Fashion isn’t about age—it’s about confidence and knowing what works for your body. As we mature, our style evolves, requiring wardrobe formulas that combine comfort, sophistication, and personal flair. I’ve gathered 20 foolproof outfit combinations that my fellow stylists and I recommend for women embracing their fabulous 50s and beyond.
1. Tailored Blazer + Straight-Leg Jeans
Honey, nothing says ‘I’ve got my life together’ quite like this power duo! The structured shoulders create beautiful lines while those straight-leg jeans elongate your gorgeous legs.
Throw on some ankle boots and watch heads turn at the grocery store. Trust me, I’ve witnessed the magic firsthand.
2. Wrap Dress + Statement Earrings
Where have wrap dresses been all your life? These figure-flattering marvels cinch at your best spots while creating a gorgeous silhouette that works for every body type.
Add those bold earrings you’ve been saving for ‘special occasions’—darling, Tuesday is special enough! The combination is unbeatable.
3. Silk Blouse + Wide-Leg Trousers
If comfort married elegance, this would be their beautiful offspring! The flowing silk creates a luxurious feel against your skin while those wide-leg trousers bring the drama.
Though initially skeptical about this pairing, I’ve converted countless clients who now swear by this combination for everything from board meetings to brunch.
4. Cardigan + Slim-Fit Pants + Shell Top
However did we survive before the invention of this holy trinity? The cardigan brings warmth without bulk, slim pants showcase your shape, and that shell top ties everything together seamlessly.
When clients feel stuck in a fashion rut, I immediately prescribe this formula—it’s my secret weapon for instant polish!
5. Monochromatic Layers in Neutral Tones
Forget what you’ve heard about ‘dressing your age’—monochromatic dressing is pure sophistication! Varying textures in the same color family create visual interest while the continuous line makes you appear taller.
Yes, even us vertically challenged fashionistas can rock this look! My clients gasp when they see the difference.
6. Statement Jacket + Simple Base Layers
Why blend in when standing out feels so delicious? A vibrant jacket transforms basic pieces into a head-turning ensemble that screams confidence.
Under that showstopper, keep things simple with solid colors. Though clients initially resist bold jackets, they quickly become addiction-level favorites—I’ve created many statement jacket converts!
7. Midi Skirt + Fitted Knit Top
Gone are the days when skirts felt fussy! Today’s midi skirts pair brilliantly with simple knit tops for an outfit that works harder than your coffee maker.
The slight waist definition flatters without constricting, while the midi length is both practical and elegant. After years of styling, I still reach for this combo myself!
8. Dark Wash Jeans + White Button-Down + Colorful Scarf
Though seemingly simple, this combination packs more style punch than outfits requiring twice the effort! Those dark jeans slim while the crisp white shirt brightens your complexion.
Meanwhile, that vibrant scarf near your face? Pure magic for enhancing your natural coloring! I’ve witnessed this transform even the most fashion-resistant clients.
9. Structured Dress + Statement Belt
If fabulous were a formula, this would be it! A well-cut dress creates an instant outfit, while that statement belt defines your waist and adds personality.
While many clients initially shy away from belts, they quickly become converts after seeing how this simple accessory completely transforms their silhouette. It’s fashion alchemy!
10. Ponte Pants + Tunic + Layered Necklaces
Whoever invented ponte pants deserves a standing ovation! These miracle workers combine the comfort of leggings with the structure of trousers.
Paired with a hip-skimming tunic and those layered necklaces you’ve been collecting, you’ll create a balanced silhouette that’s both comfortable and chic. My clients call this their ‘secret weapon outfit.’
11. Pencil Skirt + Three-Quarter Sleeve Top
Though classic, this combination is anything but boring! The pencil skirt creates a sleek line while that three-quarter sleeve length shows off your wrists—one of those areas that never ages!
When clients want to feel instantly pulled-together, I steer them toward this formula that works for literally any occasion.
12. Elevated Athleisure: Luxe Joggers + Cashmere Sweater
Who says comfort can’t be chic? Luxe joggers in fine fabrics paired with sumptuous cashmere create an outfit that feels like pajamas but looks like a million bucks!
Add some sleek sneakers and suddenly you’re the coolest woman at the farmers market. I’ve converted countless skeptical clients to this formula—they never look back!
13. Leather Jacket + Feminine Dress
Forget outdated rules about ‘age-appropriate’ dressing! The contrast between tough leather and flowing fabric creates an irresistible tension that works at any age.
Though hesitant at first, my clients who try this combination quickly make it their signature look. There’s something magical about this juxtaposition that simply works!
14. Cropped Pants + Loafers + Oversized Shirt
Sometimes the simplest formulas pack the biggest style punch! These cropped pants showcase great ankles while those loafers add polish without sacrificing comfort.
The oversized shirt balances proportions beautifully. When clients complain about nothing to wear, I prescribe this combination—it never fails to deliver effortless chic!
15. Jumpsuit + Statement Jewelry
Contrary to popular belief, jumpsuits aren’t just for the young! The right cut creates a lengthening effect while eliminating the need to coordinate separates.
Throw on some eye-catching jewelry and you’re instantly event-ready. Though initially resistant, my clients who try jumpsuits become their biggest evangelists—it’s that good!
16. Crisp White Shirt + Colorful Pants
Never underestimate the power of this dynamic duo! That pristine white shirt brightens your complexion while those vibrant pants showcase your personality.
Though white shirts intimidate many clients initially, they quickly become wardrobe workhorses. I’ve yet to find an occasion where this combination doesn’t work beautifully!
17. Maxi Dress + Denim Jacket
Whoever claimed maxi dresses aren’t flattering clearly hasn’t tried this formula! The flowing length creates drama while that denim jacket adds just enough casual edge.
The result? An outfit that works for everything from grocery shopping to gallery openings. My clients report feeling simultaneously comfortable and pulled-together—fashion nirvana!
18. Turtleneck + Statement Earrings + Slim Pants
Though seemingly simple, this combination creates a canvas for your gorgeous face! The clean lines of a turtleneck frame your features perfectly while those statement earrings draw attention upward.
Slim pants balance the proportions beautifully. When clients need foolproof elegance, this is my go-to formula that never disappoints!
19. Sheath Dress + Structured Jacket
If power dressing had a formula, this would be it! The streamlined sheath creates a beautiful silhouette while that structured jacket adds authority without trying too hard.
Though initially intimidated by this combination, my clients quickly discover its transformative effect on both appearance and confidence. It’s like wearing invisible armor!
20. Patterned Top + Solid Bottom + Coordinating Cardigan
Why choose between patterns and solids when this formula gives you the best of both worlds? The patterned top brings visual interest while solid bottoms create a sleek line.
That coordinating cardigan ties everything together beautifully. My clients love how this combination makes getting dressed practically foolproof—even on Monday mornings!