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Dressing for days at the office can be tricky. There’s the temperature to consider, of course — both outside and inside — and comfort’s a must when you’re commuting.
You want to pick outfits that are polished and put-together, but that simultaneously reflect your personal style. Certain silhouettes, lengths and fabrics just won’t fly during your 9-to-5. And on top of it all, whatever you wear to the office needs to look sharp during your after-hours plans — because who really has the time to run home and change?
In search of fresh inspiration for our fall work wardrobes, Page Six anchor Astra and I headed to Bloomingdale’s for a session with personal shopper Stacey Oliver (@ShopWithStacey). After we shared our sizes and mood boards, she put together a selection of styles she thought we’d love — and long story short, she understood the assignment.
Keep scrolling to see (and shop) what Stacy pulled for us, and if you’d like to book a free session with a Bloomingdale’s stylist either in-store or virtually, check out their Styling Services page.
Leather weather
“It’s a great, modern take on a classic suit,” Stacey said of the gold-buttoned leather L’Agence jacket and miniskirt she pulled for Astra, pairing the set with a pasta-print Alice + Olivia top.
“It’s such a great conversation piece — no need to make small talk. Your blouse does all the talking!” the wardrobe whiz added.
Stacey accessorized with Roberto Coin hoop earrings — “Every woman should own a great pair of gold hoops,” she noted — and “classic” Jimmy Choo pumps.
Shop the look:
L’Agence Jayde Leather Open Front Jacket
Bloomingdale's
L’Agence Truman Faux Leather Miniskirt
Bloomingdale's
Alice + Olivia Willa Silk Pasta Top
Bloomingdale's
Roberto Coin 18K Yellow Gold Hoop Earrings
Bloomingdale's
Jimmy Choo Romy 85 Pointed-Toe Pumps
Bloomingdale's
Pizza party
Since Astra’s petite, Stacey pulled a cropped Alice + Olivia jacket, Re/Done T-shirt and Mother jeans that “perfectly” fit her proportions — “no alterations necessary!” (Although Bloomingdale’s does offer in-house alteration services, should the need ever arise.)
“This is great for a more casual office environment; jeans and a tee, and the blazer elevates it if you have a meeting,” she shared.
It’s also a cinch to swap in a black pant like this Simkhai style for a slightly dressier look, as Astra proves in the snap above.
Shop the look:
Alice + Olivia Kidman Jacket
Bloomingdale's
Re/Done Pizza Classic Tee
Bloomingdale's
Mother Petites The Lil’ Hustler High Rise Cropped Straight Jeans
Bloomingdale's
“Red (Elana’s Version)”
Since I’m a huge fan of Taylor Swift’s style, I shared a few of my favorite street style looks of hers with Stacey as inspiration. She came back to me with a perfect pleated Sandro miniskirt, Rag & Bone sweater and faux leather Alice + Olivia jacket, all in the same classic camel color palette.
“If you like more neutral looks, adding texture is going to be great just to really bring your outfit together,” Stacey said, pointing to the skirt’s houndstooth pattern, the sweater’s tonal stripes and the jacket’s subtle gloss.
The mini’s a bit shorter than I’d typically wear to the office, but the knee-high Dolce Vita boots Stacey pulled added some welcome leg coverage — and tights would work well with the look, too.
Shop the look:
Alice + Olivia Keith Faux Leather Cropped Jacket
Bloomingdale's
Rag & Bone Tina Wool Sweater
Bloomingdale's
Sandro Cary Houndstooth Pleated Skirt
Bloomingdale's
Dolce Vita Auggie Pointed Toe High Heel Boots
Bloomingdale's
Pretty pleats
I’m a big fan of pleated skirts, blazers and dresses that accentuate my waist — so imagine my delight when Stacey found a piece that checked all three boxes! This Simkhai midi netted me copious compliments around the office, and I love the idea of pairing it with a tall boot for fall weather.
“It gives great movement, and is really put-together and polished for a work environment,” Stacey said of the dress.
She finished off the look with a “chic” woven Bottega Veneta bag that’ll easily fit my laptop and can be worn on the shoulder, across the body or carried by its top handle.
Simkhai Helena Blazer Midi Dress
Bloomingdale's
Dolce Vita Auggie Pointed Toe High Heel Boots
Bloomingdale's
Bottega Veneta Medium Andiamo Shoulder Bag
Bloomingdale's
Make like Meghan
Call it fashion kismet: Just a few days after reporting on Meghan Markle’s clothing choices from her Colombia tour with Prince Harry, I arrived at my fitting with Stacey to find that she’d pulled the exact navy Veronica Beard vest and pants the Duchess of Sussex wore in South America.
“I love Veronica Beard, because her suiting always has a nice amount of stretch in it, so it’s really comfortable,” Stacey said — ideal for a day spent running to meetings and editing copy at my desk.
For “just a little bling,” the stylist added a classic Bloomingdale’s Fine Collection tennis bracelet — “a great wear-to-work piece” because of its simplicity.
Shop the look:
Veronica Beard Orlinda Vest Top
Bloomingdale's
Veronica Beard Arte Pants
Bloomingdale's
Bloomingdale’s Fine Collection Diamond Halo Tennis Bracelet
Bloomingdale's
Saint Laurent Slingback Pumps
Bloomingdale's
Polo perfection
“I love a dress as a wear-to-work option, because it’s an outfit without having to piece anything together,” Stacey noted of the Simkhai mini she selected for Astra, pointing to the slightly longer sleeves and polo collar as details that make it particularly office-appropriate, even when paired with a bolder shoe like these Balmain boots.
Stacey further elevated the look with several dainty diamond designs, including a Bloomingdale’s Fine Collection tennis necklace and stud earrings and a Roberto Coin initial pendant.
“I love to mix and match metals; I love to layer, I love to stack,” she said, adding that all three would make great additions to anyone’s “jewelry wardrobe.”
Shop the look:
Simkhai Patricia Rib Knit Polo Minidress
Bloomingdale's
Balmain Eva Pointed Toe High Heel Boots
Bloomingdale's
Roberto Coin 18K Yellow Gold and Diamond Initial Pendant Necklace
Bloomingdale's
Bloomingdale’s Fine Collection Diamond Tennis Necklace
Bloomingdale's
Bloomingdale’s Fine Collection Four Prong Round Diamond Stud Earring
Bloomingdale's
Why Trust Page Six Style Shopping
This article was written by Elana Fishman, founding editor of Page Six Style. Elana applies her celebrity fashion and beauty expertise to shoppable content for fellow fans as the host of video series including Style Trial, Heart to Cart and Beauty Scoop — and by tracking down every Taylor Swift-worn style so you can shop it, too. Elana consults celebrity stylists on the latest street style and red carpet trends, researches which celebrity-backed brands and products are worth it, and chats with the stars themselves for beauty and fashion recommendations. Prior to Page Six Style’s inception in 2018, Elana covered celebrity fashion at Vox Media, Lucky, Marie Claire and Teen Vogue.
