
“I didn’t really know how to dress casually until I relocated to California,” shares Kelsey Keith, who spent ten years in NYC prior. “I still don my all-black attire for school pick-up, so it’s not as if the New Yorker has disappeared, but I’ve also acquired a pair of hiking shoes.” Kelsey, the creative director at MillerKnoll, contributes to one of our favorite design Substacks. Here, the Berkeley resident reveals five outfits she wore over a week, along with tips for secondhand shopping…”
Shirt: Banana Republic (check resale platforms.) Skirt: “ancient Zara.”
“I typically resort to mall brands for basic items, but Banana Republic has impressed me recently. I adore this shirt — it’s well-crafted, and the ripstop fabric is great. Their pull-on black pants are also spot on. I try to limit my new purchases, but I have my eye on several other items from their site.”
Necklace: similar. Bracelet: “designed by midcentury creator Fran Hosken, obtainable through the Hosken Archive.”
“In college, I studied abroad in Paris. While there, I ventured to Venice and then took a 24-hour ferry ride to Greece — with a deck ticket. But Greece is incredible, so any means of getting there is worthwhile. I got this Bees of Malia pendant during that journey. It’s a replica of a relic dating back to 1650 B.C.”
Cardigan: Agnes B., “purchased secondhand.” Pants: Banana Republic. Clogs: Rothy’s, “these serve as my house slippers, and they’re incredibly comfy.”
“If an item exceeds my budget, I search for it on a resale site. I utilize Gem to set alerts in my size so I get notified via email if they become available. I’m extremely patient. Gem alerts are also fantastic for gauging an item’s average pricing on the secondhand market.”
Rings: “Engagement ring by Lola Brooks, wedding bands by J. Hannah, antique quilt band ring from Oko in Portland.”
“Before our engagement, my husband and I explored options together and narrowed it down, but he made the final decision. My engagement ring is from Lola Brooks, and I feel it resembles a galaxy.”
Shirt: vintage Benetton, “incredible deal, around $30, never worn.” Jeans: DL1961. Belt: “my mom’s,” similar. Bangle: “Taxco silver, acquired in Mexico City.” Necklace: Tiffany & Co.
“One reason texture is captivating is the evident craftsmanship. With a thick wool sweater or a finely embroidered shirt, the material and construction stand out. When dressing in a single color, there’s typically a textural shift in my outfit.”
Shoes: Stoffa.
“On any given week, I’ll have 10 clothing items piled on a chair, swapping things in or out. I don’t like to be overly precious with my clothes. I seek out well-crafted items that can withstand frequent wear.”
Sweatshirt: Hey Gang. Skirt: KasMaria. Socks: Le Bon Shoppe.
“Claire McCardell was a mid-century American fashion designer who was a pioneer in integrating pockets into women’s clothing, despite male designers questioning their necessity. [She also ensured zippers were easily accessible because a woman ‘might live alone and enjoy it, but you may regret it if you strain your arm trying to reach a back zipper.’] This new book about her is incredible. Everyone should check it out.”
Shoes: Clarks.
“If your feet are in pain, enjoying yourself is impossible, regardless of everything else. Wallabies, a classic choice, provide extreme comfort. They pair well with everything since they’re a bit anti-fashion. Whenever I need a new pair, I scout resale sites like eBay — a perfect tip for timeless styles if you know your size!”
Sweatshirt: Rachel Comey, “found it on resale—set an alert on Gem. Pants: Le Bon Shoppe. Ring: “borrowed from my five-year-old daughter.” Sunglasses: Illesteva. Pouch: Dr. Max’s. Socks: Target, similar. Sneakers: Merrell Wildwood Aerosport.
“Living in California, surrounded by nature, you tend to become quite outdoorsy out of necessity, and because you’re continuously engaging in outdoor activities, casual attire becomes the norm. Merrell must immediately bring back these Wildwood Aerosports.”
“My youngest child is no longer in diapers, so I can avoid dragging everything everywhere. Sometimes I think, I’m only bringing what fits in this tiny pouch!”
“I worked for many years as a design editor, and I use that mentality for my clothing as well. I’m unforgiving about ensuring I only keep items that I truly enjoy wearing. That’s my secret.”
Thank you for sharing, Kelsey!
P.S. More women showcase their weekly outfits, including a sewing aficionado who adores clowncore, a New England grandmother sporting popped collars, and a Toronto professor rocking a pink power suit.
(Photos by María del Río for Cup of Jo.)
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**Kelsey Keith’s Weekly Outfit Guide: Navigating Style with Ease**
In the constantly changing fashion landscape, establishing a personal style that balances practicality and flair can feel overwhelming. Introducing Kelsey Keith, a celebrated fashion editor and style influencer, whose weekly outfit guide has transformed into a cornerstone for those in search of style inspiration. With a sharp eye for detail and a talent for merging trends with classic elements, Kelsey’s guide presents a refreshing perspective on everyday apparel.
**Monday: The Power Suit**
Kelsey commences the week with a salute to the iconic power suit. Mondays are meant for setting the tone, and nothing exudes confidence like a meticulously tailored suit. Choose a striking color like emerald green or royal blue to stand out. Pair it with a crisp white blouse and pointed-toe heels for a refined look that attracts attention in any meeting room.
**Tuesday: Casual Chic**
As the week unfolds, Kelsey recommends toning down the formalities with a casual chic outfit. Picture high-waisted jeans coupled with a silk blouse or a cashmere sweater. Complete the ensemble with ankle boots and a structured handbag for an elevated appearance. This outfit is ideal for those busy days filled with meetings and errands, providing comfort without compromising style.
**Wednesday: Midweek Minimalism**
Midweek calls for simplicity. Kelsey’s Wednesday selection revolves around sleek lines and neutral shades. A monochromatic outfit in tones of beige or grey can evoke a polished silhouette. A tailored coat, slim trousers, and a basic turtleneck form the basis of this style. Accessorize with subtle jewelry and an elegant watch to maintain an understated yet sophisticated appearance.
**Thursday: Bold and Bright**
As the weekend nears, Kelsey prompts the addition of vibrant colors to your wardrobe. Thursday’s ensemble is characterized by bold patterns and lively shades. Whether it’s a floral dress or a patterned skirt, embrace the fun side of fashion. Complement with neutral accessories to allow the outfit to take center stage. This day is perfect for trying out new trends and showcasing your individuality.
**Friday: Effortless Elegance**
Fridays are all about effortless sophistication. Kelsey’s guide suggests a midi dress in an opulent fabric like silk or satin. The key is selecting a dress that transitions smoothly from day to night. Pair it with block heels for the office, and switch to strappy sandals for evening plans. A striking clutch and vivid lipstick provide the perfect finishing touches for a night out.
**Saturday: Weekend Relaxation**
The weekend is meant for relaxation, and Kelsey’s Saturday outfit embodies that spirit. Go for cozy yet stylish loungewear or athleisure. Think of soft joggers matched with a fitted tee or a cozy knit set. Sneakers and a crossbody bag round off the look, making it suitable for brunch with friends or a leisurely walk in the park.
**Sunday: Classic Comfort**
Sunday is reserved for classic comfort. Kelsey suggests a timeless combination of a white button-down shirt and tailored trousers. This outfit is effortlessly stylish and perfect for a laid-back Sunday brunch or a casual outing. Add loafers and a trench coat for a touch of class.
Kelsey Keith’s Weekly Outfit Guide is beyond just a fashion blueprint; it invites you to explore and embrace personal style with confidence. By blending classic staples with modern trends, Kelsey provides a versatile wardrobe that caters to every occasion, ensuring you step out each day feeling your absolute best.

