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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Kiton
Virgin Wool Cashmere Sport Jacket
$5995
Isaia
Houndstooth Cashmere-Silk Overcoat
$7100
Mason's
Slim-Fit Torino Jersey Stretch-Cotton Pants
$300
BOSS
Double-Breasted Wool-Cashmere Overcoat
$995
Kiton
Regular-Fit Flannel Cotton Sport Shirt
$695
Isaia
Domenico Cashmere Twill Sport Jacket
$6325
Isaia
Flannel Wool-Blend Pants
$1250
Isaia
Flannel Stretch Wool-Cashmere Blend Pants
$1250
Kiton
Corduroy Cotton-Blend Jeans
$1495
Brunello Cucinelli
Long-Sleeve Cotton Piqué Sport Shirt
$645
Santoni
Duke Burnished Leather Penny Loafers
$1450
Brunello Cucinelli
Regular Fit Cotton Piqué Polo
$695
Church's
Kingsley Tassel Leather Loafers
$1450
Kilian
Intoxicated Eau De Parfum 50ml
$385
Zegna
Trofeo Wool Dress Pants
$1150
Prada
Triangle Plaque Spazzolato Leather Loafers
$1390
Ferragamo
Fosco Polished Leather Plain-Toe Derbies
$1070
Gran Sasso
Cotton Dropstitch Knitted Polo
$335
Thom Browne
Chambray Cotton Shirt
$770
Emanuel Berg
Byron 4-Flex Stretch-Cotton Performance Shirt
$278
Canali
Slim Fit Washed Stretch-Cotton Jeans
$425
Ferragamo
Fosco Leather Derbies
$1070
TOM FORD
Burnished Leather Cap-Toe Oxfords
$2490
Zegna
Torino Burnished Leather Cap Toe Oxfords
$1650
Zegna
Oasi Cashmere Crewneck Sweater
$1790
Mason's
Slim-Fit Torino Pleated Jersey Stretch-Cotton Pants
$300
Brunello Cucinelli
Polished Leather Lace Up Derbies
$1450
Brunello Cucinelli
Regular Fit Cotton Piqué Polo
$695
Eton
Contemporary-Fit Twill Dress Shirt
$295
Ralph Lauren Purple Label
Clifton Suede Trucker Jacket
$3750
BOSS
Lisbon Burnished Leather Derbies
$328
TOM FORD
Edgar Polished Leather Tassel Loafers
$2490
Thom Browne
Grosgrain Armband Button-Down Collar Oxford Shirt
$680
Kiton
Contemporary-Fit Cotton Sport Shirt
$695
Brunello Cucinelli
Suede Lace-up Derbies
$1695
Brunello Cucinelli
Suede Sheepskin Leather Jacket
$10795
Isaia
Soft Wool Sport Shirt
$1000
Giorgio Armani
Solid Twill Cotton Dress Shirt
$775
Zegna
Cashseta Light Cashmere-Silk Turtleneck
$1950
Prada
Plaque Logo Grained Leather Loafers
$1250
TOM FORD
O'Connor Bi-Stretch Wool Dress Pants
$1450
TOM FORD
Shelton Grand Hopsak Wool-Mohair Sport Jacket
$5680
Berluti
Andy Demesure Leather Loafer
$3300
Brioni
Shebha Mélange Wool Pants
$1695
Church's
Pembrey Leather Penny Loafers
$1375
Emporio Armani
Jacquard Herringbone Polo
$350
Brioni
Wool, Silk & Cashmere Sport Jacket
$5995
Santoni
Carlos Cross Hatch Double Monkstraps
$1450
Marco Pescarolo
Dox 120s Virgin Wool Pleated Pants
$595
TOM FORD
Edgar Leather Monkstraps
$2360
Eton
Contemporary-Fit Twill Dress Shirt
$295
Eton
Slim-Fit Twill Dress Shirt
$295
BOSS
Serge Virgin Wool Dress Pants
$398
Eton
Floral Dress Shirt
$295
Eton
Slim-Fit Twill Dress Shirt
$280
Moncler
Lez Field Jacket
$1780
TOM FORD
Atticus Cotton Compact Velvet Sport Jacket
$4960
Gran Sasso
Ribbed Linen-Cotton Polo
$365
Brunello Cucinelli
Mélange Linen-Cotton Polo
$1070
Kiton
Reversible Wool-Blend Coat
$9995
TOM FORD
Elkan Double Monkstrap Dress Shoes
$2740
Magnanni
Andros Leather Lace up Derbies
$598
Kiton
Regular-Fit Flannel Cotton Sport Shirt
$695
Isaia
Soft Wool Sport Shirt
$1000
Kiton
Corduroy Cotton-Blend Jeans
$1495
