3 Confidence-Boosting Date Night Looks

THE SOPHISTICATED JACKET LOOK
Why is it a Find? In general, you can never go wrong with a great navy blazer, and that’s especially true for date night. This all cotton blazer from FLYNT has an updated look with narrower lapels, open patch pockets and colorful trim under the collar. It shows you took some time to dress for the occasion and that you're not just relying on your tried-and-true conservative, work jacket.
Wear it with: Besides the outfit we’re putting together here, it looks just as good with dark wash jeans, or a twill pair in any color, and a simple white shirt.
Fit Tip: The fit is modern, ideal for most gents with just enough room to be comfortable but not slouchy.
Alternatives: If you prefer a trimmer, contemporary fit Rag & Bone’s version is so cool.

Why is it a Find? Add a subtle micro check pattern under the featured jacket with this Peter Millar shirt. The fabric is visibly luxurious and the darker blue tone gives it that right night out feel.
Fit Tip: The fit is modern, in S-XXL, so go with your normal size for the right fit.
Alternatives: J. Crew offers a trimmer, contemporary fit in a deep blue plaid that also looks great with the jacket we’re showing.

Why is it a Find? Flat front cotton twill pants are a timeless style that are always an easy go-to, and they create a classically dapper look with the navy blazer in this outfit. The charcoal grey is a nice update to your basic khaki’s, and plays up the colors in the plaid shirt, too.
Wear it with: Of course, they’re great in this look, but a pair of grey flat fronts are so versatile – they really work with all your button up shirts, polished sweaters, and sport coats.
Fit Tip: In an “everygent” modern fit, they offer a nice update to your old flat fronts, with a somewhat narrower leg, seat and thigh that still has a comfortable a mid-rise.
Alternatives: Click through the ‘shop it’ button to check out the khaki and navy versions, too.

Why is it a Find? Finish this gentlemanly look with an accessory every true gent has on a date – a simple white linen pocket square. The tipping adds a nice touch and pulls this whole look together. J.Crew’s pricing can’t be beat for an Italian linen square.
Wear it with: While it’s great popping out of your navy sport jacket pocket, it looks just as good with most any suit or sport coat. White is always an appropriate color for a pocket square.
Alternatives: There are five different tipping colors available through the ‘shop it’ button, and they’ll all pop your look to perfection.

THE CARDIGAN FOR DATE NIGHT STYLE
Why is it a Find? Shawl collar cardigans are not only a stylish statement, but their versatility gives a gent an alternative to a jacket for a relaxed and updated date night look. Rag & Bone’s textured cotton knit, patch pockets and over-sized buttons add a distinctive style that is simply cool.
Wear it with: This navy cardigan sweater not only anchors the outfit we’ve pulled together here, it can be dressed up further by adding a tie – or dressed down by pairing it with a t-shirt and your favorite jeans.
Fit Tip: The contemporary fit is trim, but not skinny, which we like for a style like this to prevent it from looking too “grandpa”. You can size up for an easier fit though, and the style will still look sleek.
Alternatives: If you prefer a pullover sweater, Rag & Bone’s timeless v-neck is just as updated looking and works with everything in this outfit.

Why is it a Find? Bugatchi’s blue plaid pattern blends perfectly with the texture of the sweater and the spread collar means you can wear this shirt with a tie, too. Though, the contrasting brown gingham pattern is such a dapper finishing detail, it looks great without one.
Wear it with: Ralph Lauren’s solid charcoal silk knit tie adds a dapper addition to this outfit if you want to show a little extra effort.
Fit Tip: The shirt is a contemporary fit, which allows this shirt to lay smoothly under the featured sweater and not bunch up.
Alternatives: If you prefer an easier, modern fitting shirt, this bolder plaid from David Donahue is a great alternative.

