There’s always that moment right before summer fully lands when you’re not quite in beach season yet, but your entire wardrobe (and mood) has already shifted there. Beach plans start to feel closer, travel dates get pencilled in, and suddenly the question isn’t if you’re going anywhere this season, but what you’re wearing when you do.
This edit is built around exactly that in-between moment. The kind of summer dressing that starts with swimwear but doesn’t end there! Think beach-to-dinner transitions, lake days that turn into patio nights, and vacation outfits that feel wearable beyond a single photo.
Consider this your starting point for building easy, flattering, and fully wearable beach date outfits for the season ahead.
SHOP THE SUMMER SWIM & BEACH DATE EDIT
WOMEN
1. Ribbon-strap pleated balconette & Serrated scallops bow cheeky bottom
Price: $29.00 CAD | $29.00 CAD
Available at: Simons
Why we love it: This matching bikini set feels flirty in the best way. The soft, textured fabric and ribbon straps make it feel feminine and playful. The soft textured fabric and ribbon straps make it feel feminine and playful. It feels perfect for the kind of beach date that turns into cocktails by sunset without needing a full outfit change.
2. Parasol stripe chambray shirt + Parasol stripe chambray short
Price: $69.00 CAD | $49.00 CAD
Available at: Simons
Why we love it: This matching striped set gives effortless coastal energy. The oversized fit feels relaxed, breathable, and intentionally undone. Because of this, it is ideal for tossing over swimwear before heading for lunch, drinks, or a long sunset walk.
3. Loose elongated printed blouse + Printed drawstring-waist wide-leg pant (ICONE)
Price: $59.00 CAD | $59.00 CAD
Available at: Simons
Why we love it: This set feels like vacation dressing done right. The flowing silhouette and soft print create an elevated but easy look. As a result, it feels romantic enough for dinner by the water while still staying comfortable in warm weather.
4. Fine crochet tie top + Fine crochet short
Price: $49.00 CAD | $39.00 CAD
Available at: Simons
Why we love it: Crochet always feels romantic in summer, and this matching set leans into that dreamy beach aesthetic. The lightweight knit texture makes it feel effortless while still looking put together enough for post-beach drinks.
5. Fine crochet lettuce-hem dress
Price: $49.00 CAD
Available at: Simons
Why we love it: This dress feels like the easiest beach-to-dinner outfit imaginable. The crochet detailing keeps it playful while the relaxed shape makes it perfect for warm evenings when you still want to feel styled without overthinking it.
6. Floral tapestry halter minidress
Price: $89.00 CAD
Available at: Simons
Why we love it: This floral mini instantly feels date-night ready. The halter neckline gives it a flattering silhouette while the tapestry-inspired print feels romantic and summery without leaning overly dressy.
7. Sweet Lilac Plunge Bikini Set – D Cup Friendly
Price: $49.95 CAD
Available at: La Vie en Rose
Why we love it: Soft lilac feels especially dreamy for summer. This plunge bikini feels flattering while still looking playful and feminine, making it ideal for beach dates that lean romantic.
8. Raspberry Red Crochet Triangle Bikini Top + Side Tie Brazilian Bottom + Long Crochet Pareo
Price: $35.95 CAD, $32.95 CAD, $39.95 CAD
Available at: La Vie en Rose
Why we love it:
This entire set feels confident and beach-club ready. The bold raspberry red instantly stands out, while the crochet pareo adds an elevated layer that makes the transition from beach towel to patio table feel seamless.
9. Ruffled Crepe Knit Cami + Crepe Knit Wide Leg Pants
Price: $34.95 CAD, $49.95 CAD
Available at: La Vie en Rose
Why we love it:
Lightweight, breezy, and effortlessly polished. This matching set feels easy enough for daytime beach wandering but elevated enough for dinner plans after sunset.
10. Polka Dot Built-In Control Plunge One-Piece Swimsuit
Price: $79.95 CAD
Available at: La Vie en Rose
Why we love it:
Classic polka dots never stop feeling chic. This one-piece feels timeless, flattering, and slightly vintage in the best way, making it perfect for a beach date that leans more elevated than sporty.
Head into your local Winners to find the best seasonal finds and these hot swim-to-dinner date pieces below. The playful patterns and bold colours make it an easy transitional piece for those sunny days, where these pops of bold in the dresses and tops keep you high fashion in your comfortable sunny-day fits.
12. Multicoloured Striped Short Set
Price: $39.99 CAD
Available at: Marshalls
Why we love it: This crochet-inspired matching set feels made for long summer weekends. The lightweight texture gives it a relaxed resort feel while still looking polished enough for brunch, patio dates, or a stroll along the waterfront. Because it works as both a cover-up and an outfit, it is one of those pieces you’ll find yourself reaching for all season long.
13. Satin Patchwork Skirt Set
Price: $34.99 CAD
Available at: Marshalls
Why we love it: This matching set brings playful summer energy to any wardrobe. The tube top and mini skirt combination feels effortless while the soft patchwork-inspired print adds a romantic touch that is perfect for vacation dinners or sunny afternoons with friends. It is an easy way to create a complete outfit without overthinking what to wear.
14. Drop Waist Printed Dress
Price: $59.99 CAD
Available at: Marshalls
Why we love it: This seashell-print dress was practically made for summer. The coastal-inspired pattern feels right at home near the water, while the breezy silhouette helps keep things comfortable on warmer days. Whether you are heading to a beachside restaurant or packing for a weekend getaway, this is the kind of dress that instantly feels like vacation.
