My Fav 9 Secrets to Always Look Stylish You Need to Know

1. Master Outfit Contrast

Stylish women understand what I’m calling “outfit juxtaposition” (I don’t even know if that’s a real phrase, but it makes sense to me). They know how to balance casual and dressy pieces: trousers with a sweatshirt, a hoodie under a blazer, a silk top with basic denim.

That mix of opposites adds interest and keeps outfits from feeling too one-note and boring. It creates the right amount of tension without looking chaotic. Honestly, this might be the secret sauce to really cool outfits. Go to your closet and just play around with this concept – something edgy with something classic, something corporate with something casual. Trust me.

2. Keep an Organized Closet

Remember those 80s and 90s movies where the cool girl has a mountain of clothes, claims she has nothing to wear, but still comes out looking amazing? Yeah, that doesn’t happen in real life.

A cluttered wardrobe makes getting dressed stressful. That’s why we end up wearing the same thing over and over – we can’t even SEE the things we actually want to wear. I organize mine by colour (my sister-in-law thinks that’s insane – she needs tops in one place, pants in another). Find what works for YOU. I’ve actually enjoyed having less clothes that actually work for my life.

3. Style Your Clothes, Don’t Just Wear Them

You’ve seen those “wearing vs styling” videos on Instagram and TikTok, right? They really show how it’s not just the shirt that makes you look good – it’s HOW you style it. Push up the sleeves. Pop the collar. Tuck it in or leave it untucked. Roll your cuffs. Add jewelry. Pull back your hair.

These little tweaks make your outfit stand out. And honestly? Tailoring. I have to get a lot of my pants tailored because they sit half an inch too low. Once I figured that out, I actually started wearing them. Game changer.

4. Be an Outfit Repeater

This might be the opposite of what Hollywood taught us, but one of the biggest secrets to always look stylish? Repeat your outfits. “Maguire, you are an outfit repeater!” – yes, and proud of it.

Stylish women have go-to outfit formulas that work for them: fitted top + wide-leg jeans + bold necklace. Straight leg jeans + silk blouse + ankle boots. They don’t reinvent the wheel every morning. They’ve figured out what works for their shape and what makes them feel confident.

5. Get Really Good at Layering

I say “work on” because this is constantly evolving – and I’m working on it too (living in Florida doesn’t give me many opportunities, but still). Layering isn’t just adding a jacket over a shirt. It’s adding texture and dimension.

Try a denim shirt under a sweatshirt. A white tee under a crew neck (I’ve got that one down). A long silk lace cami peeking out under a sweater. Bracelets OVER your sleeve instead of under. None of this requires new purchases – just creativity.

6. Invest in Standout Pieces

We all know a white tee and good jeans are staples. But women with great personal style have a few pieces that make their outfits truly unique – a statement jacket that transforms jeans and a tee, or boots that instantly add personality.

The goal: a closet that’s mostly timeless basics sprinkled with special pieces that make your outfits look personal and intentional. Think 80% classics, 20% interesting statement pieces you really love.

7. Nail the In-Between Moments

A lot of women can nail a date night or fancy event outfit, but struggle with everything else. (In my 20s, I used to dress like either a bum or a stripper – no in-between.) But it’s those casual moments – school pickup, running errands, casual get-togethers – that really show your personal style.

Stylish women have gotten rid of stained, stretched-out pieces. They’ve replaced them with elevated basics and quality knits. Think cute matching sets that feel polished, current jeans that actually flatter, and simple pieces that feel put-together without sacrificing comfort.

8. Don’t Save the Good Stuff

Stylish women don’t save the good jeans, the designer bag, the expensive shoes, the nice jewelry for “special occasions.” Clothing and accessories only have one purpose: to be worn and help you feel like the best version of yourself. Sitting in your closet? That’s not using them.

Those special pieces are often exactly what makes an outfit stand out. How many times have you heard “I’m not getting dressed up because nobody’s going to see me”? Well, YOU’RE going to see you. Stylish women find a reason to look cute – even if it’s just because they want to feel cute that day. “I’m nicer when I like my outfit” – honestly, same.

9. Treat Accessories as Essential

This is something I’ve had to work on forever. Accessories are NOT an afterthought – they’re the icing on the cake. I used to plan my outfit two weeks in advance, have it steamed and ready, then scramble for jewelry and bags five minutes before leaving. Don’t be me.

Stylish women have everyday jewelry, a few statement pieces, and great bags that feel like them. Whether it’s a signature belt, stacked rings, or a pair of hoops – these details take an outfit from good to great.