Style Guide: The Perfect Date Ensemble

Style Guide: The Perfect Date Ensemble

Thanks to the endless array of fashion forward romantic comedies and Lifetime’s cinematic gems, finding the elusive “one” has never looked easier or on trend. Unfortunately in real life not everyone gets a stylist to help conjure up the ideal date night look, thus leaving us filled with more worry, than excitement. To save yourself from staring blankly into your closet for hours in a “What do I wear?” coma, I suggest creating a mental catalog of several date worthy ensembles. If we’ve learned one thing from Hollywood, it’s that dancing around, while curling your hair and spritzing on perfume in the hours leading up to your date is way more fun than wandering frantically through a department store. A good dating rule of thumb is to always try to keep your ensembles simple and comfortable; you never want to be thinking about your outfit during your date. When it comes to hair and makeup keep it simple as well. Too much blush or bronzer could be a total turnoff to your potential beau. When it comes to first dates remember to avoid items like skinny jeans and blazers. These fashion lover staples can sometimes give off a harsh and unapproachable appearance that could be intimidating to your date.

Surprise Date
Style Guide: The Perfect Date Ensemble

As fun and exciting as “surprise” dates are, determining what to wear can be a super daunting task, especially when your guy won’t give you a clue what the night holds. When the unknown date presents itself, I always say go with a fun dress, like this floral tiered LC Lauren Conrad dress. Once you’ve got the perfect dress, it’s all about key transitional pieces. A denim jacket can instantly dress down your look if needed, while offering warmth for cool evening breezes. And a handbag big enough to hide a pair of heels or flats, is always a smart idea so you have appropriate footwear on hand.

Style Guide: The Perfect Date EnsembleLunch Date

Style Guide: The Perfect Date Ensemble

For a lunch date you want to keep your look comfy and casual with an effortless feel. Overdressing for an afternoon bite to eat can give the appearance that you have extremely high expectations, leaving your date feeling like he under delivered. Stray away from denim and go with something with a resort chic vibe like white shorts and a trendy chevron striped blouse. Keep the shoes comfy and low maintenance with a fun pair of colorful spring loafers.

Style Guide: The Perfect Date Ensemble
Dinner Date

Style Guide: The Perfect Date Ensemble

When it comes to dinner dates, a dress is always a safe bet, but for a few extra fashion points, I always suggest a classic skirt with a great detailed top. Keep in mind that you’ll be sitting across the table from your date, so wearing a texturally intriguing top, like this LC Lauren Conrad Lace Crop Top, will keep you looking stylish even when you’re half hidden by the table. If you’re someone who tends to play with your hair, be sure to pull it back so that you’re not nervously fidgeting with it throughout the meal. When it comes to jewelry, keep it simple and stylish with a stunning pair of teardrop earring and an elegant beaded bracelet. Impressionable footwear is a must for this occasion, so wear something striking, but comfortable. If you’re not a sky high stiletto girl try rocking an embellished flat.

Style Guide: The Perfect Date Ensemble
What is the best date you’ve ever been on and what did you wear for the occasion?

For more outfit inspiration check out my Sequins Trend Report ideal for a fancy night out and my Spring Cardigans post perfect for a dressy lunch date or dinner.

Fash Boulevard

You might also like…
How To Wear: Summer Neutrals
Color Code: How to Mix & Match
How To: Find the Perfect Skirt for Your Body
How To Wear: Midi Skirts

Categories: Anna James, Contributors, Style Guide, Wear
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  • Deanne Castro

    Please visit my blog. It’s about fashion and beauty!


  • Kelby Peachey

    I absolutely love this Anna!! You inspired my blog post yesterday (and you inspire me everyday!)!! I would love it if you checked it out! :)


  • Closet Fix

    Love this!

    Going on dates can be seriously nerve wracking! So, I agree with Anna, don’t over think it! It’s bad enough you have to worry about clicking with Mr. Right, or whether you have food in your teeth. You really dont want to have to worry about fashion issues too. So, be your self and stay true to your style. This wouldn’t be the time to experiment with something new unless you’re absolutely comfortable with the outcome. I generally like to keep it simple like here:

    That way by being yourself, you’ll be way more confident, and Mr. Right is sure to fall madly in love with you;) Who can resist confidence.


    Simmy P.

