Fashion week outfit planning sounds glamorous until you're mapping out show times, dinner reservations, and however many blocks stand between them. I stopped trying to plan a full month of press-worthy looks years ago and started building around a handful of pieces I actually trust to work all day into the night.
This season's diary is a mix of matching sets I could throw on half asleep, items I could style in dozens of ways, and the boots that saved me more than once. Scroll through everything I wore below and see where to shop each piece so you can build out the fall wardrobe of your dreams.
(Image credit: @_sierramayhew)I love a matching set, especially when the pieces look just as fabulous as separates. Here we have stripes in a color I actually wear that read a lot more grown-up than the black-and-white version I default to every other season. This might be the most "me" outfit of the whole week.
FAITHFULL Phylis Mini Dress FAITHFULL Jensen Pant SCHUTZ Paola Suede Pump (Image credit: @_sierramayhew)Can you tell I like matching sets? They're my fail-safe for the days when I have no idea what the schedule actually holds. The bandana print meant I didn't have to think about accessories beyond the one bag I wore probably too many times this week.
Maje Casile Cropped Embroidered Taffeta Shirt Maje Embroidered Ruffle Mini Skirt Christian Dior Lambskin Cannage Mini Lady Dior Plum (Image credit: @_sierramayhew)(Image credit: @_sierramayhew)Here's another matching set that solves the "getting dressed in a rush" problem better than almost anything else I own. This one photographs like an outfit I spent an hour on, and it took me about four minutes.
retrofête Pyna Sequin Top retrofête Pyna Sequin Pant (Image credit: @_sierramayhew)I layered what I'm calling the "It jacket of the season that gets the fashion crowd buzzing" (anything with frog fasteners) over this dress because they just had to go together. Yes, I was overheating. Yes, it was worth it.
L'AGENCE Victory Jacket L'AGENCE Lana Flare Knit Dress (Image credit: @_sierramayhew)Bouncing through cocktail parties called for the dress that truly makes a statement. If Jean Paul Gaultier is involved, I need to wear it ASAP. I needed an excuse to wear something a little dramatic, and this was it.
louvelle Ruched Lace-Up Midi Dress Naturalizer x June Ambrose Zyra Pointed Toe Sneaker Pump (Image credit: @_sierramayhew)Attempting a night out during fashion week as a busy editor is always a feat, but it's worth trying at least once a season. I attended a few parties wearing this Greek goddess–inspired dress with gold and white accessories.
nana jacqueline Marcella Cutout White Dress DeMellier The New York Shoulder (Image credit: @_sierramayhew)A show day required me to flex some of my favorite trends of the season. A lace-trimmed skirt has to be considered a must, and I love a car coat as well.
(Image credit: @_sierramayhew)A trend that kept coming up on the runways and the street style crowd was leather oxford-style shoes. After seeing them at a few shows, I had to wear them myself. A lot of industry insiders clocked that these are already set to be the shoes of the season.
J.Crew Verona Lace-Up Flats J.Crew Soho Car Coat DISSH Silvia Black Knit Tank J.Crew Fairfax Skirt (Image credit: @_sierramayhew)For a lunch meeting and show where I wanted to look polished without trying too hard, I reached for a simple dress with a sweater tied around the waist to finish it off. Rain during fashion week is inevitable at this point, and I've made peace with it.
DISSH Billie White Linen Blend Mini Dress VERAFIED Ostrich Cafe Mini Bag Loeffler Randall Marsy Angled Wedge Sandal Guizio Jolie Henley (Image credit: @_sierramayhew)Once the shows started to wind down, I defaulted to what I called my typical wardrobe—jeans I can actually sit in, a cool tank, and boots with just enough personality to still feel like fashion week. This one was for the day packed with back-to-back meetings, when comfort had to win.
Free People Mabel Tank Le Specs Work It Sunglasses Pistola Denim Evie High Rise Slim Boot Bared Footwear Tern Coffee Tan Suede & Hardware Heeled Boots (Image credit: @_sierramayhew)My unofficial fashion week uniform: a sheer top, leather shorts, and knee-high boots that hold up on cobblestones and the subway. This combination got me through two shows and a late-night interview without a single change.
retrofête Hasli Silk Chiffon Top retrofête Naya Leather Short