OOTD: What To Wear On A Date Night

You imagine her giggling at your sarcastic remarks about the necessary development of the Liberal political party. A rush of excitement flows through your body to have finally found someone who resonates with your distinctive rumour and questionable antics. After numerous ‘hanging-out’ sessions and text messages, she agrees to meet you for coffee. But not just regular coffee, a coffee date to be exact.

You have been on several dates but you are immensely nervous about this particular one. No one else, till date, has made you experience such an adrenaline with a simple smile nor  understand your pet peeve of eating rice dishes with a fork. You intend to take her to your favourite fool-proof coffee spot, where you have never experienced a bad time. With the location secured, you start pondering about your physical presentation.

The dreadful, but yet thrilling, coffee day has arrived. You see her from a distance and your heart starts uncontrollably racing. You impatiently walk up to her and say “Hey” with the widest grin on your face. She replies “Hey there!” followed by a genuine smile. You lock eyes with her and you can’t seem to stop staring at her sapphire blue eyes or smiling. Shortly, through the curated awkwardness, she giggles, breaking eye contact and catches a whiff sight of your lower half, your floral shorts and boat shoes. You examine her expression and you noticed that she was expecting more.

Admittedly, one’s appearance isn’t the primary clause for determining attraction. But you can’t deny, it does help you score a few much needed points. From failed/successful first date experiences, here are a few tips to secure the appearance factor. These tips align with the effortless and versatile theme that DWNS exudes, exhibit a serious (but not too serious) impression and ensures that you have one less thing to worry about for date.

DSC_1872First: Your darkness pair of blue jeans. Don’t go donning your dress trousers, you want her to take you seriously but don’t overwhelm her with formality. Which leads to…

Second: Your statement blazer or suit jacket. Sitting across the table, the jacket is what she’s going to notice the most. Don your favourite blazer or suit jacket, just ensure that the jacket isn’t too ostentatious – meaning one with a slight pattern weave (like his tan herringbone jacket) and preferably with patch pockets.


Third: Your most comfortable crewneck sweater or henley shirt. With the outer layer and bottom secured, feel free to wear anything under the jacket – even nothing if you are feeling extremely confident. Try to avoid anything with a collar as I feel that it will just add too much formality to the ensemble.

Fourth: Your darkest pair of boots, for the colder months, or loafers, for the warmer months. Not sure how true the statement holds up but as the saying goes “women always look at a men’s shoe first”.


Fifth: Your favourite timepiece. A watch is crucial as it tells the time, allowing you to know when to bail if the date goes south. But in all seriousness, it structures your ensemble and reflects your personality. You don’t have to wear your dress/work watch, a timepiece like the Timex Weekender will work perfectly.


Lastly: Your confidence. Remember, you rather be hated for what you are than loved for what you are not.

Good luck on your date 🙂

3 thoughts on “OOTD: What To Wear On A Date Night

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