My overriding advice for anyone of any gender is to wear what you love, what makes you comfortable, and what represents your authentic self when going on a date. You shouldn’t change your style or feel uncomfortable to try to impress someone else (no Sandy and Danny here, thank you).
However, there are some guidelines you can follow to maximize your style choices when going on that jittery first date.
Guys, I don’t mean to scare you but many females (and men, too) are quite picky when it comes to their date’s style. This doesn’t mean they’re going to judge you and cross you off the eligibility list purely based on your clothes. However, we ladies often make a considerable effort to look fabulous (for ourselves) so we are attuned to notice the effort our date puts into their own look.
Of course, a true love match overrides all of this, but the first date is “surface” by nature, so we must start from the exterior and work our way in from there.
Here is my guide for what to wear on a first date, guy’s edition.
Where to begin
If you already have a particular style that you have cultivated and are proud of, don’t change it. If you’re a fan of 3-piece suits with pocket squares and shined shoes, that’s your look!
If you’re a plaid shirt with ripped jeans and chunky boots kind of dude, run with it! She wants to see you, not the version of you that you think she wants to see. Humans, especially when dating, have a fine-tuned sense for inauthenticity and discomfort.
No matter your style, it’s all about picking the right outfits for the occasion at hand, and making a special effort when doing so. Putting in an effort is a sign to your date that you’re excited about this opportunity to hang out with them, and you want to make a good impression because you care. Now that’s attractive.
You can’t go wrong with a well-fitting pair of jeans. A slim-fit style is excellent for most body types and translates to most occasions whether super-casual or a little smarter. These Levi’s are a perfect example of a slim-fit jean that is relaxed yet refined. Black or dark blue denim is universal, and great for Fall-Winter, while pale-wash jeans have a more vintage vibe and are great in Spring and Summer.
Avoid: skinny jeans unless your look is 80s rocker or 00s emo.
Try: try a little rip or distressing for texture and street style, especially for daywear or casual nightwear (parties, gigs, movies).
If you’re heading out in Summer, shorts are a perfectly reasonable choice for daytime dating. Shorts are okay for nighttime if it’s a casual party or low-key market dinner but try to stick to long pants for evening dates when the weather permits.
If you’re going on an active date such as a beach walk or park stroll with takeaway coffee and pastries (recommended!), jersey-style or basketball shorts are great. These Nike jersey shorts are a great length and are sporty yet smart.
For parties or super-casual dinners, go for denim shorts or chino shorts. Chino shorts like these have a modern cut with a slim leg and short hemline (hey, guys can show a little leg, too!). For something a little longer and more relaxed, these have a street style vibe with a bit of throwback to 90s and 00s baggy skater style (without showing your underwear).
Avoid: the only time you should wear boardshorts is if you are going swimming.
The classic chino pant never goes out of style. They’re smart without being too “workwear”, and relaxed without being sloppy. These slim-line chinos are super-cool, with a flattering cut and style-savvy silhouette. Wear with leather shoes, a grey marle tee, and knit cardigan worn open. I tell you, your date will be well impressed.
Avoid: overly-cropped pants or drop-crotch pants unless they’re your usual, authentic style and what you’re comfortable wearing. They’re hard to pull off and can create odd proportions.
● Slim-cut blue or black jeans, a linen shirt with the sleeves rolled up, and black leather or suede Chelsea boots
● Chino shorts with a vintage-style printed shirt (top few buttons undone), with TEVA sandals or Van slip-ons
The plain t-shirt
A plain cotton t-shirt is an excellent place to begin. A marle grey t-shirt with a plain crew neck and a relaxed fit is timeless, and layers beautifully with long-sleeve shirts, cardigans, and sweaters.
Avoid: tight t-shirts or muscle tees. A slim-cut is fine, but anything tight or clingy is off-putting. Super baggy, oversized tees that look like dresses have had their moment and shouldn’t be revived. Avoid graphics or text unless it’s artistic or subtle, and definitely avoid “funny” slogans or images.
The long-sleeved tee
A long-sleeved top with a crew neck is a winter staple for guys. For example, this merino top is stylish but it doesn’t try too hard. A textured long-sleeved top in a waffle knit is a classic choice for fall and winter and adds touchable softness and texture to the look.
