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Guys, What to Wear on Your First Date

Got a first date and want a second one?

We gotta say, first impressions go beyond what you’re wearing. But, nobody ever said dressing well hurt your chances for having a good time and locking in another date. 

Depending on where you are going, you’ll have to decide for yourself how casual or formal you want to dress. See our complete First Date Style Guide.

Wantering’s Top 6 Picks for What to Wear on Your First Date:

1) Levi’s 511 Rinsed Playa Dark Denim Jeans - Dark denim is easy and goes with pretty much any color shirt, so when in doubt don’t forget this staple.

2) J. Crew Slim Fit Secret Wash Shirt in Heathered Forest Plaid - Not strictly for lumberjacks or hipsters, you can wear a plaid button down underneath a blazer or sweater and look like you tried.

3) Topman Navy Double Shawl Collar Sweater- Wear a thicker cardigan as a jacket if you’re in warmer climates. It’s cozy and comfortable but still looks dressed up because of the shawl collar detail.

4) ASOS Slim Fit Blazer in Tweed - Fancy dinner planned? Tweed, herringbone or wool blazers look way cooler than formal suit blazers. Invest in one of these.

5) Blackstone M 07 Wingtip Sneaker - Not a sneaker but not a dress shoe. High-five.

6) Anonymous Ism Chestnut JQ Crew Socks - Hey, nice socks feel good ok?


7) Aesop Moroccan Neroli Post-Shave Lotion - SMELL GOOD.

Shop more recommendations in our Wantering First Date Style Guide!

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Men’s Luxury Loungewear

You’ve probably seen them already: stylish gents wearing loungewear pieces and actually looking amazing in them. It’s a trend that quickly picked up over summer, and is only getting more popular for fall and seasons to come. Don’t try to get in on the action just by wearing your pajamas out of the house though. Read more about how to wear loungewear in different stylish ways in the full luxury loungewear trend report, and see some of the key trend pieces below.

1. Scotch & Sods Slub Henley T-Shirt

2. H&M Jersey Shorts

3. True Religion Runner Jogger Pants

4. Our Legacy 50’s Great Sweatshrt

5. Lanvin Unstructured Wool Blend Blazer

6. Phlip Kimono-Sleeve Robe

7. Dockers Nap Slippers



Fashion Blogger Street Style

How’s this for an elegant fall transition? Insider Jill of The August Diaries in a gorgeous LWD. Get the dress here:

d.ra Shanna Dress


Free People Knee High Socks: Why are they the most popular fashion item on Tumblr right now?

We’re kind of obsessed with knee high socks and the team at Free People makes them SO WELL. High enough that they won’t fall down throughout the day and thick enough that they keep your legs warm. That’s why they’re the most popular fashion item on Tumblr right now.

The key to wearing knee highs is to make sure your skirt, dress or shorts sit mid-thigh or higher, otherwise it won’t look right. You can also do some layering tricks with a pair of tights and boots.

Free People Speckled Slouch Tall Socks. GET IT HERE

Peace, love & good style,

Kathleen, Wantering Editor