1. First date outfit strategy
Before we look at clothes, I want to name two things:
- You shouldn’t try to impress women with your style. If you’re reading this, your wardrobe probably needs help, and you’re 100x more likely to succeed if you aim for “good” rather than “GQ cover model.”
- You don’t need to impress women with your style. Thankfully most women aren’t seeking guys with GQ cover model style. In fact, preoccupation with your appearance is a turn-off for many women.
Basically, you just want to:
- Look above-average so women either think your style is good, or don’t consciously think about your style, and…
- Minimize complexity so you don’t sweat what to wear, and can focus on having fun on your date!
Before we move on to actual outfits, if you forget everything else in this article, just remember…
Your clothes should fit.
I don’t care that you’re wearing Balenciaga, baggy looks bad. Same goes for Mr. Muscles, who’s bulging out of his shirt!
2. The best first date outfits for men
Spoiler alert, there’s no one “best” first date outfit.
There are infinity combos of tops, bottoms, shoes, and accessories that can knock women’s socks (and more 😜) off. We’ll look at dozens in this article.
Still, if I had to recommend just one “best” first date outfit?
It’d be something like:
- 👕 Plain, casual, button-down shirt
- 👖 Nice dark jeans
- 👟 Simple white sneakers
This outfit is a winner because it’s elevated yet casual; it’s insanely simple yet versatile; and girls like it!
If it speaks to you…
- Get a plain, casual, button-down shirt. These styles from Everlane, J. Crew, and Mr. P are all solid! You choose short or long sleeves (and whether to wear an undershirt), though the “right” answer is often weather dependent.
- Get a pair of nice dark jeans. I’m a fan of Madewell and Rag & Bone. Invest in a pair you’re proud of, minimize distractions (i.e. not these), and dry clean to retain color + crispness.
- Get a pair of simple white sneakers. You can’t go wrong with Jack Purcell, Veja, or Common Projects. Similar story as jeans, but instead of dry cleaning, clean ’em yourself (this can help).
3. What color to wear on a first date
🥴 “Wear red on a first date!”
I’ve heard this claim many times, but does it really matter if you wear red, or another color?
I examined the research, and it traces back to a famous (and questionable) 2010 academic study that claims:
“Women perceive men to be more attractive and sexually desirable when seen on a red background and in red clothing…”
Here’s one of the so-called experiments in the study:
- 10 female students scored a photo of a man wearing a plain shirt on a red background 🤔
- 11 female students scored the same photo, edited to have a white background 🤨
- Red background scores averaged 6.8, while white background scores averaged 5.7 😑
Pardon my lack of a PhD, but that’s not exactly “case closed” for red.
4. Casual vs less-casual first date outfits
Good first dates are usually casual, so good first date outfits are usually casual, too 😃
Still, depending on your lifestyle, your relationship with the woman you’re taking out, and the date you planned, you may want to dress up or down a bit!
Let’s look at both ends of the spectrum…
Casual first date outfits
You’ve already got your dark jeans and white sneakers covered, so to remake both of these outfits, you just need a couple of pieces:
- Get a good henley. I like Everlane and Todd Snyder. Black, white, and grey are always safe color options.
- Get some good t-shirts. Once again,Everlane and Todd Snyder are strong here. Recently my husband has been obsessed with Vuori.
- Get a bomber jacket. Zara has dirt cheap options that look good. Alternatively, this Rag & Bone will never go out of style.
Let’s skip the shorts for now, as we’ll cover them shortly 😜
Also, heads up…
These are just two of many casual options.
Aside from less-casual looks up next, most of outfits throughout this article are varying degrees of casual, too!
Less-casual first date outfits
These fits obviously contrast with the outfits we’ve looked at so far, but they can work in certain cases, for example:
- You usually dress like this. Not trying to be ageist, just flagging in case it helps — most guys I work with in their 20s don’t usually dress like this, and many of the guys who are 40+ do.
- The situation warrants it. You shouldn’t deliberately plan fancy first dates, but I can imagine situations where a nice outing makes sense (e.g. you met in first class on your flight from LAX to JFK…)
Basically, don’t buy a blazer for your next first date just because you read this, but absolutely get one if it feels authentic to you.
Want to nail this look?
- Get a blazer. As usual,Zara is great for inexpensive options. If you can invest more, I’ve heard good things about Suit Supply. Blazer pro tip: stick to grey or navy unless you know what you’re doing!
