What To Wear On A Gray Day In May

What’s the best thing about fashion over 40? You already own a pair of ankle crop flare jeans in your closet … from the year 2000! However, the worst part is figuring out what to wear to stay on trend but not look silly for your age. Especially when the season is changing and you may have a bit of fashion dread about the warmer weather. Start by wearing pieces that are comfortable and fit well. Lately I find oversized pieces to be a great solution to this dilemma! They skim over body flaws and make you feel confident, covered up and appropriate. The day of skimpy and uncomfortable clothes are gone for me, and I’m glad.

I picked up a Topshop Boutique Oversized Biker jacket and it comes in so handy for spring’s unpredictable weather from chilly days to rainy nights. Yet then there are those unexpected days which get much warmer so a t-shirt is the way to go! I’m wearing a colorblocked Thakoon for DesigNation top I found at Kohl’s last fall. Sorry, it is no longer available, but I stumbled upon this very similar Extended Stripe Hem Tee which also happens to be from TOPSHOP. I tell you TOPSHOP is not just for your daughter!

I kept my James Cured by Seun crop flare jeans because I always liked the silhouette, but I did have to practically wait a 17 year cycle to wear them again. These Current/Elliott The Kick Jeans are identical and I tell you you do need a pair this season! Cropped jeans are lighter and cooler to wear in warm weather and they highlight your shoes. A slingback bootie makes a good transitional shoe in spring when you aren’t quite ready for sandals. My shoes are from Vince but these Chinese Laundry Try Me Pointed Toe Booties are similar and at $59.97 you can’t beat the price. I am in love with my Barneys New York Duffel Bag! It holds everything I need and keeps my phone handy in an outer zipper pocket. It also has a cross body shoulder strap for city (shopping) excursions. I am wearing only one piece of jewelry (I tend to do that when I have a bit of craziness going on elsewhere i.e., my top) which is a huge statement ring. Lele Sadoughi offers a wonderful selection of statement rings like this Sandbar Ring.


* indicates required




carol-calacci-casual-outfit-side view-may-2016



Are you following Fountain Of 30 on Facebook, Twitter, Instagram and Pinterest? We’ve got lots going on, so join in on the fun! Subscribe to our newsletter here. Oh and we are now on Snapchat too!

Photos: Tyisha Liddell for Fountain Of 30

Leave a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.