Timeless Style: 11 Resort, Winter & Holiday Outfits; Elegant Classic Wardrobe Finds / Fashion Over 50

(ABOVE) Three of the classic and pretty looks I show in this post for winter 2024-2025.

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For YouTube Video & Outfit/Makeup Details Scroll to Bottom of Page

(NOTE: Some links that I provide in this post are affiliate links, which means if you follow that link and make a purchase I may possibly earn a small commission, at no extra cost to you. More information here.

November 24, 2024 / Video Post Notes

RESORT, WINTER & HOLIDAY OUTFITS

Wintering in Florida

If you are planning your first trip to Florida this winter, you might be wondering what sort of clothing to pack. The short answer is resort wear, which is summer clothing that is worn during the winter in beach resorts like Naples or Palm Beach, Florida. In this post and video, I show 11 outfits; several are resort outfits that you  might want to bring with you for a vacation here (outfits #3, #5, #6, and #7).

I often am asked if I wear resort clothing or fall/winter clothing during the fall and winter months. Because I live in Naples year-round, I wear both. On one day, I might wear a resort look; on another, a more wintery look. It just depends on my mood, the weather, the occasion, and where I am going.  Although I do wear winter-white or ivory pants, skirts, dresses or shoes during Naples’ winters, I save my bright white items for summer. If I lived in Naples only during the winter and up north only during the summer, I probably would wear white items during the winter, just like Florida vacationers. I do carry a bright-white bag year round, and I also wear white jeans year-round, no matter where I am–in Florida or up north.

Thanksgiving and December Holiday Looks

The other seven outfits I show in this post and video will work beautifully this winter no matter where you live. All are comprised of timeless pieces that will serve you well year after year; they are classic designs that never go out of style. Plus, the chili-red sweater and tweed jacket I show are perfect for pairing with jeans or dressy trousers during the holidays.

My Savings Codes

If you are interested in shopping for any of the items I feature in this post from Goelia, LilySilk, Ally Shoes, or Gingiberi Jewelry, you might find the following savings codes helpful (all updated as of December, 2024):

Goelia (excludes discounted items) 10JLJ for $10 off order or 20JLJ for $20 off order over $169 (Items I show in this post from Goelia were gifted to me.)

LilySilk (*Excludes Discounted Products): JLJ20, 20% off or JLJ25, 25% off over $/€/£480 (Items I show in this post from LilySilk were gifted to me.)

AllyShoes: JANIS10, 10% off first purchase (The tan flats I show in this post from Ally were gifted to me; I purchased the brown slingbacks from Ally with a discount code.)

Gingiberi 18k Gold, Diamond, Pearl Jewelry: Janis15, 15% off site-wide; free 30-Day returns (Items I show in this post from Gingiberi were gifted to me.)

Thank you, as always,  for visiting my blog. I hope you have a wonderful week ahead.

~ Janis

Janis Lyn Johnson
Classic-Style Lover. Happily Married. Born in 1960. Fan of Understated, Timeless Fashion and Healthy Living.
Editor
JLJ Back To Classic

Previous Posts:

Timeless Style: Ferragamo Sofia Bag, Ivory Ruffle Blouse, Ivory Jeans, and Pastel-Blue Cardigan OOTD
Blog Post, YouTube Video

Timeless Style: Refurbishing My 1994 Louis Vuitton Monogram Speedy 30; Plus My Brown Cardigan, Ruffle Shirt, and Khaki Pants OOTD
Blog Post, YouTube Video

Timeless Style: Nine Elegant, Understated Fall-Winter Outfits
Blog Post, YouTube Video

Timeless Style: Longchamp Leather Le Pliage XS Bag and Camel Sweater-And-Skirt Set OOTD
Blog Post, YouTube Video

Timeless-style Favorites: Six Outfits Featuring Classic Summer-To-Fall Transition Staples
Blog Post, YouTube Video

Timeless style: 10 Classic Summer Wardrobe Staples, Five Outfits, Pairing Navy and White With Red
Blog Post, YouTube Video

Vlog-Timeless Style: Louis Vuitton Bandouliere Malletage Speedy 25; Black Tee, Pink Pants; Brunch and Shopping David Yurman
Blog Post, YouTube Video

Timeless Jewelry: Five Cherished, Vintage Heirloom Pieces; And Six Classic New Pearl Finds
Blog Post, YouTube Video

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Scenes From The Video

(Note: I am 5’8” tall; size XXS or XS or 0-2 in most tops; size 2, 4 or S in most bottoms and size 27 in most jeans; size 9.5-10 in most shoes.)

