Tessa Faye O’Connell is a contributor known for her work at various fashion houses, specializing in media and public relations, currently working at Coach as its global PR director. She’s a mom of two, working to expand her influence in the fashion space through styling while also just making it out the door on time.
After the birth of my second daughter, I came back from maternity leave, and my first week back to reality was a business trip for an event. I started packing and couldn’t put any outfits together because I didn’t have the right shoes for what I was going for. In all honesty, coming back from maternity leave was hard enough, and then to feel like I couldn’t put a decent outfit together that felt good… (Real ones know!) Clothes strewn all over the floor, definitely crying, I vowed that I would be getting my shoe game together. I love clothes but have never been one to collect shoes; I’ve always being more partial to sweatersor jackets. My go-to has always been Birkenstock clogs thrown on in a pinch, but as I was determined to feel more put together, it was time to address what was missing: a lineup of shoes for work that I could count on. On top of that, working in New York City added a layer to the project: I wanted shoes that were cute and comfortable—that I could run around to meetings in but also feel like myself.
While I’m still very much on this journey, in searching the right shoes that can mix and match with multiple pieces, I found I could elevate what I was wearing and more easily get dressed in the morning. Being able to find some must-have classic styles has alleviated 75% of my stress in getting ready, and I’m not sure why I didn’t have this realization sooner. Ahead, my current roundup for winter.
Flat, Brown (Semi-Pointy) Boots
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Dare I say these Tony Bianco boots saved me (dramatic, I know!). Having a brown boot that is flat but still chic in a chocolate brown suede has been the biggest upgrade to my wardrobe. Easy to throw on under jeans or peek out of trousers, it goes great with any color and makes me feel instantly put together.
Reformation
Dominique Ankle Boots
Steve Madden
Dusty Chocolate Brown Suede Boots
Staud
Wally Flat Ankle Boots
Adidas Sneakers
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Nothing has saved me more on a rainy day than a variety of Adidas sneakers that don’t make an outfit feel too casual, as you can dress up appropriately. It is now becoming a problem that I can never have enough sneakers.
Adidas
Gazelle Lo Pro W Sneakers
adidas Originals
Handball Sneakers
adidas Originals
Samba OG
adidas Originals
Gazelle Lo Pro
Thick-Soled Boots
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A friend recommended these chunky Alexander McQueen ones, and at first opposed, I’ve come to see the magic in their ways. Good for winter weather but still elevated, they are comfortable and have been my go-to on many a snow day trekking into the city. Depending on what color suits you, there’s a variety of black or brown boots that would fit any need. A good alternative is Blundstone’s, which I wear often on the weekend.
Ganni
Cleated Low Chelsea Boots Suede
Prada
Chocolate Suede Chelsea Boots
Margaux
The West Chelsea Boots
Blundstone
Women’s Thermal Boots
Loafers
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There is nothing more necessary than a chunky loafer, and a comfortable one at that. Wear socks in winter and still be good for work. Pair with sweaters, or a button-down, you can’t go wrong. I cannot recommend these enough with their buttery smooth leather.
Jamie Haller
Thee Bit Loafers
Gucci
Sylke Horsebit Loafers
Larroudé
Suki Lugsole Loafer in Brown Suede
Square-Toe Ballet Flats
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Perhaps controversial, but one of my favorite new core items is a square-toe ballet flat. I find the rounded toe to be too specific of a look, whereas this shape can be dressed up or down. These black Margaux ones are beyond comfortable (size a half-size down), and I have a suede brown Mansur Gavriel pair that are divine. Either way, my notion that all ballet flats are uncomfortable was completely wrong, and they look adorable with dresses or jeans for the office.
Margaux
The Fonteyn Flats
FREDA SALVADOR
Jada Square Toe Ballet Flats
AEYDE
Delfina Leather Ballet Flats
Black Mules
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Forget the little black bag. The little black mule! These have saved me more times than I can count, and they go with everything.
Jamie Haller
The Trap Clogs
Toteme
Square Leather Kitten Mules
Proenza Schouler
Trap Slippers
ZARA
Slingback Mule Shoes
Stuart Weitzman
Stassi Mules
Tony Bianco
Harriet Mules
Booties
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If you need a flat boot, it only makes sense that you would also need a heeled boot. There are some days that you need that extra lift to fake it until you make it, and you need the right shoes for the job. I prefer a little bit of a chunkier heel, but there are a variety of different options depending on what your vibe is.
madewell
The Dimes Chelsea Boots
Alex Mill X Margaux
The Inga Boots
Shearling Flats
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My favorite item for years has been the Birkenstock shearling clog, so I’ve made it my mission to find shearling flats that could be an elevated swap in for work days.
Larroudé
Verona Ballet Flats in Cocoa Leather and Natural Shearling
margaux
The Demi Jane Flats
ALAÏA
Ballet Flats in Merino Shearling
Prada
Shearling Ballerinas
Madewell
Remy Teddy Mary Janes
More Sneakers
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We already know comfort is key, and therein lies the power of the dad sneaker. New Balance makes a variety of styles that I live in, and they are my other go-to option on inclement-weather days when I need to get out of the house and get going fast. Or throw them on as your commuter sneaker and change when you get to the office.
Golden Goose
Women’s Dad-Star Sneakers
Salomon
Unisex Xt-6 Sportstyle Low Top Sneakers
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