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Weekly Wardrobe Wisdom November 2, 2025 issue cover from Styled by Jenn featuring the title and topics: Confidence in Every Outfit, Behind the Scenes: Building Styled by Jenn, Quick Win (5 Minutes), and What Happens When You Start Dressing for Yourself.

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November 06, 20254 min read
Weekly Wardrobe Wisdom newsletter cover for November 2, 2025, by Styled by Jenn. Featuring stylist Jennifer Whitacre in a blue-green blouse, black jeans, and black flats. The issue highlights building confidence in every outfit, upcoming Amazon Winter Favorites, and holiday gift card ideas. Includes section on style packages with closet edits, shopping trips, and custom look books.

Behind the Scenes: Building Styled by Jenn

This week, I took a moment to pause and appreciate how far I’ve come — and honestly, I’m so proud of it.

When I started Styled by Jenn, I wanted to help women feel confident through their wardrobes. What I didn’t realize was how much I would grow, too. From learning Google Ads and search optimization to setting up analytics and improving my online presence, it’s been a mix of trial, error, and plenty of “I did it!” moments.

I’ve also created and designed my own website — something I update weekly with new photos, outfits, and resources. Just last night, I added new looks to the gallery page, and it’s such a great reminder of how much Styled by Jenn has evolved.

It’s exciting to see Styled by Jenn showing up on Google searches and seeing my ads reaching more women who want to feel confident and stylish. Each step — big or small — is proof that progress happens when you keep showing up for your goals. 💖

If you’re working on something new or learning a new skill, keep going. You’ll surprise yourself with how capable you really are.

Every update tells a story — new outfits, new inspiration, and new confidence.
Explore what’s new in the Styled by Jenn gallery

View the Gallery Page Here


Quick Win (5 Minutes)

5-Minute Polish: Add 1 Statement

Sometimes confidence is one piece away.
Tonight, pick one standout item to wear tomorrow — maybe a textured sweater, a bold necklace, or a chic belt that makes your outfit feel intentional instead of accidental.

It doesn’t need to be dramatic — just something that feels you.
One hero piece can transform your look (and your mindset) in minutes. 💕

See a few of my favorites below

Jennifer Whitacre of Styled by Jenn wearing a Loft burnt orange sweater layered over a denim shirt, paired with dark wash bootcut jeans, black boots, and silver accessories — a chic fall outfit for effortless confidence and everyday style.

Textured & Confident

This Loft red sweater brings warmth and personality to a classic fall look. Layered over a chambray shirt and finished with a long silver necklace, it adds both texture and shine — the perfect reminder that one statement piece can elevate even the simplest outfit. ❤️

Jennifer Whitacre of Styled by Jenn wearing a WHBM pink cashmere-blend sweater layered over a white blouse, styled with a silver four-strand necklace, dark wash bootcut jeans, and black boots — a polished, feminine winter look from White House Black Market.

Soft Sophistication

A pop of pink makes everything feel brighter. This WHBM cashmere-blend sweater layered over a white blouse adds instant polish in under five minutes. The peek of white at the neckline and hem keeps the look fresh, while silver jewelry ties it all together — cozy, confident, and completely put-together. ✨


👗 What Happens When You Start Dressing for Yourself

The biggest shift happens when you stop dressing to please others — and start dressing to express who you are.

When you wear something that makes you feel good, everything changes: your posture, your energy, your confidence. You stop second-guessing yourself and start showing up as the best version of you.

Personal style isn’t about following every trend — it’s about finding what feels authentic and powerful. Whether it’s your favorite color, a polished jacket, or that one outfit that always makes you stand a little taller, dressing for yourself is the ultimate confidence move. 💕

➡️ Find more confidence-boosting outfit ideas →

Jennifer Whitacre of Styled by Jenn wearing a WHBM teal tweed jacket over a light teal Loft V-neck top, paired with WHBM black bootcut jeans, black boots, and gold jewelry — a chic, polished outfit perfect for work or evening outings.

💙 Teal Tweed Confidence

Why it works:
The structure of this WHBM teal tweed jacket instantly adds polish, while the light teal Loft top underneath softens the look for balance. It’s a great example of how mixing textures and tones in the same color family creates sophistication without feeling too formal.

Confidence message:
When your outfit blends strength and softness, confidence feels effortless. 💫

Jennifer Whitacre of Styled by Jenn wearing a Loft black cardigan paired with altered leopard print jeans, a brown stone statement necklace, and black Rothy’s flats — a stylish casual look that blends comfort with modern sophistication.

🐆 Leopard Print Confidence

Why it works:
The bold leopard print brings instant personality, while the black cardigan and gold accessories keep it refined. The tailored fit of these altered jeans makes all the difference — when your clothes fit just right, your confidence naturally follows.

Confidence message:
A perfect fit doesn’t just flatter your shape — it lifts your mood, too. ✨

Jennifer Whitacre of Styled by Jenn wearing burgundy coated denim jeans with a long-sleeve burgundy top, a long silver necklace, and matching burgundy flats — a chic monochromatic fall outfit that blends polish, comfort, and confidence.

🍷 Burgundy Boldness

Why it works:
Head-to-toe color instantly makes a statement. The rich burgundy tones of the WHBM top and coated denim jeans create a sleek monochrome look that’s modern and sophisticated. Silver jewelry and matching flats add shine and balance, showing that confidence can look both bold and comfortable.

Confidence message:
Owning your style — and your favorite color — is the ultimate power move. 💪✨

Styled byJennWeekly Wardrobe WisdomPersonal Stylistconfidence in styledressing for yourselfstyle inspirationcloset editsfashion confidencefall outfits
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Jennifer Whitacre

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

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