What to Wear on a Date: Four Expert- Approved Looks.

I met Emily Holmes Hahn (the founder of white glove match-making service Last First) at a party in the Hamptons this summer and we instantly hit it off. We immediately bonded over our mutual handbag obsession. I drooled over her white Goyard, she complimented my vintage red Chanel. The girl has style, and she is also really nice. That can be hard to find. And when I found out that she was a professional matchmaker, I instantly (of course) had a million questions for her. Fast forward to a few weeks later, I’ve finally managed to rope her into helping me out with a little blog post.

Emily was kind enough to answer some fun dating related questions for us (scroll to the bottom) AND put together four really cute date outfit ideas. (I’m particularly obsessed with the whole daytime outfit… I want every single thing she featured). Then, to keep things budget friendly, Kelly then came in and tracked down some more affordable alternatives for each look. Enjoy!

What to Wear on a Date! Workday Lunch. Dating Advice (+ Outfit Ideas) with Emily Holmes Hahn, founder of LastFirst.

I chose a feminine, preppy-with-a-twist look for the workweek lunch date. Keep it simple with minimal accessories, or layer on the ear cuffs and/or hat if those speak to you. The Ganni skirt should be properly tailored, because that pop of skin between boot and hem is essential!” – Emily

Get the lookMaje Top // Ganni Leather Mini Skirt // Stuart Weitzman Boots // Mansur Gavriel Patent Mini Bucket Bag // Eugenia Kim Georgina Fedora (optional) // Accessorize this look with delicate ear candy like this, this, or this.

The look for less: Reformation Eden Top // Free People Vegan Leather Skirt // Sam Edelman Boots // Baggu Drawstring Bag // Sensi Studio Hat // BaubleBar Ear Crawlers

What to Wear on a Date! Weekend Brunch or Activity Date. Dating Advice (+ Outfit Ideas) with Emily Holmes Hahn, founder of LastFirst.

“Brunch is a fun and relaxed time, so a swingy slip of dress is a great pick. Layer on  this herringbone blazer or fringed scarf, or both, to make the look weather-appropriate. Finish the look with these Rag & Bone Harrow boots and Self-Portrait sunglasses, both on-trend and practical.” – Emily

Get the Look: Madewell Printed Mini Dress // Rag & Bone Harrow Booties // Halden Chevron Jacket // Sapphire Ear Cuff // Self-Portrait Sunglasses // Rebecca Minkoff Bag // Isabel Marant Scarf

The Look for Less: Forever 21 Dress // Charles by Charles David grey suede boots // ASOS New Look Blazer // BaubleBar Ear Crawlers // Festival Round Sunglasses // Leather Satchel Co. Saddle Bag // Forever 21 Scarf

What to Wear on a Date! Uptown Dinner Date. Dating Advice (+ Outfit Ideas) with Emily Holmes Hahn, founder of LastFirst.

For a more formal dinner date, a LBD is a great place to start. This one by IRO is the kind of dress that makes you look in-the-know but not runway crazy. Finish the outfit with a dainty Are You Am I choker tied up in a bow (for a little flirt) and sparkly, but discreet, jewelry, which you could do in gold or silver.” – Emily

Get the Look: IRO Dress // Christian Louboutin Pumps // Nina Ricci Bag // Ear Jackets // Choker // Catbird Threadbare Ring // Crystal Ring // Catbird Bracelet

The Look for Less: Y.A.S. Dress // Daya Pumps // BCBG Feather Clutch // BaubleBar Ear Jackets// BaubleBar Choker //BaubleBar Crystal Ring // BaubleBar Hand Chain


What to Wear on a Date! Downtown Dinner Date. Dating Advice (+ Outfit Ideas) with Emily Holmes Hahn, founder of LastFirst.

For a downtown dinner date, try a look that’s clean and dressy-casual. Winter white is always a “do” when balanced out with darks, and the cut of the Elizabeth and James top will flatter any figure. I did red accents with this look but you could keep it easier with only blacks and whites, too; or go for a more trendy “pop” of olive green or airy blue.” – Emily

Get the Look: Maje Jacket // Elizabeth and James Peplum // ACNE Skinny Jeans // Gianvito Rossi Plexi Pumps // Red Envelope Clutch // Delfina Delatrez Earrings

Look for Less: Urban Outfitters Duster Poncho // ASOS Black Peplum Top // Articles of Society White Jeans // BCBGeneration PVC Heels // Red Envelope Clutch // Lip Ear Jacket

I also got Emily to answer a few dating-related questions for me… enjoy!

Grace: Getting ready for a date can be daunting – what’s the best advice you have to offer?

Emily: The most important thing is to wear something that makes you feel confident. If you’re confident, you’ll be more relaxed and alluring. A great formula for achieving that confidence level is to wear something that (a) is spot-on for the occasion and (b) accentuates your favorite feature.

