You only get one chance to make a first impression. Perhaps you’ve been out of the dating game for a while and are heading off on your first date in a long time. Or maybe you’re going out for a long-awaited date with your significant other. Either way, you’ll find plenty of inspiration in this article on how to dress on first date.

What to think about when choosing how to dress for a first dat

First what should you consider when putting together your first date outfit?

#1 Wear what you’re comfortable in

How to dress for a first date - Abi in a jumpsuit | 40plusstyle.com

While you’ll want to choose something special, you’ll want to make sure you feel comfortable. You don’t want to be fidgeting with a neckline or feeling that your waist is digging in.

Abi @stealmystyle40 above looks very stylish but also relaxed in her print jumpsuit.

Recreate her outfit with this similar jumpsuit (another option here), sandals and necklace.

#2 Stay true to your style personality

Not only do you want to be comfortable, you’ll also want to express yourself as you really are. After all, you’ll want to the other person to like you for YOU. Stay true to your unique style personality.

So if natural is normally your style personality, stay true to that and just glam it up a bit.

Of course it’s perfectly fine to show up as the best version of you or the most sexy version of you, but stay true to yourself.

#3 Add an on trend piece

You want to look current on your first date. Even if your style personality is classic. In that case, make sure your classic style is current. Adding just one new item to your outfit can make all the difference.

#4 Mix and match formal and casual

Patricia in a skirt and denim jacket | 40plusstyle.com

To look great yet as if you haven’t tried too hard, mixing formal and casual pieces is a good formula.

Patricia @madamechicbcn above (read her style interview here) adds a casual element to her otherwise formal look with her denim jacket.

Check out this similar tank top, denim jacket, skirt (another option here), pumps, crossbody bag (another option here), sunglasses and headband.

#5 Think about where the date is

For example, if you’re having dinner, you’ll want to concentrate on your top half. But if you’re having a picnic, you’ll want to make sure you can sit down comfortably.

#6 Wear tactile fabrics

Sylvia in a silk dress | 40plusstyle.com

If you want to give your outfit a romantic feel, then wearing tactile fabrics like silk, satin or leather is perfect.

Sylvia @sylviacolella above (read her style interview here) opts for a silk slip dress and cozy cardigan.

Recreate her outfit with this similar dress, cardigan, sandals and shoulder bag (another option here).

#7 show off whatever you’re most confident about

What to wear on a first date - Nikki in a black dress | 40plusstyle.com

If there’s anytime you want to feel confident, it’s on a date. So, if you want to add some subtle sex appeal to your outfit, think about showing off the area of your body you like the most, whether that’s your shoulders, your legs or your decolletage.

Nikki @40notfrumpy above shows off her legs in her little black dress.

Steal her look with this similar dress (other options here and here), handbag, sandals and necklace.

how to dress for a first date a first date

Now, let’s look at how to dress for a first date and some specific outfits you could put together. You’ll find a first date outfit capsule at the end so you can look at how you can mix and match all the different clothes, shoes and accessories.

tops

Ted Baker London Trisca Boxy Cargo Crop JacketNordstrom Drape Neck Short Sleeve TopCareste Georgia Silk SkirtNina 60 Pointy Toe PumpChrysansmile Leather Quilted Crossbody BagOpen Edit Twisted Link Collar Necklace

You could also think about cowl neck tops which always look stylish and have some sex appeal. A print will draw attention to your upper half while if you like your shoulders, you could choose a halterneck top.

First date tops | 40plusstyle.com

Nordstrom Drape Neck Short Sleeve TopVICI Collection Cowl Neck Satin BlouseTed Baker London Harper Floral Tie Front BlouseVICI Collection Satin Halter Neck Blouse

jackets and Coats

Karen Millen Compact Stretch Single Breasted JacketFraiche by J Wrap Front Long Sleeve DressCushionaire Alba Block Heel SandalReiss Arden Basket Weave ClutchOpen Edit Twisted Link Collar NecklaceJennider Helena Chain Drop Earrings

You could always add some drama with your coat and keep the rest of your look simple. Or, you can choose a classic choice like a blazer or a trench coat. A moto jacket or a denim jacket can add a casual element to your outfit.

