Lindsay Weiss on What to Wear When You Don’t Know What to Wear

As a former fashion and accessories editor, Lindsay Weiss knows a good buy when she sees it. Now a content creator and Upper East Side mom of two, she’s taken to sharing those buys over on Instagram, where she posts her latest pickups—a beaded Dries clutch, our new Dual-Tie cardigan, a buttery-looking leather bomber from Khaite, to name a few—almost daily. (Needless to say, she’s a fun follow.)

It might not seem like it, but even Weiss struggles with getting dressed sometimes. We asked her how she deals in those moments, and much more, below.

A Conversation with Lindsay Weiss

Do you build outfits around a single piece, a mood, or an occasion?

It usually starts with a certain piece I want to wear. I always tell people that if you choose a focal point and build the outfit from there, it becomes so much easier to get dressed. Mood and location are definitely factors, but I do tend to overdress in general. My husband is always saying that it never looks like we’re going to the same place because we’ll be down the shore where it’s super casual, but I don't want to wear flip-flops to dinner—I want to put on a nice heeled sandal and my Valentino bag because that’s what I have, and that’s what I like to wear.

When was the last time you felt sartorially stuck?

Being in between seasons, like we are right now, is the hardest for me. I’m so sick of summer clothes at this point, but fall is just beginning. I’m so ready for it, you know?

What is one existing piece in your wardrobe that you can’t wait to wear this fall?

I have this long, chocolate-brown suede coat from The Row that I bought at the very end of the season last year and didn’t get to wear enough, so I’m excited for that.

One new piece you’re looking forward to styling?

I just got this tweed bag from Valentino. I normally wouldn’t go for the Rockstuds, but I liked how unexpected they are with the top-handle silhouette.

Do you have any tips for getting unstuck? Walk us through your decision-making process.

It goes back to picking that hero piece and then just trying different things. For example, I have on a cute pair of Posse shorts today—but I’m sitting in my house, and the sun keeps going in and out, so I’m cold. So I took off the tank top I was wearing earlier and put on a white baseball tee, and was like, You know what? This is better. Because I actually felt like I looked too summery before. And then instead of wearing a sandal, I put on a white Mary Jane.

I’ve done this many times before where I’ll get dressed and leave the house to get coffee, and in my head, I’m like, Something’s not working. Then I realize, Oh, I should have switched out my shoe or shirt or whatever it is. So I go back home and do that, and then I’ll feel the whole outfit click into place.

Is there a formula or a uniform you fall back on when you’re feeling uninspired?

I don’t, really. I love getting dressed. It’s my favorite thing. But I know a lot of people don’t, so I think a formula can work really well if you know certain silhouettes look great on you. You can just stick to those pairings and switch it up by adding different accessories so it doesn’t look like you’re wearing the same thing every day.

Are there pieces you believe can solve the “nothing to wear” problem for most people, regardless of personal style?

I love jeans. I did a collaboration with AGOLDE, which we actually just restocked. We made a straight-leg, ankle-length style that I love for daytime, and we also did a wider pair that’s more for night.

I love a grey cardigan. I feel like I can never have too many. It’s funny—I actually just got the new GWYN ones delivered.

I’m really into a grey boot. Last year, I bought a pair of grey leather boots from Toteme and ended up wearing them more than my black or brown boots because they matched everything.

So I just got another pair from Chloe. They’re rib-knit; they look like sweaters for your feet.

And then I think a barn coat is such a great piece for fall, and you can do those at any price point, from J.Crew to Prada or The Row.

What’s a sign that someone's closet is working against them rather than for them?

I remember I once had a styling client who liked this particular button-down, so she went out and bought, like, 14 of them. And it was like, sure, this works…but then she was committed to styling the same thing over and over. That’s how you get bored. I think it's better to own fewer pieces overall, and to make sure that those pieces are things you really love. Then you can have fun mixing and matching.

I also think staying organized is so important. This might sound crazy, but I label my jeans now because I was sifting through about 50 pairs every morning just to get dressed. It was like, which is the Lana? Which is the Baretta? Which is the low-slung curve? I don’t f*cking know! So now I label every single hanger with what style it is so I can get ready fast. I also switched all my pant hangers over to children's hangers, so the jean takes up the whole length of the hanger and nothing slides around. It's so much better.