How to Style Hats: Tips and Tricks

(Because a good hat can change the whole mood.)

There’s something about a hat that just does it for me.

It’s giving: main character walking down Lenox.
It’s giving: coffee in hand, lip gloss on, sunglasses low.
It’s giving: I didn’t try that hard (but I absolutely did).

Whether it’s a baseball cap on an errand day, a structured fedora in the fall, or a cozy beanie in the middle of a Harlem snowstorm — hats are one of the easiest ways to elevate an outfit without overcomplicating it.

And as someone who lives in New York City year-round, I can tell you: hats aren’t just fashion. They’re strategy.

Let’s get into it.

1. Start With the Vibe, Not the Hat

Before you grab the hat, ask yourself:
Who am I today?

• Off-duty creative running around the city? → Baseball cap.

• Soft, romantic, fall-in-NYC energy? → Wide-brim felt hat.

• Cozy but cute on a winter coffee run? → Knit beanie.

• Summer farmer’s market girl? → Straw hat.

The mistake most people make is choosing the hat first and trying to force the outfit around it. Instead, build your outfit as usual, then use the hat to finish the story.

Think of it like the final sentence of a paragraph. It ties everything together.

2. Balance Is Everything

Hats add volume up top — so balance the rest of your look accordingly.

If the hat is structured or wide:

Keep the outfit clean and streamlined.
Tailored trousers. A fitted knit. A long coat.

Structure + structure = powerful.

If the hat is casual:

Lean into relaxed pieces.
Oversized blazer. Straight-leg denim. Sneakers.

Baseball cap + blazer is forever that girl.

If the hat is chunky (hello, winter beanie):

Keep layers sleek underneath so you don’t feel bulky.

In NYC winters, I love a fitted turtleneck, wool coat, scarf, and beanie. It looks intentional instead of “I just ran out.”

3. Mind Your Hair (But Don’t Stress It)

Hats will flatten your roots. It’s okay. We live here now.

Here’s what works:

• Low bun or low ponytail under baseball caps

• Loose waves with wide-brim hats

• Middle part with a slight tuck behind the ears

• Slicked-back bun for a chic, minimalist look

Sometimes I’ll style my hair with the hat on — especially if I know I’m keeping it on most of the day. Work smarter, not harder.

Pro tip: a little texture spray saves everything.

4. Play With Proportion

If you’re petite, avoid hats that completely overwhelm your frame.
If you’re curvier (hi, me), don’t be afraid of a slightly wider brim — it actually balances beautifully.

This is especially true with structured wool hats in the fall. A bit of width adds drama in the best way.

The key is trying it on in a full-length mirror. Not just a selfie.

5. Color Coordination Makes It Look Intentional

If you want your hat to look styled (not random), connect it to at least one other thing in your outfit:

• Match it to your shoes

• Echo the tone in your bag

• Pair it with similar undertones (warm with warm, cool with cool)

In winter, I love doing a monochrome moment — cream beanie, cream scarf, camel coat. It feels soft and elevated without trying too hard.

6. Use Hats as a Confidence Tool

Listen.

Some days, I don’t feel like doing my hair.
Some days, the wind in Manhattan is disrespectful.
Some days, I just want to feel a little cooler than I actually am.

A hat fixes that.

It gives you something to hide behind — but also something to step into.

When I throw on a hat with sunglasses and gloss, I walk differently. Shoulders back. Chin up. Like I have somewhere important to be (even if it’s just Trader Joe’s).

And honestly? That’s reason enough.

7. Seasonal Hat Staples (NYC Edition)

Here’s what I personally think every girl should have:

Spring:

• Neutral baseball cap

• Lightweight bucket hat

Summer:

• Straw hat

• Sporty cap for sweaty subway days

Fall:

• Structured wool fedora

• Classic beret (so chic with a trench)

Winter:

• Neutral knit beanie

• Slightly oversized cozy option for snow days

If you’re building slowly, start neutral. Black, camel, cream, navy. You’ll get the most wear.

8. Try It On and Leave the House

The biggest tip?
Actually wear the hat.

Not just in your apartment mirror. Not just for photos.

Leave the house in it.

Walk the block. Grab coffee. Let it feel normal.

Confidence comes from repetition.

The first time you wear a statement hat, you might feel like everyone is staring. They’re not. And even if they are? You look good.

Final Thoughts

Styling hats isn’t about following strict rules. It’s about intention.

It’s about finishing your outfit in a way that feels like you.

And if you’re in your NYC era — walking through Harlem, downtown for dinner, or just romanticizing your errands — a hat is one of the easiest ways to add personality without adding stress.

So next time you’re getting dressed and something feels like it’s missing?

It might just be the hat.