Kiton
Corduroy Cotton-Blend Jeans
$1495
Isaia
Domenico Cashmere Sport Jacket
$6325
Brunello Cucinelli
Regular Fit Cotton Piqué Polo
$695
Brunello Cucinelli
Regular Fit Cotton Piqué Polo
$695
TOM FORD
Officer Wool Peacoat
$6240
Berluti
Equilibre Leather Stitch Cutout Double Monkstraps
$3850
TOM FORD
Cotton-Linen Gabardine Leisure Shirt
$1240
Eton
Slim-Fit Twill Dress Shirt
$280
Eton
Slim-Fit Twill Dress Shirt with French Cuff
$280
Brunello Cucinelli
Ribbed Cotton Polo
$950
TOM FORD
Leather Cap-Toe Oxfords
$2240
Giorgio Armani
Lambskin Leather Sport Jacket
$6295
TOM FORD
O'Connor Stretch-Wool Dress Pants
$1450
Loro Piana
André Striped Pattern Linen Polo
$1100
Emporio Armani
Slim-Fit Stretch Cotton Sport Shirt
$395
Moncler
Camicia Stretch-Cotton Overshirt
$1065
Isaia
Wool-Cashmere Twill Walking Coat
$4800
Brunello Cucinelli
Mélange Camp Shirt
$1195
TOM FORD
Hybrid Canvas Sport Jacket
$4860
Zegna
Triple Stitch Suede Slip-On Sneakers
$1295
Brioni
Shearling Collar Lambskin Leather Jacket
$14995
BOSS
Hal Jersey Dress Shirt
$178
Brioni
Brushed Cashmere Overcoat
$14995
TOM FORD
Yarn Dyed Mikado Wool-Silk Trousers
$2110
TOM FORD
Slim Fit Organza Dress Pants
$1890
Brioni
Jersey Cotton Cashmere Military Shirt
$1495
Brioni
Stretch-Wool Cotton-Blend Overshirt
$1395
Brioni
Wool, Silk, & Cashmere Overshirt
$4995
Zegna
Torino Burnished Leather Oxfords
$1610
Brioni
New Plume Cashmere, Silk & Linen Sport Jacket
$11995
Emanuel Berg
Byron 4-Flex Stretch-Cotton Performance Shirt
$278
Kiton
Lightweight Wool Coat
$3995
Thom Browne
4-Bar Chambray Shirt
$770
Tiger of Sweden
Tenuta Wool Twill Suit Pants
$329
TOM FORD
Sean Patent Leather Tassel Loafers
$2740
Kiton
Virgin Wool Cashmere Sport Jacket
$5995
Isaia
Houndstooth Cashmere-Silk Overcoat
$7100
Mason's
Slim-Fit Torino Jersey Stretch-Cotton Pants
$300
BOSS
Double-Breasted Wool-Cashmere Overcoat
$995
Kiton
Regular-Fit Flannel Cotton Sport Shirt
$695
Isaia
Domenico Cashmere Twill Sport Jacket
$6325
Isaia
Flannel Wool-Blend Pants
$1250
Isaia
Flannel Stretch Wool-Cashmere Blend Pants
$1250
Kiton
Corduroy Cotton-Blend Jeans
$1495
Brunello Cucinelli
Long-Sleeve Cotton Piqué Sport Shirt
$645
Santoni
Duke Burnished Leather Penny Loafers
$1450
Brunello Cucinelli
Regular Fit Cotton Piqué Polo
$695
Church's
Kingsley Tassel Leather Loafers
$1450
Kilian
Intoxicated Eau De Parfum 50ml
$385
Zegna
Trofeo Wool Dress Pants
$1150
Prada
Triangle Plaque Spazzolato Leather Loafers
$1390
Ferragamo
Fosco Polished Leather Plain-Toe Derbies
$1070
Gran Sasso
Cotton Dropstitch Knitted Polo
$335
Thom Browne
Chambray Cotton Shirt
$770
Emanuel Berg
Byron 4-Flex Stretch-Cotton Performance Shirt
$278
Canali
Slim Fit Washed Stretch-Cotton Jeans
$425
Ferragamo
Fosco Leather Derbies
$1070
TOM FORD
Burnished Leather Cap-Toe Oxfords
$2490
Zegna
Torino Burnished Leather Cap Toe Oxfords
$1650
Zegna
Oasi Cashmere Crewneck Sweater
$1790
Mason's
Slim-Fit Torino Pleated Jersey Stretch-Cotton Pants
$300
Brunello Cucinelli
Polished Leather Lace Up Derbies
$1450
Brunello Cucinelli
Regular Fit Cotton Piqué Polo
$695
Eton
Contemporary-Fit Twill Dress Shirt
$295
Ralph Lauren Purple Label
Clifton Suede Trucker Jacket
$3750
BOSS
Lisbon Burnished Leather Derbies
$328
TOM FORD
