Style GirlfriendStyle Girlfriend is the go-to destination for guys seeking not just fashion advice, but lifestyle tips, tricks, and shortcuts - all from a friendly, female editorial team’s perspective. Each week, Team SG will round up the clothes, grooming products and more men need to live their most stylish lives.  

Ah, day dates. The safety zone of romantic plans, where chemistry goes to die. Just kidding! Day dates are fine! But, if you ask us, they’re not as easy to dress for as an after-dark rendezvous. You want to nail a look that says, “I put in effort” and “I realize it’s 3 p.m. on a Saturday” at the same time. Like you might have plans later… Or you might not. Anything’s possible! You’re breezy!

In our book, a button-down shirt isn’t required on dates before 5 p.m. Instead, use your outerwear to step up the style factor, and make sure your footwear is spiffed up and ready for broad daylight. Your day date outfit formula can rely on colors, patterns and layers to telegraph your open-minded, cheerful mood and sunglasses to literally put your best face forward.


Bonobos jeans, $108

Bonobos - The Blue Jean
Graphic: Shep McAllister

Light out, light jeans. Dark out, dark jeans. It sounds simplistic, but we really like this approach to date dressing. These jeans from Bonobos in the ‘Lanier’ wash get our vote because of the clean blue hue and that 1% touch of Spandex for a little stretch. (It’s the weekend, after all. Comfort is king!)

Uniqlo henley, $20

Uniqlo - Waffle Henley
Graphic: Shep McAllister

Team SG has always been pro-henley, but no more strongly so than on dates. That trail of buttons, when it divides a soft, waffled cotton, really does something for the pectoral… area. So yeah, throw this cozy long-sleeve tee on under your shirt jacket for your trip to the museum. (But she won’t have her eyes on the art, trust us!)

Faherty Durango shirt jacket, $112

Faherty - Durango shirt jacket
Graphic: Shep McAllister

An outing like a Sunday afternoon “coffee walk” is the perfect excuse to debut your finest fall outerwear, best admired in the waning light of a leisurely stroll at dusk. Speaking of sunsets, this Faherty shirt jacket totally reminds us of dusk in the American Southwest, which is like, very romantic.

Greats Royale perforated sneaker, $179

Greats - Royale perforated sneaker
Graphic: Shep McAllister

We are all for sneakers on a date (day or night, actually) as long as they look both a) clean, and b) cool. A smart move is to invest in a classic pair of leather sneakers, like this perforated pair from Greats, because they can be spiffed up over and over, and aren’t likely to go out of style anytime soon.

Ray-Ban Keyhole sunglasses, $140

Ray-Ban Keyhole sunglasses, $140
Graphic: Shep McA

Not that you need it, but studies show the symmetry of sunglasses makes any face look more attractive. No shame in using yours to build a little courage when stepping outside after your day date and steeling yourself to ask for a second outing. When you look so good, how could she say no?