The Essential Wardrobe Checklist: Top Timeless Classics

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Welcome To The Essential Checklist Series!
Whether you’re shopping for basics or looking to level up, these lists will be your guide!
Over the next two months, a Top Timeless Classics category will be released each week! There will be shopping links for each itemized suggestion, as well as new merchandise added to the WWTNT Shop that will help you fill your wardrobe with the basics you need.
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Top Timeless Classics
No matter what your signature style, there are timeless classics every wardrobe needs. Think of them as the foundation of your wardrobe upon which you build. Because they are timeless, they’ve been around for ages and you probably know several of them already. But some of them are not what you would expect.
Do I Need All of them?
This list provides suggestions for your foundation. You don’t need every item. Consider your lifestyle, your shape, and your climate when deciding which ones apply to you. For instance, a pencil skirt may not be a flattering cut for your figure, or a top coat isn’t necessary for where you live.
But Which Style?
Your signature style will dictate which style to purchase. For example, if you favor minimalism, your white shirt will be simple, with an emphasis on a modern cut. But if you tend to be more romantic, you’ll choose a white shirt with ruffles or another feminine detail.
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White Button Down Shirt
A white shirt is one of the most versatile items in your wardrobe. Under a jacket or cardigan, it provides a frame for your face. Worn alone, it goes with virtually every color out there. Go with something structured, or one that’s relaxed, or something light and gauzy (or even all three!) Whatever fits your signature style.
- Theory Tenia Long Sleeve Blouse
- Theory Riduro Organic Cotton Button Down Shirt
- Universal Thread Gauze Button Down Shirt
Blue Chambray Shirt
Durable, colorful, and more interesting than a t-shirt, this workhorse can be worn alone or even as a “jacket” over a tank or tee.
- Frank & Eileen Chambray Button Up Shirt
- Rails Carter Dip Dye Denim Shirt
- Universal Thread Labette Denim Woven Shirt
Navy/White Striped Tee or Knit
The navy and white striped shirt is a nautical, timeless classic and is a staple of any Francophile wardrobe. Wear it alone or peeking out from underneath outerwear.
- Vince Striped Short Sleeve Rib Top
- Theory Stripe Cuff Tank
- Caslon Ballet Neck Knit Elbow Sleeve Tee
V-Neck Black Knit
You might have expected a turtleneck, and can certainly substitute one here. However, a turtleneck emphasizes the jawline and depending on your skin’s elasticity, it can draw attention to your age. A v-neck, scoop neck, or crew neck offers a more flattering, lower neckline.
- Maje Short Sleeve Sweater
- ATM Cashmere V-Neck Long Sleeve Sweater
- Charter Club V-Neck Cashmere Sweater
Cardigan Sweater
A cardigan is a comfortable topper that adds interest to your outfit. It can immediately take you from “around the house” to “out and about”.
- Reiss Summer Wool and Cashmere Blend Cardigan
- Theory Preen V-Neck Merino Cardigan
- Barefoot Dreams Cozy Chic Circle Cardigan
Cashmere Hoodie
This is another unexpected topper that is really quite versatile. A zip up hoodie can be dressed up (with a blouse and skirt) or down (jeans and t-shirt). It’s softness and longevity are worth the investment.
- Maje Cashmere Blend Zip Hoodie
- Theory Relaxed Cashmere Hoodie Sweater
- Charter Club Cashmere Zip Front Hoodie
Dark Denim Jeans
Think of dark denim as your “dressier” jeans. It lends itself to being dressed up more than medium or lighter versions. You’ll want to wash it infrequently to help maintain its rich color.
- Joe’s The Charlie Ankle Skinny Jeans
- Paige Manhattan High Waist Bootcut Jeans
- AG The Prima Ankle Cigarette Black Jeans
Light Denim Jeans
These are your “casual” jeans and they go with everything. They are more forgiving than white pants, while offering the same contrast to any darker colors you pair with them.
- Mother Looker High Waist Ankle Skinny Jeans
- Hudson Jeans Barbara High Waist Bootcut Jeans
- 7 For All Mankind Dojo Tailorless Flare Leg Jeans
Black Slim Pants
Substitute slim black pants for leggings or yoga pants. It’s a more polished look and can be just as comfortable when made from stretchy fabrics like ponte.
- Lauren Ralph Lauren Skinny Pants
- Theory Thaniel Trousers
- INC International Concepts Ponte Skinny Pants
Cropped Pants or Jeans
A nostalgic throwback to the fifties and sixties, there’s no better way to show off a knockout pair of shoes.
