Date Night Outfits
Putting together the perfect date night outfit can be challenging, especially if it's your first date. Here, we've curated a selection of styles sure to impress your special someone on any occasion.
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Isaia
Pure Silk Jersey Shirt
$1350
Isaia
Pure Silk Jersey Shirt
$1350
Brioni
William Micro Houndstooth Dress Shirt
$895
Kiton
Cashmere Knitted Sweater
$3150
Isaia
Pure Silk Jersey Polo
$1450
Isaia
Wool Piqué Jersey Shirt
$995
Isaia
Wool Piqué Jersey Shirt
$995
To Boot New York
Retro-Inspired Sneakers
$530
Berluti
Classic Patinated Leather Belt
$960
Brunello Cucinelli
Easy Fit Cotton Corduroy Western Shirt
$1380
Isaia
Wool-Blend Pants
$995
Isaia
Wool-Blend Pants
$995
Isaia
Wool-Blend Pants
$995
Berluti
Classic Scritto Leather Belt
$1050
Prada
Spazzolato Leather Tassel Loafers
$1450
TOM FORD
Atticus Sharkskin Pants
$1690
TOM FORD
Straight Fit Pleated Wool Pants
$1690
Brioni
Check Cotton-Cashmere Shirt
$1295
100 Hands
Brushed Cotton Dress Shirt
$765
Brioni
Sustainable William Striped Shirt
$995
Jacob Cohen
Bard Stretch-Cotton Blend Jeans
$565
Brunello Cucinelli
Herringbone Wool, Silk & Cashmere Overcoat
$7795
TOM FORD
Grain Leather Biker Jacket
$12810
Brax
Chuck Corduroy Hi-Flex Pants
$268
Brax
Chuck Relax Flex Cotton-Blend Pants
$258
Paige
Danford Slim Fit Stretch-Cotton Chino Pants
$315
Bontoni
Vittorio Leather Oxfords
$1525
Bontoni
Polished Leather Derbies
$1875
Isaia
Glen Check Wool Pants
$1295
Marco Pescarolo
Muno Stretch-Cashmere Drawstring Pants
$1125
Isaia
Argyle Cashmere-Wool Turtleneck
$3087
Ralph Lauren Purple Label
Tartan Plaid Sport Jacket
$2495
Isaia
Gingham Check Cotton Dress Shirt
$795
Isaia
Gingham Check Cotton Dress Shirt
$695
Marco Pescarolo
Stretch-Cashmere Jacket
$1695
TOM FORD
Silk Charmeuse Sport Shirt
$1820
Brunello Cucinelli
Nubuck Calfskin Sneakers
$1150
Zegna
Triple Stitch Tonal Suede Slip-On Sneakers
$1295
Zegna
Leather Triple Stitch Sneakers
$1440
Brunello Cucinelli
Italian-Fit Virgin Wool Pants
$1195
Maurizio Baldassari
Quilted Cashmere Suede Trimmed Vest
$1595
Henderson
Suede Leather Penny Loafers
$795
Tod's
Nuovo Gommino Leather Loafers
$895
Balmain
Virgin Wool Reversible Bomber
$3990
Eleventy
Silk-Cashmere Reversible Vest
$1995
Ferragamo
Foster Double Gancini Bit Pebbled Leather Loafers
$1090
Zegna
Oasi Cashmere Full Zip Cardigan
$4350
Brunello Cucinelli
Mélange Virgin Wool Sport Jacket
$3995
Ferragamo
Foster Double Gancio Leather Loafers
$1090
Brax
Chuck Corduroy Pants
$268
Canali
Calfskin Captoe Derby
$675
Brunello Cucinelli
Suede Tassel Loafers
$1300
Brunello Cucinelli
Padded Leather Flight Jacket
$11495
Zegna
Triple Stitch Leather Sneakers
$1440
Samuelsohn
Plaid Wool-Blend Sport Jacket
$1595
Kiton
Plaid Flannel Overshirt
$1495
Ferragamo
Fermin Polished Leather Oxfords
$1210
Paige
Stafford Straight Fit Transcend Pants
$318
Polo Ralph Lauren
Relaxed Fit Cotton Chinos
$228
Marco Pescarolo
Nerano Stretch Cashmere 5-Pockets Pants
$1125
BOSS
Lisbon Leather Lace-up Derbies
$348
Emporio Armani
Micro-Check Bamboo Sport Jacket
$1675
Brunello Cucinelli
Cashmere Jacket
$5595
Samuelsohn
Twill Wool Sport Jacket
$1495
Kiton
Flannel Houndstooth Cotton Sport Shirt
$995
TOM FORD
Regular-Fit Cotton Polo
$610
Anderson's
Grained Leather Dress Belt
$290
Bugatchi
Leaf Stretch-Cotton Sport Shirt
$250
Canali
Extra-Fine Merino Wool Sweater
$375
Zegna
Triple Stitch Secondskin Leather Sneakers
$1820
Canali
Wool-Silk Knitted Polo
$950
Zegna
Triple Stitch PELLETESSUTA Nubuck Leather Sneakers
$1820
Brunello Cucinelli
Easy Fit Medallion Print Cotton Sport Shirt
$1195
TOM FORD
Icon Cotton-Blend Denim Jacket
$1880
Bugatchi
Geometric Stretch-Cotton Sport Shirt
$195
Canali
Wool-Silk Knitted Polo
$950
Ferragamo
Funes Leather Penny Loafers
$1070
Windsor
Serpo Wool Pleated Pants
$595
Marco Pescarolo
Nerano Stretch-Cashmere 5-Pockets Pants
$1125
BOSS
Genius Cotton-Blend Trousers
$298
TOM FORD
Regular-Fit Cotton Polo
$610
Emporio Armani
Houndstooth Dress Shirt
$550
JOOP!
