Fashion Fridays Mondays: The Classics

*Sorry some of the font/spacing is wonky. I’m not sure how to fix it!
Today’s Fashion Friday Monday post focuses on the classics. These are quality pieces that every woman should have in her wardrobe to build a foundation for timeless looks. The inspiration is obviously Jackie O, one of the biggest fashion icons in history. Her grace, beauty, and flair has continued to influence looks.

Jackie O

Michelle Obama has carried on this tradition of donning clean, classic clothing and can provide inspiration as well.

Michelle Obama

Taking these ladies as inspiration for a classic look, I’ve narrowed down the list of necessary items to 12 key pieces:
1. Button-up

Rachel Stretch Cotton Shirt

Slim-Fit Stretch Poplin

A crisp button-up can do wonders for an outfit. It can be dressed up (as seen above left) or down (above right) according to what it’s worn with (pants, skirt, accessories). A button-up can also be sexy as well!
Rachel Stretch Cotton Shirt: Ralph Lauren Black Label $325
Berlynn Slim-Fit Stretch Poplin Shirt in Lilac/White: Ralph Lauren Black Label $145

2. Flats

Tods Flat

Tory Burch Flats

A cute pair of flats can be both fashionable and functional! They come in every color, finish, and price point, but the styles above from Tods and Tory Burch have become really popular, chic choices.
Tods Flats: Saks $215
Tory Burch Flats: Saks $195
3. Perfect Pumps

Cole Haan Pumps With Nike Air Technology

Every woman needs a perfect pair of pumps to go with everything from a suit to jeans . The heel shouldn’t be too high and the shoe should have classic styling (no side cuts or toe cleavage). Cole Haan makes my absolute favorite shoes because they are made with Nike Air technology and are super comfortable. I’ve had a pair for 5 years now and I still love them! They are (almost) like wearing my running shoes!
Cole Haan Talia Pump w/Nike Air: Zappos $128
4. LBD/LD (or an impeccably tailored little dress no matter the color or print)

Tahari Ruffle Dress


Tahari Wrap Dress

The importance of a LBD goes without saying. A basic black shift dress can be updated with a bib necklace or scarf. The options above are cute takes on the LBD that include somewhat different stylings: ruffles and wrap style.  Tahari has the cutest LBDs at all price points and offers great choices for work and leisure.
Elie Tahari Ruffle Dress: Bluefly $227
Tahari ASL Wrap Dress Bloomingdales $128
5. Pencil Skirt

J. Crew Bi-Stretch Wool Pencil Skirt


Superfine Cotton Pencil Skirt

I hope pencil skirts never go out of style. If they did, my choices for what to wear to work would be dramatically cut in half! They flatter almost every shape and if well-made, a pencil skirt can be just as comfortable as wearing pants! I especially love tucking in a pretty blouse or button-up. J.Crew (along with Banana Republic, Ann Taylor, Theory) has great options.
Bi-stretch Wool Black Pencil Skirt: J.Crew $118
Superfine Cotton Pencil Skirt in Smokey Graphite: J.Crew $98

6. Bootcut Jeans

Citizens of Humanity Kelly Boot Cut Jeans

7 For All Mankind Skinny Boot Cut

While jean trends come and go, a great pair of bootcut jeans will last the test of time. They flatter all shapes and sizes and can be dressed up or down. I highly recommend investing in a few quality pairs in a darker wash that are unadorned in the front and back (no back pocket craziness). Good options include: 7 for All Mankind, Citizens, Paige, Current/Elliot, Rich&Skinny, or for a little less $$ Madewell).
Citizens of Humanity Kelly Boot Cut Jeans: ShopBop $150
7 For All Mankind Skinny Boot Cut Jeans in Rinsed Indigo: ShopBop $155
7. Sleek and Slimming Dress Pants

Theory "Max C" Flat Front Trousers

Theory "Eleisha" Ankle Pants

A  great-fitting, quality pair of trousers can be indispensable. Theory makes some of the best suits/pants and they will last you forever! Make sure to invest in both a classic boot cut and cropped style as shown above. Keep in mind that you will probably have to tailor your pants (especially the hem), but it’s worth it for a great fit!
Theory “Max C” Flat Front Trousers: Bloomingdales $245
Theory “Eleisha” Ankle Pants: Bloomingdales $295

8. Fitted Blazer

Black Boyfriend Blazer

Chambray Blazer

While oversize boyfriend blazers have become popular in the past two years, a well-tailored blazer that nips you in at the waist is a timeless piece that can worn over anything dresses, button-ups w/jeans, and blouses w/skirts. These blazers are pretty much ubiquitous now, but you can get really nice quality one for a little bit under $100.
Silence & Noise Boyfriend Blazer: Urban Outfitters $78.00
Chambray Blazer: Anthropologie $88.00
9. Boyfriend Cardigan

CeCe Oatmeal Cashmere Cardigan

Tory Burch Cardigan


A boyfriend cardigan that’s slightly longer and looser fitting can be a perfect topping for a pretty blouse, tank, or shirt. It’s a great, chic coverup for chilly spring or fall days.
CeCe Oatmeal Cashmere Cardigan: BlueFly $139 (down from $268!)
Tory Burch “Simone” Cardigan: Bloomingdales $225
10. Trench

Anne Klein AK Ruffle Collar Trench

Burberry Short Poplin Trench

A trench will always be a classic way to cover-up whether it’s raining outside or not. Invest in a really nice coat now and it will last you forever!
Burberry London Poplin Short Trench: Bloomingdales $1,095
AK Anne Klein Ruffled Collar Trench Coat: Macy’s $99

11.Satchel or Hobo

Cole Haan Vintage Valise Claire Mini Black Satchel

Tory Burch Amanda Hobo in Cognac

A leather satchel or hobo in a neutral color will complement any outfit. I didn’t pick the Cole Haan satchel above because it is named “Claire” (well that wasn’t the only reason 😉 but because it is a classic shape in a lovely black leather that will go with anything and will last forever!

Cole Haan Vintage Valise Claire Mini Black Satchel: Zappos $348
Tory Burch Amanda Hobo in Cognac: Bloomingdales $465

12. Clutch

Henri Bendel Debutante Assymetrical Clutch in Dark Red

Halston Heritage Jenny Fold Clutch in Black Sequins

Finally, a clutch is a perfect accessory for nighttime looks. I recommend something with a bit of sparkle or a little something extra that can dress up a look so you can go from day to night easily if need be.

Halston Heritage Jenny Fold Clutch in Black Sequin: ShopBop $195

Henri Bendel Debutante Asymmetric Clutch in Dark Red (looks pink above): Henri Bendel $168.75 (on sale!)

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2 Responses to Fashion Fridays Mondays: The Classics

  1. Several things . . .
    I love the word “wonky.”
    I love Jackie O.
    I love every piece in this post!
    I love YOU!

  2. Awww thanks!! I’m soooo excited for this weekend 🙂 Hopefully I can still stay over Fri night???

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