unusual father's day gifts
t-shirt: Hugo Boss, lounge pants: Hugo Boss

This post has been updated with new items for Father’s Day 2021.

Allow me to introduce you to my dad! He is a retired Silicon Valley engineer, famous for sporting his socks with sandals and free t-shirts. Come to think of it, I don’t believe he has purchased a shirt for himself in over 20 years. He adores free things, so when I explained to him Hugo Boss wanted to dress him for my Father’s Day blog post, he emailed back, “Sounds interesting.” This would be a good time to tell you that my dad has never used an exclamation point in his life. He is also a man suspicious of all good things, so “sounds interesting” is a top drawer comment from him. Interesting is also an apt word, as a modeling job is probably one of the more unusual Father’s Day gifts he has ever received.

After confirming his participation in the collaboration, I asked him what he needed. He replied, “modern pants.” I replied, “What kind of modern pants, like for going out to dinner or more for home?” He returned with, “Not dressy. Smart casual.” Although my dad speaks many languages, conversation has never been his strong suit.

Since he is retired, and we are in a pandemic, I requested comfortable loungewear: a regular fit t-shirt in soft cotton, regular fit pants with a drawstring in pique jersey, and a two-tone structured jacquard sweater in recycled yarn for dressier occasions. Since he lives in San Jose and I live in San Diego, when the Hugo Boss box arrived at his door a couple of weeks ago, we jumped on a video call so I could watch him open it up.

unusual father's day gifts

There are few things that give me more joy than watching my father open up a present. No one is more present than my dad when he opens a present. He analyzes the packaging, inspects any tags, and immediately puts to use or wears whatever it is that has been given to him. And he speaks the entire time, narrating every thought, feeling, and realization as he examines his new possession.

Here is his commentary upon unfolding the Hugo Boss t-shirt, “Oh look at this. Soft. What size is this? Large, okay good. What is this made of? Where is the tag? I can’t find the tag? Left side? Okay, okay. No tag there. I don’t know what this is made of, something soft. I can’t guess it. This looks small. This is a large? Looks like a medium. How do I wash it? Soft though. Let’s try it on. What do you say?”

The shirt is now on him. “Oh this is nice. This is expensive. Does this fit right? Is it supposed to be this tight? Are my nipples showing? This is a good shirt. Let’s show Debi.” He takes the computer so I can accompany him and his newly applied t-shirt into the kitchen to show his partner of 20 years, “Debi, what do you think? This is a nice shirt!” Debi enthusiastically agrees that it is fantastic.

Time for the pants. Dad really goes nuts for these pants, “Ooh are these slacks? What are they made out of? What are these? Where do I wear them? Do I wear them to a restaurant?” “No Dad, these are lounge pants. You can wear them around the house,” I reply. “What? No. Are these jogging pants? Dressy jogging pants? Only for the nice runs? They have pockets. These are a large. They look like a medium. I can’t gain a pound. These are good pants.”

unusual father's day gifts

He thought the lounge pants were so nice he genuinely wanted to wear his dress shoes with them for the photoshoot. Dress shoes. I said, “No, Dad, you’re going to wear your sandals. These are casual pants.” He only jokingly asked if he could wear his socks with the sandals because even he knows men wearing socks with sandals is ill-advised.

Of course, he loved the jacquard sweater as well: “This feels expensive. I look good!” My dad has never looked better actually. It is seriously refreshing to see him in nice clothes, which brings me to the topic at hand. The best unusual Father’s Day gifts are stylish or self care items your dad wouldn’t buy himself, like modern pants. On the list below, you will see all sorts of fashionable gifts to make your dad look and feel more fresh. More like a man, and less like a dad.

Sizing Tip: My dad is wearing larges in all the garments. He is 5’9″ and 189 lbs. He has a 43-inch chest and a 35-inch waist. Like many stylish brands, Hugo Boss runs slightly slim, so order a size up if you’re not sure of your father’s size. Boss provides free shipping and free returns, so feel free to order multiple sizes.

Fun Fact: After trying everything on, Dad said, in all seriousness, that he would “take a shower” for his Hugo Boss modeling debut. LOL.

Hugo Boss Regular-fit T-shirt in soft cotton

unusual father's day gifts
Hugo Boss $68

Is it just me or does my dad look way better in this t-shirt? This model is quite scrawny and this shirt is meant for athletic or bigger men. Not that my dad is ripped; he just barely fills out the sleeves himself.

Vuori Strato Tech Polo

unusual father's day gifts
Vuori $54

This polo by Vuori is super soft. Every single one of my clients adores the fabric Vuori uses — and your dad will too. As an added bonus, this polo also offers extra protection in the sun with UPF 30+. Plus, they are a San Diego-based company, which you know I love.