- Wit & Wisdom Ab-Solution Ankle Skinny Pants
- Majestic Filatures French Terry Pull On Cropped Pants
- FRAME Le High Ankle Skinny Jeans in Poe
A-Line Skirt
An a-line skirt is universally flattering. It balances out a figure that is fuller on top and makes a figure that is fuller on the bottom seem smaller because it bells out at the hemline. And it offers curves to someone with a straight shaped body.
- Gibson x Hi Surgarplum Positano Denim Skirt
- Mango Wrap Floral Mini Skirt
- Club Monaco Pleated Flounce Skirt
Pencil Skirt
A pencil skirt is sophisticated and feminine. Ideally, the hemline should hit just above knee. Look for something with some elastin (stretch) that will help keep its shape.
- Vince Camuto Stretch Knit Midi Tube Skirt
- Spanx The Perfect Black Pencil Skirt
- Mango Pencil Belt Skirt
Navy Blazer
A navy jacket is an ideal topper that can easily be dressed up or down. Whether you choose one that’s structured or more cardigan-like, its flattering, neutral color and polish will elevate your outfit.
- Capsule 121 Hailey Triple Pocket Jacket
- Boss Joanita Mixed Media Hooded Blazer
- Joie Neville Knit Blazer in Navy
Blue Denim Jacket
You can top virtually anything with a denim jacket and immediately create an edgy, yet approachable look. The bolder the blue, the more it will light up your face.
- AG Jeans Robyn Button Front Denim Jacket
- Lauren Ralph Lauren Patch Pocket Denim Jacket
- Universal Thread Freeborn Denim Jacket 29.99
Anorak Raincoat
The main reason to go for an anorak style is the drawstring waist. Be sure to cinch it in to create a flattering, hourglass silhouette.
- Blanc Noir Camo Print Hooded Anorak Jacket in Black
- Joules Loxley Waterproof Padded Raincoat
- Sam Edelman Water Repellent Hooded Parka
Trench Coat
A lightweight, mid-length, belted trench coat creates a beautiful hourglass shape as well. Choose one that fits in the shoulders, but doesn’t have too full a “skirt” and wear the belt tied in a clean knot, not belted.
- Lauren Ralph Lauren Belted Water Resistant Trench Coat
- Club Monaco Maite Trench Coat
- Cole Haan Signature Hooded Trench Coat
Peacoat
With its strong shoulder, the masculine, military style of a peacoat adds strength and structure to your outfit, while playing beautifully against feminine lines.
- Nili Lotan x Target Black Double Breasted Coat
- Michael Michael Kors Double Breasted Olive Peacoat
- Lauren Ralph Lauren Faux Shearling Coat
Top Coat
A top coat finishes your outfit. Choose something lightweight in a neutral color. Look for a structured shoulder to balance your shape. And keep your hemlines in mind when choosing a length for skirts or dresses. The coat should end just below the hemline.
- Lauren Ralph Lauren Belted Wrap Coat
- Lauren Ralph Lauren Wool Blend Coat
- Sam Edelman Notched Collar Wool Blend Coat 240.
Shift Dress
The shift dress or sheath dress follows the natural lines of your figure. Look for one that defines your waist, whether it’s with gathered fabric, a belt, or some other design detail. The most flattering styles drop straight from the hip and slightly taper to just above the knee.
- Tahari Knot Neck Sleeveless Stretch Crepe Sheath Dress
- Tahari Mock Neck Stretch Crepe Sheath Dress
- Harper Rose Gathered Neck Belted Sheath Dress
One Piece Swimsuit
As we get older, we sometimes look for more coverage in swimwear, but we don’t have to sacrifice style. Avoid large prints and instead go for solid colors or small patterns. Belts, gathered fabric, wide set straps, and deep v necklines can all be very flattering and are details you can use to direct the eye to your best assets.
- Tory Burch Side Tie Swimsuit
- Jets Australia Jetset Solid Tank Swimsuit
- Kate Spade New York Cherry Print Bandeau Swimsuit
Two Piece Swimsuit
You can wear a bikini for as long as you like, as long as you choose one with great support and coverage in the right areas. Helen Mirren was sporting one at 65 and looked fantastic. Solid colors or small prints are most flattering. Use deep v necks, gathered fabric, ruffles and other design elements to direct the eye to your best assets. And don’t forget sunscreen!
- Sea Level Cross Front Multi Fit Bikini Top
- Sea Level Frill Bikini Top
- Shan Classique Solid Bikini Top
Swimsuit Coverup
Do not go without a swimsuit coverup. Not only is it sophisticated and appropriate, but it completes your outfit and is much more flattering than a towel wrapped around your waist at the tiki bar. Choose a length the same way you would choosing a dress.
