10 Ways To Be a 20 Year Old Grandpa

Hi. My name is Chelle, and I’m sort of a fashion icon. That is, I have all the tips and tricks you will ever need as long as next season’s looks include being a quirky grandpa. I have that look on lock. So, stick around and take a look at some of the key pieces of my wardrobe:

1. Oversized Flannel T-Shirt

This is the only part of Kylie’s wardrobe that is attainable to the college student / grandpa figure. My sister has lovingly addressed my flannel attire as “Construction Worker Chic,” which is a title that I have embraced with open arms. It’s very easy to convert into a warmer outfit when our weather is so unpredictable. When the morning is cold, just throw on a flannel. You’ll be able to rip it off and toss is in your bag after your first class and be good to rumble until after your comedy show lets out at 1 am. 

2. Loose V-Necks


V-Necks are a staple for my yearly wardrobe because you can wear them without having to worry about matching. This is a common theme in my wardrobe because I like to sleep more than I care about fashion. If all your clothes match each other, then you have nothing to worry about! Bonus points if they’re a dark color, so when you inevitably spill on yourself throughout the day you’re all good. Also, I get them a little loose so I don’t have to worry about if I’m bloated or if I’m just not feeling myself.

3. Long Sleeved Tee

You need to be able to dress for spring without a jacket! It’s essential. I am a person who is ready to party like 40% of the day so I want to be able to do that uninhibited. This means I don’t need the seam of a jacket telling me how excited I’m allowed to be and rolling the sleeve back twice of a long sleeve t-shirt will give you circulation to cool down later in the day. Another huge factor in being a Grandpa is embracing things you like. For example, if you like the Incredibles, wear an Incredibles long sleeve. Life is too short to wear things that don’t make you better when you hold them.

4. Jeans (that you only sort of like)

I was at Forever 21 in the spring and found a pair of cute jeans on sale of $10 so I was like yeah I need these. Then, I realized they were on sale because they had frayed bottoms which I’m not sure who told them that they were in style. But I just cuff them whenever I wear them because I don’t pay full price.  My grandfather was raised by immigrants during the Great Depression, my $10 clearance jeans are thriving just as well as my $30 pair from Old Navy.

5. Ugly Cute Construction Boots

This pair of boots from Payless is currently on clearance for $20, and they will high key change your life. I’ve had them since fall and they’re great for trekking through snow, spur of the moment trips to the Lincoln Park Zoo, and for pick-up games of frisbee in the quad. My number one tip for maximum old person effect….


...is to wear a pair of cat socks underneath them. The trick is for the cats to have ears. They will stick up slightly above your boots and people will ask about them whenever they see them. Now, you get to share your really cute socks with all of your loved ones!! Also, socks are the one item that will always fit you whether you’re bloated, on a health kick, or all your best friend’s have turned 21 within a span of 30 days.

6. Socks That Make You Happy

When I was in 9th grade, I bought a pair of socks that still physically make me smile whenever I see them. They are pieces of literal French toast! Socks are cheap and are mostly unseen. Might as well be something you like.

7. Caps for your NL and AL team


This White Sox hat is a two for one because it also represents the University of Illinois that my sister went to. Representing your family is another total Grandpa move that I am all about.


8. A Cross-Body Purse

I am a person who requires full use of my hands to live up to my full potential. Therefore, I need a cross-body bag so I can keep my supplies on me.

9. Phone Case


Also, now that you are a grandpa, you can get whatever you want. Any quirk can be your thing because no one expects you to be trendy. Obsessed with the best artist that has ever walked this earth? Get a phone case about her!  Want to have a favorite checkout line at Jewel? Yeah, ask them how their kids are when they scan your yogurt. You also have to have a phone case because having a cracked phone would ruin your elderly aesthetic.

10. Snacks

Most grandpas can’t afford to be lacking in their snack game because of their blood sugar, but I can’t afford to lack in my snack game because I turn into a hangry monster. First grandpa snack I rock at least twice a week?


The humble rice cake. Lightly Salted Quaker Rice Cakes will make your world go round.


Also, I’ve recently started making green tea with lemon juice in a mason jar and taking it with me. Mason jars are the most versatile thing you will ever own. Going to a party? Bring your mixer. Want to bring a salad for lunch? Pack the dressing on the bottom, the goodies in the middle, and the greens up top. You’re out of rice cakes? Pack yourself some dry roasted almonds. There isn’t a thing your mason jar and you can’t handle.

As you can tell, I am a spring fashion icon. Make sure to follow me on instagram at @sassmastershell so that you can see my chic nature in action.