The linen shirt
One of the most attractive articles of clothing a male can wear is a linen shirt, rolled at the sleeves. Linen is soft, stylish, and elegant without being too formal or on the “work shirt” route. A deep navy, sky blue, or white linen shirt is flattering to all skin tones and goes with everything from blue jeans to caramel chinos.
A soft wool knit or cotton sweater worn with slim jeans or chinos is a cool (and sexy) aesthetic. Look for a simple crew neck and don’t be afraid to try a pop of colour. For example, this rich green crew neck sweater would look great on absolutely anyone.
Sometimes avoid: hoodies are fine when you’re on an active date or super-casual coffee date. Grey marle, charcoal, or navy hoodies are flattering and timeless.
The open cardigan
A knit cardigan, worn open shares the same 90s-style aesthetic as the classic plaid shirt. This green cardigan is a cool mix of dapper, grungy, and refined. It’s slightly androgynous and signals stylishness as well as a cool-casual vibe.
Listen and learn: shoe choice is critical. Your choice of shoe is a clear indicator of your overall style-savvy. You would be surprised at how many people who are attracted to males, especially women, take note of their date’s shoe choice. Why? I can’t quite explain it, but it’s true.
Leather lace-ups: if you’re wearing smart chinos or dress trousers, leather lace-ups are the clear choice. Smart Oxford shoes such as these are sleek, stylish, and show that you’ve made an effort. Not only have you made an effort, but you’ve got fine taste and you take pride in your aesthetic.
Leather slip-ons and loafers: not everyone is comfortable with ultra-smart lace-up shoes, and that’s fine. If you’re into a more relaxed look but you want to remain smart, try a pair of leather loafers such as these. Wear with any formal or smart-casual long pants and your look finishes on a high note.
Chelsea boots: Chelsea boots are something you should consider adding to your wardrobe if you don’t already have a pair. They’re more casual than leather brogues or lace-ups, but they’re much smarter than Chucks or Vans. A plain black or deep brown pair of Chelsea boots (such as these) look excellent with almost any long pants. Boots on guys are a clear indicator of great taste.
Trainers or sneakers: if you’re going on an active date with your tee and jersey shorts, clean trainers are fine. For casual dates, Vans or Converse are timeless and show that you’ve got a classic, youthful, streetwear style.
Sandals: there’s nothing wrong with a good pair of sandals in Summer. Leather sandals such as these classic Birkenstocks are no-fail. This may seem a little controversial, but TEVA’s are on-trend in a big way (and thank goodness because boy are they comfy). They used to be considered a little nerdy and “Dad-style”, but now fashion has deemed them as cool, and certainly Summertime casual date appropriate.
Avoid: big, chunky skate shoes with loose laces, very old and dirty trainers, or wrinkled, peeling, faux-leather “town shoes”. Sloppy flip-flops (or thongs, or jandals depending on where you are in the world).
Note: if you are vegan or follow a leather-free life, there are plenty of excellent vegan leather options on the market.
When it comes to accessories and extras, wear what you usually wear. Now’s not the time to suddenly decide you’re into necklaces and scarves, you’ll just end up feeling unsure and awkward. In saying that, accessories are a great way to show that you’ve put in extra thought and you’ve got an eye for detail.
Hat: wool beanies in winter are a hit, especially if they’re your go-to style. Don’t go for costume-style hats such as bowlers and trilbies unless you’d wear one out with your friends on a regular night out. They can overkill a perfectly great look.
Watch: a nice watch is always timeless, and it gives off a little hint of old-fashioned style. A leather-strap analog watch is a nice touch.
Jewellery: many people are drawn to a male’s hands, wrists, and forearms. For this reason, a simple hammered gold or bronze bangle, or a leather tie bracelet is a chic touch. Jewellery on guys is also a handy conversation starter, especially if there’s a fun story behind them, or if they’re a gift from family.
Scarf: a scarf in winter is not only cozy and sometimes essential, but it suggests a certain refinement. A cashmere or wool scarf has a Parisian style to it and lets your date know that you know a thing or two about how to dress, and you’re not afraid to show it. (Who knew a simple piece of fabric could hold so much meaning?!).
The way you wear your facial hair is personal to you. If you feel at your best with a clean-shaven face, go with that. If you’re proud of your bushy beard, rock it. If you’re unsure? Many girls and guys love a light stubble or well-groomed facial hair.
As long as you smell great and your hair is washed, you’re good to go.
Good luck on your first date! Wear what makes you comfortable, confident, and lets your authentic “you-ness” shine through.