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How to Dress Old Money Style for a Cocktail Party – Gent’s Guide

Hey there, gents. We are back to help you navigate the tricky waters of cocktail attire.

With over three decades of experience styling Old Money looks for young men like yourselves, we’ve got plenty of tips and tricks up my well-tailored sleeve.

So, let’s dive in and get you looking your best for that fancy cocktail party!

Old Money Cocktail Attire Essentials

When it comes to Old Money style, it’s all about understated elegance.

You want to look polished and put together without being too flashy or over-the-top.

Investing in high-quality, timeless pieces that will serve you well for years is key.


For a strict cocktail dress code, a well-fitted suit is your best bet.

Opt for a slim-fit style in a dark, neutral color like navy or charcoal.

If the event is more relaxed, you can go for a lighter shade like gray or a subtle pattern like plaid.

Remember, the fit is everything – ensure your suit is perfectly tailored.

Jackets and Blazers

A jacket or blazer is a great alternative if a full suit feels too formal.

A classic navy blazer is a must-have in any Old Money wardrobe.

Pair it with well-pressed trousers in a complementary color, and you’re good to go.

For a more casual vibe, try a textured jacket made of material like wool or linen.

Classic Shirts

When it comes to shirts, simplicity is key.

A crisp, white dress shirt is always a safe choice, but don’t be afraid to experiment with subtle patterns or muted colors.

Avoid anything too bold or flashy – remember, Old Money style is all about refined taste.

If you’re feeling daring, a classic polo shirt can work for a more relaxed cocktail event.

Roll Necks

Want to stand out from the sea of dress shirts?

A roll-neck sweater is a smart and sophisticated choice.

Opt for a lightweight material like merino wool or cashmere to avoid overheating.

A roll neck in a dark, neutral color will pair perfectly with your jacket or blazer.

Tailored Trousers

Your pants should be the foundation of your cocktail attire.

Stick with well-fitted, tailored trousers in a dark color like navy or charcoal.

If you’re feeling adventurous, a pair of cream or light-colored pants can be a great summer option.

Just make sure they’re pressed to perfection – no wrinkles allowed!

Dress Shoes

When it comes to shoes, you can’t go wrong with a classic pair of dress shoes such as Oxfords or loafers.

Choose a style in a dark, neutral color like black or brown, and make sure they’re polished to a shine.

Avoid sneakers or anything too casual – this is a cocktail party, not a backyard barbecue.


The right accessories can take your Old Money cocktail attire to the next level.

A sleek watch, a pair of cufflinks, or a subtle pocket square can add just the right personality to your look.

Keep it simple and tasteful – less is definitely more.

What to Avoid – Cocktail Attire Faux Pas

Now that you know what to wear, let’s discuss what to avoid.

Avoid anything too casual, like jeans or sneakers.

Leave the bow ties and cufflinks at home – they’re too formal for a cocktail event.

And please, resist the urge to over-accessorize.

Unlike a walking advertisement for your favorite brand, you want to look stylish.

Styling Tips

In my years of styling, I’ve seen countless young men transform their confidence and social interactions by nailing their Old Money cocktail attire.

One memorable client, a shy twenty-something, arrived at a summer garden party in a perfectly fitted seersucker suit, crisp white shirt, and classic penny loafers.

His polished appearance turned heads and gave him the self-assurance needed to engage in meaningful conversations and make lasting connections; here are some tips you need to look like him.

Dress for the Occasion

When choosing your cocktail attire, it’s crucial to consider the event’s location, time of day, and season.

Opt for lighter fabrics and colors for an outdoor summer party, such as a cream linen blazer paired with well-fitted khaki trousers.

A dark wool suit or a navy blazer with flannel trousers will keep you looking sharp and warm for a winter evening event.

Fit is King

In achieving the old-money look, proper fit is everything.

Invest in a good tailor who can ensure your suits, jackets, and trousers fit like a second skin.

When assessing fit, look for:

  • Suit and blazer shoulders that lie flat.
  • Jacket sleeves that hit the wrist bone.
  • Trousers that gently skim your shoes without pooling.

Grooming Matters

Your appearance extends beyond your clothing.

Classic haircuts, clean shaves, and subtle fragrances are essential to nailing the Old Money aesthetic.

Keep your hair neatly trimmed and styled, and if you opt for facial hair, ensure it’s well-maintained.

A light, fresh cologne will complement your look without overpowering the room.

Must-wear Old Money Brands

When shopping for Old Money-approved pieces, look to brands known for their timeless quality and craftsmanship.

Ralph Lauren, Brooks Brothers, and J.Press offer suits, blazers, and accessories that embody the understated elegance of the Old Money aesthetic.

These brands can serve as a starting point as you build your cocktail attire wardrobe.

Style Old Money Like an Expert

If you’re still unsure how to take your cocktail attire to the next level and create a classic Old Money look, let The VOU’s expert stylists help.

Our personalized styling packages will have you looking and feeling your best, no matter the occasion.

Trust me, investing in your style is one of the best decisions you’ll ever make.

You’ll confidently walk into that cocktail party, knowing that you look like a million bucks (even if you didn’t spend nearly that much).

So go ahead, treat yourself – you deserve it!

With over twenty years of front-row fashion and styling events, collabs with haute-couture houses, and a PhD in Luxury Fashion, Laurenti is an expert in crafting personalized looks that depict old-money sophistication.

With years of expertise in high-end fashion collabs and a PhD in Sustainable Fashion, Ru specializes in curating eco-luxe wardrobes for the modern gentleman seeking understated refinement.

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  1. Adorable collection! These all outfits are looking amazing. These are perfect looks for day night and weekend outings. I’m so excited to try them. Thanks a lot for sharing.

  2. Beautiful selection of cocktail outfits, the ensembles are all gorgeous, especially the dinner gala-like combo for him and her.

  3. My partner was invited to a work cocktail party and we both had no idea what to wear. Did a google search, this article came up and it was an absolute life saviour as I was ready to go in jeans and sneakers!


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