Coats for a first date | 40plusstyle.com

BLANKNYC Suede Leather Moto JacketKaren Millen Compact Stretch Single Breasted JacketTed Baker London Trisca Boxy Cargo Crop JacketKaren Millen Compact Stretch Stud & Eyelet Statement Coat

jeans and pants

Cathy in wide leg jeans | 40plusstyle.com

Cathy @themiddlepageblog above (read her style interview here) chooses a pair of on-trend wide leg jeans. She adds a classic white shirt and moto jacket, and her print heels add sexiness and playfulness to her outfit.

Check out this similar shirt, moto jacket, wide leg jeans, sandals, bag, necklace and sunglasses.

You can always wear a pair of jeans if you don’t want to look like you’ve tried too hard. Or a pair of black or white pants will always be on trend. You could also think about print pants, but keep the rest of your outfit simple.

Pants and jeans for a first date | 40plusstyle.com

Wit & Wisdom ‘Ab’Solution Itty Bitty Bootcut JeansBoden Richmond 7/8 PantsVICI Collection Belted High Waist Wide Leg PantsNatori Boro Cotton & Silk Ankle Pants

dresses and skirts are perfect for first dates

What to wear on a first date to feel confident and look amazing | 40plusstyle.com

Dresses or skirts would be a natural choice if you want to create an impact. Lizzy @whatlizzyloves above (read her style interview here) chooses a dress that would be perfect for a summer date.

Check out this midi dress (another option here) that you can wear with this similar pair of pumps and clutch.

A red dress is ideal if you want to create a big impression, and a little black dress will, of course, always be appropriate.

Skirts and dresses for a dinner date | 40plusstyle.com

Fraiche by J Wrap Front Long Sleeve DressKay Unger Raven Draped Sheath Midi DressTed Baker London Kiylie Floral Satin Asymmetric SkirtCareste Georgia Silk Skirt

shoes for a first date

Karen Millen Compact Stretch Single Breasted JacketVICI Collection Satin Halter Neck BlouseWit & Wisdom ‘Ab’Solution Itty Bitty Bootcut JeansCalvin Klein Beeta Pointy Toe FlatReiss Arden Basket Weave ClutchOpen Edit Twisted Link Collar Necklace

Your shoe choice can make a big difference to the look of your outfit. You could choose a classic option like a pair of pumps or block heel sandals, or opt for an edgier look with a pair of ankle boots or pointed toe flats.

Shoes for a dinner date | 40plusstyle.com

Calvin Klein Beeta Pointy Toe FlatCushionaire Alba Block Heel SandalNina 60 Pointy Toe Pump27 EDIT Naturalizer Florentine Bootie

accessories

Julie in a statement necklace | 40plusstyle.com

Julie @stylishparadox above (read her style interview here) opts for statement gold jewelry that draws the attention up to her face.

Steal her look with this similar dress (another option here), earrings, necklace and bracelet.

Karen Millen Compact Stretch Single Breasted JacketKay Unger Raven Draped Sheath Midi DressCushionaire Alba Block Heel SandalChrysansmile Leather Quilted Crossbody BagOpen Edit Twisted Link Collar NecklaceJennider Helena Chain Drop Earrings

Choose clutch bags and statement jewelry. If you want to add extra warmth, you can always add a pashmina over your shoulders.

Clutch bags and statement jewelry | 40plusstyle.com

Chrysansmile Leather Quilted Crossbody BagReiss Arden Basket Weave ClutchOpen Edit Twisted Link Collar NecklaceJennider Helena Chain Drop EarringsQBSM Pashmina Wrap

Your first date outfits together in one capsule

You can see the clothes and accessories from above together in one capsule below so you should find plenty of ideas when considering what to wear on a first date. You can always mix and match the tops, jackets and shoes to create lots of different looks. If you have any semi formal event to attend this year, you should find inspiration below.

First date outfits | 40plusstyle.com

shop some of the first date outfits above here:

Continue reading:

  1. What To Wear To The Races
  2. How To Choose The Perfect Little Black Dress For Your Body Type
  3. What To Wear To A Casual Wedding In Summer

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What to wear on a first date to feel confident and look amazing | 40plusstyle.com

Feature image by Lizzy @whatlizzyloves

Sylvia

Sylvia is 40+style’s editor-in-chief and has been helping women find their unique style since 2011. An alumni of the School of Color and Design, she is devoted to empowering women of any age to look and feel their best. Read more about Sylvia and 40+style on this page.

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