What to Wear on a First Date
When you're dressing for a first date, you're dressing to impress. This certainly adds extra stress to the process of choosing the right outfit, which is painful enough as it is. You want to look nice, but not too polished; stylish, but not peacocky; effortless, but without an I-don't-care vibe.
The most important rule of dressing is dressing according to the setting. So, the first thing you should do is look up the date venue online or stop by there beforehand to take a glimpse of what the atmosphere is like. (That is, of course, if you haven't been to that place before.) This will help you decide if you should opt for something smart or more casual.
That said, whatever attire you end up choosing for your first date, this should be something you feel comfortable and confident in.
Hopefully, this collection of date-ready combinations for men will take some stress off of you.
Wear a black double breasted blazer with white chinos and you'll assemble a proper and sophisticated getup. Brown leather double monks will immediately dress up even the simplest of getups.
A navy blazer and navy dress pants make for the ultimate stylish outfit. A nice pair of black leather tassel loafers pulls this look together.
For an ensemble that's city-style-worthy and effortlessly smart, consider wearing a navy blazer and khaki chinos. Feeling experimental today? Spice things up by sporting a pair of brown leather tassel loafers.
To put together a casual look with a modern take, you can rock a blue chambray long sleeve shirt and black jeans. Grey low top sneakers serve as the glue that brings this outfit together.
Rock a tan blazer with khaki dress pants for seriously dapper style.
Pairing a grey houndstooth blazer with navy dress pants is an on-point choice for a classic and sophisticated outfit. When it comes to shoes, introduce a pair of brown leather loafers to the equation.
If the occasion calls for an elegant yet killer menswear style, you can easily rock a black blazer and khaki chinos. Introduce dark brown suede desert boots to your outfit and ta-da: the outfit is complete.
Such staples as a brown cardigan and khaki jeans are the perfect way to infuse some cool into your day-to-day styling rotation.
This off-duty combo of a tobacco military jacket and grey jeans is perfect when you need to look stylish in a flash. A pair of white low top sneakers immediately bumps up the street cred of this look.
A multi colored short sleeve shirt and khaki chinos are essential menswear items, without which our wardrobes would be incomplete. Slip into white plimsolls and ta-da: this ensemble is complete.
Wear a navy suit and a blue chambray long sleeve shirt for a sleek elegant look.
If you're a fan of casual pairings, then you'll love this pairing of a white polo and blue jeans. Feeling bold? Switch things up with brown leather chelsea boots.
Consider wearing a tan suit and a green cardigan for sharp style with a twist. Brown leather loafers will be a stylish complement to your outfit.
A grey wool suit and a white dress shirt are among the fundamental elements in a versatile man's wardrobe. Does this ensemble feel too dressy? Let a pair of brown suede desert boots jazz things up.
Stand out among other guys by wearing a navy barn jacket and khaki chinos. Let your expert styling truly shine by finishing with a pair of brown leather desert boots.
You'll be surprised at how easy it is for any gent to get dressed this way. Just a beige field jacket married with a light blue long sleeve shirt.
A brown corduroy barn jacket and blue jeans are essential in any man's versatile casual wardrobe.
If you feel more confident in comfortable clothes, you'll like this off-duty pairing of a white long sleeve shirt and black chinos. You could perhaps get a bit experimental in the shoe department and complement your getup with a pair of burgundy leather casual boots.
Dress in a white blazer and a blue long sleeve shirt and you'll pull together a proper and sophisticated look.
For a casually cool look, go for a beige military jacket and black chinos — these items play nicely together. Get a little creative with footwear and spruce up this ensemble by rounding off with dark brown leather brogues.
Combining a burgundy v-neck sweater with grey jeans is a wonderful option for a casual yet stylish look. On the shoe front, this look is complemented well with tan suede desert boots.
Team a white and navy vertical striped long sleeve shirt with dark green dress pants for sharp style with a modernized spin. If you want to immediately dress up your ensemble with one item, why not complete your look with tan leather derby shoes?
