Shoes and bags are two of the categories I’m asked about most. Which shoes are actually comfortable? Which bags are worth the money? What do I carry every day, and what would I buy again?
These are my year-round favorites: the shoes I can walk in, the bags I carry repeatedly, and the pieces I recommend most often. Some are practical everyday staples, while others are more significant purchases, but they are all things I own, use and genuinely love.
As we move through the year, I’ll add separate seasonal editions featuring the shoes and bags I rely on specifically for fall, winter, spring and summer.
Flats
Margaux has become one of my favorite shoe brands. They are a splurge, but I don’t think you need a closet full of flats. A few beautifully made, classic styles will take you far:
MARGAUX The Phoebe | $385
A modern take on the ballet flat, with a square toe and slim instep strap. The shape feels current without losing its classic appeal, and it is available in narrow, medium and wide widths.
MARGAUX The Demi | $290
The quintessential ballet flat, with a rounded toe, adjustable bow and soft, flexible construction. Handmade in Spain and available in several widths, it is the kind of shoe you can wear for years.
Classic White Sneaker
My favorite sneakers cover a wide range of prices. The right pair does not have to be expensive, and I wear each of these for different reasons:
M.Gemi The Palestra Due | $298
The splurge of the group and one of the most comfortable sneakers I own. The soft Italian leather, cushioned footbed and lightweight sole make them easy to wear all day, while the sleek shape keeps them from looking bulky.
VEJA Campo Leather | $175
A classic leather sneaker with a slightly more substantial shape. The simple design works year-round with jeans, trousers, skirts and casual dresses, and there are plenty of color combinations to choose from.
Keds Contest Lace-Up | $74.95
An excellent option under $100 with a vintage-inspired shape and a comfortable, removable footbed. They have the look of a classic court sneaker and feel current without being overly chunky.
Shop the M. GEMI The Morena , the VEJA Campo Leather , and the Keds Contest Lace Up
Best Rain Boot
HUNTER Women’s PLAY Tall Rain Boot | $140
I cannot tell you how often I grab these, and every single time I’m so happy I bought them. Rainy school drop-offs, running errands, soaking-wet sidelines, whatever the day brings. They are one of those purchases you do not realize you need until you own them.
Shop the HUNTER Women’s PLAY Tall Rain Boot
Sandals & Flip Flops
When it comes to sandals, I keep it pretty simple. I want an inexpensive flip-flop, a comfortable heeled sandal that works for dinners and events, and something minimal for when I need a proper heel:
J.Crew Factory Easy Summer Flip-Flops | $29.50
I do not spend a lot on flip-flops, and these are my go-to. They come in a great range of colors and prints, so they are easy to replace or add to as needed.
MARGAUX The Paloma Sandal | $375
A beautiful leather sandal with a walkable 2.5-inch block heel. The straps hold your foot securely, and the classic design works for everything from dinner out to a summer wedding. I have these in black and dune.
Dolce Vita Ramia Heels | $110
A simple, minimal heel with slim straps, a square toe and a manageable two-inch height. These are ideal when you want a heel that disappears into the outfit and works with almost anything.
Shop the J.CREW Factory Easy Summer Flip-Flops , the MARGAUX The Paloma Sandal , and the Dolce Vita Ramia Heels
Cozy Slippers
Brunch Essential Slipper | $98
I wear these around the house and always pack them when I travel because I refuse to walk barefoot on a hotel room floor. They are comfortable, easy to slip into a suitcase and one of those small things that makes a trip feel much better.
Pumps
For a classic pointed-toe pump, these are the two I recommend most. Both have a similar heel height and timeless shape, with one at a higher price point and one that stays closer to $150:
INEZ Alta Pump | $285
INEZ designs heels with comfort in mind, and the Alta has a cushioned insole with arch support and a 3.5-inch heel. It is beautifully made and a great investment if you wear pumps regularly.
Sam Edelman Hazel Pointed-Toe Pump | $150
The Hazel is a dependable classic available in a huge range of colors, materials and prints. The pointed toe and high heel give it a clean, elegant shape, and the lower price makes it easier to add a color or finish beyond basic black.
Shop the INEZ Alta Pump and the Sam Edelman Hazel Pointed Toe Pump
Athletic Sneaker
My go-to athletic sneaker for workouts, long walks and days when I know I’ll be on my feet for hours. The Clifton 11 has plenty of cushioning, a lightweight feel and a breathable mesh upper. They are incredibly comfortable right out of the box.
Kitten Heels
A kitten heel is one of the most useful shoes to have on hand. You get the look of a classic pump with a heel height that makes sense for a full day or long event:
Sam Edelman Summer Pointed-Toe Pump | $150
A simple pointed-toe pump with a two-inch kitten heel. The leather across the toe is designed to stretch with wear, and the clean shape works with everything from trousers and jeans to skirts and dresses.
SARAH FLINT Perfect Kitten Pump 50 | $495
The investment option, thoughtfully designed with a wider toe box, built-in arch support, extra footbed padding and a stable flared heel. If you wear pumps often and comfort is the priority, this is an exceptional shoe.
Shop the Sam Edelman Summer Pointed Toe Pump and the SARAH FLINT Perfect Kitten Pump 50
Work Bag
MAISON de SABRÉ The Zipped Soft Tote | $458
This is my favorite work bag. It holds a laptop up to 16 inches, has a full zip across the top, and includes compartments for the smaller things that usually disappear at the bottom of a tote. The full-grain leather is beautiful, the shoulder straps are comfortable, and it carries everything I need for a day of work or travel.
Shop the MAISON de SABRÉ The Zipped Soft Tote
Best Casual Tote
L.L.Bean Boat and Tote, Open-Top | $32.95–$59.95
My forever favorite. I have several in different sizes and use them for everything: the beach, travel, groceries, sports, hauling things between home and the shore, and all the general chaos of family life. They are practically indestructible, hold an unbelievable amount and only get better with age.
Shop the L.L.Bean Boat and Tote
Best Crossbody Bags
MAISON de SABRÉ The Zipped Bucket Bag | $478
This is a great everyday bag. It is roomy enough for everything I tend to bring with me, the zipper keeps it all secure, and the crossbody strap leaves my hands free. Love it in the brown.
Lo & Sons Pearl Convertible Crossbody Bag | $258
I have carried the Pearl for years, it’s great for everyday and travel. It sits close to the body and has separate compartments, so I am not digging around for my phone, wallet or passport while standing in an airport and also is chic and stylish to carry wherever you land.
Shop the MAISON de SABRÉ The Zipped Bucket Bag and the Lo & Sons Pearl Convertible Crossbody Bag
Clutch
Tuckernuck MODA LUXE Black Victoria Clutch | $95
This is such a great find. Skip the collection of just-okay evening bags from Amazon and buy one great-looking black clutch you can carry to everything. It holds the essentials, goes with almost any outfit and looks much more expensive than $95.
Shop the Tuckernuck MODA LUXE Black Victoria Clutch
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