Published on July 6, 2018 — Leave a comment

How to Wear the Same Skirt All Week Without Anyone Noticing

share this:


When you see a top that catches your eye, what makes you put it back on the racks versus taking it to the register? For all of us at team thrEDIT, the definitive question between an enthusiastic “YASS!” and a hard “Nope!” is, “How can I wear this?”. 

When shopping, it’s always hard to imagine creative ways to style what we want with what we have. That’s why we’ve challenged our stylish thredUP staffers and influencers to wear a single item five ways. Let’s styleUP!

Our first brave stylite to take on the challenge is our Brand Marketing Coordinator, Cassandra Moua! We asked her to style a single summer skirt for five different days. Let’s see how she managed to balance versatility, style, and a (very) full social/work calendar.


Hi, I’m Cassandra! You may know me from my Staffer Spotlight a couple of months back and I show up a lot on Facebook/Instagram too. I’m a fan of brands like Zara, J. Crew, and ASOS, and I get a lot of my inspiration through fashion blogs and scrolling through IG all day. I wanted to give myself an extra little challenge and chose to style a bold pink pencil skirt all week. I got a lot of compliments on my outfits, and everybody was none the wiser because every look was so different! I bought the skirt for only $9 and I got SO many wears and outfits of it! Here’s how I pulled it off…

Monday: The All-Business Outfit

I hit the ground running on Mondays! I’m always on the move from one meeting to the next, so I needed an outfit that would be comfortable and professional. I love this outfit because it’s so “me” but also perfect for work. I added character by wearing a herringbone printed blazer with my bold pink skirt, then I threw on jet black slingbacks to anchor the whole look.



— I chose two pretty bold pieces to wear that day so I balanced the look by wearing a white Linen blouse underneath to keep things neutral since I’m wearing two statement pieces. A white top with a bold skirt really evens out the look.

Block heels are super comfortable for the office, highly recommend these if you will be on your feet all day in the office! The pencil skirt hits just above the knee so a lower heel is a more demure option for ever day. Slingbacks are also very trendy this season.


— If you’re looking for something that makes a statement, shop thredUP and filter by pattern AND color to get exactly what you want.

Wednesday: The On-Wednesdays-We-Wear-Pink Outfit

I thought I would have a little fun with this one (it was Wednesday after all)! I had a networking event that night and I wanted to come off elegant and not too showy. I love LOVE the monochrome look during the summer/spring time! The best way to tackle this look is to play around with textures and tones.



— For a monochrome outfit, the details are key! I wore a light pink top with pearl embellishments to add texture. Monochrome doesn’t have to be boring.

— Metallics are an eye-catching addition to plain looks. I reached for a rose gold clutch from Marc by Marc Jacobs to add a little POP to my look.


— Have a certain texture in mind for your monochrome look? Shop at thredUP and filter by the type of item and accents (which includes everything from glitter to frayed edges) to find exactly what you want.

Friday: The TGIF Outfit

Whew! I had been rocking the skirt the WHOLE week and was feeling a little fashion fatigue, but I loved how I got a lot of compliments! I had Happy Hour plans that night and was excited to blow off some steam. A leather jacket is my go-to going out layer, and the pencil skirt’s length was the perfect match with dressy nude block sandals!



— Leather jackets make any outfit a little edgier. Since this skirt is so bright and bubbly, I wanted to tone it down for a night out with my leather jacket.

— In order to break up the black vs. bright color scheme, I wore a window pane printed top underneath.


— Did you know you can search skirts by not only type but also length as well? I wanted a skirt I knew I could pair with block heels, which meant a longer length, so I chose to filter by midi and calf length skirts to find what I had in mind.

Saturday: The Easy Errand Outfit

Saturdays are my errand days. This was a hard outfit to do since pencil skirts are so tied in with workwear. My fave combo lately has been these slip-ons and skirts, so I decided to downplay the business vibe. It’s the weekend so I gave it a fun twist with a complementary bright pink bag!



— SF rule of thumb: Always bring a jacket. Plus, a jacket can be tied around the waist to emphasize your figure, especially something like a high-waisted pencil skirt!

— Wearing a dress or skirt doesn’t require to heels or booties. Throw on a pair of a sneakers and make your outfit casual. Trust me, wearing these on my walk to Bart. Lastly, SF rule of thumb: always bring a jacket.


— My loose-fitting tank top is what really makes this outfit casual. You can shop for the perfect top by filtering according to neckline, pattern, condition, and even accents.

Sunday: The Brunch Bunch Outfit

I REALLY wanted to show off my latest thredUP find (peep that cute basket bag!) at brunch with the girls, but I didn’t want overload my outfit with colors. A grape purple J.Crew pullover (scored from my Goody Box!) and flats made the perfect colorblock frame, so I could bring more shades to the outfit. I paired it with printed head scarf to add a pop of pattern and my fave new basket bag that holds everything I need for my Sunday afternoon plans.



— It’s important to colorblock with two colors that have similar color tones.

— My go-to for styling tops with a high-waisted skirt is to tuck, but I thought I’d kick it up a notch by knotting my T-shirt! It adds a little visual interest which really made the look pop!


— You can filter and shop by color on thredUP, but go a step further! If you’re building a colorblock outfit, you’ll want to look at individual pieces. Filter by type of clothing! I found my perfect style by filtering pink AND pencil skirt.


And that’s a wrap! So, how did Cass do? We’d love to hear your thoughts below and any styling trade secrets YOU have to changing up your favorite skirt. Let’s get brainstorming!