    Personal Style Blog:



    Instagram: @ClosetFix

  • Anna James

    Oh my goodness, Kelby. You are too sweet. Thank you so much for the amazing shout out. I feel so honored. I love all the pieces you pulled. You have amazing taste!

    Thanks again for the support, love. xo

  • Hailey Anderson

    I love how sure an confident all your solutions are! They are so fool proof and absolutely perfect. Loved this post and love your blogging! You are perfectly put together all the time. Love, love, love.

  • Jessica E

    What wonderful looks. I just adore the “”lunch Date”” look.

    You all are so creative and fashion forward. And for someone who is “”fashion troubled”” this tips are just want the doctor ordered :)

  • Rebekah W

    wow, love every single outfit :) but especially the last one! so classy and girly and a great combination of sexy and cute!

    good work!


  • Rachel Trampel

    Love this Anna! Great advice :) I definitely love the dinner date outfit… that is my go-to always on dates with the boyfriend! :)


  • Dory Geelkerken
  • laura wagner

    What brand is that hot pink bag? I love it! Lovely post as always Anna!

  • Amanda Kennedy

    love the pink bag and the dinner date outfit!

  • Kellie Norton

    Love all of those outfit selections!! The dinner date is definitely my fav though :-) love the detailing on the back of the shirt! Great post Anna!!


  • Melissa LaRose

    Love these outfits… Totally perfect for date night {or day!} I have a huge problem preemptively planning out outfits and am also rushing around at the last minute… My new goal is going to have to be “”plan ahead”” Thank you for the suggestions! :)

    <3 Melissa

  • Giselle Escamilla

    Wow thanks Anna!! I can never find something to wear haha but now I know better!! Btw I love the outfits so cute!:)

  • Amber Welles

    Anna, this post is amazing. So many great tips. I love the Lunch Date outfit. Very cute.

  • Melissa Panici

    I love ALL of those outfit ideas! They are simply gorgeous:) To be honest Anna, I couldn’t even attempt to remember what I wore on my best date! lol It’s been way too long! Thanks for the tips girl!

  • T Girl

    Wow, girl. These looks are fab. I look forward to your post all week and this one did not let me down. I can totally see myself in the first dress. Where’s it from?

  • priscilla frehe
  • Shannon H

    Love all of these outfits. Your post are always so smart and fun, Anna. I never know what to wear on suprise dates. The idea of bringing back up shoes is great. The best date I ever had was last year when my then boyfriend suprised me with dinner on a boat he rented. I wore heels, and really should have had flats with me. lol. Boat+heels=nightmare

  • Claire Pitrof
  • Petra Zeller

    Love all Outfit. Special love your amazing pink bag. Love it. Great Post lovely Anna. Its so great to read your amazing posts.
    xo, Petra

  • DancesWithHooves

    Adorable outfits and thank you for sharing thoughtful elements of your choices in your post (such as the handbag big enough for a change of shoes and dressing to eleminate the “”appearance that you have extremely high expectations.””).

    I enjoy your posts! Thanks so much!

  • Kristina Rovtar

    Thanks for this post, it really is hard sometimes to think of the perfect date outfit, but I will be using your tips.

    follow me on pinterest:

  • Bunhead

    This is so helpful. I love all of these tips and outfits, Anna. You look incredible.

  • Umbrella Drink

    Great ideas! I like the dinner date. It’s so classic.

  • Jaclyn Schler

    I love that lace crop top! So beautiful and classy.

  • Cassidy Short

    all of these looks are adorable!



  • Valerie Lynn

    deff love them all, but the first look is my favorite! thanks anna :)

  • Ally Powell

    Great post, Anna. Every outfit is beautiful. If I had to pick one, it would be the lunch date outfit. Those shoes are tots adorbs.

  • Penelope G

    Thanks for including our Mai Earrings Anna! Gorgeous as always!!

  • Larissa Wilhelm

    I definitely needed this! Thanks Anna!

  • GraceyCleo

    Hi Anna. These are perfect tips. I’m always rushing to put an outfit together so these really helped. I want that cheveron top. You look fab.

