Stylish Dad Style: The Father’s Day Shopping Guide

Here at Style Girlfriend we believe that there are few things better than a well-dressed, doting dad. The kind of dad who shows up to his kid’s school play in a three-piece suit (gotta dress up for a night at the theatre!). Or the one who’s ready to run to the drugstore at midnight to scoop up a prescription for his offspring’s ear infection in the perfect sweats co-ord. 

We also know that whether you’re a dad of little ones, grown children, or even fur babies, it can be tricky to find the time to shop for stylish dad style for all occasions. 

Luckily, our friends at Hugo Boss have your back.

Just in time for Father’s Day, we’ve compiled their best stylish, dad-friendly outfits that are equal parts cool and comfortable.

You’ll find looks for the pre-planned date night with your significant other, for PTA meetings, and everything in between. And when you’re a dad, there’s a lot of in between… 

Feel free to pass this shopping guide along with a ‘nudge nudge’ to your spouse and kids, or simply treat yourself to a l’il Father’s Day shopping spree.

Below, 11 outfits for nailing stylish dad style:

jacket | tracksuit bottoms | t-shirt | boots (similar)

What this outfit says about you: You’ve got two kids under the age of 10 and they keep you on the move on the weekends.

In this outfit, you’re grabbing brunch at a casual spot with your no-makeup makeup wife, dipping into your son’s hash browns while you sneak sips from your daughter’s hot cocoa.

After brunch, the whole family hits the park, where you’re the slickest dad watching the slide.

suit jacket | pants

What this outfit says about you: You work a corporate job, but not the stuffy kind. Your office has jars of candy and a few bean bag chairs thrown around.

You’re a certified Cool Dad^TM without having to work at it.

This is the look you rock on the rare night you steal out with your smoking hot spouse at the newest local restaurant – you’re both adventurous eaters, always ready to try a new cuisine.

sweatshirt | sneakers

What this outfit says about you: You’re a no-fuss dad, who will one day be the father that falls asleep watching the History Channel. And your family loves you for it.

You’re not super fashion-conscious—you’re more comfortable in your pajamas than a suit—which makes it all the most impressive when you turn out a great ‘fit.

This is your go-to casual look for when you’re running errands, or cheering your kids on during their weekend soccer games and swim meets.

letter jacket | t-shirt

What this outfit says about you: You are the it dad. Your tween keeps you up to date on all the latest TikTok trends, and you’ve even been known to join in on filming a video or two.

When you’re in charge of carpool, your kids’ friends know that the music selection is going to be choice.

sport coat | loafers

What this outfit says about you: You’re a numbers guy with a fancy shmancy office job and a team of people that look up to you…and that includes admiring your on-the-clock style choices.

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At home, your kids dip into your closet more than you’d like (but you’ll admit it feels pretty good when they want to steal your clothes).

short-sleeve shirt | sneakers

What this outfit says about you: You’re the easy-breezy dad.

No ego or pretense, and you always smell good.

Your family has the best group photos because you always effortlessly match without even coordinating beforehand.

You’ve got taste and class, but at home you love a good slapstick comedy and aren’t above a cartoonish impression to get a laugh out of your kids.

hoodie sweatshirt | tracksuit bottoms

What this outfit says about you: You’re the sports dad. Your free time (using the term loosely) is spent shuttling your kids from basketball courts to soccer fields, and shoveling heaps of McDonald’s into the back seat of your big SVU for all their friends.

Thankfully, sporty style comes naturally to you. After all, you’re super active yourself! Hence a closet full of stylish dad athleisure looks.

Your idea of a great date means tickets to a minor league baseball game or going on a hike, not a fancy dinner where you have to get all gussied up.

striped collar polo shirt | sneakers

What this outfit says about you: You are a dog dad. No father of actual human children would be able to wear an all-white ensemble anywhere! You and your spouse dote on your Vizsla, Roberto.

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This is your go-to travel outfit – again, because you don’t have little ones you two are free agents and love to visit the most pristine places in Europe.

Anywhere they go on Succession–that’s where you two like to be and this look is perfect for dinner on Lake Como.

shorts | sandals

What this outfit says about you: You are the dad of a newborn.

This outfit says I am literally too tired to tie my shoes, so I need to strap this baby to my chest and go to the coffee shop. But make it fashun.

You can be seen wearing this look while pushing the stroller through the park on weekends, zooming through the grocery store because it’s only the first of approximately thirty things on your to-do list, or falling asleep on the couch with your partner fifteen minutes after dinner.

turtleneck | loafers

What this outfit says about you: You are the high fashion dad. You and your spouse are a perfect match because you’re both high maintenance (no judgment!) and you wouldn’t have it any other way.

This is your favorite outfit to wear on Thursdays because that’s date night, when you go straight from the office to the flower shop down the street and pick up their favorite: white peonies. Then, onto the local steakhouse where you and your significant other have a standing weekly reservation.

You enjoy martinis together and catch up on the latest neighborhood gossip.

straight-fit jeans | sandals

What this outfit says about you: You are the creative dad. The thought of corporate America makes your skin crawl.

You’re a little unconventional in your style and your parenting.

You couldn’t explain a sports metaphor if you tried, but your kids talk to you about everything, and you hope it stays that way forever.

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Happy Father’s Day to all who celebrate, and thanks for supporting the brands, like Hugo Boss, that make Style Girlfriend possible!