Dressing for Date Night: Outfits, Shoes & Bags

Off on a date? Wear shoes to guarantee you a second one.

split image with female model on the left and male model on the right

When did date night become a ‘thing’ – maybe when Michelle Obama announced that her and Barack never missed their weekly rendezvous. Now this isn’t to suggest that date night is exclusively for married couples – date night is for everyone, whether you’re off on a nervy first date or your 400th. Date night outfit ideas are important when you’re single and mingling – because it’s all about first impressions and putting your best foot forward. It’s so key to feel your best self when dating, from the colour of your outfit to what pair of shoes is going to give you a little more oomph.

Calming First Date Nerves

Feeling nervous before a first date is inevitable, but even though your stomach might be churning, you can still look cute despite of that. A stylish first date outfit is the good way to boost your confidence, whether you’re out for a chic dinner date or a casual coffee catch-up, we’ve got first date outfit ideas for every occasion and the perfect shoes to match.

Date Shoes For Every Occasion

Just imagine the perfect date scenario – what does it look like? An early evening get-together over drinks followed by the must-see arthouse film, a laidback artisanal coffee and endless conversation, or a uber-romantic night out dressed up to the max accompanied by a Michelin Star dinner. Date night outfits for men and women can be anything style-wise as long as you keep the location in mind – and never forget about your shoes on a date because accessories always make the outfit.


1.The Dinner Date: Classy Dinner Date Outfit

split image with model couple on the left and Russell and Bromley Kitty shoes

When it comes to a dinner date, a classy date night outfit is the only way to go. For ladies the dress is the best and easiest option – embrace an LBD with an edge and up the drama with a backless detail or a high thigh slit – for extra cover pair with a leather blazer or a boxy cropped jacket. Shoe-wise, if you’re keen to make a statement, a sculptural platform sandal will be a sure-fire instant confidence boost and a great option when you’re planning to take an Uber straight your date. Classy date outfits for the guys mean giving the denim a break and embracing a classic smart pair of trousers, wide leg looks particularly fresh when paired with a collarless button-down shirt and of course a blazer to finish. For men's date footwear, why not do something a little different and refamiliarise yourself with monks or tassel detail loafers.

Russell and Bromley Cake shoe


Russell and Bromley Candy shoe


Russell and Bromley Birch shoe


Russell and Bromley Keeble 3 shoe
Keeble 3



2.Valentine's Day Date: Valentine's Bags

split image with pink and purple valentine's day bags

Valentine’s Day calls for following a bit of a theme and for a Valentine’s Day date, it’s worth embracing those red and pink hues to really stand out. Why not match your footwear to your bag AND your dress choice to really impress your date in a tonal outfit. Your pink bag choice could have chain details, be covered in glitter, or quilted, but keep your Valentine’s date bag on the smaller side, so it doesn’t overwhelm your outfit, whether it’s casual or a little more dressed up.

Russell and Bromley pink On The Rocks bag
On The Rocks


Russell and Bromley red Icon Mini bag
Icon Mini


Russell and Bromley pink Top Pouch bag
Top Pouch


Russell and Bromley purple Quiltbox bag



3. Casual Coffee Date: Day Drinks Date

split image female model taking selfie next to wooden table wearing Russell and Bromley Miley caged fisherman platforms

The casual coffee date is somewhat underrated, everyone focuses on the glamour of dating after dark, but during the daytime you can actually see your date, plus the lighting’s much better. Dress for your coffee date in denim and if you want to be a little edgy “double-denim it” and team your all denim look with a statement trench coat or an oversize leather bomber. Look suitably cool for a daytime date and pair with a fisherman sandal on a sunnier day and if it’s a little chilly a statement loafer works well. A super chic date look to team with your oat milk latte.

