Valentine's Day is already right around the corner (how has 2025 flown by so fast?!) and you might be feeling the pressure to plan something elaborate...
While we can't read your girlfriend's mind, we're here to help you on this high pressure holiday with a few outfit ideas - so you don't have to do too much thinking.
Check out these simple outfit ideas for a fun and fashionable Valentine's Day!
1. Prince Charming
This Valentine's Day look is built to impress. Pair our Pique Polo 2.0 with stylish slacks, leather shoes, and a classy gold watch to look sharp for your dinner date. Pairs well with a dozen roses and a glass of Pinot Noir...
2. Hiking Heartthrob
Planning an active Valentine's Day date? Come prepared with a look that won’t just keep you comfortable while you hike but will have your valentine sneaking looks at you while you trek;). Pair our Athletic Shorts - designed to keep you cool and hug all the right places—with our new Athletic 1/4 Zip, tennis shoes, a trusty water bottle, and a ball cap. And don't forget to surprise her with flowers!
3. Hot & Steamy
Hoping to get lucky this Valentine's Day? Be the gift your girlfriend gets to unwrap ;). Pair some fun goofy boxerswith our Jogger Sweatpants and a casual Stripe Tee for the ultimate “Netflix & chill” date. (And we also highly recommend The Adventure Challenge: In Bed for some extra fun!)
4. Cozy Coffee Date
A classic, great option we had to include! Dress to impress for your humble coffee date because nothing beats conversation over coffee. We love pairing our Long Sleeve Henley (in a fresh new color) with a Flannel Overshirt, jeans, and stylish boots. Don't forget a cozy coffee cup and your favorite brown HeyDudes to complete the look.
5. Dreamy Dinner In
Underrated Valentine's Day date? A dreamy dinner in. Find a fancy recipe, get the groceries, and surprise your sweetheart with a home-cooked meal she'll love. Bonus with this date? You can dress in whatever’s comfy - think Everyday Shorts, a soft Cotton Tee, and a Midweight Pullover Hoodie. Top it off with some slippers, a scented candle, and a warm blanket for the ultimate cozy vibe.
Don't overthink it tall guys - just be yourself and think of creative ways to show your valentine how much you love them, and everything will go just fine. Looking for more advice? Check out a few of our other resources...
Best Valentine's Day Gifts for Your Tall Girlfriend
35 Easy At-Home Valentine's Day Date Night Ideas
The Best Tall Undershirts for Men
Before you go, make sure to check out a few of our bestsellers during love season below!
^^ Looking for the perfect blend of style and warmth? Our Tall Flannel Shirts are tailored for your build, making them the ideal choice for a cozy yet stylish Valentine's Day look. Order here!
^^ Want to keep things laid-back but still look put-together? Our Fleece Crew Neck offers ultimate comfort while keeping you warm on your date. Order here!
^^ Keeping it casual? Our Tall Cotton Tees are the perfect go-to for effortless style and comfort, designed to fit your tall frame perfectly. Order here!
