First Date Outfits

First date outfits should strike the perfect balance between comfort and style, ensuring you feel confident and at ease. Whether you're planning a casual coffee outing or a more formal dinner, our selection of versatile clothing options will help you create an effortlessly charming look. From timeless classics to modern favorites, find the ideal ensemble that showcases your personality and makes a lasting impression.

Sort by:

Filter & Sort

504 Items

Women's Cloud Gauze Midi Dress

A lightweight white cotton midi dress with a crinkled gauze texture, V-neckline, and adjustable waist.
Men's Premium Double L® Polo Banded, Short-Sleeve Without Pocket

A super-soft, all-cotton navy polo that resists wrinkles, fading, shrinking, and pilling.

Pros: High quality Perfect fit Durable fabric Softness Comfortable fit
Women's True Shape Jeans, High-Rise Straight-Leg

A high-rise straight-leg jean in black denim with superior shape retention and a classic fit.

Pros: High quality Soft material Versatile design True to size Comfortable fit
Perfect Fit Pants, Straight-Leg Crop

A pair of gray cropped pants with a high-rise, straight-leg design made from stretchy jersey-knit cotton.

Pros: Perfect fit Versatile style Flattering design High-quality fabric Comfortable fit
Women's True Shape Jeans, High-Rise Slim-Leg

A pair of high-rise, slim-leg jeans in black premium stretch denim with superior shape retention.

Pros: Attractive color Perfect fit Well-made Comfortable Holds shape
Women's Perfect Fit Pants, Denim Straight-Leg

A pair of high-rise, straight-leg black jeans made from 96% cotton and 4% spandex for ultimate comfort.

Pros: High quality Perfect stretch Great for work No shrinking Comfortable fit
Women's Summer Knit Dress, Short-Sleeve Print
Price was from: $59.95 now: $44.99

A versatile, flattering A-line summer dress in bright mariner ditsy floral, made from a soft rayon-spandex blend.

Pros: High quality Stylish Versatile Comfortable Good fit
Women's L.L.Bean Interlock Turtleneck, Long-Sleeve Stripe

A slightly fitted, cream and navy striped turtleneck made from soft, substantial 100% combed cotton.

Pros: Great fit High quality Soft material Warmth Comfortable
Women's True Shape Jeans, High-Rise Bootcut

A high-rise bootcut jean in rinsed denim that retains shape, made from a cotton-polyester-elastane blend.

Pros: High quality Perfect fit Durable Comfortable Soft fabric
Women's True Shape Jeans, High-Rise Straight-Leg Colors

A high-rise straight-leg jean in tan denim, maintaining shape with a cotton-polyester-elastane blend.

Pros: Versatile and stylish Lovely color options Comfortable and stretchy Consistent fit High quality and durable
Women's 207 Vintage Jeans, High-Rise Boyfriend

A pair of high-rise boyfriend jeans in light indigo denim, offering relaxed fit and vintage appeal.

Pros: Great look High quality Perfect fit Softness Comfortable
Women's Summer Knit Dress

A versatile black summer dress with a flattering empire waistline, made from soft jersey-knit rayon and spandex.

Pros: Versatile for various activities Flattering fit Comfortable and stylish Great for hot weather Lightweight and soft
Men's L.L.Bean Wool Peacoat

A classic black peacoat made of 100% Italian wool with Thinsulate™ Insulation for added warmth.

Pros: Fit Quality Warmth Appearance Versatility
Women's True Shape Jeans, High-Rise Skinny-Leg Colors
Price was from: $69.95 now: $49.99

A pair of high-rise skinny jeans in washed indigo, designed to retain shape after frequent washings.

Pros: Great fit Perfect fit Bug repellent Stylish Comfortable
Women's Signature Utility Dress
Price was from: $119 now: $89.99

A relaxed-fit green utility dress with a soft cotton-TENCEL blend and convenient front pockets.
Women's Cloud Gauze Midi Dress
Price was from: $79 now: $44.99

A breezy white midi dress made from 100% lightweight cotton gauze with a relaxed fit and side slits.
Women's Signature Castine Cotton Popover Dress
Price was from: $119 now: $89.99

A soft, white cotton popover dress with a fit-and-flare silhouette and elasticized waist.
Women's Summer Knit Maxi Dress, Print
Price was from: $69 now: $44.99

A versatile blue print maxi dress with a flattering fit-and-flare silhouette and soft jersey-knit fabric.
Women's Beech Point Dress
Price was from: $69.95 now: $44.99

A midnight black A-line dress with UPF 50+ protection, made from a soft, stretchy synthetic blend.
Women's L.L. Bean Heritage Washed Denim Shirt Dress

