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Styled by Jenn Weekly Wardrobe Wisdom newsletter cover for August 31, 2025. Topics include Style Made Simple fall transitions, fall denim refresh, pops of color for late summer and early fall, one base two looks, Real Style for Real Life week 3, and style for every woman.

Weekly Wardrobe Wisdom August 31

September 22, 20253 min read
August 31 Weekly Wardrobe Wisdom newsletter cover by Styled by Jenn. Focus on Style Made Simple for Fall with effortless outfit ideas, seasonal wardrobe tips, and confidence-boosting fashion advice.

✨ Ready to make your style simple and stress-free? Click below to explore my styling packages and find your perfect fit.

Check out my Styling Packages here!


🍂 Fall Denim Refresh

White jeans are a summer staple, but as the weather cools down it’s time to swap them for deeper fall tones. In this week’s video, I’m showing how I styled black skinny jeans and sharing why now’s the season to reach for dark denim, burgundy, gray, or black. And for an extra edge, try coated denim to give your look a sleek finish.

✨ Watch the video for outfit inspiration and easy ways to keep your denim style fresh this season.


🌟 Can You Still Add Pops of Color in Late Summer & Early Fall?

The answer is absolutely yes! Just because the seasons are shifting doesn’t mean you have to pack away all your brights. Pops of color are a fun way to transition your wardrobe and keep your style feeling fresh.

In this look, I’m wearing the same base outfit from my Fall Denim Refresh video — black skinny jeans, a white graphic tee, and white sneakers — but I added a bright blue moto jacket. Instantly, the outfit goes from simple to standout.

✨ Pro tip: Choose one colorful piece — a jacket, blazer, or handbag — and let it do the talking while keeping the rest of your look neutral. It’s an effortless way to bring energy and personality into your early fall outfits.

Styled by Jenn outfit featuring a WHBM bright blue moto jacket, WHBM anniversary graphic tee, black WHBM jeans, and a leopard print belt for a chic pop of pattern.

Styled by Jenn outfit featuring a WHBM bright blue moto jacket, WHBM anniversary graphic tee, black WHBM jeans, and a leopard print belt for a chic pop of pattern.

👗 One Base, Two Looks

It’s amazing how one small swap can totally change your outfit!

In both of these looks, I’m starting with the same black short-sleeve cardigan sweater (buttoned at the top) and the same black G Gradual pants. But here’s the twist:

  • Look 1: Layered with a black + white print top underneath, finished with black sandals.

  • Look 2: Swapped for a leopard print top underneath, finished with black flats.

✨ Just by changing the top, the vibe of the outfit shifts completely — proof that your wardrobe basics can work harder for you when you style them smartly.

Styled by Jenn Canva graphic showing two outfit ideas: WHBM black short sleeve cardigan with G Gradual black pants layered over a leopard print top, and a second look featuring a black and white printed top for a polished style swap.

👗 Real Style for Real Life: Week 3

How to Shop with Confidence

Ever come home from a shopping trip with nothing—or with a bag full of things you’ll never wear? The secret to shopping confidently isn’t about buying more. It’s about knowing what to buy and why.

Here’s how to shop smarter, not harder:

📝 Make a style plan before you shop.
Know what’s missing in your wardrobe (like layering pieces, better basics, or shoes that match your lifestyle). This prevents impulse buys and duplicates.

🎯 Look for pieces that mix and match.
If you can wear it at least 3 different ways, it’s a keeper. Try to visualize it with pieces you already own.

Fit first, then style.
A trendy piece means nothing if it doesn’t fit right. Always prioritize flattering fits and comfortable fabrics.

👗 Bring intention to the dressing room.
Don’t ask, “Is this cute?” Ask: “Does this align with my style, my life, and my goals?”

✨ Ready to shop with a plan?
Check out my style packages—from closet edits to shopping trips and personalized look books, there’s an option that fits your needs.
👉 Explore my style packages here

Next week in the series: Feeling Stylish Again (At Any Age or Stage)

Styled by Jenn Canva graphic showing 4 ways to wear a Tommy Hilfiger yellow tee: paired with jeans, shorts, G Gradual pants, and white jeans styled with a light-colored printed scarf as a belt for a versatile summer-to-fall outfit guide.

Styled by Jenn Canva graphic showing 3 ways to wear navy G Gradual pants: styled with a red short sleeve cardigan, paired with a yellow Tommy Hilfiger tee, and with a blue striped Tommy Hilfiger tee for versatile outfit inspiration.

✨ Because Style Belongs to Every Woman

I used to think that styling only “worked” if you had the budget, the body, or the brand.
But that’s just not true.

I created Styled for Success because every woman deserves to feel good in what she wears—no matter where she’s starting from. Inside the course, I’ll walk you through how to define your style, dress for your shape, and finally feel aligned in your own skin.

Founding Member Price: $597
Be one of the very first to join and lock in this exclusive rate as a Founding Member.

⚡ Founding Member spots are limited — secure your place today!

👉 Get Styled for Success Today

Styled for Success course by Styled by Jenn — screenshot of page 1 showing the course introduction, modules, and student login layout for personal style transformation

fall style tipsstyle made simplefall wardrobe transitionspop of color outfitsdenim refresh fall 2025real style for real lifestyled by jenn fashion advice
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Jennifer Whitacre

Jennifer Whitacre is the CEO and Personal Stylist at Styled by Jenn, LLC.

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