In this week’s episode, Holly is diving headfirst into the stylish side of what she calls your “Post-Career Lifestyle” - because who really wants to use the word retirement, anyway?
Whether you're downsizing your work hours or declaring a permanent vacation, your wardrobe deserves a glow-up just as much as your mindset.
Holly’s giving you permission (and the blueprint) to evolve your style, refresh your closet, and dress intentionally for this exciting new chapter of life.
If you've ever stared into your closet wondering how to dress for days without board meetings, packed schedules, or uncomfortable office wear, this episode is your stylish lifeline. Head on over to your Pinterest board to see all of the examples discussed!
Key Style Areas Covered in This Episode:
Shoes: Comfortable AND Cool
Shoes that DON'T kill your feet don’t mean boring. From New Balance 327s to Superga classics and Vejas, we discuss favorite “lifestyle sneakers” that go with everything—from jeans to dresses.
Need a comfy yet chic sandal? Listen or head on over to our YouTube channel to watch, listen, and learn.
Pants: Fit, Fabric & Flattering Cuts
Terrible polyester, pants that are too short, or stores that skew to "mature" customers are things to steer clear of. Structured fabrics, proper pant lengths (above the ankle, please!), and the magic of a good tailor are things that are a non-negosh.
She gives a big shoutout to *linen blends* for summer style—breathable but not wrinkle-prone—and urges everyone to ditch the iron and invest in a steamer!
Tees & Blouses: Quality Over Quantity
T-shirts aren’t just for lounging. A flattering tee is also a must—think fitted, vibrant, and logo-free—and why your souvenir shirts from that trip to Aruba should probably stay home.
For blouses, try different sleeve styles and colors, and avoid overly flowy tops that can actually add bulk. Just say "no" to schmata tops.
Dresses & Skirts: Casual, Chic & Ageless
From sporty polo dresses at Lacoste to stylish skirts and shorts, make sure you listen to the full episode for options that are comfy, casual, and stylish at any age.
There's even genius layering tips—like wearing a tee under a strapless dress—and how to style a maxi skirt with sneakers for instant fashion cr
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