Gary Wool-Blend Coat
$1295
Kiton
Regal Cashmere Crewneck Sweater
$2995
AG
Aiden Cotton Western Shirt
$298
Marco Pescarolo
Nerano Stretch Cashmere 5-Pockets Pants
$1125
PT
Slim-Fit Stretch-Cotton Chino Pants
$345
Brunello Cucinelli
Mélange Virgin Wool Sport Jacket
$3995
TOM FORD
Double Face Shearling Blouson
$9440
Zegna
Oasi Cashmere Mélange Polo
$2450
TOM FORD
Reversible Grain Leather Textured Belt
$1070
Moncler
Bess Short Down Jacket
$3505
TOM FORD
Cashmere-Silk Knitted Polo
$2150
TOM FORD
Prince of Wales Cotton Dress Shirt
$1340
Canali
Wool-Silk Knitted Polo
$950
TOM FORD
Silk-Blend Long-Sleeve Military Polo
$2690
Ferragamo
Funes Penny Loafers
$1070
Brioni
William Geometric Shirt
$1195
Brunello Cucinelli
Basic Fit Oxford Cotton Button-Down Shirt
$870
BOSS
Leather Pin-Buckle Belt
$98
Isaia
Pure Silk Jersey Shirt
$1350
Isaia
Pure Silk Jersey Shirt
$1350
Brioni
William Micro Houndstooth Dress Shirt
$895
Kiton
Cashmere Knitted Sweater
$3150
Isaia
Pure Silk Jersey Polo
$1450
Isaia
Wool Piqué Jersey Shirt
$995
Isaia
Wool Piqué Jersey Shirt
$995
To Boot New York
Retro-Inspired Sneakers
$530
Berluti
Classic Patinated Leather Belt
$960
Brunello Cucinelli
Easy Fit Cotton Corduroy Western Shirt
$1380
Isaia
Wool-Blend Pants
$995
Isaia
Wool-Blend Pants
$995
Isaia
Wool-Blend Pants
$995
Berluti
Classic Scritto Leather Belt
$1050
Prada
Spazzolato Leather Tassel Loafers
$1450
TOM FORD
Atticus Sharkskin Pants
$1690
TOM FORD
Straight Fit Pleated Wool Pants
$1690
Brioni
Check Cotton-Cashmere Shirt
$1295
100 Hands
Brushed Cotton Dress Shirt
$765
Brioni
Sustainable William Striped Shirt
$995
Jacob Cohen
Bard Stretch-Cotton Blend Jeans
$565
Brunello Cucinelli
Herringbone Wool, Silk & Cashmere Overcoat
$7795
TOM FORD
Grain Leather Biker Jacket
$12810
Brax
Chuck Corduroy Hi-Flex Pants
$268
Brax
Chuck Relax Flex Cotton-Blend Pants
$258
Paige
Danford Slim Fit Stretch-Cotton Chino Pants
$315
Bontoni
Vittorio Leather Oxfords
$1525
Bontoni
Polished Leather Derbies
$1875
Isaia
Glen Check Wool Pants
$1295
Marco Pescarolo
Muno Stretch-Cashmere Drawstring Pants
$1125
Isaia
Argyle Cashmere-Wool Turtleneck
$3087
Ralph Lauren Purple Label
Tartan Plaid Sport Jacket
$2495
Isaia
Gingham Check Cotton Dress Shirt
$795
Isaia
Gingham Check Cotton Dress Shirt
$695
Marco Pescarolo
Stretch-Cashmere Jacket
$1695
TOM FORD
Silk Charmeuse Sport Shirt
$1820
Brunello Cucinelli
Nubuck Calfskin Sneakers
$1150
Zegna
Triple Stitch Tonal Suede Slip-On Sneakers
$1295
Zegna
Leather Triple Stitch Sneakers
$1440
Brunello Cucinelli
Italian-Fit Virgin Wool Pants
$1195
Maurizio Baldassari
Quilted Cashmere Suede Trimmed Vest
$1595
Henderson
Suede Leather Penny Loafers
$795
Tod's