- Get a pair of loafers. For solid classics on a budget, check out G.H. Bass. For less guesswork, check out what’s available at Todd Snyder. Loafer pro tip: don’t buy anything your grandpa wouldn’t have worn.
- Get a pair of chinos. You can’t go wrong with Bonobos, and just remember that pleat = dressier!
We’ll cover polos later!
5. Daytime vs evening first date outfits
Don’t waste brain cells pondering the distinction between daytime and evening first-date outfits.
There aren’t rules here, though:
- 🌞 Good daytime outfits may be more casual, may show more skin, and may bias toward lighter colors
- 🌚 Good evening outfits may be more formal, may cover up more, and may bias toward darker colors
Daytime first date outfits
Notice how dissimilar these outfits are?
That’s the point!
Either of these looks can work for a daytime first date. You could wear either outfit at night too, though you’d look silly in shorts if it’s not warm out 😊
Evening first date outfits
Again, note the contrast.
The outfit on the left is more classically “evening” given the heavy palette and leather. The outfit on the right is more versatile for either day or night.
To nail all of the outfits above…
- Get a leather jacket. Schott has stylish options for relatively entry-level prices (leather jackets are expensive…) but if money is no object, go Tom Ford.
- Get a pair of Chelsea boots. My husband swears by R.M. Williams. I’ve also heard good things about Thursday Boots, and they’re half the price!
- Get some good shorts. They should land above the knee. Try Bonobos or Mr P.
- Get some light outerwear. I love all of the Corduroy and Denim shirt options on Mr Porter.
6. Cool weather first date outfits, for fall and winter
Weather cooled down? You’ll want to layer up:
To streamline your first date wardrobe choices for fall and winter:
- Get a plaid flannel shirt. They never go out of style. Madewell and RRL have great options, and the shirt the model on the right is wearing is Mr P.
- Get a puffer jacket. This can be your outer layer with basically any outfit. Invest in something plain from a good brand like Canada Goose, Patagonia, or Moncler.
You don’t need much else. Fashion-forward pieces like trenchcoats and peacoats are great, but not required, for dating!
7. Warm weather first date outfits, for spring and summer
Weather warmed up? Layer back down:
To streamline your spring and summer wardrobe choices:
- Get a good printed shirt. A few of my favorite brands are Saturdays NYC and Kenny Flowers.
- Get good polo. These Zara knits are affordable, and these Mr P options are classic if also pricier.
- Get a pair of huaraches or espadrilles. Huaraches are woven sandals from Mexico. Try Nisolo’s. Espadrilles are their canvas cousins from Spain. The most famous brand is Castañer.
8. Accessories to wear on a first date
PSA: You don’t need to wear any accessories on a first date.
Accessories can detract from an outfit just as easily as they can add to one, so I’d err on the side of not accessorizing. Still, let’s look at examples…
- 🧣 SCARVES. Scarves are the only accessories I can wholeheartedly endorse. They’re useful in winter, plus they can add spice to a dull outfit. Obviously only wear a scarf if it’s cold, and if you’re unsure how to tie one, check out 10 masculine ways to tie a scarf.
- 🧢 HATS. You can wear a hat if it’s functional (e.g. afternoon date to the park) but please skip the hat if you’re trying to hide hair loss. You’re not fooling anyone!
- 🎒 BAGS. Unless you need a bag (e.g. you’re picnicking), avoid bringing one on your first date. Toting your workbag to dinner can signal lack of boundaries, and backpacks especially can make you look childish.
- ⌚ WATCHES. Absolutely wear a watch you already own and love on a first date. But you don’t need to buy a watch for dating purposes if you don’t already own one. I informally surveyed 102 women about men’s accessories in 2021, and 55% said they don’t even notice if a guy is wearing a watch. My husband literally doesn’t even own one.
- 📿 JEWELRY. Same story as watches.
9. Outfits to avoid on a first date
I’ll never say never, but please be wary of wearing:
- 👔 Anything you wear deliberately for work. Wearing your startup hoodie (or your O.R. scrubs) can signal lack of boundaries.
- 🥴 Anything purposefully showy. Do you really want to date a woman who likes you for your $800 Gucci logo t-shirt?
- 🦄 Anything you wouldn’t normally wear. A first date isn’t the right time to pilot an outfit you’re unsure of.