  • Sarah Lawson

    Hey girl. Love every single outfit. You can tell you put a lot of time into this. Thanks for all the wonderful suggestions. Wish my bf would plan suprise dates, lol. #lazy

    – Sarah

  • Martin M

    I loveyour outfit for the surprise date :) The blue looks really amazing! Perfect look for it!! Would have been perfect for Berlin Fashion Week last week as well ๐Ÿ˜‰ XOXO from Germany :)

  • Chelsea Underwood

    1) I totally wrote a blog post for the site I am intern for about date night outfits last night

    2) the “”Lunch date”” outfit is a def NO NO. ew!

  • Sabrinchen

    Where is the top from the Lunch Date outfit from?

  • Varsi Stockwell

    Yes, now this is style. You look striking, Anna. I love the lunch date look the best and then the dinner date. Both are great for every girl. Love all your post. xoxo

  • Christa Hampton

    Best post yet, Anna. You look like a movie star. Keep on inspiring, girl. You’re doing great. I’ve been a fan since day one.

  • Dy Shiny

    Others beautiful outfits to add to my Pinterest’board of Anna!!! Compliments Anna, great outfits!!! :)

  • Alliaon Chiffon

    This post is awesome. My friends sent me your way and I’m very glad. I’ve never gone on a suprise date, but I would wear that first outfit to any date. You look great.

  • Dapper Look

    This is just awesome. I lke the dinner date fasion. Love all of it.

    Find fashion for dudes. Dapperlook lets guys share, find and recommend fashion!

  • Deanne Castro

    Please view my fashion and beauty blog!


  • Rebecca Bakofsky

    I would wear every single one of these looks, great post!!

    My Blog (I just started):

  • Leslie Arriaza

    i love the dinner date ensemble! i’m not a dress/skirt type tho but it’s not too much. i’ll def be on the look out for a skirt like that. Amazing as always Anna! <3

  • Tiffani Stuart

    Didn’t even know your tiered dress was from LC Lauren Conrad!! No wonder I adore it!

  • jill s

    great blog post, check out our facebook page for more on fashion, trends and style “”like us”” on FB at

  • Linh Ly

    Anna! I love all the outfits. Great post! Of course my favorite is your surprise date outfit. It’s perfect and flattering.


  • Rachael Yanta

    These are such great date night choices! I love them :) Happy Friday!

  • Kimmy S

    Love all of these looks, espeically the last one with that top. SO CUTE! It’s from Kohl’s right? I am totally ordering in… Thanks Anna! Xo

  • Paloma Ortiz.

    These looks are amaizing, & they are perfect for dates. I’m definitely buying clothes like that.

  • Deanne Castro

    I think Anna’s outfit choices are perfect! SO FAB!

    Congratulations on your win as well! :)

    please also view my blog for fashion and beauty advice:

  • Cheyenne Weimer

    These are wonnderful tips and great outfits. You really know you’re style. You’ve got a new fan. Can’t wait to see more.


  • Amy Breckenridge

    i can’t choose between the surprise date and the dinner date – both are gorgeous and i could see myself wearing either look! also, love your arm candy!!


  • Amanda DeWitt

    love the dinner date look!!! simple with beautiful textures!!

  • soupforthegirlysoul

    that Chevron top is to die for!!! I love it! :)

  • Meg Acquavella

    love,love, & love all of the outfits. those LeBunnyBleu shoes are to die for, i’m on the link now & are ordering them. thanks anna!!

  • lila k

    so many lovely looks!!i cant decide which one is my favorite!!so cute!!

  • Amber Welles

    Anna, where did you get the pink purse from? I love it.

  • Emily Broughton

    looooooooooove the looks :) I’v written a lil article on top fashion bloggers, so if you love this one then def check out the list….

  • Jacqueline

    So cute, i love this!!!

  • Melissa mould

    i love the cute lace detailed top. looks really pretty.

    I’ve featured lots of summer inspired looks on my blog too :)

    Mel x

  • Amenah Hussein

    Lovely combination of sweet and sexy but not too out there :) Fash Love!

  • Amenah Hussein

    I loved eah and every single one of them equally but my favorite part of it all was the fact it contained pieces from my all time favorite LC Lauren Conrad line typically the best!

  • Kendrra Thoms

    I love how simple you made this stressful task! You used pieces that every girl has and provided some killer ideas. Great post!

  • Lauren

    i love the dinner date outfit. it is simple but very elegant. i wanna try something similar but probably with my Chinese Laundry pumps <3
    any thoughts?

  • Bridget

    Who sells the heels that went with the surprise date outfit?



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