What to Wear on a First Date

1. Movie Night

An unstructured cotton jacket is a great Spring piece for looking smart but relaxed.

By “unstructured” or “unconstructed” I mean a jacket without a chest canvas, lining or shoulder pads/sleeve heads . It’s really just a shell of a jacket. It feels very lightweight and “moldable” because it’s sewn more like a shirt than a traditional tailored jacket.

With slim chinos and a sharp tee (preferably long-sleeve) it’s one of those dressy-casual looks that is appropriate to go just about anywhere.

Leather driving shoes are sharper than sneakers without the stiffness of leather-bottom office loafers.

They’re also very comfortable and great for walking – which is important when the nerves are running up on a first date.

On Dan: Black cotton jacket by Theory. Grey l/s cotton tee by RichInClothing. Cotton chinos byMichael Andrews Bespoke. Loafers by Gucci. On Karyn: Top is a vintage 1950s bathing suit. Pants by American Apparel. Shoes by Urban Outfitters. Vintage earrings. Ring by Just Charmed from Yumi Kim store. Jacket by Stile Benetton.  

2. Brunch & Walk in the Park

There’s confidence in simplicity.

A simple combination that will look proper and easy on just about any guy: button-down shirt + slim fitted v-neck + jeans or chinos.

Keep the palette neutral, you don’t need to make any bold color statements.

On Dan: Brown v-neck by Hugo Boss. Shirt by Michael Andrews Bespoke. Jeans by Ralph Lauren Polo. Saddle shoes by Bass. Alligator belt by Ralph Lauren Purple Label. Shades by Archie Brower. Watch by Montblanc. On Karyn: Jersey knit dress from Tokio 7.  Loafers by Kelsie Dagger. Hat thrifted. Ring by Just Charmed.

3. Drinks & Night Out

A lightweight black leather jacket is meant for a night out, and it’s hard to go wrong with slim, but not skinny, jeans in a dark indigo wash.

Whether you like it or not, it’s true. She’s definitely going to notice your shoes.

Scratch that. She’s not only going to notice your shoes – she’s going to look at them and pass a small judgement of some kind. Depending on the girl, this judgement might go a long way.

Don’t take your chances. Wear a sharp shoe if you’re stepping out somewhere nice for the evening. My first choice is usually a black leather loafer or dressy boot.

On Dan: Leather jacket by Ralph Lauren Purple Label. Cardigan by Rag&Bone. Shirt by Steven Alan. Loafers by Johnston & Murphy. Jeans by JCrew. On Karyn: Hat by Stetson. Shoes by JCrew. Jacket by Peppe Peluso. Top: Alexander Wang. Vintage Ring.

4. Bike Ride & Picnic 

For an active afternoon date all you need is a simple knit crewneck, slim chino and white low-top sneakers.

I can’t say enough about purchasing a quality pair of sunglasses that flatter your face.

It’s one of those purchases you shouldn’t skimp on since you wear them almost everyday and they’re front and center on your face.

On Dan: Top by St. James. Trousers (part of suit) by Michael Andrews Bespoke. Leather sneakers by Converse. Shades by Matsuda Eyewear. Watch by Montblanc. On Karyn: Shoes by Dolce Vita. Jeans by H&M. Onesie by American Apparel. Jacket by Urban Outfitters. Necklace by Urban Outfitters. Hairbow is a vintage scarf.

5. Reservations for Dinner

If it’s a “fancy” date you can wear a suit, but you don’t want to look like a suit.

Drop the socks, the belt, and a couple shirt buttons (or three if you’re not afraid of a little cleavage).

A suit in a textured fabric looks more “chic” and less “office”, as does a shirt with a darker base color.

On Dan: Grey hopsack suit by MAB by Dan Trepanier. Shirt by Michael Andrews Bespoke. Oxblood loafer by Scarpe di Bianco. Vintage pocket square. On Karyn: Tee by Target. Pants by American Apparel. Necklace by Urban Outfitters. 

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