here, I really like it.

I can’t resist a star print.