Outfit #1

18k-Gold and AAA-Pearl Removable-Drop Earrings

Organic Cotton Long Pajama Set, Bagheera (I’m in size Tall, S)

Suede Mules, Black

 

Outfit #2

18k-Gold and AAA-Pearl Removable-Drop Earrings

Eco-Friendly Bamboo-Viscose Long Robe, Bagheera (I’m in L)

Suede Mules, Black

 

Outfit #3

18k-Gold, Diamond, and AAA-Akoya Pearl  Bow Earrings

18k-Gold, Diamond and AAA-Akoya Pearl Leaf Necklace

Tapestry Midi Dress, With Belt (I’m in size S)

Ray-Ban Sunglasses, Round Double Bridge

Prada Re-Edition 2005 Bag, Black (mine was purchased at Saks in 2022)

Suede Mules, Black

 

Outfit #4

18k-Gold and AAA-Pearl Removable-Drop Earrings

Pima-Cotton 3/4-Sleeve Bateau-Neck Tee, Ivory (I’m in size PP)

Pima-Cotton Long-Sleeve Crewneck Tee, Ivory

Faux-Suede Skirt, Brown (I’m in size 4)

Ray-Ban Sunglasses, Round Double Bridge

Louis Vuitton Trouville Bag (mine was purchased at Louis Vuitton in 2006)

Leather Skinny Belt,  Brown

Brown Suede Kitten-Heel Slingbacks (JANIS10 for 10% off your first purchase; more colors available)

 

Outfit #5

18k-Gold and AAA-Pearl Removable-Drop Earrings

18k-Gold and AAA-Pearl Station Necklace

Short-Sleeve Tweed Shift Dress, Frozen Blue (I’m in size 2)

Sleeveless Boucle Tweed Shift Dress & Coat, Windowpane Fiddle Leaf Green

Short-Sleeve Tweed Shift Dress, Capri Blue (more colors, prints available)

Long-Sleeve Tweed Shift Dress, Hot Pink (more colors, prints available)

Sunglasses, Rosewater (narrow, medium, wide widths)

Ray-Ban Sunglasses, Round Double Bridge

Chanel Timeless CC Shoulder Bag (circa 2004; mine was purchased preloved in 2011)

MCM Visetos Aren Small Hobo, Soft Pink (10% off first purchase)

MCM Himmel Laurentos Small Tote, Silver-Pink (10% off first purchase)

Salvatore Ferragamo Shoulder Bag, Pink

Salvatore Ferragamo Varina Ballet Flats, Pink

Cashmere Crewneck Sweater, Bright Pink

Cashmere Crewneck Cardigan, Bright Pink

 

Outfit #6

18k-Gold, Diamond, and AAA-Akoya Pearl  Bow Earrings

18k-Gold and AAA-Pearl Station Necklace

Sequin-Plaid Short-Sleeve Sweater (I’m wearing size XS)

Sequin-Plaid Cardigan (I’m wearing size PP)

Jeans/Jeggings, White (I’m in size 2)

Ray-Ban Sunglasses, Clear Frame

Warby Parker Sunglasses, Clear Frame

Louis Vuitton New Wave Bag, White (mine was purchased at Louis Vuitton in 2019)

Leather Slingback Flats, Metallic Gold

Stuart Weitzman Emelia Flats, Light Gold (also Neiman Marcus; Nordstrom; Saks)

 

Outfit #7

18k-Gold, Diamond, and AAA-Akoya Pearl  Bow Earrings

18k Gold and AAA-Pearl Station Necklace

Wool-Blend Short-Sleeve Sweater (I’m wearing size XS)

Wool-Blend Cardigan (I’m wearing size PP)

Puffer Jacket, Pearlescent White

Silk Trousers, Off White (I’m wearing Size 6)

Leather Belt, Ivory (more colors available)

Christian Dior Medium Lady Dior Bag, Latte (mine was purchased at Saks in 2019)

Ray-Ban Sunglasses, Clear Frame

Warby Parker Sunglasses, Clear Frame

 

Outfit #8

(ABOVE & BELOW) These Wool Wide-Leg Sweater Pants (I’m in size M) are so cozy and comfortable. They’re just perfect for wearing at home in the evening with a sweater. I show them here with flats, which I like for indoors. If I were going to wear them out, however, I’d choose a little bit higher heel–either a boot or pump–so that they don’t touch the ground. They are a little long on me. 