Lab Series Future Rescue Repair Serum

unusual father's day gifts
Lab Series $65

Skincare products may seem like unusual Father’s Day gifts, but they need it — and will appreciate it. There was a time when it was believed that men got better looking as they age, while women not-so-much. My god, the tables have turned. We look phenomenal. Men are looking weathered. Even men as young as 39 are looking haggard. The reason is education and exploration. We are taught skincare young and explore the products that best work with our skin for decades. Men are grossly behind and it shows. Get your dad a serum to refresh that skin. I highly recommend Lab Series. It can be used day and night. (Read my full Lab Series review on my fashion blog for men).

23andMe Health + Ancestry Service

unusual father's day gifts
23andMe $149

The 23andMe DNA testing kits are a fun way for your dad to find out more about his ancestry and health. Plus, if you buy two the second kit is half off, so you can pick up one for yourself too and learn more about what genetic traits you got from your dad.

Montarbo Skincare Daily Moisturizer Broad Spectrum SPF 30

unusual father's day gifts
Montarbo $33

One of the main reasons men look like a crumpled up shirt is the sun. I know many men hate the feel of sunscreen, so get your dad this sunscreen from my esthetician Cody Montarbo. It is 100% non-greasy, lightweight, will not break him out, and it feels absolutely fantastic on. This is the sunscreen I personally use on my sensitive skin, from my face and chest to shoulders and hands. You may recognize it for my post on My Summer Essentials. I have been using it almost daily for six years and it is the only sunscreen I allow to touch my face.

Hugo Boss Regular-fit T-shirt in soft cotton

unusual father's day gifts
Hugo Boss $68

This is my dad’s t-shirt, but in a different color. I have no idea why they had these skinny guys models these regular fit shirts. They look like children in them. If your dad isn’t too skinny, he will rock this tee.

Hugo Boss Regular-fit T-shirt in mercerized cotton

unusual father's day gifts
Hugo Boss $78

I have put this Hugo Boss v-neck on many clients for years. Men love the high v-neck to cover their chest hair.

Juniper Books Book Set

unusual father's day gifts
Juniper Books $195

Juniper Books has the most beautiful special collections that look great on any bookshelf. Gift your dad a set of books by his favorite author or make your own collector’s set of his favorite books. You can find them on Amazon or Juniper Books.

Zint Collagen Powder Peptides

unusual father's day gifts
Zint $39.99

After I found out Jennifer Lopez was 50, I picked my jaw up off the ground and looked into her beauty regime. The main takeaway was consuming collagen. I started putting a scoop of top-notch Zint collagen powder into my water every morning. Within 30 days, my knees hurt less and my skin was radiant. Radiant! This is one of the more unusual Father’s Day gifts, but if you can get the bugger to digest it every morning he will love the results!

Hugo Boss Slim-fit T-shirt with long sleeves in waffle cotton

unusual father's day gifts
Hugo Boss $88 $70

Here is another color of my favorite long sleeve tee by Hugo Boss. As mentioned, this is great for the taller dads.

Hugo Boss Regular-fit pants with drawstring in piqué jersey

unusual father's day gifts
Hugo Boss $148 $103

Every man needs these pants. They are fun, yet casual. No, he can’t wear them to a restaurant, but he can wear them around the house and about town.

Hugo Boss Two-tone structured jacquard sweater in recycled yarn

unusual father's day gifts
Hugo Boss $178 $106

This shorter sweater is great for men 5’9″ and under who struggle with sweaters being too long. As you know, it is difficult and ill-advised to hem a sweater, so if a sweater is too long you have to skip it.

Hugo Boss Relaxed-fit shorts with layered metallic logo

unusual father's day gifts
Hugo Boss $128 $89

These are soft, luxurious lounge shorts. And no, your dad can’t wear them to a restaurant.

Hugo Boss Slim-fit T-shirt in cotton with collection print

unusual father's day gifts
Hugo Boss $88 $61

Hugo Boss used to be my go-to designer for unusual graphic tees, which make for great Father’s Day gifts. It looks like they’re coming up with some goodies again.

Hugo Boss Slim-fit shorts in anti-wrinkle fabric

unusual father's day gifts
Hugo Boss $178

Maybe this is more for the younger fellas, but I had to share these fabulous shorts.

Hugo Boss Slim-fit jogging pants with layered logo

unusual father's day gifts
Hugo Boss $148 $103

Pandemic anyone? Every man wants some stylish sweatpants they would never buy themselves.

My blog posts are my honest and personal opinion. Sometimes my content includes products sent from brands or PR firms. In this case, Hugo Boss gifted clothes to my dad. If I am sent something that is unimpressive or boring I don’t write about it.