what-would-holley-wear-2It’s Holley’s turn to take over the keyboard today…sharing tips on how on how to be “One Hip Grandma” in the fashion department…

Talk about twist, this week is definitely a “fashion twist” for me!  Why?  Because we are babysitting our 18-month old grandson for a week.  This is exciting and scary at the same time…not because of the baby but because of me.  What will I wear all week?  I will be trading in ladies luncheons, shopping trips, and committee meetings for playdates, train rides and a trip to the zoo.

So, two thing you will need to know about me:

  1.  I’m a Grandmother to three precious children
  2.  I don’t dress like a Grandmother (or at least that’s my goal)

That being said, I have learned over the past nine years how to dress in my own “grandmotherly” way when I am with my three grandchildren. We spend a lot of time on the floor, going up and down stairs, playing with balls, riding scooters and bikes, and taking walks.

Here is my Grandmother uniform for this week and pretty much anytime I am hanging out with my grandchildren…

  1.  Shoes.  My three favorite pairs are my Nike running shoes, my Converse sneakers and a pair of leather dressy sneakers I purchased in Aspen this summer.  When it comes to my sneakers I don’t skimp on the price or quality.  When it’s cold outside, I have a great pair of flat Aquatalia boots from Stanley Eisenman’s Fine Shoes that I run around in.  When I say “these boots are made for walking” I really mean it!

Mrs. Twist has seen Lolly about town in this. Pink Nikes for sure.


Converse Sneakers are on-trend

2. Bottoms — Nylon walking pants, jeans and a midi skirt are my go-to’s.

Mrs. Twist’s turnDon’t let the athletic pants scare you.  Spanx has just launched an entire line of leggings — both active and everyday guaranteed to make you look like Gisele Buendchen. Check out their leggings guide here.

I love jeans.  If I could I would wear them everyday.  Do you know why? Because I have found jeans that fit me and are comfortable. If you don’t think you can wear jeans — you are WRONG! You may have to make a day of it, but visit places like Chico’s, Gap, Talbots, and Nordstrom where you can find someone to help you try on, and try on until you find the right pair for you.  They are perfect with Converse kicks, boots and heels.  Dress up or down.

tie-waist-look3.  Tops — t-shirts, a casual tuck in blouse, or a long tunic.

4.  Jackets — sports jackets, jean jackets, blazer, or puffer vest.  One of my favorite trends is to tie a shirt or jacket around my waist or drape it over my shoulders.  I may start out the day wearing the jacket if it is cool outside, but once it warms up, I tie it around my waist or drape it.  It serves three purposes — keeps me warm, keeps me from losing it, and has a slimming effect (covers the derriere).



Mrs. TwistI like puffer vests.  I have been inspired recently with monogrammed vests.  What a fun way to personalize your outfit and it would make a darling gift for Christmas.  You can find inexpensive vests everywhere and spend about $10 for monogramming.


monogrammed puffer vest


Leggings, sweater, vest, boots and scarf. It’s all about layering.

bandana-scarf5.  Accessories — sun shades, baseball cap, backpack or shoulder strap or cross-body bag A scarf is the perfect all-weather accessory either an infinity scarf when it’s cool (like the above photo) or another way to jazz up my playground style is with a blanket scarf you can wrap around your shoulders.  If you want to look super trendy, tie a bandana around your neck (choker style), or on your backpack and even around your wrist.

sunnies-and-baseball-capSunshades are not only a necessity but an accessory with a lot of pop! There are so many options and price points.  Back in the day, I only purchased expensive designer shades.  But after losing or breaking them, I started buying less expensive brands.  Backpacks are so in style now and there are great embellished ones.  Though, I tend to stick with my classic Longchamp backpack that’s great for travel and the playground. One of my absolute go-to fashion accessories is a baseball cap.  My three favorites are my plaid Burberry, my monogrammed cap and my Yale University cap (a gift from my youngest son).  Truthfully, I wear them on bad hair days, but it’s comforting to know they also make me look stylish and smart!


Merona for Target Suede Tote

Mrs. Twistmy favorite accessory for the fall is a suede tote.  You can throw everything in it from your tablet to sippy cups and cheerios.  I saw this one at Target the other day. $39 and comes in seven chic colors including my favorite for fall burgandy!  Makes me want to put a bottle of wine in there…

Believe it or not, we actually do go with our grandchildren to church, movies and restaurants and that’s when I “might” make a few style substitutes.  For example, I might exchange out the sneakers for a pair of flats or boots, wear black jeans or slacks, add a blouse or tunic, a blazer or coat and a few accessories.  On warm days, I might wear a light weight midi skirt, a blouse that I tie at the waist or a t-shirt and add flats or flat boots.  The main idea is to be comfortable and adaptable to a child’s world. Because no matter what I wear when I’m babysitting, it has to meet the shake, rattle and roll test but with a “fashion twist” of course!

Be sure to check out this week’s updated Pinterest style board to show you how to add some style to your everyday look, even if you are just hanging out on the playground with your kiddos.


Holley Williams is a personal stylist specializing in closet inventory, seasonal shopping, closet organization and wardrobe consultation.  Contact Holley at [email protected].