- Robin Piccone Michelle Tunic Cover Up
- Eberjey Sardinia Tessa Cover-Up Dress in Peacoat
- Poupette St Barth Clara Ruffled Mini Dress
Pajama Set
This is something you do just for you and it makes you feel pretty. These are loungewear “outfits” you can change into early in the evening as things wind down and wake up in feeling elegant (not dumpy). It really makes a difference in your attitude toward your appearance.
- Nordstrom Lingerie Moonlight Pajamas in Blue Air
- Eberjey Gisele Long Sleeve Pajama Set
- Desmond & Dempsey Leopard Print Classic Short Pajama Set
Matching Bras & Panties
Like pajamas, this is something you do just for you and it really does change your mindset toward taking care of yourself. Do yourself a favor, and when you buy your next bra, buy a few matching panties to complete the set. Be sure to line dry your lingerie, as the heat from the dryer will break them down faster.
- Natori Bliss Perfection Bralette
- Chantelle Invisible Memory Foam T-Shirt Bra
- Calvin Klein Seductive Comfort Lotus Floral Demi Bra
- Natori Bliss Perfection Thong
- Chantelle Lingerie Soft Stretch Seamless Hipster Panties
- Calvin Klein Seductive Comfort Lotus Floral Bikini Panty
Sneakers
These are different from gym shoes in that they have a little more elevated style for your nonathletic daily outfits. Wear them with everything from jeans to casual skirts and dresses.
- Veja Campo Bicolor Leather Low Top Sneakers
- Converse Chuck Taylor Shoreline Sneaker
- UGG Dinale Leopard Print Lace Up Sneakers
Espadrille Sandals
This timeless sandal is perfect with summer dresses and skirts. It offers lots of support and sophistication.
- Kate Spade New York Fab Wedge Sandals
- Tory Burch Espadrille Wedge Sandal
- CC Corso Como Penelopy Platform Sandal
Black Pumps
As versatile as a Little Black Dress, and available in endless styles. The goal is something as elegantly refined looking as the Manolo Blahnik. But if you’re on your feet all day, a block heel offers more support.
- Manolo Blahnik BB Pointed Toe Pump
- Nine West Astoria Suede Block Heel Pumps
- Schutz Boris Suede Slingback Pumps
Boots (Tall or Booties)
A must have for any closet, these are something you’ll look forward to taking out each season.
- Frye Veronica Harness Knee High Boot
- Nine West Hiya Heeled Boots
- Nine West Orleeh Heeled Boots
Rain Boots
Whether you choose a tall or shorter pair, look for slip resistant treads for traction on wet surfaces.
- UGG Shaye Tall Rain Boots
- Joules Print Molly Welly Rain Boot
- Joules Collette Waterproof Rain Boot
Snow Boots
If your climate calls for it, it’s a smart idea to invest in durable, timeless snow boots. The lace up “duck boot” never goes out of style and is expertly sealed against everything cold and damp. Shearling and faux fur help to keep your feet cozy and dry.
- Sorel Tofino Curry Fawn Waterproof Winter Boots
- Sorel Joan of Arc Suede Shearling Boots
- UGG Adirondack III Waterproof Boots
Tote Bag
This handbag is made for running errands. It’s spacious enough for all you need and keeps your outing hands free.
- Rebecca minkoff Megan East West Tote Bag
- Longchamp Roseau Leather Shoulder Tote
- Tory Burch Perry Leather Tote Bag
Crossbody Bag
A truly hands free bag, the crossbody bag offers you freedom of movement while shopping, enjoying a concert, or other weekend fun.
- The Marc Jacobs Snapshot Colorblock Camera Bag
- Strathberry Mini Ace Leather Crossbody Bag
- Kate Spade New York Kent Pebble Crossbody Saddle Bag
Leopard Print Clutch
Treat leopard print like a neutral pattern: it goes with everything. A leopard print clutch is chic and elegant and can be dressed up or down.
- Clare V. Calf Hair Leopard Foldover Clutch
- Rebecca Minkoff Leo Animal Print Envelope Clutch
- INC International Concepts Luci Leopard Print Clutch
Evening Bag
Don’t take a regular handbag to a cocktail party. You deserve a bag fit for the occasion, and there are many affordable options. Consider these special bags as jewelry for your outfit.
- Nina Minaudiere with Crystal Clasp
- Whiting & Davis Envelope Shoulder Bag
- Nina Desyre Crystal Minaudiere
Beach Tote
Summery beach totes are bags you look forward to taking out when the season hits. Look for strong weaves that will stand the test of time (and sand!).