For a relaxed getup, choose a navy field jacket and white jeans — these pieces work really well together. Brown suede derby shoes are an effortless way to power up this outfit.
For an effortlessly stylish ensemble, pair a tan wool blazer with blue jeans — these items play pretty good together. Finish off with tan suede desert boots and you're all done and looking spectacular.
This pairing of a navy chambray long sleeve shirt and tobacco chinos is hard proof that a pared down casual outfit can still be really interesting. Not sure how to round off this look? Wear a pair of burgundy leather casual boots to bump it up.
An olive military jacket and black jeans are the perfect way to introduce effortless cool into your daily rotation. For something more on the daring side to round off this ensemble, add a pair of grey suede low top sneakers to the equation.
This combo of a navy plaid long sleeve shirt and tobacco chinos is hard proof that a safe off-duty look can still look really interesting.
This combo of a blue chambray long sleeve shirt and navy jeans is hard proof that a simple casual look can still be really interesting. In the shoe department, go for something on the relaxed end of the spectrum with brown leather work boots.
For an outfit that's very straightforward but can be styled in plenty of different ways, wear a white blazer and blue jeans. Let your styling expertise really shine by complementing this ensemble with brown suede desert boots.
An olive military jacket and burgundy chinos teamed together are a match made in heaven for those dressers who appreciate casually stylish styles. Look at how well this look goes with dark brown leather casual boots.
Go for a pared down but on-trend getup marrying a navy blazer and beige chinos.
Why not try teaming a charcoal crew-neck sweater with navy jeans? As well as totally functional, both items look amazing when worn together. Our favorite of a variety of ways to complement this ensemble is with brown leather desert boots.
You'll be amazed at how easy it is for any man to pull together this laid-back ensemble. Just a red cardigan and navy chinos. Why not add a pair of tan leather brogues to the equation for a hint of refinement?
Pair a white long sleeve shirt with green chinos for a casual and stylish outfit. Finishing with brown leather loafers is a fail-safe way to add some extra definition to your outfit.
Rock a camel duffle coat with orange chinos to create a dressy, but not too dressy ensemble. For a more relaxed feel, add a pair of burgundy suede low top sneakers to your ensemble.
Master casual in a navy crew-neck sweater and yellow chinos. Black leather derby shoes are guaranteed to give a sense of polish to your outfit.
This smart pairing of a navy blazer and blue chinos is super easy to throw together in no time, helping you look amazing and ready for anything without spending a ton of time combing through your wardrobe. Feeling venturesome today? Break up this look by finishing with a pair of grey plimsolls.
As you can see here, it doesn't require that much effort for a man to look casually sleek. Just pair an olive wool blazer with mint chinos and be sure you'll look amazing.
This pairing of a black blazer and yellow chinos is truly jaw-dropping, but it's super easy to replicate too. Avoid looking too casual by rounding off with a pair of brown leather derby shoes.
This combination of a grey v-neck sweater and navy jeans is definitive proof that a safe casual ensemble doesn't have to be boring. Tan suede desert boots are a goofproof footwear option here that's also full of character.
Try pairing a tan crew-neck sweater with blue jeans to pull together a truly sharp and modern-looking off-duty outfit.
The combo of a navy field jacket and navy jeans makes for a solid casual look.
If you're a fan of off-duty getups, why not opt for this combo of a tobacco military jacket and beige chinos?
A tan blazer and navy chinos make for the perfect base for an outfit. You can get a bit experimental when it comes to shoes and elevate your ensemble by rocking a pair of olive suede double monks.
You'll be surprised at how extremely easy it is for any gent to get dressed this way. Just a beige pea coat matched with navy jeans.
Why not opt for a grey crew-neck sweater and navy jeans? These two pieces are super practical and look cool when teamed together. Add a pair of burgundy leather desert boots to the equation to tie the whole look together.
Super dapper and comfortable, this off-duty combo of a tan cardigan and aquamarine chinos will provide you with variety. Wondering how to round off your ensemble? Wear brown leather tassel loafers to dress it up.
If the setting calls for a classy yet neat outfit, dress in a beige blazer and blue chinos.