"You can’t help but wonder does this scream “I’m trying too hard?” My colleague Sarah was doing a slow circle in my office doorway last Tuesday, modeling a very optimistic (for Boston in February) wrap dress. Her first date tonight – a consultant she’d connected with on Bumble – had clearly brought out the pre-date jitters in full force.
“Hypothermia,” I said, glancing away from my spreadsheet. “And didn’t you buy that dress for dates? That’s always a warning sign.” Sarah groaned and quickly made her exit down the hallway; presumably to try on outfit #6.
I’ve sort of become an accidental authority on first date fashion ; mostly because every female coworker seems to believe I have some magic formula for pulling off the perfect first date look. And while my own dating history has been… irregular, I have watched enough coworkers experience wardrobe-induced anxiety attacks to recognize the signs, and honestly, most of the advice out there is absolute garbage.
Magazines love to tell you what to wear on first dates, but they’re usually written by people who have not taken part in an actual first date since Bill Clinton was president. Dating coaches promote their silly psychological games based on clothing choices. And then there are the Instagram influencers who seem to think every first date takes place at some Instagram-perfect rooftop bar instead of, say, the kinds of dive bars where most of us actually meet people.
In reality, first date dressing is far more complex than anyone wants to admit ; particularly when you are attempting to balance looking pretty with looking professional with avoiding desperation with being able to speak coherently. Throw in the added pressure that you’ll likely be meeting this person right after work, so your outfit needs to easily switch from conference room attire to whatever restaurant this person chose, and you get into the middle of this massive strategic headache.
I began paying attention to all of this partially due to my professional environment – working in finance makes every social interaction potentially impact your job, including dates – and also because I got sick of watching smart and successful women completely freak out over something that’s ultimately just … clothes. However, as I continued to observe this trend, I realized that there were actually several universal guidelines that apply regardless of style or budget.
One of the biggest mistakes I see women make? Wearing something entirely new for the date. I literally can’t stress this enough – DO NOT WEAR SOMETHING YOU’VE NEVER WORN BEFORE TO MEET SOMEONE NEW. You have NO IDEA how that material will act after 2 hours. You won’t know if those shoes will blister your feet. You won’t know if that top will remain in position when you lean forward to pick up the check.
My friend Lisa found this out the hard way when she wore a beautiful new silk blouse to meet a lawyer from Hinge. What a beautiful top, looked fabulous for precisely thirty minutes, and then started slipping downward like it was covered in butter. She spent the remainder of the dinner trying to casually tuck it back into position without anyone noticing she was experiencing some sort of wardrobe malfunction. “He probably thought I had some bizarre tick,” she explained later. “I kept rubbing my collarbone.”
Rule Number Two: Wear something that represents your personal style ; simply dressed-up a bit. This may appear simple, however I’ve seen numerous women change their entire sense of style for dates. If you typically wear jeans and T-shirts, don’t break out the body-hugging cocktail dresses because some magazine wrote that men prefer curvy figures. You’ll be dressed up like you’re wearing a costume and that feeling is going to come through.
Instead take your current style and polish it a bit. So if your typical uniform is business casual (lucky you), that automatically translates to dates. You can replace your work blouse with a silk model rather than cotton, or put on the blazer that actually fits as opposed to the one you purchased three years ago and never got tailored.
Over the years I have developed what I refer to as my “Date Night Formula” mainly through trial-and-error and observing what truly works vs. what looks good in theory. The components include: dark jeans that I know fit perfectly and don’t sag or distort, a silk cami or well-fitted blouse, my good blazer, and ankle boots with a block heel. Essentially it is my standard work uniform minus corporate accessories and better jewelry.
This uniform has worked for me throughout various coffee dates, dinner dates, drinks dates, and yes even the memorable awkward mini-golf outing where I could at least walk correctly. It’s both comfortable and reflects how I want to be perceived. More importantly I am not worrying about how I’m dressed during the date which enables me to concentrate on determining if this individual has any meaningful opinions about anything.
The type of venue plays a huge role. Boston is unique regarding date logistics ; you’re most likely going to be somewhere that is either freezing cold or scorching hot; the seating arrangements vary greatly; and you have a reasonable chance of ending up walking farther than intended due to Boston’s somewhat erratic public transportation system. Therefore your outfit must endure these conditions without needing constant adjustments.
Layers are vital here. How many times have I seen someone shivering through a date merely because they placed aesthetics above temperature control? No one is attractive while visibly shivering and you cannot carry on an intellectual conversation while distracted by the need to avoid rattling your teeth. A nice blazer or cardigan that complements your outfit resolves this issue.
Comfort extends beyond mere temperature factors. If you are uncomfortable (either physically or mentally) it impacts every aspect of how you represent yourself. During my initial years of dating I was still learning what “professional yet inviting” meant outside of the workplace realm. I would wear these outfits that appeared stunning in front of the mirror but felt wrong against my body. Thus I would spend the entire duration of the date feeling self-conscious.
