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
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
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
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
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 Jacket – Nordstrom Drape Neck Short Sleeve Top – Careste Georgia Silk Skirt – Nina 60 Pointy Toe Pump – Chrysansmile Leather Quilted Crossbody Bag – Open 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.
Nordstrom Drape Neck Short Sleeve Top – VICI Collection Cowl Neck Satin Blouse – Ted Baker London Harper Floral Tie Front Blouse – VICI Collection Satin Halter Neck Blouse
jackets and Coats
Karen Millen Compact Stretch Single Breasted Jacket – Fraiche by J Wrap Front Long Sleeve Dress – Cushionaire Alba Block Heel Sandal – Reiss Arden Basket Weave Clutch – Open Edit Twisted Link Collar Necklace – Jennider 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.
BLANKNYC Suede Leather Moto Jacket – Karen Millen Compact Stretch Single Breasted Jacket – Ted Baker London Trisca Boxy Cargo Crop Jacket – Karen Millen Compact Stretch Stud & Eyelet Statement Coat
jeans and pants
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.
Wit & Wisdom ‘Ab’Solution Itty Bitty Bootcut Jeans – Boden Richmond 7/8 Pants – VICI Collection Belted High Waist Wide Leg Pants – Natori Boro Cotton & Silk Ankle Pants
dresses and skirts are perfect for first dates
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.
Fraiche by J Wrap Front Long Sleeve Dress – Kay Unger Raven Draped Sheath Midi Dress – Ted Baker London Kiylie Floral Satin Asymmetric Skirt – Careste Georgia Silk Skirt
shoes for a first date
Karen Millen Compact Stretch Single Breasted Jacket – VICI Collection Satin Halter Neck Blouse – Wit & Wisdom ‘Ab’Solution Itty Bitty Bootcut Jeans – Calvin Klein Beeta Pointy Toe Flat – Reiss Arden Basket Weave Clutch – Open 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.
Calvin Klein Beeta Pointy Toe Flat – Cushionaire Alba Block Heel Sandal – Nina 60 Pointy Toe Pump – 27 EDIT Naturalizer Florentine Bootie
accessories
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 Jacket – Kay Unger Raven Draped Sheath Midi Dress – Cushionaire Alba Block Heel Sandal – Chrysansmile Leather Quilted Crossbody Bag – Open Edit Twisted Link Collar Necklace – Jennider 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.
Chrysansmile Leather Quilted Crossbody Bag – Reiss Arden Basket Weave Clutch – Open Edit Twisted Link Collar Necklace – Jennider Helena Chain Drop Earrings – QBSM 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.
shop some of the first date outfits above here:
Continue reading:
- What To Wear To The Races
- How To Choose The Perfect Little Black Dress For Your Body Type
- What To Wear To A Casual Wedding In Summer
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Feature image by Lizzy @whatlizzyloves
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Personally I usually wear my favorite pair of jeans, white top, black blazer and black flats (day) or black heels (night). If it is cold outside I also wear a nude trenchcoat or my coat. It is very simple outfit that guys like. I like it because my date focuses on my personality and not on my appearance. Second date is different. You can dress more flirty or sexy as dates go on.
I’m still single at 46 (too busy for a relationship and dating is fun) so I go on a LOT of first dates! I do have a lot of life experience, but I still don’t know what I want…I’ve dated men of all ages, shapes and sizes and can’t seem to pick just one (or maybe it’s because there are so many great men out there).
I tend to not think about how sexy I am dressing because I’m comfortable in my skin and as an athlete am frequently stripped down in public places and am used to having strangers looking at my body. I’ve stopped caring what people are thinking else I’d have massive anxiety and body issues. Who needs that in their life?
Totally agree with points 3,4 and 5! Being physically comfortable is key–especially an old favorite! And point 5: wearing nice underwear…I don’t know WHY this makes me so happy. If the conversation starts to get boring, I think about the cute undies I’m wearing and can’t stop smiling.
Depending on the time of year, I have four go-to outfits:
– a loose chiffon tank in a color that looks great on me (burgandy) with black leggings and cute black boots. It’s cute and comfortable enough to wear to practically anything (museum, spontaneous midnight hike, dinner at a nice restaurant, go-carting, dancing at a club)
– a darling floral print sundress. Great for salsa dancing, dinner, brunch, any non-active activity where I want to look cute and feminine.
– khaki shorts and white tanktop. Anything that is a bit more active–rock climbing, backpacking, kayaking.
– a black spandex dress that you feel gorgeous in that won’t shift, ride up, wrinkle, show stains (for me it’s a cap sleeve, scoop neck minidress)
Thanks for sharing these tips! They were really great!
I have been married 20 years and I still try and dress like it was our first date when we go out (even for a lunch date) Love this post.
Thanks for your feedback Bella Curious to know how you dress then.. Do you follow some of the directions above or are you going for a more sexy look?
I too haven’t gone on a first date in 20 plus years, but I think your advice is sound. I think if I had to go on one I’d be a little glam and wear a drapey knit jersey dress. I would want to be sexy without being too sexy.
Great advice. Thanks for your input Heather!
Ha. I have blind dated within the last year (at 43) and, yeah, it sure is interesting. Top priorities until you know someone are full coverage, freedom of movement and good ground connection through your feet. My ideal first date outfit is a fitted but not movement-constricting jacket, over a pretty top or graphic tee, and pants or jeans with a heavy belt. I wear comfortable, flat shoes that stay on my feet securely — hip leather sneakers are my favorites. Outfit #3 would do, except for the shoes, but I’d be a little overdressed for the socioeconomic circles I run in.
Thank you so much for your feedback Cynthia! It’s great to hear from someone who is actually dating at the moment. Great advice and good luck in finding someone special!
I sincerely hope I never have to go on a “first date” again. I and my 4 closest friends have each been married for 23 to 28 years. 🙂 I have no experience with dating. But I love what you said about dressing to show your confidence, not showing too much skin, and making sure you are comfortable in your outfit – physically and mentally. Be your best self and you will attract the person you deserve. I like all four looks you posted above and would wear those clothes. They are simple and clean but the accessories make them current.
I’m happy I got it right in your opinion. It’s actually quite fun to think about what I WOULD wear on such an occasion..