Grace: Are there any absolute dont’s? For example, I’ve had friends tell me things like… “don’t wear red lipstick,” “Don’t carry a designer bag or he will think you are shallow,” “Don’t wear heels in case he’s not as tall as his profile says..

Emily: I don’t like a “don’t” rule if it interferes with your personal style. But, I suppose you should avoid coming on too strong in any one direction. I always say to my women clients, “balance your look.” If you have to have Gwen Stefani red lips (amazing if you can pull it off!), just go very light on the rest of your make-up. If you do carry a structured designer bag, go for a more effortless-chic outfit. And always, if you wear a super short skirt, pick a more covered-up top.

Grace: If you remember… what did you wear on your first date with Ross?

Emily: It was early September so I did a dark summery look. I wore a short, slinky black trapeze dress from Maje (which if you couldn’t tell from my outfit picks, is one of my favorite brands!), and these black leather-and-cork wedge sandals that I got as “wardrobing” when I worked at Ralph Lauren. I’d be lying if I said I remember how I accessorized, but let’s say I had some awesome rose gold stacked rings, and dainty layered necklaces! I love little pops of twinkly jewelry on a date because they’re unassuming but still eye-catching. So I probably wore those!

Grace: Any parting advice?

Emily: On a first date—or one in which you don’t know your date well—wear something you love, but also something slightly classic. A little black dress for dinner or a jeans-and-heels combo may sound “basic,” but it is really spot-on. You want your personality and gorgeous face to shine, and your outfit to play a supporting role!

Leave a Comment


  1. Rachel says 9.9.16

    Amazing! Loving every sets!


    • graceatwood says 9.9.16

      So happy to hear that, Rachel! Have a great weekend!!!

  2. Jenn Lake says 9.9.16

    So many cute looks! Happy Friday!

    • graceatwood says 9.9.16

      Thanks Jenn – back atcha! Have an amazing weekend!

  3. Tracy Schwartz says 9.9.16

    What a great post! And thank you for sharing the look for less! As someone on a tight budget and just starting out dating this will really help!

    • graceatwood says 9.9.16

      Aw thank you so much, Tracy! And you are welcome. Kelly did such a good job recreating Emily’s looks on a budget – I am super impressed! Have a great weekend!

  4. I am all about that second outfit! SUPER cute!

    • graceatwood says 9.9.16

      That one is my favorite, too!

  5. Josephine says 9.9.16

    Love this!!! First look is killer. Those boots.

    • graceatwood says 9.9.16

      I know, it’s so good! Confession: I ended up ordering the Ganni skirt – it fits really well! x

  6. Ah, you nailed this post, Grace (and Emily and Kelly)! I really appreciate the fact that you included links to more budget friendly options. As much as I would LOVE to treat myself to a pair of Louboutins, they’re not in the cards for me just yet. Someday!

    Natalie Was Here

    • graceatwood says 9.9.16

      I am so happy to hear that you enjoyed it, Natalie! It’s always good to have budget-friendly alternatives 🙂 🙂 Have a great weekend!

  7. Dana says 9.9.16

    This was such a fun post to read, love it!

    Pink Champagne Problems

    • graceatwood says 9.9.16

      So happy you enjoyed it lady! xx

  8. Thuy says 9.9.16

    Love the brunch and dinner date looks. I could do the lunch date look but maybe slightly different colour palette.


    • graceatwood says 9.9.16

      Thanks, Thuy! That one was my favorite too.

  9. Meghan says 9.9.16

    omg LOVE this post format! It’s so fun to see what an expert would pick (I’m obsessed with that brunch outfit) but also to have more affordable options to easily do a high/low look. Happy Friday!

    • graceatwood says 9.9.16

      So glad you enjoyed it, Meghan!!! Emily has the best taste. Have a great weekend! 🙂 x

  10. Lisa Tran says 9.9.16

    This was SUCH a cute post!!! I love all the styling options! Maybe next time, you can get her to spill some dating tips… such as how to LAND a date 😉 so I have an excuse to wear all those cute pieces 😉

    Also loved Kelly chiming in with her affordable pics – super cool idea!


    • graceatwood says 9.11.16

      Haha, great idea! Thank you Lisa – hope you had a great weekend!!!

  11. Annie says 9.9.16

    Grace! Longtime daily reader. Just FYI, you have never looked more beautiful. You are simply glowing. I think you are about to attract some really positive energy (likely in the form of a man). Mark my words:you’re radiant. You’re powerful. Good things are coming soon

    • graceatwood says 9.11.16

      Aw, that is so sweet of you to say, Annie! Thank you 🙂 xx

  12. Shannon Waisath says 9.13.16

    Oh my god the Brunch date outfit is my absolute fav! So so so cute!


    • graceatwood says 9.13.16

      Mine too!!