Why is it a Find? Bonobos is a go-to resource for all kinds of pants. And now Nordstrom carries it. They are priced really well, especially once you check out the quality, and offer a variety of fits so they work for every gent. They use a washed cotton twill for these dark grey (called Chino Grigios), flat fronts that have the right casual, yet updated feel to work in this outfit. Whether you’re headed to a restaurant or an early or late night drink, these will have you fitting right in.
Wear it with: These pants are a basic, so when you want to look pulled together and don’t know what to wear…just wear these.
Fit Tip: Started as a pants line, Bonobos nails fit, which is available in 3 options: Tailored (the trimmest, contemporary fit we’re suggesting today), Straight (a modern “everyman” fit that is still updated and current), and Slim (which is in between the two, and what we're showing here). Besides choosing your waist size, you can also choose an inseam length that is right for you.
Alternatives: Nordstrom also carries the Tailored fit in a bunch of great neutrals. On Bonobos' own website, you can stock up on multiple colors and choose from any of their 3 different fits right here.

Why is it a Find? We always advise to make sure you’ve got a good-looking belt on. It’s one of those things that are only noticed if it doesn’t look good…and we can’t have that on date night. This pebble grained leather belt with a brushed silver buckle from Will Leather Goods has a 1 ¼” width that is updated and completes the outfit.
Fit Tip: A gent usually buys a belt one size larger than his waist size.
Alternatives: The belt is also available in brown and tan through the ‘shop it’ button. Tip: Match your belt to your shoes.

THE RIGHT WAY TO DO JEANS
Why is it a Find? Any good date can appreciate a gent in a great-fitting pair of jeans. And these Joe’s are the ones that will do it. The dark wash has just the right amount of distressing along the edges, and whiskering in all the right places, for that nonchalant air of confidence.
Wear it with: The outfit we’re showing you here is just an example of all the great ways to wear these jeans. We really can’t think of anything they won’t look great with, so go ahead and dress ‘em up with a sport coat or down with a t-shirt. You’ll wear them all the time.
Fit Tip: These Joe’s Brixton fit, which is one of their most popular contemporary cuts. They have a narrower straight leg and lower - but not too low - rise. It is the ideal fit for a gents who wants a modern, updated look but not a truly skinny pair of jeans.
Alternatives: A pair of jeans in a simple and clean black twill are also a great date night go-to, and these AG’s have a similar fit.

Why is it a Find? You’ll simply never go wrong with a plaid button up shirt, for any occasion, including a special night out. This one from Zackery Prell has a rich, modern look in it’s dark, muted tones that feels sophisticated and rugged at the same time.
Wear it with: It can easily stand on its own, especially with the dark jeans we’re showing in this outfit, and looks great with charcoal wool dress trousers, too. Besides the sweater we’re showing below, you can also wear it under a navy or charcoal blazer. And, of course, it’s certainly good-looking enough to stand on its own.
Fit Tip: The fit is contemporary, creating a trim silhouette that allows the shirt to be worn tucked or untucked and still look polished.
Alternatives: For a more relaxed, modern fit, Robert Graham’s navy plaid will never disappoint.

Why is it a Find? J.Crew does a great job producing high quality cashmere, and this lightweight crewneck (shown in “night vision”) is a great layer over the shirt in this outfit during the Winter. It’s adds a beautifully soft texture to your look, but since it’s lightweight, you won’t get too hot.
Wear it with: Wear it with all your button up shirts and jeans of any wash.
Fit Tip: The fit is typical J.Crew - modern and universally flattering for most gents. It comes in Tall, too. If you prefer a more relaxed fit, size up.
Alternatives: It comes in a ton of great looking colors through the ‘shop it’ button. We also really like the black version for a night out.

Why is it a Find? Sure, your oxfords will look great with this outfit. But step up your style with these Frye shoes, instead. The perfect blend of boots and a stylish pair of sneakers (so current and acceptable everywhere these days), they have a hand-burnished, black leather chukka style upper and a sneaker bottom - such a cool look that will impress any date.
Wear it with: From the dark jeans we’re showing here to your favorite broken-in pair, these will have you walking in style.
Fit Tip: We find them to fit true to size.
Alternatives: Frye also offers the same look in a true chukka boot style.