6 Things To Keep in Mind as You Outfit Yourself This Fall (And Forever)

Hello again sweaters and red wine

Sip Sip is a weekly newsletter dedicated to making moms feel SEEN in the realm of mental health. 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 life right.

Happy Tuesday Friends!

Clearly I can’t get it together to send the newsletter out on Sundays. This weekend was filled with socializing, wine, and apple picking, which clouded my sleep-deprived brain even further. And because Sip Sip is all about making mental health work fun, I guess I was just practicing what I preach.


Fashion has been on my mind lately — so much so that I’ve been having dreams of going shopping and picking out the perfect silk jumpsuits + kimonos + sexy/sporty streetwear that fit my bod juuuuuuuust right. They are the best dreams, and they are where I get my best style inspiration these days — both for my own fashion sense and for my clothing brand in-the-making.

What does this have to do with YOU, you ask? Kind of everything, as September is a month synonymous with who we want to be and goals we want to achieve for the remainder of the year.

That said…if you aren’t in the fashion industry yourself, knowing how to dress can be a serious daily struggle, and THAT IS FRUSTRATING. And because we’ve been out of practice thanks to the plague, it feels especially daunting this season.

However! Figuring out a style that feels right to you can (and should) be a fun pursuit. While you can get inspiration from Pinterest, Instagram, and IRL street style, you can’t obtain a style that truly speaks to you without your own trial and error.

For this reason, here are some keen reminders to ensure you are buying the right clothes for *you* whilst shopping and/or recreating new outfits from your wardrobe:

1. Your body isn’t the problem — the clothes you’re wearing are.

Experiment with different sizes, silhouettes, and textures to find what speaks to you. And please, disregard sizing. The “But I’m an XS” complex needs to stop.

2. When you come across a “cool brand” on Instagram that seems too good to be true, it is more than likely too good to be true.

In my opinion, you should always be skeptical of a low price point.

3. Ask questions about fit, function, and fabric when shopping online.

When you can go straight to the source through a seller on Etsy, Poshmark, or customer service rep from a brand you’re eyeing, ask all the questions you can about how the item fits and feels. No one wants to deal with returns.

4. Fit is the most important factor in buying new clothes.

If you absolutely love something but it doesn’t fit right, don’t buy it. You won’t wear it and it will make you sad every time you see it hanging in your closet.

5. Do not give a f*ck about trends.

Seriously. We are too old to be following trends. Why anyone would want to look like someone else — let alone everyone else is something I’ll never understand. Create your own style.

6. Shopping in person will always override shopping online.

If you care about your appearance — and your mental health and your confidence and your job and everything else happening in your world that’s directly tied to your appearance — you will make time to shop in-store. View it as the necessary investment it is.

See you next week!

If you’d like to support this newsletter further, that would be SO FABULOUS. Proceeds from memberships will go toward my clothing line, VALT, whose mission is to help moms reclaim their identity through fashion. You can get the full scoop here.

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Be you.

Xo, Ash