Russell and Bromley Isola chunky clean sole fisherman in brown


Russell and Bromley Miley caged fisherman platform in black


Russell and Bromley Smoking slipper dress flat in beige


Russell and Bromley Cleopatra 3 ring loafer in black


4. Date Night Out: Cinema Date Outfit

cinema date outfit

Date night looks can be tricky, especially a cinema date – what do you wear to sit in the dark with a potential love interest? Honestly the answer is something that you’re happy for your date to see you in the light too. A cinema date has a cool, relaxed vibe, so make sure you don’t feel or look too trussed up. A cute cosy co-ord with a cool jacket will look good paired with some sweet and salty. For your shoes, complete your cinema date night look with smart leather sneaker or an easy-wear slip-on/sandal, for that cute and cosy vibe.

Russell and Bromley Trax sandal in black


Russell and Bromley Sandy - woven strap sandal in brown


Russell and Bromley Retro -  contrast sole lace up sneaker in white


Russell and Bromley Hourglass  - Flared Sole Sneaker


5. Lunch Date: Casual Date Outfit

split image with male model walking down the stairs and female model standing on the street on the right

Perfecting the casual date outfit is easier said than done. How casual do you want to go? Do you want to look trend-led with a twist, or simply classic 'smart casj.' Really that’s all up to you – just make sure you’re feeling good. Whether you opt for a classic white tee with vintage denim for a lunch date or a boxy leather jacket over a knitted dress, you can tie together your daytime date look with some head turning footwear. For a spring-ready ensemble, think ankle boots. For something more summer appropriate? Embrace an espadrille or a chunky flat sandal of some sort. And for the boys? Cargo pants and a lightweight knit is a failsafe yet still refreshing option. Try pairing this look with a leather lace up featuring a gum sole or a high-top sneaker for extra style points – easy, breezy.

Russell and Bromley Cash - Heeled Western Boot in black


Russell and Bromley High Sky - multicolor platform sandals
High Sky


Russell and Bromley Hove M - mens Soft Lace Up Derby in green
Hove M


Russell and Bromley Park Hi M - mens high lace up sneakers
Park Hi M




6. Adventure Date: Date Sneakers

split image left - Russell and Bromley Charleston mens shoes right - woman Park Stich shoes

The adventurers amongst you may think all these sit-down dates sound dull, so if you like to cycle, run, play a sport or perhaps get yourself a little freaked out on a date, this bit’s for you. Your outfit needs to match your activity, so dress accordingly – but maybe have a little fun with flashes of colour since were going for a sporty feel on an adventure date. For the shoes, you can't beat women's and men's date sneakers. You can go classic, in an all-white sneaker, but it’s worth having a little more fun in a range of colourways and patterns, so your date can get a real sense of your personality – before they find out just how competitive you are.


7. Date Bag Delights

split image left - white Russell and Bromley Shopstar bag right - Icon XXL bag

Date night bags are simple – make a bit of a statement with your bag choice. There is so much fun to be had with a bag. If you’re in a black dress, go for eye popping colour. If your outfit has a cool casual vibe, dress it up with a clutch covered in sparkling diamante. Off on a romantic Valentine’s Day walking date around town? Embrace a statement oversized bag. Make sure your date bags are as stylish as your date fits.

Russell and Bromley Shopstar bag in white


Russell and Bromley Valentine bag in purple


Russell and Bromley Glisten - rhinestone knot shoulder bag


Russell and Bromley Icon - chain east/west grab bag


8. The Perfect Date: Second Date Outfits

split image left - female model standing on the street right - male model sitting between wooden tables

You’ve made a great impression and the second date is inked into your diary. It’s official, you’re busy Saturday night – but how do you keep impressing your date on your next meeting? Ladies, second date outfits should be laidback and cool. If you want to keep it dressy, team leather trousers with an oversize blazer and pack a punch with a striking fashion-forward heel. For the guys – be bold and team crisp white jeans with a classic shirt, sharp blazer, and smart/casual slip-ons – you’ll have the third date practically in the bag.

Russell and Bromley Kitty women shoes in green


Russell and Bromley Sunrise heels


Russell and Bromley Zeno mens shoe in navy blue


Russell and Bromley Carmel mens suede loafer in beige