How I Get Dressed: Sai De Silva

Sai de Silva gets dressed at least three times on Sunday. One of the new additions to The Real Housewives of New York City cast, de Silva has been a fashion content creator since before content creation was a thing. It works because she’s funny, genuine, and unafraid to admit that her real life is a bit messier than the perfectly polished ‘fits she shares on Instagram. 

Case in point: On Sundays, de Silva traverses New York City to shoot fashion content and makes use of an unexpected changing room. “I use my car as a mobile dressing room,” she tells InStyle. “We shoot anywhere between three to six different looks. I'll pile all of the garment bags on top of each other in the car, and I use this wonderful car as my beautiful mobile dressing room.”

Regardless of whether she’s shooting new content for her followers or taking her daughter to high tea, de Silva’s process of getting dressed starts with a bit of meditation. “I dress according to my mood and how I'm feeling, and I'll visualize it in the shower,” she shares. “It's my time to think about what I want to wear that day. I do it every single morning.” 

With the day’s outfit firmly visualized, de Silva heads into the “organized chaos” of her closet. “My closet is pretty tidy,” she says, though she’s quick to add that organization, chaotic or otherwise, is often in the eye of the beholder. “I tend to take things off and kind of put them everywhere, but if you were to walk into my closet, you would think it is very organized just because my wonderful housekeepers put everything back for me. I guess you could say I'm kind of organized, but with help.”

It’s this level of transparency that makes de Silva so engaging as an influencer in the fashion space. She may slay, but she’s also willing to admit that fashion, as any art form, takes work. Like her closet, shoot days and fashion week are, for de Silva, “very chaotic. Nothing is seamless or smooth. The only thing that is organized are the looks.” Ahead, she talks all things fashion, from outfit troubleshooting to power pieces she’ll never give up and the fashion eras she’s never going back to. 

Who She Gets Dressed For

I get dressed for myself and other women. I don't dress for men. Never ever. I don't dress for my husband. The things I pick and I like, other women compliment me on versus my husband who won't necessarily understand trends, why I'm wearing this, or why it goes together. He’d have no idea. 

I'm also not a sexy dresser per se, which I think men gravitate towards. For example, I love oversized bottoms and while men might not like that, a woman will see me and say, "I love your trousers."

On Former Fashion Eras 

I have some eras that I never ever want to see ever again. I used to love to wear bandanas around my neck. I don't understand what I was going through. It was the vibe at that moment, but looking back at it…I have very big curly hair, I was in my blonde phase and it wasn't flowing very well, let's just say that. I was really sad when the skinny jeans era kind of went away, but now I look back at it and I really just never want to see it again. 

There are certain eras that I am happy to give up, but the ‘90s are back which I'm really, really loving. I remember myself in high school always wearing a baggy jean with a crop top, but now it's a little bit more refined. 

In All Things, Seek Flow 

Right now, my “thing” is definitely flow. Quiet luxury is trending right now, but I feel like it's just a classic look that's been around forever and as my style evolves and I get a little bit older, I feel like being put together in a quiet luxury ensemble. I love trousers that flow very well, a little bit larger, accented with a fitted top. I love shoes that tend to have more of a kitten heel or a block heel, something that I can walk around in for long periods of time, but still very much flow with my outfit.

On Finding Comfort in Fashion

Being comfortable is a big aspect of getting dressed. Obviously there are times during Fashion Month when I'm very uncomfortable, but in my day-to-day outfits, I don't wear high Louboutin Pigalles anymore. I think sometimes when we see the word “comfortable,” we automatically think it looks frumpy and it can't look good, but it’s the complete opposite nowadays. 

Jeans, sneakers, slides, flats — there's so many options. You can dress comfortably and look chic and curate some really, really beautiful pieces. It depends on what the look is, but you can make almost anything comfortable and still be on trend. Think of sneaker style. I used to work in corporate America and you just had to come in looking a certain way, but now it's evolved. Nowadays, a nice pair of sneakers with oversized trousers? Actually quite nice. 

Her Power Pieces

Trousers, trousers, trousers. They go with so many things. You can wear them belted, a little bit loose, a bit tighter. There are endless possibilities on what you can do with trousers. I like adding a blazer, belted or not. You can also never go wrong with a white button-down. I promise you, it really does transform a look when you add jewelry and some beautiful sunglasses. I'm a big fan of mixing and matching, especially if I'm traveling and I know that I can't pack too many things, a white button-down and a blazer will always be something I [pack].

On Second-Guessing, and Troubleshooting an Outfit 

I'm usually spot on about visualizing an outfit, but if it’s not exactly going the way I’d envisioned, what I typically do is take a picture of myself. Nine out of 10 times, it looks different on camera than it does in the mirror and that helps me pinpoint exactly what needs to be changed. 

The other day, I had on a very fitted mini-dress and a pair of Chanel slides and it didn't look right. I opened up my camera, took a photo, and immediately saw it needed a blazer and a different shoe. I made it a completely different look.

Fashion as a Family Affair 

A family that slays together stays together, so I love that my family is a little bit more stylish and just more put together. If I know that I am going to Central Park with my daughter, nine times out of 10, we do afternoon tea, something we’ve done for so long. I need our outfits to be very cohesive — something that can go from the park to afternoon tea and still look polished and put together.

Dressing together is something that me and my daughter have been doing since she was probably two years old, when my blog first started. I tend to gravitate towards things that are kid-friendly, but fashion-forward, and because we bonded over fashion, she [developed taste] that is kid-friendly, but fashion-forward. She sees what I wear and she matches what I do, even to the point that she's into trousers now, actually. It's quite shocking.