5 Outfit Ideas for Date Night

Every guy needs to look good for date night. Obviously not overpowering her, but you gotta be the handsome to the pretty, no? 

To all my not-so-single lads, Valentine’s Day is approaching, and who wants to be that guy, struggling to find an outfit? That guy who eventually settles for a wrinkled shirt and gym shoes. Nah brah! 

(Gotta look fly while paying the meal, no?) All jokes aside…

…and while romantic dates and gentle gestures should happen more frequently, if not daily or weekly, Valentine’s Day gives us the opportunity to reflect and celebrate the good, bad , and the ugly parts of the relationship. Because let’s be honest…not everyone has time to inwardly reflect on their relationship for hours. Every. Single. Day. Not even a random day. 

Thought I should spill that thought, since so many people give the holiday insignificance!!

Some guys go waaaaay sloppy (please no) and some look 10x hotter than the other half, which I don’t recommend, either. No offense!

Here are five outfit ideas to consider:

1. Smart Casual

Basic at its finest. Sometimes a simple, low-budget date can be the most intimate thing. It keeps the focus right where it should be: love. This look captures any casual setting, down to the fast food chain restaurants. I love it because it truly is simple, but still has an elevated feel to it. A simple cashmere crewneck will ALWAYS do the trick, paired with a medium wash denim and worn-out leather shoes (casual penny loafers for the win!). Don’t forget the leather watch!

2. Fireside Fancy
For low-key dates/dinners at home. I always fancy those perfectly disheveled loungewear, which I find to be the awesomest thing ever! Wear a pair of fuzzy socks and match it with a “fireside” look. This apr├ęs-ski-inspired shawl sweater, paired with a nice french terry jogger, screams cabin chic with a touch of modernity. An outfit that can go from kitchen cooking to couch canoodling! Lol.

3. Bistro Dine
From upscale restaurants to fancy bars, this look is truly cool for the occasion. No need to go all out (AKA matchy suit per se?) if  you don’t want to. This outfit, my friend, is sharp without the overly done look. Throw on a sports blazer (I like to keep it solid), with a business casual shirt, lived-in chinos and your go-to leather belt. Cheers!

4. Motion Explore
Physically active date nights are downright romantic. Take her out for a touristy run. Take silly pictures, stop by local ice cream shops and treat-up. A lot of movement might transpire, so a pair of stretchy jeans is your best bet. A striped tee can add to all the running/jumping/dancing! Just keep it airy and carefree! I think a quilted shirt-jacket would top the look so well.

5. Romantic Getaway
So you’re on vacation and the weather is more than likely superb. If not, don’t forget to pack a parka! Now’s the perfect time to sport those crazy patterns! (even cooler  if you add a standout blazer). Silver watch to add pizzazz, if you want. Tee shirt, oxford shirt, or polo shirt under the blazer? you call the shots! I love matching the scenery (not in a camouflage way) to fully grasp that perfect moment, ya feel me? Take her someplace scenic, and just have a ball with those outfits!



I'm Ian, the writer behind CharlesTucket (a mix between Charleston & Nantucket, two of my favorite places). My hope is to inspire every man to live a wholesome & whimsical life, one quirk at a time.


"Be watchful, stand firm in the faith, act like men, be strong. Let all that you do be done in love." | 1 Corinthians 16:13-14


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