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Featured Article

Madison's Most Stylish

Celebrating some of Madison's most fashionable, creative, and confidently authentic personalities.

Madison is home to an array of unique styles and personalities. Anywhere you go, you’ll see people embracing their own uniqueness with their personal style. From timeless classics to the latest trends, these local fashion lovers show that confidence and creativity is always in style. 

Tiffany Pack, Dream Key Realty

What is a fashion staple in your wardrobe?
Heels, without a doubt. I love them all, but I definitely have a soft spot for a pair of red bottoms.

What is your fashion advice?
Wear what makes you feel confident. If you feel good in it, you’ll look good in it.

What is one trend you’d love to see make a comeback?
Denim on denim. It’s classic, effortless, and always makes a statement when done right.

Where does your style inspiration come from?
My personality. My style is eclectic and reflects whatever mood I’m in that day.

Where is your favorite place to shop?
I love a good mix of local boutiques, Amazon finds, and Nordstrom staples.

When did your love for fashion begin?
In my early twenties, when I realized fashion was a form of self-expression.

What can we catch you wearing most days in town?
Something uniquely me, usually a skirt or dress paired with heels.

What’s one fashion trend you’d never try?
Crocs. 

How has your style changed over the years?
The older I get, the more I appreciate classic, timeless pieces.

What’s a style era you love?
The 70s. I love the bold fashion, confidence, and individuality of that era

Yunus Hassan, Providence Bar and Loonas 

What is a fashion staple in your wardrobe?

Watches. I start by looking at my day and choosing a piece that matches my activities and the watch tones and material will guide my subsequent wardrobe decisions.
 

What is your fashion advice?

Fashion is personal, but it’s what everyone sees. My advice is to find people that inspire you and use your inspirations to create your own looks!  

Where does your style inspiration come from?

My style inspiration comes from English Premiership soccer coaches,  and my trips to Tokyo.

Where is your favorite place to shop?

My favorite places to shop are freeflyapparel.com, Zappos.com, vintage watch stores, concert merch when seeing a band I like, and Hermes and Burberry.

When did your love for fashion begin?

My love for fashion started when I first saw the Victoria’s Secret fashion show on TV.

What can we catch you wearing most days in town?

Most days in town I’m wearing relatively relaxed clothes that I can take to the gym and then make my rounds at the restaurants. 

What’s one fashion trend you’d never try?

Skinny jeans.

How has your style changed over the years?

My style has changed from slightly more urban to much more professional, with light all weather blazers and pull overs so I can feel a bit more age appropriate.

What’s a style era you love?

My favorite era is early 90s hiphop culture.

Kenyonna James

What is a fashion staple in your wardrobe?
A great pair of statement pants will always have a place in my closet. They make even the simplest outfit feel intentional and are the easiest way to look put together without trying too hard.

What is one trend you’d love to see make a comeback?
I will always vote for more 90s fashion. It was the perfect mix of effortless, sporty, and timeless.

When did your love for fashion begin?
I’d say it started back in middle school with a pair of bell bottoms I wanted to wear almost every day. Looking back, that was probably the first sign that getting dressed was going to become one of my favorite forms of self expression.

Where does your style inspiration come from?
I’d say it comes from somewhere between streetwear with a feminine edge. I love relaxed silhouettes with soft colors, bold prints, and pieces that make getting dressed feel fun.

Where is your favorite place to shop?
My closet is a mix of Amazon, Old Navy, Fashion Nova, and ASOS. I love finding affordable pieces that look elevated when they’re styled well.

How has your style changed over the years?

Now that I’m a toddler mom I keep it easy but fashionable. Matching sets, oversized shirts, and easy pants have become my go to because they make mom life easier without sacrificing personal style.

What is a style era you love?
The 90s will always be my favorite style era. It mastered the balance between casual and cool in a way that still feels relevant today.

What can we catch you wearing most days town?
You can almost always find me in a patterned or animal print pant, an oversized button up, and my Adidas Sambas.

What is one fashion trend you’d never try?
Y2K coded low rise jeans + mini crop tops are one trend I will happily leave in the past.

Sahara Embry, CRUE Realty


What is a fashion staple in your wardrobe?
A great blazer! I love a blazer-and-jeans look for my day-to-day at work. One of my favorite staples is a green Aritzia blazer I bought a couple of years ago.

What is your fashion advice?
Wear what makes you feel confident and comfortable. Comfort goes a long way, but so does wearing pieces that make you feel your best. Try different styles until you find what truly feels like you.

What is one trend you’d love to see make a comeback?
I’ll say it… skinny jeans! Especially in the winter with tall boots.

Where does your style inspiration come from?
A lot of it comes from Pinterest. I search words that describe my style and save looks that inspire me.

Where is your favorite place to shop?
Aritzia and DISSH are my favorites. Honestly, Abercrombie has made such a great comeback too.

When did your love for fashion begin?
I didn’t really get into fashion until I started working. Over time, I learned to trust my own style and wear what I love instead of dressing for other people’s opinions.

What’s one fashion trend you’d never try?
I just can’t get into jorts…

How has your style changed over the years?
Completely! My style is so much more “me” now. I’ve become more confident in knowing what I like and sticking to it.

What’s a style era you love?
The ’90s, for sure!

Style has nothing to do with size. Every color and pattern can work on every body when you find the silhouettes that make you feel your best.

Over time, I learned to trust my own style and wear what I love instead of dressing for other people’s opinions.