(Packed To Perfection)

Let This Fashion Insider’s Milan Wardrobe Be Your Fall Shopping Guide

So many good outfit ideas.

Written by Alison Syrett
Originally Published: 
TZR; Tiffany Reid; Akela/Stocksy
Tiffany Reid wearing a buttoned-down white shirt tucked in a black mini skirt in Milan.
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In our Packed To Perfection series, TZR follows industry tastemakers to local haunts and far-flung destinations alike to see — and shop! — what they’re wearing while out and about in the world. Up next? Bustle Digital Group’s senior vice president, Tiffany Reid, and her expertly planned lineup of looks for Milan Fashion Week Spring 2023.

Here’s a little something you should know about the street style outside of runway shows: It takes a lot of time and effort to coordinate all those photo-ready outfits. “I plan all my looks ahead of time and take pictures of everything, so I remember if something is not working,” explains BDG’s senior vice president of fashion, Tiffany Reid — who, at this point in her career, has fashion month style down to a science. Any given season she can have upward of three or four international cities to dress for, and she takes the prep work for each very seriously.

Before each trip, Reid explains, she creates a different look for every day she’ll be running from event to event, and meticulously choreographs potential bag, shoe, and top changes for each. “Organizing everything ahead of time leaves me peace of mind because [during the week] I’m out late, somethings until 2 a.m., and then shows start the next morning at 9 a.m.; I want to just get up, steam my clothes, and head out!”

This past September, Reid’s thoughtful approach to packing certainly paid off when she touched down in Milan to take in the Italian shows. Her wardrobe for the week, which she describes as having a “professional-sexy” vibe, struck a delicate balance between business-savvy professional and someone who’s ready for a good after-party. Her looks are also a source of serious inspiration for anyone planning their go-to outfits and style approach for the new season. Keep scrolling to see how she put everything together and to shop the same (or similar) pieces for yourself.

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Fresh From Flight

courtesy of Tiffany Reid

“This is my airport look. I wore it on the plane. Basically I had to wear the coat and boots because those were the biggest things that I had to carry with me, and so I was trying to preserve my luggage space. So, although [the jacket is] not comfortable, I wore it anyway. And then I wore a T-shirt, pleated pants — they’re Issey Miyake Pleats, Please and super cozy. You can curl up in them, and when you get off the plane, you’re not wrinkled.”

Hitting The Ground In Heels

Darrel Hunter

“This is first day of shows [in Milan]. I’m that type of person who wears the band tee to the concert, so I’m in Fendi for the Fendi Show. And then the shoes are my trusty Alexandre Birman croc boots. They have a heel, and I’m always in a heel — even if it’s a baby heel, I still have something! These boots are super comfortable, and I wear them all the time, so they are a little bit worn in. They’re good for first day of shows, when I’m easing into the things.”

She’s Got Layers

courtesy of Tiffany Reid

“So I love shirting, but I also like to be sexy. I think I [mix the two] with a little bit of taste. This look is the shirtdress with a little miniskirt over it — it kind of gives the illusion that it’s all one piece, but I just layered one on top of the other. And this was Prada day, so I wore the Prada shoes that I just bought [for the show].”

Day-To-Night, Done Right

courtesy of Tiffany Reid

“This was my nighttime look later that day [that I wore the shirtdress]. I kept the same skirt, but as you can see, it looks very different with my jacket and crop top, which is actually a sports bra. I had a lot of evening events. That photo was taken at an event with Mytheresa. After that I had a big dinner with Armani, and that team likes to party, so I knew we would go out after. I wore this so I could take the jacket off and have a cropped top and a little skirt. The sports bra is perfect because you can wear it all night long dancing and sweat in it and you’ll be fine.”

On The Scene In Green

courtesy of Tiffany Reid

“This was after the Loro Piana presentation across the street [on Day Three]. They had a flower truck, and were giving people flowers — it was super cute. This was Gucci day, so I wore this Gucci printed G Blazer. It’s a little subtle. You can’t really see the G’s on it. I [paired it] with the little white Gucci bag, high-waisted boot, and a short skirt. Obviously I’m into minis because I wore one two days in a row. I think this white one looked really nice with the brown boot because it gives the illusion that I’m showing my leg, but it’s more covered up. And then I changed up my hair look with a little playful ponytail.”

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