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The Fairway Tailored Shorts

Name: The Fairway Tailored Shorts
Brand: Henry Grayson
Price: 44.99 USD
Availability: InStock

$44.99

📦 $4.99 tracked shipping

🔒 Secure checkout

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Standard Shipping

$4.99 flat rate on all orders. Tracked from dispatch to delivery.

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Delivery Time

Processed within 1 to 2 business days. Delivery takes a further 3 to 10 business days.

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Order Tracking

A tracking number is emailed as soon as your order ships.

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Considered Materials

Carefully chosen fabrics, selected for feel, durability, and the way they wear over time.

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Built to Last

Designed to be worn for years, not seasons. Every detail placed with care.

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Designed in Northern Ireland, Sold in the United States

Rooted in the heritage and craft traditions of the north of Ireland.

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30 Day Returns

Send it back within 30 days. Unworn, tags attached, original packaging.

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Easy Process

Email us with your order number. No restocking fees, ever.

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Quick Refunds

Processed within 3 business days to your original payment method.

Description +

The Fairway Tailored Shorts bring clean structure to warm-weather comfort. With their refined silhouette and understated character, they’re an easy choice when casual shorts feel too relaxed but full trousers are more than the day calls for.

Tailored, Not Stuffy

Designed with a smarter profile, these shorts create a polished appearance while keeping the easygoing feel you want during warmer weather. They work naturally across holidays, lunches, weekends and summer evenings.

How to Wear Them

Pair with a tucked-in polo or lightweight button-down and loafers for a classic summer look. For something more relaxed, add a simple tee and clean sneakers.

Product Features

• Smart tailored silhouette
• Clean, refined appearance
• Comfortable warm-weather styling
• Easy to dress up or down
• Ideal for holidays, weekends and summer occasions
• Pairs naturally with polos, shirts and lightweight knitwear

Product Care

• Follow the garment care label for best results
• Wash gently with similar colors
• Avoid excessive heat
• Reshape after washing where necessary
• Allow to dry naturally where possible

Details and Care +

Designed with attention to every detail. Look after your piece and it will look after you.

Spot clean with a damp cloth
Reshape while damp if needed
Air dry away from direct heat
Do not machine wash or tumble dry
Store flat or in original packaging

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Tracked Shipping

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30 Day Returns

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N. Ireland

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Real Support

Flat Caps · Newsboy Caps · Beanies

Measure around the widest part of your head, just above the ears and across the forehead. Between sizes? Take the larger.

Size	Head (cm)	Head (in)	UK / US Hat
S	54 – 55	21.3 – 21.7	6 3/4 – 6 7/8
M	56 – 57	22 – 22.4	7 – 7 1/8
L	58 – 59	22.8 – 23.2	7 1/4 – 7 3/8
XL	60 – 61	23.6 – 24	7 1/2 – 7 5/8

Jackets · Shirts · Knitwear · Blazers

Measurements in inches.

Size	Chest	Sleeve Length
XS	33 – 34	33
S	36 – 38	33.5
M	39 – 41	34
L	42 – 44	34.75
XL	45 – 48	35.5
XXL	49 – 53	36.25
XXXL	54 – 58	37.5

Pants · Trousers

If the inseam length isn't what you were looking for, reach out to support@henrygrayson.com and we may be able to arrange a custom size.

Size	Waist (in)	Inseam (cm)	Inseam (in)
XS	28	80	31.5
S	30	80	31.5
M	32	81	32
L	34	81	32
XL	36	81	32
XXL	38	83	32.5
XXXL	40	83	32.5

Footwear

All men's footwear at Henry Grayson is offered in US Men's standard sizing. Measure your foot length and match it to the closest size below.

