Meghan Ashley Styling

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Basic Doesn’t Have to Mean Boring: 5 Stylish Options to Make Winter Life Easier

When we start to dive in with the goal of redoing our wardrobes, it can be easy to have lofty goals. We can easily over-complicate ourselves. I see it nuuuuuuuuuumerous times with my clients. We get all tussled up and we buy... and buy... and… feel like our closet is utter chaos. 

That’s when I just have to unravel their closets and go back to the basics. 

So if you find yourself feeling like you have too many clothes and nothing to wear, then I encourage you -- for the next two months (just 60 days) -- and go back to the basics!

The basics are our foundation for style and we can’t have style without good quality basics that know how to flatter our body type. 

So here are a few categories for you to use as a checklist that I promise will help you simplify your wardrobe and lead straight to Winter season chic-ness!

Black, navy or white jeans/pants/slacks

  1. Do you feel comfortable wearing them? Are there any parts digging in, or slouching and slipping?

  2. Does the fabric flatter you? Is it of a good quality and does it cut a sharp appearance?

  3. Do you like the style? Between straight, flared, boot-cut, skinny, etc.,you’ve got a lot of options - do you like your choice?

Frame Buttoned Jeans

Black ankle bootie

  1. Are they comfortable? Or will you be in a foul mood after enduring them for four hours?

  2. Does the style match up with most of your favorite pants and dresses?

  3. Are they appropriate for a variety of occasions?


Sam Edelman Daysie Bootie

Neutral sweater (camel, black, grey, cream, or navy)

  1. Does the cut (boat, crew, scoop or V-neck) flatter your body type? 

  2. Is the fabric (cashmere, wool, etc.) in good condition and of high quality?

  3. Do you feel comfortable wearing it? Does it feel like “you”?

French Connection Rolled Mock Neck Sweater

Classic jacket/coat

  1. Does its practicality work withr the weather you live in?

  2. Can this jacket suit a multitude of occasions?

  3. Does your jacket flatter your body type and personality?

Reiss Longline Coat


Neutral dress

  1. Is this dress flattering to your body type?

  2. Can it work with a variety of scenarios depending on how you accessorize it?

  3. Will the style and lines of this dress still be chic seven years from now?

Theory Stretch Wool Blend Dress And of course you could layer a thin turtleneck and tights with this dress

There you have it! I hope my outline will help you get closer to your style goals. 

For a full guide to redoing your wardrobe, please check out my new book The Catholic Wardrobe, available on Amazon now!

Question: What Winter clothing piece is a life-saver for YOU?!