All occasions

What to Wear on Father's Day

Father's Day tends to mean a barbecue, a long lunch or a day out, so the outfit wants to be relaxed but clearly considered. A polo or oxford shirt, chinos or tailored shorts, a light overshirt and clean leather trainers or loafers cover most plans, in navy, stone, olive and white.

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A man wearing a forest green Donegal tweed sport coat, cream and navy striped cotton dress shirt, charcoal grey wool blend pleated trousers and polished brown leather wingtip brogues — a men's old money outfit.

The edit

Complete looks for the occasion

Looks from the lookbook that work here. Each one links back to the aesthetic it came from.

Start with a proportion that suits the setting, then let the finish and accessories carry the formality.

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A man wearing a forest green Donegal tweed sport coat, cream and navy striped cotton dress shirt, charcoal grey wool blend pleated trousers and polished brown leather wingtip brogues — a men's old money outfit.AI-styled model — see it on you instead

Heirloom Hues

Why this look works

Drawing on "Deep Seasonal Hues," this outfit leverages rich, grounded tones for a confident everyday appeal. The forest green Donegal tweed sport coat with its tailored fit creates a sharp yet comfortable silhouette that provides structure without being restrictive. This is complemented by charcoal wool blend pleated trousers, which offer a clean, straight line. A subtle striped dress shirt beneath adds a layer of classic detail, resulting in a cohesive and confident ensemble for an elevated casual occasion.

From the men's old money lookbook

Prices checked 15 September 2026. Availability and price change — confirm at the retailer.

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A man wearing a hunter green subtle windowpane check wool-blend sport coat, ivory merino wool v-neck sweater, tan flannel pleated trousers and dark brown leather wingtip brogues — a men's old money outfit.AI-styled model — see it on you instead

Country Club Confident

Why this look works

A substantial yet refined sport coat in a distinctive pattern adds visual interest and structured elegance.

From the men's old money lookbook

Prices checked 15 September 2026. Availability and price change — confirm at the retailer.

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A man wearing a fine-gauge merino wool knit polo shirt in deep forest green, relaxed-fit pleated front cotton twill chinos in a stone beige, structured navy wool blend blazer and dark brown suede penny loafers — a men's old money outfit.AI-styled model — see it on you instead

Country Estate Casual

Why this look works

This ensemble draws from the "Elevated Menswear Casual" trend, infusing a relaxed yet refined sensibility ideal for travel within the old money aesthetic. The fine-gauge merino knit polo offers a comfortable alternative to a traditional shirt, while the tailored chinos provide a relaxed fit suitable for movement, maintaining a polished appearance. A classic navy blazer completes the look, adding structure and confidence, making it versatile for various travel scenarios.

From the men's old money lookbook

Shoppable pieces

Prices checked 15 September 2026. Availability and price change — confirm at the retailer.

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More ways to wear it

We're still sourcing some pieces in these looks. Linked pieces are ready to shop; the rest are marked still sourcing.

A man wearing a white mercerized cotton crew neck t-shirt, burgundy suede overshirt, tan slim-fit tailored cotton trousers and dark brown leather Chelsea boots — a men's smart casual outfit.AI-styled model — see it on you instead

Vivid Tones

Why this look works

This "Deep Seasonal Hues" look harnesses a rich burgundy suede overshirt to create a confident and fashion-forward smart casual statement. The deep color provides a striking focal point, complemented by the warm tan tailored cotton trousers, offering a contemporary twist on classic menswear. This palette ensures a memorable date night ensemble, where the distinct color pairing works harmoniously for a sophisticated and assured presentation.

From the men's smart casual lookbook

Shoppable pieces

Prices checked 15 September 2026. Availability and price change — confirm at the retailer.

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A man wearing a forest green fine-gauge merino wool turtleneck sweater, dark khaki cotton pleated chinos, brown suede chukka boots and gold-tone classic watch — a men's old money outfit.AI-styled model — see it on you instead

Heritage Hearthside

Why this look works

Embracing the "Essential Knitwear for Men" trend, this look offers a confident yet comfortable presence, perfectly suited for fall work within the "old money" aesthetic. The fine-gauge forest green merino wool turtleneck provides a sleek, refined base. Paired with crisp dark khaki pleated chinos, the ensemble maintains a tailored edge. This rich, earthy palette creates a sophisticated and grounded composition.

From the men's old money lookbook

Shoppable pieces

Prices checked 15 September 2026. Availability and price change — confirm at the retailer.

