Style  •  01.14.26

The 7-Day Daily Looks Challenge

Day 1: Finish The Look

Add one extra "finishing touch" you'd usually skip.

Day 2: Repeat Player

Style something you wore in the last two weeks in a new way.

Day 3: Texture Play

Mix at least two textures today—knit, denim, leather, silk...

Day 4: Monochrome-ish

Build a full look using just one color family. Shades welcome!

Day 5: Pattern Play

Pair two prints that share a color or live in the same family.

Day 6: Back of the Closet

Wear something you haven't touched in months.

Day 7: Vacation Energy

Style a piece that reminds you of a place or mood.

Inside the 7-Day Daily Looks Challenge

As the new year begins, it felt like the perfect moment to take a fresh look at what’s already in rotation. That idea sat at the center of the 7-Day Daily Looks Challenge, a week-long styling series that unfolded inside Trade-Off’s Substack Chat.

Each day introduced a single prompt designed to open up new ways of getting dressed — revisiting favorite pieces, rediscovering what had been sitting in the closet, and trying combinations that hadn’t been explored yet. Over the week, a clear story took shape — not just of what people wore, but how they approached their wardrobes.

Finish the Look

AYR ShirtGuest In Residence SweaterHouse of Dagmar JeansAlaia FlatsComme Si SocksDestree Bag, Hermes Scarf (similar here), Sherman Field Necklace (sold out, similar here)

Repeat Player

LilyEve Jacket (similar here), Alemais Shirt, Attersee Skirt (old, similar here), Chanel Flats (similar here), JB x Jennifer Behr Necklace

Day One: Finish the Look

Prompt: Add one extra “finishing touch” you’d usually skip.

The opening prompt was simple: add one detail you usually skip. A belt. A scarf. Jewelry. A cuffed sleeve. A pin.

This is one of the questions that comes up all the time — why a look can be made up of great pieces and still feel like it’s missing something. The answer is almost always in the final layer. A scarf at the neck, a belt at the waist, a piece of jewelry that pulls the eye in — once it’s there, the whole outfit suddenly clicks.

Starting here set the tone for the entire week.

Day Two: Repeat Player

Prompt: Style something you wore in the last two weeks in a new way.

This day was all about taking something you already love and seeing it in a new way.

Personal style grows through experimentation — wearing the same piece differently, shifting where the color sits, changing how something is layered. It’s how favorites keep feeling fresh instead of familiar.

As someone shared in the chat, “Today I decided to add a bit of color and tie a scarf around my waist.” That one small change turned a well-worn outfit into something completely new.

Texture Play

AYR Shirt, Plain Goods Sweater (similar here), Donni Pants, Chanel Flats (similar here), Hermes Bag (similar here), LGR Sunglasses

Monochrome-ish

LilyEve Jacket, Doen Tank (similar here and here), Chloe Pants, Chanel Flats (similar here and here) & Necklace (similar here)

Day Three: Texture Play

Prompt: Mix at least two textures.

Sometimes an outfit works, but it still doesn’t feel special — and that usually comes down to texture. When everything is too similar in finish, the look can fall flat, even if the pieces are good. Mixing fabrics like suede, tweed, and silk creates contrast in a way color alone can’t, giving the outfit depth and movement. 

One of my favorite reflections from the chat: “This challenge has really allowed me to think outside of the box.”

Day Four: Monochrome-ish

Prompt: Build a full look using one color family.

This day was all about using color in a way that feels pulled together from the start. When an outfit stays within one tone, everything relates — the eye reads it as one continuous story instead of separate pieces.

From there, contrast becomes even more fun. A necklace, a shoe, or a brighter shade stands out beautifully because the base is already working.

Pattern Play

Missoni Top, Gucci Skirt (old, similar here), Hermes Belt (similar here), Chanel Flats

Back of the Closet

Chanel Sweater, Celine Jeans (old, similar here), Chanel Bag (old, similar here), Chanel Flats (similar here)

Day Five: Print Friends

Prompt: Pair two prints.

This is the easiest way to start playing with pattern.

Florals, stripes, animal prints — when two prints share a color or a rhythm, they begin to work together instead of competing. Anchoring them with something embellished through a shoe or accessory keeps the mix feeling styled and wearable.

This was one of those days where outfits felt full of personality.

Day Six: Back of the Closet

Prompt: Wear something you haven’t touched in months.

This day was such a favorite. It’s all about reframing what you already own.

We all have pieces waiting for their moment — a statement bag, a jacket you’ve been saving, something you love but haven’t quite figured out yet. And then the chat delivered this gem:

“This necklace belonged to my great-grandmother, and I had actually never worn it before. So today was the day.”

That’s exactly what this prompt is about — letting one piece finally take center stage.

Vacation Energy

Anine Bing Jacket (similar here), Similar Embroidered Jacket, Perfect White Tee, AYR Jeans (similar here), Chanel Flats (old, similar here)

Day Seven: Vacation Energy

Prompt: Style a piece that reminds you of a place or mood. Vacation energy encouraged.

Vacation dressing always works because we’re more open to trying things — brighter, lighter, more playful. This final prompt asked what happens when you bring that same energy into everyday life.

The bracelet you save for trips. The breezier blouse. The shoe that changes how you walk. As someone shared in the chat, “I stepped out of my comfort zone with this outfit today that I wore to a birthday party.”

That’s exactly the spirit we wanted to end on.

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