Nowadays I use a very basic method: If I can sit comfortably for two hours in something, it passes my first date criteria. If I find myself constantly adjusting it during regular daily routines it fails. If it necessitates specialized underwear or constant supervision ; it is eliminated. As previously stated: Life is too short to waste a first date fretting about whether your bra is visible or your skirt keeps creeping upwards.
Color selection is much more critical than individuals realize ; particularly for women of color in professional environments. Over time I have come to strategically select colors that photograph well under restaurant lighting; colors that compliment my complexion in a manner that provides increased confidence; and colors that fade into the background. For dates I now choose my go-to palette: Deep blue colors; Rich green hues; Classic Black; And rarely a bold red when I’m feeling particularly confident.
Jewelry decisions merit consideration too. I have certain items that I refer to as my “date jewelry” ; items that represent a step above my regular everyday jewelry, but not expensive enough that I fear damaging them. My grandmother’s old gold bracelet is one such piece that I pull out for serious potential connections. It has become this little ritualistic tradition that boosts my confidence ; although rationally speaking it shouldn’t.
Footwear selections are arguably the most significant decision you’ll ever make and I’ve witnessed more first dates destroyed by ill-chosen footwear options than any other single factor. High-heeled shoes are acceptable if you actually feel more confident in them and you know you can walk normally; however hobbling is unattractive. In Boston I opt for block-heeled shoes that are functional or exceptionally good flats when the weather is uncertain.
There is an equally applicable new-shoe rule. Using new shoes on a first date is a distinctively masochistic activity. When I wore nice-looking boots in the store that seemed okay initially, but ultimately proved to possess an architectural flaw causing blisters within sixty minutes, trying to smile charitably while your feet screamed was virtually impossible.
Weather-based considerations create additional complexities. Summer dates in Boston are often brutally humid but restaurants heat/cool to extreme levels. Winter dates pose the additional challenge of appearing appealing while bundling up like you’re preparing for polar expedition travel; followed by a quick transition indoors to heated spaces capable of powering small greenhouses.
To address these issues I have incorporated into my Date Wardrobe building blocks items that adapt seamlessly between temperature ranges. Lightweight blazers that are visually pleasing yet provide warmth; scarves that can be removed without ruining the overall appearance; Waterproof boots designed with functionality yet lack any overtly outdoorsy design elements.
Perhaps the largest realization for me was realizing how much confidence affects your ability to successfully execute a first date regardless of what you wear. I have experienced great dates in seemingly plain outfits and mediocre dates while wearing attire that probably costs more than most people pay per month for rent. The only consistent factor among successful dates was not what I wore but how comfortable I felt wearing what I did.
This may sound as obvious as sunshine is bright ; but it took me longer than I wish to acknowledge to understand this concept. Previously I would over analyze each and every decision ; Is this too corporate? Too casual? Too eager? Not eager enough? Nowadays I focus on whether an outfit makes me feel like the best possible version of myself ; and nearly everything else falls into place.
Another lesson I’ve learned is that men tend to notice significantly less about your outfit than you think they do ; but they certainly notice confidence levels. Throughout my life, I’ve received more compliments for simple outfits where I felt confident wearing them than for elaborate ensembles that needed constant adjustment. There is something inherent about wearing clothes that enable you to disregard them and engage with conversations.
Having said this ; I do think there is merit in marking the occasion with some degree of extra effort ; not necessarily through purchasing something or wearing something radically different from your daily routine ; but through showing respect for the person’s time and signaling that you are taking seriously the possibility of forming some level of connection.
For me this manifests itself as higher quality accessories than usual, more attentiveness toward my grooming habits, and ensuring all elements fit properly and are clean. Essentially this is the distinction between rolling out of bed and actually getting ready to meet someone new ; without crossing over into trying too hard territory.
Additionally, there is something fascinating about regional differences as well. Boston has its own unique challenges when it comes to dating ; weather-wise; stylistically (the general New England understated aesthetic); and because we all work in finance or technology or biotechnology and have nearly identical wardrobes ; finding that sweet spot between blending-in while standing-out requires balancing multiple variables at once.
As such, I have noted that what works in Boston may not translate elsewhere. On rare occasions when I’ve had dates while traveling for work, I have had to modify my usual formula based on location-specific requirements. New York demands greater polish; Miami affords greater exposure of skin; Smaller towns/cities sometimes demand more conservative attire. These variables contribute another layer of complexity to an already complicated puzzle.
However regardless of location ; the core concepts remain unchanged: Wear something you feel confident in; Ensure you can move freely; Dress according to venue/weather conditions; Avoid experimenting with your appearance when you’re already anxious/nervous about meeting someone new. Everything else is simply detail.
Sarah eventually opted for dark jeans and a cashmere sweater ; her standard WFH attire albeit in better-quality fabrics; she saw him again last weekend ; and thus sometimes the best advice is simply: Stop overthinking it
