Winter Outfit Ideas - My 5-Day Closet Challenge Results
My 5-Day Style Challenge: Fresh Outfit Ideas from Your Existing Wardrobe
In today’s post, I'm sharing the 5 outfits I created during my closet challenge, complete with styling tips, shopping links, and the surprising confidence boost that came from thinking creatively about getting dressed. Plus, find out which unexpected color combo became my favorite!"
What if I told you that you don't need new clothes…you just need new eyes? Last week, I challenged myself (and you!) to a 5-day style experiment that completely changed how I see my closet. The results? Eye-opening, confidence-boosting, and honestly... a little addictive. Today I'm sharing all five looks, the styling tricks I discovered, and why this simple challenge made me feel more put-together than I have in months.
Day 1 Challenge - Choose two items you love but have never worn together. Let them surprise you.
My Take…How to Style Brown Corduroy Pants in Winter
Day 1 Outfit - for this challenge, I chose brown corduroy pants and a grey cardigan sweater. I love both pieces and have worn the grey cardigan often. I really thought when I bought the pants that I would wear them more than I have but for some reason, I always thought they were too “fall” looking to wear in winter. That’s because I was styling them with other fall colors instead of thinking outside the box.
I had just gotten the bandana scarf from Free People and added that because it tied the look together nicely. I have a tee on underneath the sweater for warmth. The short leopard jacket was perfect and I choose the off-white bag from Lancel Paris that I’ve had forever, because the color of the trim matched the pants, and also because it lightened up the look. And…how absolutely perfect are these green suede booties that Baldy gave me for Christmas? Voila…a cute look with pieces that I would have never put together! Next…I’m styling those pants with pink!
Day 2 Challenge - Let one beloved piece lead the way today.
My Take…Layering a Suede Tunic: 70s-Inspired Outfit
Day 2 Outfit - the “one beloved piece” I chose was a suede tunic from Sezane that I purchased in the fall. I had only worn the tunic with nothing underneath and decided it might be really great with a lightweight silk blouse. I love the 70’s vibe of the tunic and the blouse along with longer slightly flared jeans…they just added to the whole vibe.
I tried several long necklaces but none of them seemed to work, however, the malachite necklace from Hart added a small pop of color and pulled the look together. My long leopard coat from Simon Miller (other options linked below) along with older suede Veronica Beard booties and a suede bag completed the look. I just love this one! I’m going to try the tunic styled with a scarf next time!
Day 3 Challenge - Revisit an old favorite and give it a new mood.
My Take…Styling a Denim Jacket Year-Round (Not Just Spring!)
Day 3 Outfit - The “old favorite” I chose for this look was a denim jacket from Veronica Beard that I’ve had for about three years. For some reason, I’ve only ever worn it in the spring with white jeans. I love the jacket (similar here) and it wasn’t inexpensive, so I have no idea what the block about wearing it all year has been about because I wear my other, more classic denim jackets year round! So…I decided to add a white peplum blouse (that I’ve hardly worn at all) under the jacket, my leather pants (several years old) and some fun jewelry from French Kande.
I adore the black lug sole boots with this look along with my new faux fur vest from Apparis. The cheetah bag from Tory Burch added texture and interest. I wore this out and about and got lots of compliments! I think this jacket would be so much fun with leopard pants so I’m going to try that next. It would also be great with the brown corduroy from the look above!
Day 4 Challenge - Introduce color where you normally wouldn’t…just enough to change the feeling.
My Take…Bold Color Combo: Red & Blue Winter Outfit
Day 4 Outfit - This look may be my favorite because one of my goals for January has been to wear more color! This look was actually inspired by an outfit I saw on Pinterest that used blue and red together. I got the red gloves recently…I’ve been wanting them for over a year and finally pulled the trigger (you can see them styled differently here). The blue sweater from H&M is actually new as well and I love the color…and it’s great with the gloves. If you order the sweater, I would recommend sizing up as it runs small.
The shimmery coated jeans are from Pistola and fun for Valentine’s Day and really any day! Camel is definitely a neutral and the coat from J. Crew from last season was a no brainer here! I’ve had the LOVE bag from Lancel for many years and it’s the absolute perfect accessory!
Day 5 Challenge - Choose one expressive piece and let everything else stay effortless - a long strand of pearls, a black leather jacket…whatever you feel is elegant but doesn’t try too hard!
My Take…Elegantly Undone: Pearls, Fur & Rhinestone Jeans
Day 5 Outfit - I wrote a whole post over on Substack called The Grace of Being Undone! When I envisioned the concept of Elegantly Undone…this was the vibe I had in mind! Pearls (see another pearl styling idea here), vintage furs, an older much loved grey sweater combined with a pair of comfortable but fabulous jeans and stilettos…that’s the look! But, having said that, I know the concept of being elegantly undone would be different for everyone, so make this challenge as “you” as you want! As far as my look goes, it’s just me! If you love vintage furs…be sure to check out this post!
Wearing my moms fur coat always makes me feel good - it actually still smells like her a little. I added two strands of pearls…one vintage and one new and love the look of those with the crewneck sweater that I tucked into the jeans. I have had my eye on these jeans from Veronica Beard for a while now and nabbed them when they went on sale! Why not wear rhinestones all year! Stilettos forever is my mantra and love them with jeans! My bag was a splurge from 2 years ago and I have absolutely no regrets! I’ll keep it for the rest of my life (similar here)!
A few takeaways…
If you see something you love and it seems a little “out there”, get it anyway - I promise you’ll wear it! I’ve pulled this bag out numerous times and it always surprises me! These are the pieces that really show your personality and give your outfits interest!
Don't be afraid to mix unexpected colors (red + blue!)
One statement piece can transform a basic outfit
Style pieces outside their "season"
Investment pieces are worth it if they make you feel amazing
This challenge was truly life-changing. I felt confident, got compliments everywhere I went, and noticed people were more helpful when I was out shopping—funny how putting out good energy works! But more than that, I loved the creativity of the style challenges. They forced me to think outside the box and really wear my clothes.
The truth? I don't need new things, I just need to reimagine what I have. I'll still add a piece here and there (spring refresh, anyone?), but I'm looking at my closet with totally new eyes now.
Your turn! Did you try even one day of the challenge? Which look would you actually wear? I'm planning to do this seasonally…let me know in the comments if you'd join me!
Also…let me know - which look is your favorite? Would you wear the rhinestone jeans?
Thanks so much for reading today and as always…I would love a comment or two!
~XOXO Suzanne