Why Dressing "Cool" is Essential To Your Mental Health

You can't be a badass in sweatpants.

Personal shopper & wardrobe stylist Lindsey Hutter, pictured above

Personal stylist Bree Jacoby (aka Queen Bree) and Founder & CEO of BREE JACOBY, INC. reminds women often of this simple power statement: “You need to dress cool. You just do.”

And I have to agree. Because when you dress like a badass, you feel like a badass. And when you feel like a badass? You guessed it. You act like one. This is the point I’m always trying to drive home to women who say things like, “But I work from home. No one sees me.”

My response to that is always: You can’t be a badass in sweatpants.

While Bree means that quite literally — referring to “cool” as sleek, chic, badass, and effortless — “cool,” while usually associated with sister terms like “edgy” and “fashion-forward,” means something different to everybody.

What Does Dressing Cool Mean To You?

This is dependent on three major things:

  • Personal preference

  • Personality

  • Lifestyle / Occasion

I’ll use myself as an example: I’m a freelance writer. I spend most of my days working out of coffee shops on my laptop, taking phone calls here and there. Because I am alone most of the day, it is IMPERATIVE I look the part so I can BE the part.

Because I favor bold outfitting — give me anything that’s oversize, different, and that which makes people do a double take — vibrant colors, silky fabrics, unexpected silhouettes, and weird patterns speak to my cool vibe soul — while Plain Jane outfits repulse me. Because….How can I expect to be the next Anna Wintour in a white tee and jeans?

2 Questions For You!

(1) What is most important to you when shopping for new clothes?

(2) What does your dream wardrobe look like as a Boujee-Cool Mom who needs standout outfits for her social life?

Let me know your answers by hitting reply to this email!


Dressing cool is essential to your mental health because it makes you feel like an elevated version of yourself, leading you to act like an elevated version of yourself. You deserve to look and feel like a badass, every day. Don’t forget it!

As a Feel Good Expert, I’m here to help you look cool. Because it matters.

Sip Sip is a weekly newsletter dedicated to making millennial moms feel seen in the realm of mental health + wellness + fashion. As the editor, I’m committed to easing your mom woes — one newsletter at a time — through advice, lessons, and humor on how to live your one and only life right.

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Thank you so much for being here! Stay fabulous.

Be you.

Xo, Ash

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