Summer, summer, summertime. Time to sit back and unwind, party, tan and go on dates. Everyone knows that summer is the time when people come out of hibernation and look to get out, reconnect with old friends and more importantly make new ones. With Spring being break-up season, its only fitting that summer is matting season, make-up season, dating season…you get the idea. Summer offers some great options on what you can do when planning a date, from afternoon picnics, late night dinner, to casual walks by the water. Unlike winter where you are confined to being indoors, summer definitely opens the doors to possibilities, which can only work in your favour.

Once you’ve got the girl and activity nailed down, pardon the innuendo, the next step is to figure out what you’re going to wear. Your outfit is key in ensuring that you put your best foot forward, because there is no doubt that she will be paying attention. To help you in that department we reached out to our stylists to put together some of their best “Summer Date” outfits.

Neal: My inspiration for my Summer Date outfit was a nice day in the park or on the beach. I wanted a look that would be nice and fashionable yet light and airy. To start with I picked these great shorts by Parke and Ronen, they offer a great fit and are made of a nice light weight cotton making them very breathable and comfortable for long walks. I paired that with a Parke and Ronen mesh cardigan which I layered with a fun stripped tank by Benson. Mesh cardigans are on trend right now and offer a nice twist to classic sartorial style.

No picnic or beach date is complete without the appropriate accessories. For this outfit I included a large tote bag from benson for all your sunscreen, towels, hats and flask incase you get “thirsty”.  I also added a light John Varvatos scarf so you’re prepared incase it gets a little cooler in the evening.

Benson Beach Bag: $150
Parke & Ronen King’s Mesh Cardigan: $220
Parke & Ronen Slim Board Shorts: $138 Shop Now
Strellson Skinny Leather Belt: $120 Shop Now
Benson Stripe Jersey Tank: $60 Shop Now
Goorin Streetwise Paper Straw Fedora: $75
Maians Sisto Clasico Spanish Canvas Shoe: $120
Samy Stripe Scarf: $110
In God We Trust Flask: $60

Daria: My Summer Date outfit revolves around going on a nice dinner where you want to dress up but not look overly stuffy. It’s all about keeping it summery and light, yet sophisticated. I started with a classic navy Oscar shirt. This shirt is a no-brainer as it goes with everything and require very little finessing.  Same is true of the sport jacket, the great check pattern allows the wearer to pretty much pair it with any colour or style. You can dress it up, as we’ve done here with a pair of Hiltil trousers or down with a nice pair of jeans for a casual afternoon brunch.

One of my favourite items in this look are the light grey brogues from John Varvatos. These shoes are simply great, the light shade offers a nice twist to a smart summer shoe, while still being versatile enough that you can wear them with trousers or jeans. It’s a perfect example of  what we like to call “sophisticated casual”.

Anderson’s Textile Woven Belt: $135
Oscar Solid Slim Fit Shirt: $198
Hiltl Piacenza Check Pant: $228
Sand Wool/Linen Blazer w/ Suede Elblow Patches: $698
Base London Catch Suede Shoe: $175
A Christensen Pocketsquare: $45

Nicole: My inspiration is based on a man that is very well put together, he has a good full time job and someone who takes a lot of pride in the way he dresses. For that man there was no other option than our stunning double breasted jacket. This isn’t your fathers old double breasted jacket, it’s modern, stylish and sure to make you stand out from the crowd. What makes this blazer great is that its 1/4 lined making it light weight and ideal for warm summer dates on the boardwalk.

But let’s not forget that any well dressed man knows the importance of details, which is why I added this great WOOD watch which goes perfectly with our monk strap shoes. And for the cherry on top, I threw in one our floral print linen pocket squares…just cause!

 

Hilton Double Breasted Peak Lapel Jacket: $730
WeWood Metis Watch: $120
Haight & Ashbury Slim Fit Shirt: $120
Strellson Belt: $108 Shop Now
Matteo Massimo Monk Strap Shoe: $450 Shop Now

 Joel: I think the best dates are spontaneous and you never know where they are going to lead you, so I picked an outfit that would be very versatile and literally take you anywhere. You could go to a fancy dinner or a walk in the park, there are no limitations to where you can go in this outfit.

Wearing colour is on trend right now, which is why I chose these cotton trousers as they are very easy to wear. I paired it with a lot of neutral so that it wasn’t overwhelming in colour. The other main feature of this outfit is the cotton blazer because it adds that bit of formal edge while keeping the look very light weight and easy going. I also love the shoes because even though they seem a little trendy they are a classic and can be worn in the future.

 

Tiger Of Sweden Evert Blazer: $499
Tiger Of Sweden Rodman Chinos: $199
Rogue Rodman Distressed Wingtip Shoe: $250
Strellson Suede Belt: $108
Haight & Ashbury Slim Fit Shirt: $95
A Christensen Linen Pocketsquare: $45

 Lindsay: Mid-Summer night picnic in the park was my inspiration behind my Summer date outfit. With the great summer weather, dates in the park are always a sure bet at being romantic. Keeping that in mind I started with this sport jacket just incase it gets a little chilly as the evening progresses. We added some pop of colour under jacket with with a cool pink shirt (real men wear pink) and green scarf. No picnic is complete without some “beverages” which is why I included our great flask set, incase you guys get a little thirsty.

To round it off I paired this outfit with a nice WOOD watch, AG denim, and classic canvas brogue shoes.

 

 

Ted Baker: Rolando Cotton Check Blazer: $498
Strellson Scarf: $98 Shop Now
Adriano Goldschmied Jean: $310
WeWood Voyage Watch: $140
Oscar Shirt: $198
Wolverine Two-Tone Brogue Shoes: $300
Daines & Hathaway Triple Bar Set: $358

Shop the brands:
A. Christensen, Strellson, Ted Baker, Tiger of Sweden, Hiltl, Sand