Signature Look: Dennis Lindsay

Signature Look is a new project asking the question; ‘If you could only wear one outfit for the rest of your life, what would it be?’

The idea explores why we gravitate to certain looks; outfits that work for the various aspects of our life—work, home, hobbies, going out with friends—, whilst also showcasing our personalities. In this series, we ask people of different styles, professions and ages to think about what they wear and why one outfit is the best fit for their life.

As a test, I have photographed myself and answered the questions that will be put to each person. I look forward to seeing the styles and answers to why each interviewee came up with their particular outfit ahead of all other available choices.

If you could only wear one outfit, what would it be and why?

Starting with my feet, I like traditional leather shoes, especially these Alden cordovan brogues in oxblood. Socks are an opportunity to add some visual interest and I wear either burnt yellow or navy with a subtle pattern. Dark indigo denim from Japan acts as a base for this outfit; the key is the quality of the material as good jeans age beautifully over time. Belts always match the shoes to provide continuity while oxford cloth button-down shirts in white or blue/white stripe are harmonious in terms of both colour and formality. A waistcoat made in a less formal fabric like tweed, linen or denim is both flattering and keeps my core warm, while a navy quarter lined blazer elevates the overall look.

How does this collection of clothes allow you to move between the various aspects of your life?

I spend my life between travelling to the city for appointments,—mostly held in cafes, restaurants and bars—, whilst living in the country, walking around the lake and spending time with family and friends. Almost everything I do in a week can be done in this outfit by adding or subtracting the blazer or tie. I love that the way this outfit straddles the formal aspects of business and city life, yet I can sit on the ground or go for a walk in the county and not feel fussy about my clothes. Similarly, it is easy to adjust to the weather by removing the blazer and tie for the summer months.

Describe this style:

Tailoring combined with robust fabrics and smart leather shoes.

List what you are wearing:

Cool weather version:
Blazer: Canali
Shirt: Canali
Waistcoat: RRL
Tie: Margaret Howell
Jeans: Freewheelers
Socks: Uniqlo
Shoes & Belt: Alden
Watch: IWC

Warm weather version:
Waistcoat: Weber & Frey
Shirt: Hilfiger
Jeans: Freewheelers
Socks: Uniqlo
Shoes: Crockett & Jones
Belt: Ferragamo
Bag: Hardgraft
Watch: IWC

If money was no object, what is the ultimate version of this outfit?

This is my ultimate version. I bought the key pieces over the past ten years and they all have aged well.

What is the origin of this look for you?

There was quite a journey to settle on this outfit. It began with seeing images of Giorgio Armani as a teenager and deciding that one day I would wear those flowing suits. In my early twenties I spent a ridiculous amount of my limited income on a black Armani suit that I wore to death. The suit made me feel confident, and I knew that I stood out for the right reasons.

Over time, however, the fine fabrics meant that the expensive suits did not last. This bothered me as I was brought up with a view of buying quality, spending money on well made, long lasting products. After Armani, I explored the sharp but less formal offerings of Prada in the late 90s and early 2000s. It was an exciting time, however, Prada proved too ‘fashion’ for me as I got into my middle 30s. This lead me to explore tailor-made suiting which I liked very much, yet it found it constrictive and a little precious as I always felt I had to change after work into something else which did not suit my lifestyle of going out straight after work.

During the 2010s I explored workwear, discovering the joys of Japanese denim which I still love to this day. However, workwear was not for me. It felt like I was wearing a costume and I missed the elegance of Italian tailoring. The solution came in the merging of quality tailoring, beautiful leather shoes and robust denim which offered the balance I was seeking.

How do you feel when you wear this?

I feel as though I can go anywhere, be well presented and appropriately attired. This outfit is also an authentic representation of me. By contrast, at times I wear beautiful, tailored suits, one that a younger me would have imaged I would be wearing. I know intellectually that this is a sharp look, however, I often feel as though I am wearing a costume. The outfit I have chosen above has none of that. I always feel confident and ready for the day ahead.

Imagine you were put in charge of designing a capsule wardrobe based around your style. What would it comprise? 

Navy quarter lined wool blazer, single breasted, notch lapel, patch pockets with minimal shoulder padding
Denim waistcoat
Oxford cloth button down shirts: White, Blue & Blue/White stripe
Blue striped tie
Chocolate cashmere turtleneck
Japanese indigo denim jeans, higher waisted with a wider cut
Grey wool, pleated high waisted trousers
Oxblood brogues and belt
Chocolate brown suede loafers and belt
Burnt yellow & Brown/grey socks
Beige overcoat
Brown leather tote bag