Edgar Polished Leather Tassel Loafers
$2490
Thom Browne
Grosgrain Armband Button-Down Collar Oxford Shirt
$680
Kiton
Contemporary-Fit Cotton Sport Shirt
$695
Brunello Cucinelli
Suede Lace-up Derbies
$1695
Brunello Cucinelli
Suede Sheepskin Leather Jacket
$10795
Isaia
Soft Wool Sport Shirt
$1000
Giorgio Armani
Solid Twill Cotton Dress Shirt
$775
Zegna
Cashseta Light Cashmere-Silk Turtleneck
$1950
Prada
Plaque Logo Grained Leather Loafers
$1250
TOM FORD
O'Connor Bi-Stretch Wool Dress Pants
$1450
TOM FORD
Shelton Grand Hopsak Wool-Mohair Sport Jacket
$5680
Berluti
Andy Demesure Leather Loafer
$3300
Brioni
Shebha Mélange Wool Pants
$1695
Church's
Pembrey Leather Penny Loafers
$1375
Emporio Armani
Jacquard Herringbone Polo
$350
Brioni
Wool, Silk & Cashmere Sport Jacket
$5995
Santoni
Carlos Cross Hatch Double Monkstraps
$1450
Marco Pescarolo
Dox 120s Virgin Wool Pleated Pants
$595
TOM FORD
Edgar Leather Monkstraps
$2360
Eton
Contemporary-Fit Twill Dress Shirt
$295
Eton
Slim-Fit Twill Dress Shirt
$295
BOSS
Serge Virgin Wool Dress Pants
$398
Eton
Floral Dress Shirt
$295
Eton
Slim-Fit Twill Dress Shirt
$280
Moncler
Lez Field Jacket
$1780
TOM FORD
Atticus Cotton Compact Velvet Sport Jacket
$4960
Gran Sasso
Ribbed Linen-Cotton Polo
$365
Brunello Cucinelli
Mélange Linen-Cotton Polo
$1070
Kiton
Reversible Wool-Blend Coat
$9995
TOM FORD
Elkan Double Monkstrap Dress Shoes
$2740
Magnanni
Andros Leather Lace up Derbies
$598
Kiton
Regular-Fit Flannel Cotton Sport Shirt
$695
Isaia
Soft Wool Sport Shirt
$1000
Kiton
Corduroy Cotton-Blend Jeans
$1495
Kiton
Corduroy Cotton-Blend Jeans
$1495
Isaia
Domenico Cashmere Sport Jacket
$6325
Brunello Cucinelli
Regular Fit Cotton Piqué Polo
$695
Brunello Cucinelli
Regular Fit Cotton Piqué Polo
$695
TOM FORD
Officer Wool Peacoat
$6240
Berluti
Equilibre Leather Stitch Cutout Double Monkstraps
$3850
TOM FORD
Cotton-Linen Gabardine Leisure Shirt
$1240
Eton
Slim-Fit Twill Dress Shirt
$280
Eton
Slim-Fit Twill Dress Shirt with French Cuff
$280
Brunello Cucinelli
Ribbed Cotton Polo
$950
TOM FORD
Leather Cap-Toe Oxfords
$2240
Giorgio Armani
Lambskin Leather Sport Jacket
$6295
TOM FORD
O'Connor Stretch-Wool Dress Pants
$1450
Loro Piana
André Striped Pattern Linen Polo
$1100
Emporio Armani
Slim-Fit Stretch Cotton Sport Shirt
$395
Moncler
Camicia Stretch-Cotton Overshirt
$1065
Isaia
Wool-Cashmere Twill Walking Coat
$4800
Brunello Cucinelli
Mélange Camp Shirt
$1195
TOM FORD
Hybrid Canvas Sport Jacket
$4860
Zegna
Triple Stitch Suede Slip-On Sneakers
$1295
Brioni
Shearling Collar Lambskin Leather Jacket
$14995
BOSS
Hal Jersey Dress Shirt
$178
Brioni
Brushed Cashmere Overcoat
$14995
TOM FORD
Yarn Dyed Mikado Wool-Silk Trousers
$2110
TOM FORD
Slim Fit Organza Dress Pants
$1890
Brioni
Jersey Cotton Cashmere Military Shirt
$1495
Brioni
Stretch-Wool Cotton-Blend Overshirt
$1395
Brioni
Wool, Silk, & Cashmere Overshirt
$4995
Zegna
Torino Burnished Leather Oxfords
$1610
Brioni
New Plume Cashmere, Silk & Linen Sport Jacket
$11995
Emanuel Berg
Byron 4-Flex Stretch-Cotton Performance Shirt
$278
Kiton
Lightweight Wool Coat
$3995
Thom Browne
4-Bar Chambray Shirt
$770
Tiger of Sweden
Tenuta Wool Twill Suit Pants
$329
TOM FORD
Sean Patent Leather Tassel Loafers
$2740