Lindsay Brooke Weiss is the former editorial director of Haute Living. She now lends her eye for style to private clients, and to us all, thanks to her blog. This year, she also became a mom. As you can see, both mother and child—the now six-month-old Colette Artie Weiss—are rather adorable and dress for whatever the day might hold. —Kate Guadagnino
Look 1: Strolling and lunching in the hood
J. Crew tissue tank: They’re my favorite basics and fab for layering.
TSE knit shorts.
Vintage suede booties: They’re comfy and look chic and unexpected paired with shorts.
Chanel charcoal gray lambskin flap bag: Perfect for day to night and holds a ton! One of my best investment pieces.
Prada sunnies: I never leave the house without sunglasses—ever! Even in the winter I have a pair with me at all times. Hey, that white snow is bright!
Look 2: A friend’s rehearsal dinner
Zara striped dress: There’s a wire and crinoline in the skirt, so it stands away from the body. Also, stripes are so in right now. I was going for a chic nautical look!
YSL patent wedges: I saw these last winter at Jeffrey and fell in love with them. I’m a sucker for a nude patent, and the five extra inches are a bonus.
Zara Terez red leather printed croc clutch
Vintage YSL chain link necklace: This was passed down to me from my great aunt. They just don’t make substantial gold chains like they use to!
Rose cut diamond, gold, and enamel earrings: My husband brought these back from India as a birthday gift for me a couple years ago. He (sadly) had to be away from me on a business trip, but the gift made up for it!
Look 3: Charity event
Stretta bandage dress: This dress speaks for itself. I love the asymmetric hem and the silver ombré.
Manolo Blahnik Sedaraby heels: These are my wedding heels. I love that I get to wear them again.
Giorgio Armani clutch: I wore this clutch to my wedding as well. Surprisingly, it holds a lot!
Diamond hoops: These were my “push present” from my wonderful husband. I was completely surprised and completely thrilled.
Look 4: BBQ with friends
A.L.C cropped sweater: Cropped sweaters are in style right now, but be careful not to show too much skin. A little bit leaves a lot to the imagination!
Aqua skirt: I got this on sale at Bloomie’s last summer. It looks best paired with a cropped sweater or a white button down tied at the waist.
Sergio Rossi wooden wedges: I scored these at a press sample sale that occurred before the sale to the public. I’m not so into sample sales and the pushing that goes along with them, but this was civilized—I was the only one in the room!
David Yurman dog tag necklace: My husband and I have matching stingray necklaces. I’m so into men’s jewelry—sometimes more so than women’s.
Diamond necklace: This was a birthday present from my parents for my 17th birthday. It’s one of those little necklaces that are perfect for layering with others.
Look 5: Traveling or lounging
Aritzia jumpsuit: I live in this. It’s flattering and can be worn with wedges or flats. It’s also my go-to plane outfit. I put on a cardi and a pair of Yosi Samra foldable flats, and it’s easy and comfy travels from there.
Colette in Estella dress: Colette’s like my little accessory. Sometimes I’m more into dressing her than myself! This Estella dress (from Estella in the West Village) is lightweight and so easy for her to wear. She is constantly crawling and moving around, so she needs to wear things that aren’t constricting. Plus, most garments end up in her mouth anyway, and this floral print doesn’t show drool!