Nuovo Gommino Leather Loafers
$895
Balmain
Virgin Wool Reversible Bomber
$3990
Eleventy
Silk-Cashmere Reversible Vest
$1995
Ferragamo
Foster Double Gancini Bit Pebbled Leather Loafers
$1090
Zegna
Oasi Cashmere Full Zip Cardigan
$4350
Brunello Cucinelli
Mélange Virgin Wool Sport Jacket
$3995
Ferragamo
Foster Double Gancio Leather Loafers
$1090
Brax
Chuck Corduroy Pants
$268
Canali
Calfskin Captoe Derby
$675
Brunello Cucinelli
Suede Tassel Loafers
$1300
Brunello Cucinelli
Padded Leather Flight Jacket
$11495
Zegna
Triple Stitch Leather Sneakers
$1440
Samuelsohn
Plaid Wool-Blend Sport Jacket
$1595
Kiton
Plaid Flannel Overshirt
$1495
Ferragamo
Fermin Polished Leather Oxfords
$1210
Paige
Stafford Straight Fit Transcend Pants
$318
Polo Ralph Lauren
Relaxed Fit Cotton Chinos
$228
Marco Pescarolo
Nerano Stretch Cashmere 5-Pockets Pants
$1125
BOSS
Lisbon Leather Lace-up Derbies
$348
Emporio Armani
Micro-Check Bamboo Sport Jacket
$1675
Brunello Cucinelli
Cashmere Jacket
$5595
Samuelsohn
Twill Wool Sport Jacket
$1495
Kiton
Flannel Houndstooth Cotton Sport Shirt
$995
TOM FORD
Regular-Fit Cotton Polo
$610
Anderson's
Grained Leather Dress Belt
$290
Bugatchi
Leaf Stretch-Cotton Sport Shirt
$250
Canali
Extra-Fine Merino Wool Sweater
$375
Zegna
Triple Stitch Secondskin Leather Sneakers
$1820
Canali
Wool-Silk Knitted Polo
$950
Zegna
Triple Stitch PELLETESSUTA Nubuck Leather Sneakers
$1820
Brunello Cucinelli
Easy Fit Medallion Print Cotton Sport Shirt
$1195
TOM FORD
Icon Cotton-Blend Denim Jacket
$1880
Bugatchi
Geometric Stretch-Cotton Sport Shirt
$195
Canali
Wool-Silk Knitted Polo
$950
Ferragamo
Funes Leather Penny Loafers
$1070
Windsor
Serpo Wool Pleated Pants
$595
Marco Pescarolo
Nerano Stretch-Cashmere 5-Pockets Pants
$1125
BOSS
Genius Cotton-Blend Trousers
$298
TOM FORD
Regular-Fit Cotton Polo
$610
Emporio Armani
Houndstooth Dress Shirt
$550
JOOP!
Gary Wool-Blend Coat
$1295
Kiton
Regal Cashmere Crewneck Sweater
$2995
AG
Aiden Cotton Western Shirt
$298
Marco Pescarolo
Nerano Stretch Cashmere 5-Pockets Pants
$1125
PT
Slim-Fit Stretch-Cotton Chino Pants
$345
Brunello Cucinelli
Mélange Virgin Wool Sport Jacket
$3995
TOM FORD
Double Face Shearling Blouson
$9440
Zegna
Oasi Cashmere Mélange Polo
$2450
TOM FORD
Reversible Grain Leather Textured Belt
$1070
Moncler
Bess Short Down Jacket
$3505
TOM FORD
Cashmere-Silk Knitted Polo
$2150
TOM FORD
Prince of Wales Cotton Dress Shirt
$1340
Canali
Wool-Silk Knitted Polo
$950
TOM FORD
Silk-Blend Long-Sleeve Military Polo
$2690
Ferragamo
Funes Penny Loafers
$1070
Brioni
William Geometric Shirt
$1195
Brunello Cucinelli
Basic Fit Oxford Cotton Button-Down Shirt
$870
BOSS
Leather Pin-Buckle Belt
$98