18k Yellow-Gold, Diamond Bar-Stud  Earrings With 4-5mm Double Pearls

18k Rose-Gold, Diamond, and 10-11mm AAA-Pearl Necklace

18k Rose-Gold Station Bracelet with 7-7.5mm AAA Pearls (the pearls can be placed where you wish on chain)

18k Yellow-Gold, Diamond, and 4.5-5mm AAA-Pearl Ring

Polo Shirt, White (I’m in size XXS)

Wool-Blend Cableknit Sweater, Pale Pink (I’m in size XS)

Sunglasses, Rosewater (narrow, medium, wide widths)

Wool Wide-Leg Sweater Pants, Light Melange Beige (I’m in size M)

Cashmere-Wool Blend Wrap Coat, Heather Brown (I’m in size S)

Prada Double-Bag Tote, Cammeo

Ballet Flats, Tenacious Tan Suede/Bossy Beige Leather  (JANIS10 for 10% off first purchase; more colors available)

 

Outfit #9

18k Yellow-Gold, Diamond Bar-Stud  Earrings With 4-5mm Double Pearls

18k Rose-Gold, Diamond, and 10-11mm AAA-Pearl Necklace

18k Rose-Gold Station Bracelet with 7-7.5mm AAA Pearls (the pearls can be placed where you wish on chain)

18k Yellow-Gold, Diamond, and 4.5-5mm AAA-Pearl Ring

Mohair-Wool Blend Sequins Sweater, Foggy Grey (I’m in size XS)

Silk Tie-Neck Blouse, Winter White (I’m in size XXS)

Straight-Leg Jeans, Dark Cherry

Versace Small Medusa 95 Bag, Burgundy (also Saks 5th Ave.,  Neiman Marcus, Nordstrom)

Leather Ballet Flats, Midnight Burgundy

 

Outfit #10

18k Rose-Gold, Diamond, and 3-7mm AAA-Pearl Earrings

18k Rose-Gold, Diamond, and 10-11mm AAA-Pearl Necklace

Silk Ruffle Stand-Collar Blouse, Cream (I’m in size XXS)

Wool-Tweed Sparkle Long Jacket, Chili Red (I’m in size XXS)

Crepe Straight Ankle Pants, Black

Ponte-Knit Wide-Leg Pants, Black

Chanel Small Chevron Chic Bag, Black (mine was purchased at Saks in 2018)

Black Silk Pumps (mine were my mother’s, from the 1960s; similar also here)

Sunglasses, Black (narrow, medium, wide widths; more colors available)

Satin Hair Scrunchie, Large, Burgundy Red (set of 3 small, 3 large)

 

Outfit #11

18k Rose-Gold, Diamond, and 3-7mm AAA-Pearl Earrings

18k Rose-Gold, Diamond, and 10-11mm AAA-Pearl Necklace

Silk Ruffle Tie-Neck Blouse, Winter White (I’m in size XXS)

Mohair-Wool Blend Sparkle Cardigan, Chili Red (I’m in size S)

Satin Hair Scrunchie, Large, Burgundy Red (set of 3 small, 3 large)

Silk Trousers, Off White (I’m wearing size 6)

Leather Belt, Ivory (more colors available)

Christian Dior Medium Lady Dior Bag, Latte (mine was purchased at Saks in 2019)

Ray-Ban Sunglasses, Clear Frame

Warby Parker Sunglasses, Clear Frame

 

My New Sunglasses

(ABOVE & BELOW) These are my first Ray-Ban Sunglasses purchase! What makes them unique is that you are able to design them yourself. You choose the frame color, lens color, and more.

Ray-Ban Sunglasses, Round Double Bridge

Silk Ruffle Stand-Collar Blouse, Cream (I’m in size XXS)

 

My Makeup & Hair Products (Clean, Low in Toxicity)

(ABOVE & BELOW) I am wearing the same makeup and hair products throughout this post and video. For details on all of the items, including the tools I used, scroll down the page.

Lip Pencil, Spice

Lip Gloss, Mocha Latte

Gold Dual-Ended Retractable Lip Brush (for lining and filling-in lips with lip color)

Eye Pencil, Black/Brown

RMS Beauty Unpowder Powder (applied to eyelids before and after eye pencil as primer/setting powder; also Amazon)

Makeup Brushes/Sponge/Case (to apply my face, eye, and cheek makeup)

Pacifica Mascara, Black/Supernova

Set of Four Portable Eyelash Combs, Pink (to comb out mascara)

 

Vaseline Triple Purified, 100% Pure Petroleum Jelly  (applied to cheeks and cheekbones as highlighter; also Target)

1-Ounce Glass Jars (set of 6, for storing Petroleum Jelly, Shea Butter, etc.)

Organic Argal Oil (EWG-rated well/low toxicity/low allergies)

Hair Comb

Hot Rollers (available in blue or coral)

Hair-Styling Mousse (listed 2/low toxicity at EWG Build Your Own Report and listed 1/low toxicity at EWG Skin Deep)