- Tory Burch Ella Straw Basket Tote Bag Floral Applique
- A New Day Straw Circle Handle Tote
- Naghedi St Barths Large Tote
Weekender Bag
Again, don’t use the wrong bag for the occasion. You deserve better than stuffing your fun weekend looks into an old duffel bag. Start your getaway on the right foot and show up in style.
- Delsey Chatelet Plus Duffel Bag
- A New Day XL Duffel Weekender Bag
- Paravel Grand Tour Duffel
Diamond Studs
These are your go-to everyday earring that goes with everything. Cubic zirconias are wonderful imposters as long as you keep them on the smaller side.
- Nordstrom Precious Metal Plated Cubic Zirconia Stud Earrings
- Raye Earrings in Gold
- Jennifer Meyer Three Bezel Set Drop Earrings
Metal Bracelet
Whether you stack a set of bangles, wear it alone, or with a watch, a gold or silver metal bracelet or two draws attention.
- Tory Burch Kira Stackable Enamel Bracelet
- Jennifer Zeuner Maggie Chain Bracelet
- Brook & York Wren Initial Bracelet Set
Bracelet Band Watch
Because our phones have stepped in to tell the time, the watch has become even more of a decorative piece. Choose one with a bracelet band to add some shine to your outfit.
- Tissot Tradition Bacelet Watch 31mm
- Gucci G-Timeless Bracelet Watch
- Longines Conquest Classic Bracelet Watch
Right Hand Ring
If you’re right handed, that hand is doing most of the moving. Find something special to add to the attention it’s taking anyway.
- Arabella Sterling Silver Cubic Zirconia Three Row Ring
- Jennifer Meyer Marquise Stone Ring
- Anna Beck Cross Ring
Pendant Necklace
Pendants come in all shapes and sizes. If you’re smaller chested, a long necklace ending in a statement pendant is a beautiful choice. Those with a fuller bust, look knockout with a pendant that ends mid decollete.
- Madewell Amazonite Pendant Necklace
- Tai Mother-of-Pearl Pendant Necklace
- Knotty Layered Necklace
Statement Necklace
No matter what size a statement you’d like to make, there’s a necklace for you. A bold necklace can be dressed up or down and should be the star of the show. Keep other jewelry to a minimum.
- BaubleBar Kew Crystal Collar Necklace
- Jules Smith In Chains Necklace
- Anthropologie Beaded Collar Necklace
Tortoiseshell Sunglasses
There are three pairs of sunglasses you need: Brown, Black, and Metal Frames. Tortoiseshell refers to the speckled shades of brown in these sunglasses. The variation is flattering against your skin and goes with all your warm colors, dressy or casual.
- Tom Ford Lauren Sunglasses
- A New Day Tortoise Shell Square Sunglasses
- Oliver Peoples Marianela Cat Eye Sunglasses
Black Sunglasses
Black plastic framed sunglasses are very chic and a must have for any black outfits. Look for something substantial that works with the shape of your face. Here’s a post to help!
- Valentino Rockstud Gradient Cat Eye Sunglasses
- Tom Ford Alistair Gradient Sunglasses 475.
- A New Day Oversized Round Sunglasses
Aviator Sunglasses
Metal framed glasses, like the classic aviator, are excellent for any sporty outfits. The masculine feel of these glasses is right at home with jeans and t-shirt.
- Rag & Bone Gradient Aviator Sunglasses
- Ralph Lauren Ralph Polarized Sunglasses
- A New Day Bronze Aviator Sunglasses
Black Belt
A black belt is a trick for helping your waist “disappear”. It’s a trick stylists use to darken out that area and shift focus to other parts of the body. Corset belts are especially nice. Try one around the waist of a dress or skirt.
- Frye Campus Leather Belt
- Isabel Marant Black Lonny Belt
- Raina Vixen Asymmetrical Velvet & Leather Belt
Brown Belt
A brown belt is the other must have for your wardrobe. It’s a classic with jeans. Knotted leather and leopard print add more interest to your outfit.
- Isabel Marant Lecce Belt
- A New Day Leopard Calf Hair Belt
- Frye Studded Leather Belt
Beach Hat
A beach hat is a must for protecting your skin. Look for tighter weaves and versions that are packable. Here’s a post to help you.
- Eric Javits Classic Squishee Packable Fedora
- Frye Raffia Cybil Telescope Bolero Hat
- Brixton Joanna Straw Hat
If you’re a WWTNT subscriber, head over to the Subscriber Page to see the new Other Accessories category in the Take It To The Next Level Checklist.
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And since this is the last installment of The Essential Checklist: Top Timeless Classics, I’ve included a checklist download of all the categories to have at your fingertips.