A soft-washed, 100% cotton denim shirt dress with a relaxed fit and vintage appeal.
Women's VentureStretch Seersucker Dress
Price was from: $79 now: $54.99

A lightweight orange seersucker dress made from stretchy, moisture-wicking recycled polyester with UPF 50+ protection.
Women's 207 Vintage Corduroy Pants, High-Rise Wide-Leg

A pair of dark khaki high-rise wide-leg corduroy pants, offering vintage appeal and all-day comfort.
Women's Summer Knit Maxi Dress
Price was from: $59.95 now: $44.99

A versatile black maxi dress with a fit-and-flare silhouette, crafted from soft jersey-knit fabric.
Women's Cloud Gauze Cover-Up Dress, Stripe
Price was from: $74.95 now: $29.99

A cloud-soft, crinkled cotton cover-up dress in sienna brick micro stripe, perfect for casual or beach wear.

First Date Outfits

When it comes to planning for a first date, choosing the right outfit is about more than just style—it’s about feeling at ease, ready for anything, and confident in every moment. The best first date outfits are those that balance comfort with timeless appeal, allowing you to focus on making memories rather than fussing with your clothes. Whether you’re heading out for coffee, strolling through a local park, or meeting up for a casual dinner, ll bean inspired outfits offer the kind of versatility and durability you can rely on. For women, a first date casual outfit might mean pairing soft, well-made jeans with a cozy sweater or a crisp button-down, finished with a layer like a classic jacket or fleece for November’s chill. For those who prefer a first date dress, look for options crafted from quality materials that move with you, offer all-day comfort, and are easy to care for—perfect for everything from a relaxed lunch to an evening out. Men can reach for ll bean style clothing options that include chinos or classic denim, paired with a flannel or a pullover that feels just right for the season. The key is to choose pieces that feel authentic, practical, and ready for whatever the day—or night—might bring.

Thoughtful outfit choices also make wonderful gifts, especially as the holidays approach. A well-chosen shirt, sweater, or outer layer can be a meaningful gesture for someone gearing up for a special outing or looking to refresh their wardrobe with pieces that stand the test of time. The appeal of ll bean outfit selections lies in their lasting value and problem-solving details—think pockets in all the right places, layers that work together seamlessly, and timeless colors that never go out of style. As autumn deepens and the air turns brisk, layering becomes especially important. A lightweight jacket or vest adds just the right amount of warmth without feeling bulky, while a classic scarf or hat can be the finishing touch that pulls the whole look together. These clothing options are designed to be relevant and comfortable, so you can focus on enjoying your first date, whether you’re laughing over coffee or exploring a local trail.

No matter how you define your personal style, the right first date outfit should help you feel like yourself—relaxed, confident, and ready to enjoy good company. When browsing for the perfect look, consider the setting and season, and opt for pieces that offer both comfort and lasting value. Classic denim, soft sweaters, and sturdy boots are always a smart choice for November outings, while dresses and skirts made from easy-care fabrics keep things simple and enjoyable. For more inspiration on putting together an outfit for a special evening, you can also explore our curated selection of Dinner Date Outfits. With timeless, versatile clothing options designed for real life, you’ll be ready for any first date adventure that comes your way.

FAQs

When choosing a first date outfit for fall, look for pieces that offer warmth, comfort, and versatility. Layering is important, so consider lightweight sweaters, shirts, or jackets that can adapt to changing temperatures. Opt for durable fabrics that hold up well throughout the day and timeless styles that work for a variety of settings.

A relaxed yet polished look often comes from combining classic pieces, like a well-fitted pair of jeans with a comfortable button-down or a simple dress with a cozy cardigan. Neutral colors and subtle prints can help your outfit feel effortless, while comfortable shoes ensure you’re ready for any activity.

Solid colors and subtle patterns are generally a great choice for first dates, as they tend to be versatile and easy to accessorize. Earthy tones, soft blues, and classic neutrals can complement the season and create a timeless look that feels approachable and welcoming.

For cooler months, consider outerwear like a lightweight jacket, fleece, or a classic pullover. These options provide warmth without being too bulky and are easy to layer over shirts or sweaters. Look for styles that are easy to move in and pair well with the rest of your outfit.

Absolutely. High-quality, versatile clothing items such as sweaters, shirts, or jackets make thoughtful gifts for friends or family members who are preparing for a first date or looking to update their wardrobe. Choose timeless pieces that are comfortable and easy to style for a variety of occasions.

It's time to upgrade your browser

First Date Outfits