US Size	Foot Length (in)
2	7.6
2.5	7.8
3	7.9
3.5	8.1
4	8.3
4.5	8.5
5	8.6
5.5	8.8
6	9.0
6.5	9.1
7	9.3
7.5	9.5
8	9.6
8.5	9.8
9	10.0
9.5	10.2
10	10.3
10.5	10.5
11	10.7
11.5	10.8
12	11.0
12.5	11.2
13	11.3
13.5	11.5
14	11.7

How to Measure

Stand with your heel against a wall on a hard floor. Measure from the wall to the tip of your longest toe. Measure both feet in the evening, when they're at their largest, and use the bigger measurement. If you fall between sizes, we recommend sizing up.

Flat Caps · Newsboy Caps · Beanies

Measure around the widest part of your head, just above the ears and across the forehead. Between sizes? Take the larger.

Size	Head (cm)	Head (in)	UK / US Hat
S	53 – 54	20.9 – 21.3	6 5/8 – 6 3/4
M	55 – 56	21.7 – 22	6 7/8 – 7
L	57 – 58	22.4 – 22.8	7 1/8 – 7 1/4
XL	59 – 60	23.2 – 23.6	7 3/8 – 7 1/2

Dresses · Tops · Knitwear · Blazers

Measurements in inches.

Size	Bust	Waist	Hips
XS	31 – 32	23 – 24	33 – 34
S	33 – 34	25 – 26	35 – 36
M	35 – 36	27 – 28	37 – 38
L	37 – 39	29 – 31	39 – 41
XL	40 – 42	32 – 34	42 – 44
XXL	43 – 45	35 – 37	45 – 47
XXXL	46 – 48	38 – 40	48 – 50

Pants · Trousers · Skirts

If the inseam length isn't what you were looking for, reach out to support@henrygrayson.com and we may be able to arrange a custom size.

Size	Waist (in)	Hip (in)	Inseam (cm)	Inseam (in)
XS	23 – 24	33 – 34	76	30
S	25 – 26	35 – 36	76	30
M	27 – 28	37 – 38	77	30.5
L	29 – 31	39 – 41	77	30.5
XL	32 – 34	42 – 44	77	30.5
XXL	35 – 37	45 – 47	78	31
XXXL	38 – 40	48 – 50	78	31

Footwear

All women's footwear at Henry Grayson is offered in US Women's standard sizing. Measure your foot length and match it to the closest size below.

US Size	Foot Length (in)
2	6.4
2.5	6.6
3	6.7
3.5	6.9
4	7.0
4.5	7.2
5	7.4
5.5	7.5
6	7.7
6.5	7.9
7	8.0
7.5	8.2
8	8.3
8.5	8.5
9	8.7
9.5	8.8
10	9.0
10.5	9.2
11	9.3
11.5	9.5
12	9.6
12.5	9.8
13	10.0
13.5	10.1
14	10.3

How to Measure

Stand with your heel against a wall on a hard floor. Measure from the wall to the tip of your longest toe. Measure both feet in the evening, when they're at their largest, and use the bigger measurement. If you fall between sizes, we recommend sizing up.

Henry Grayson packaging with knitwear and heritage details

The Grayson Word

A handshake still means something here.

Thirty days. Our word. Kept the old way.

I.

Nothing Leaves Unchecked.

Every piece passes through careful hands before it sets off to you. Where we come from, you don't put your name on something you haven't looked over.

II.

Thirty Days, No Quibbles.

Not right for you? Send it back within 30 days for a full refund. No restocking fees, nothing marked final sale, and no need to explain yourself. Want a different size or colour? Return it and reorder, simple as that.

III.

A Person, Not a Robot.

Sizing questions, returns, or anything in between, write to support@henrygrayson.com and a real person answers. Monday to Friday, 8:00 AM to 6:00 PM EST.

Our Conviction

"My great grandfather crossed the Atlantic with almost nothing. But he never stopped dressing like the man he was. That quiet pride is what we build every piece around. Not trends, not seasons. Just the belief that the things worth wearing are the things worth keeping."

Adam Grayson

Founder, Henry Grayson