TGSS™ - Whitney Port

The queen of sweats

Oct 31, 2024

I want to start off by acknowledging that there wasn’t a Bitesize last week. Some of you may have missed it, a lot of you probably didn’t. Either way, I hope there will be one this weekend. I’m just going through a really rough time right now and it’s hard to know what I have energy for in advance. If you’ve been through a rough time too then you probably know what I’m talking about. Anyways, I am finally in the mood to talk a little fashion again. So, here we are.

Have I talked about my obsession with Whitney Port? I think maybe I’ve mentioned the fact that I listen to her podcast religiously, but that’s not even the half of it. I, like so many of us millennials, never missed an episode of The Hills or The City but to be honest I always saw Whitney as the kind-hearted best friend. It was Lauren and Olivia who were my #1 back then. I guess I was still in the phase where you really want the cool girl to like you, maybe even more so than investing in truly great friendships.

Cut to a few years later and I discovered Whitney’s youtube channel where she spoke candidly about how she loved her baby but hated pregnancy. I was hooked. They way she spoke so openly about both mental and physical struggles, the way her husband (the adorable Timmy) supported her in her different emotions, the way the both of them tackled these challenges together. Ugh - obsessed.

It’s no secret that Whitney has always been a chic fashionista™, but I must say she’s come a long way since the Topshop mini skirt with statement necklaces-era that we all endured during the 2010’s. She’s still a part of the NYFW squad and wears incredible, creative looks for all events she attends. But that’s not really what makes me swoon over her wardrobe. What I really love are her everyday looks, running errands around LA. Let’s take a closer look, shall we?

There’s something about nailing a sweats look that just hits right. We all love sweats, but a lot of the time they feel inappropriate for anywhere outside the comfort of our own home. Or maybe that’s just me. Anyways, I feel my absolute most clever fashion-wise when I manage to really hit a sweet spot with my sweats, where I feel comfortable and put-together enough to actually take myself outside. The key is usually (like pictured) a perfect balance between a sturdier/more classic accessory - the leather bag - and an intentional shoe choice - the modern sneaker. If this look featured a canvas tote and birks or worn in frumpy sneakers it just wouldn’t be the same.

This is a pretty similar formula - fashion handbag and modern sneakers. An instant elevation of the grey sweats.

In this look, the bag is swapped for a more practical tote, I’m guessing since she’s actually out getting groceries or whatevs. But we still have the modern sneaker as well as some really cool dad shades and a few layers of necklaces. Whitney is also a certified colour-pairing expert.

I have a feeling this image is slightly older than the ones above, just because I feel like her style has evolved slightly from this. But I’ve had this image saved for a really long time. Even though this isn’t my style per se, there’s something about the Canadian tuxedo together with another layer of jacket (although carried), paired with some pretty funky zebra shoes, and a yellow (!) Chanel bag that feels yummy to me. I love when someone feels truly relaxed in their style, enough so to put on something that isn’t going to make it into a fashion magazine but still feels authentic and personal and thoughtful. This is infinitely more inspiring to me than a full The Row-look.

Nowhere close to rocket science. Simply a great sweater paired with great socks — a colour pairing that kind of makes the whole look. This with an oversized leather jacket and a pair of sunglasses would make me feel super great.

When Whitney does feminine, there’s always a twist. Unfussy hair, cool girl-sneakers, a nonchalant coffee. (Yes, sometimes a coffee cup is an accessory).

Okay so that’s all I had for you today. I hope you found this inspiring in one way or another. I don’t know when my obsession with really basic, yet creative looks will fade but it hasn’t yet so I guess there will be a few more of these Truly Great Street Style™ posts. Let’s just agree to wear our clothes and not feel like we have to look perfectly styled all the time, yeah? Great, thanks.

Talk soon, xx