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A man wearing a crisp white cotton poplin button-down shirt, dark navy stretch cotton chinos, deep burgundy unstructured cotton twill blazer and dark brown leather Derby shoes — a men's smart casual outfit.AI-styled model — see it on you instead

Assertive Elegance

Why this look works

This look grounds a confident statement piece – the rich burgundy blazer – with classic smart casual elements. The unstructured nature of the blazer provides comfort for a night out, while the crisp shirt and well-tailored trousers maintain a polished aesthetic. The interplay of textures and colors offers a fashion-forward sensibility.

From the men's smart casual lookbook

Shoppable pieces

Prices checked 15 September 2026. Availability and price change — confirm at the retailer.

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A man wearing a white crisp poplin dress shirt, hunter green fine merino wool V-neck sweater vest, charcoal grey tailored wool trousers and dark brown polished leather cap-toe Oxford shoes — a men's old money outfit.AI-styled model — see it on you instead

Varsity Luxe

Why this look works

Embracing the "Essential Knitwear for Men" trend, this look combines classic collegiate style with refined textures for a confident date night. A crisp white poplin shirt provides a clean base, while a richly textured V-neck sweater vest in hunter green adds a sophisticated layer and a traditional old-money vibe. The clean lines of charcoal tailored wool trousers create a sharp, polished profile that suits a lean frame, while the deep green pairs well with warmer skin tones.

From the men's old money lookbook

Shoppable pieces

  • Roundtree Yorke V-Neck Solid Sweater Vestat dillards.com$55
  • White crisp poplin dress shirt with a classic collar and French cuffs,…still sourcing
  • Charcoal grey tailored wool trousers with a flat front, slim fit, and a…still sourcing
  • Dark brown polished leather cap-toe Oxford shoes with a stacked heel.still sourcing

Prices checked 15 September 2026. Availability and price change — confirm at the retailer.

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A man wearing a fine gauge knit polo shirt in a rich olive green, unstructured blazer in a charcoal grey tweed, relaxed fit tailored trousers in a camel wool blend and dark brown suede loafers — a men's smart casual outfit.AI-styled model — see it on you instead

Tailored Ease

Why this look works

This look embodies the "Elevated Menswear Casual" trend, balancing tailored elements with comfortable pieces suitable for a family gathering. The relaxed tailored camel trousers maintain a clean, modern line that works well with his balanced physique.

From the men's smart casual lookbook

Shoppable pieces

  • Reiss Manor Merino Wool Polo Shirtat macys.com$107
  • Unstructured blazer in a charcoal grey tweed, featuring soft shoulders and…still sourcing
  • Relaxed fit tailored trousers in a camel wool blend, with a straight leg and…still sourcing
  • Dark brown suede loafers with a penny slot detail and a stacked heel.still sourcing

Prices checked 15 September 2026. Availability and price change — confirm at the retailer.

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A man wearing a charcoal pinstripe wool blazer, deep teal silk blend button-down shirt, black wool crepe pleated trousers and black polished leather derby shoes — a men's old money outfit.AI-styled model — see it on you instead

Urban Heritage

From the men's old money lookbook

Shoppable pieces

  • Men's Suede Penny Loafersat kohls.com$80
  • Charcoal pinstripe wool blazer, single-breasted, two-button, with peak lapels…still sourcing
  • Deep teal silk blend button-down shirt, long sleeve, with a subtle sheen and a…still sourcing
  • Black wool crepe pleated trousers, featuring a relaxed fit, straight leg, and…still sourcing
  • Silver minimalist cuff bracelet, crafted from solid sterling silver, worn on…still sourcing

Prices checked 15 September 2026. Availability and price change — confirm at the retailer.

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Questions

What should a dad wear on Father's Day?
Something relaxed that still looks chosen. A knitted polo or an oxford shirt with chinos and clean leather trainers suits a barbecue, a pub lunch or a family walk. Add a light overshirt or a cotton jacket for the evening, and the outfit works from noon until late.
What do I wear to a Father's Day barbecue?
Breathable and easy to move in. A short-sleeved shirt in linen or cotton, tailored shorts or light chinos, and a canvas or leather trainer handle heat and a garden. Darker colours hide the inevitable sauce far better than white does, which is worth remembering.
What is a good Father's Day outfit for a restaurant?
Step up one notch from the barbecue: an oxford shirt or a fine-knit polo, flat-front trousers in stone or navy, and a loafer or clean leather shoe. An unstructured blazer finishes it without making it formal, and it can come off once the table relaxes.
Are shorts acceptable on Father's Day?
Yes, for most daytime plans in warm weather. Keep them tailored rather than athletic, with a hem just above the knee, and pair them with a collared shirt or a knitted polo. That combination reads grown-up where cargo shorts and a sports top do not.
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