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

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. The shipment cut off date for items to arrive by Father’s Day is June 14th.

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.

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.

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).

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.

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.

Cody is one of the most generous people I have ever met, so of course he is giving my readers 20% off his whole website with code VSTYLE.

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

unusual father's day gifts
Hugo Boss $88

This shirt is absolutely gorgeous and great for those tall dads.

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.

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 T-shirt with long sleeves in waffle cotton

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

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

Hugo Boss Slim-fit casual chinos in brushed stretch cotton

unusual father's day gifts
Hugo Boss $128 $64

Hugo Boss does basically everything well. Their pants are fabulous, and this color is awesome.

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.

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!

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.