15. Palm Printed Swimsuit + Palm Printed Shorts + Embroidered Palm Tree T-Shirt
Price: $24.99 CAD | $34.99 CAD | $19.99 CAD
Available at: Marshalls
Why we love it: This fit brings all the vacation vibes with the palm patterns and accents, but easily allows you to cover up ad head up in a high-fashion outfit that doesn’t sacrifice on comfort.
MEN’S
Price: $87.00 CAD
Available at: Manmade
Why we love it: A clean, elevated swim short that feels polished without trying too hard. The tailored fit makes it easy to go from swimming to drinks without feeling underdressed, which is exactly what a beach date outfit should do.
Price: $48.00 CAD
Available at: Manmade
Why we love it: This feels like the perfect beach-date basic. Soft, easy to wear, and cut in a way that feels intentional instead of sloppy, it works equally well over swim shorts or paired with linen pants after sunset.
Price: $39.99 CAD
Available at: Simons
Why we love it:
Minimal and classic in the best way. These swim shorts feel timeless, easy to style, and polished enough to wear beyond the beach when paired with a breezy button-down.
4. 100% European linen short-sleeve shirt – Comfort fit
Price: $79.00 CAD
Available at: Simons
Why we love it: Nothing says beach-date energy like linen. Lightweight and breathable, this shirt feels effortless while still looking intentionally styled for patio drinks or dinner by the water.
5. Striped seersucker swim short
Price: $59.00 CAD
Available at: Simons
Why we love it: The subtle stripe texture instantly gives these a more elevated, vacation-ready feel. They lean coastal without feeling costume-y and work especially well for summer weekends near the water.
👉 SHOP HERE
6. Exotic flower linen shirt – Comfort fit
Price: $79.00 CAD
Available at: Simons
Why we love it: This shirt brings just enough personality without feeling over the top. The tropical print feels playful and vacation-ready while still looking elevated enough for summer dinner plans.
This geometric-print short sleeve shirt is an easy way to elevate a warm-weather outfit. The lightweight design keeps things comfortable while the eye-catching pattern adds a modern touch. Pair it with shorts, linen pants, or swimwear for an effortless vacation-ready look.
Find your closest Winners here.
BEACH ACCESSORIES THAT COMPLETE THE LOOK
WOMEN’S
Price: $22.95 CAD
Available at: La Vie en Rose
Why we love it: The wedge heel and crochet touches give them that nostalgic Y2K vibe, while the wide strap keeps things comfortable all day long.
Price: $22.95 CAD
Available at: La Vie en Rose
Why we love it: Phone, sunnies, lipstick… Just slide them into this straw clutch and you’re set for the beach, brunch, or a market wander.
3. Pearl and hammered-nugget necklace: Exclusive Simons x Pilgrim collection
Price: $79.00 CAD
Available at: Simons
Why we love it: Beach jewellery should feel effortless, and this necklace does exactly that. The pearl and hammered detailing feel coastal and romantic without becoming too formal.
Price: $15.00 CAD
Available at: Simons
Why we love it: A subtle nod to beach styling without feeling cheesy. These instantly make a simple outfit feel more playful and summer-ready.
5. Large iridescent Hawaiian flower clip
Price: $9.00 CAD
Available at: Simons
Why we love it: The easiest way to make beach hair feel intentional. This oversized flower clip feels playful, tropical, and unexpectedly chic for sunset drinks.
6. Crocheted straw tote bag
Price: $79.00 CAD
Available at: Simons
Why we love it: A crochet straw tote immediately gives “summer romance” energy. It feels effortless, coastal, and perfect for carrying towels, SPF, and last-minute patio essentials.
7. Beaded Mini Bag
Price: $49.99 CAD
Available at: Marshalls
Why we love it:
This statement beaded handbag brings colour and texture to any summer outfit. The detailed beadwork gives it a special occasion feel, making it just as suitable for weddings and date nights as it is for vacation evenings. Sometimes all it takes is one standout accessory to elevate an entire look.
8. Platform Sandals
Price: $59.99 CAD
Available at: Marshalls
Why we love it: These chunky slides combine comfort and style in one easy piece. The slip-on design makes them perfect for beach trips, pool days, and everyday summer errands. They are practical enough for all-day wear while still feeling on trend.
UNISEX
1. Sonny full aviator sunglasses
Price: $150.00 CAD
Available at: Simons
Why we love it: Aviators never stop feeling cool. These work equally well with swimwear, coverups, or relaxed dinner outfits, making them an easy beach-date essential.
2. Amiga colourful tote
Price: $99.00 CAD
Available at: Simons
Why we love it: Bright, practical, and large enough to carry everything you actually need for a beach day. It feels playful while still looking elevated.
3. Portable Handheld Fan
Price: $12.99 CAD
Available at: Marshalls
Why we love it: This portable handheld fan may be one of the most practical summer finds in the collection. Small enough to fit inside a tote bag, it helps make hot afternoons, outdoor festivals, and beach days much more comfortable. When temperatures climb, this is one accessory you’ll be glad you packed.
MEN’S
1. Colourful natural stone bracelet
Price: $115.00 CAD
Available at: Simons
Why we love it:
Small details matter. This bracelet adds personality to a beach outfit without feeling overly styled, making casual summer looks feel more intentional.
2. Arizona EVA sandals – Men
Price: $70,00 CAD
Available at: Simons
Why we love it:
Easy, comfortable, and classic. These sandals work for beach mornings, casual afternoons, and sunset walks without sacrificing comfort.
Planning more summer dates? Discover even more beach escapes, patio spots, weekend getaways, and romantic experiences on It’s Date Night. Your next favourite date idea might be just a click away. ☀️💕
