What to buy (in this order)
If you only buy a few things, start at the top.
- 01Tailored suit
- 02Dress shirts
- 03Shoes + belt
- 04Leather jacket
- 05Casual pants
- 06White sneakers
01The suit (for dinner dates)
Get a blazer, dress shirt and trousers custom-fitted at a made-to-measure (MTM) showroom. For dinner-type dates, this is where I would spend first. Your suit photo will almost certainly be your lead dating app picture anyway, so you get the wardrobe and the profile handled in one shot.
If none of these brands has a showroom near you, look for a local tailored-suit shop in the $1,000–$2,000 range (the price sweet spot). If nothing good turns up, set up a virtual consultation with Proper Cloth (my favorite brand) instead.
Tell the person measuring you that you plan to leave the top blazer button open. You want a relaxed business-casual look, not an office suit. Get a dark color (navy, charcoal, dark brown, etc.) but not black. A black suit looks like you came to the date straight from the office.
Always order the blazer and trousers together, in the same fabric. If the fabrics don't match exactly, women will notice, and the outfit loses 10–20% of its appeal.
A tailored suit takes 3–4 weeks: roughly 2 weeks for production, then 1–2 weeks for final alterations.
02Extra dress shirts
If you got a custom suit above, use those measurements to order more shirts from the same brand. Depending on who you went with, you'll either have an online profile with your exact measurements saved (so reordering takes a minute) or a paper record from your visit. Either way, a fitted dress shirt looks far better than anything off the rack.
If you didn't go the custom suit route, you have two options: get measured at any of the brands above and order a custom shirt on its own, or buy an off-the-rack shirt and have a local tailor adjust the waist and sleeves. If you go off the rack, get the shoulders right in the store, because a tailor can't really fix them. The shoulder seam must end exactly where your natural shoulder does.
Also get shirt stays: elastic straps that clip your shirt tails to your socks and keep the shirt tucked in all night. It won't bunch at the waist, and you won't be re-tucking in the restaurant bathroom. For $35, your shirt just looks cleaner. Get the Y-style military shirt garters on Amazon.
03Leather shoes, boots and a matching belt
Only wear these on dates. They stay date-worthy for roughly 50 outings, so keeping them out of daily rotation is worth it. Shine and store them properly between wears, and match your belt to the shoe color exactly. Wear the shoes in warm months and the boots when it's cold.
Buy whatever fits your budget. If money is no object, get the pair marked My pick in each table.
04Leather jacket (casual dates)
For more relaxed dates, a leather jacket carries the whole outfit. It looks absurdly good in person, much better than it photographs, which is why stylists rarely recommend it.
Wear it over a crisp white tee (like these Amazon Essentials) or a simple crewneck sweater. Cheap tees are the right call because the shirt has to be spotless, and at that price you can toss one the moment it gets stained or faded.
If you can swing it, I'd strongly recommend either the Theory Morvek or Theory Wyatt. They look better than the rest of this list by a wide margin. If you have non-standard sizing (tall, long torso, short arms, etc.), go for the Falcon MA1 instead.
05Casual pants to go with the jacket
06White sneakers (keep them for dates only)
They must be 100% white: no stripes, accent colors or colored soles. Once they lose that clean look, retire them from dates. Expect about 20 good wears before it's time for a fresh pair. Because that lifespan is short, cheaper options are often the smarter buy.
Unless you live somewhere very dry, go waterproof. One rainy walk can ruin a non-waterproof pair.