Surely, every man aspires to leave a positive impression on a date, from first encounters to standing date night with the wife. For the most part, women are just looking for a little effort, especially given that how you present yourself tends to correlate with how much you care. A hasty fit says you grabbed whatever was on the chair — or worse, the floor; an overdone one says you’re trying way too hard. You want to land somewhere in between: put together, comfortable and maybe even a little memorable.
Few people have thought about at how we look and shop for clothes as Sreya Halder. A Stanford grad with an advanced degree studying AI, she is a co-founder of The Mall, an app that tracks sales, restocks and new drops from your favorite brands in one place. (Halder also previous worked in Hollywood, on Star Wars and DreamWorks properties.)
Building the platform, Halder has found that men shop more like women than you’d think. They know their exact fits, they’re loyal to their brands and, as she puts it, they “actually do want to feel like they have taste and not just go to Zara or Target for really basic stuff.” Here are her thoughts on date-night outfits, as told to InsideHook.
What She Notices First
I love when a man can really balance a cool and casual vibe but still keep it elevated. Your outfit should be flexible — we could sit down at a nice restaurant for dinner and not get kicked out, but we could also go to a dive bar afterward and not look crazy. Layering always looks really smart. A sweater, like a timeless cable knit, is very chic — not too bulky or oversized and not too tight. Obviously that’s what I see when I’m sitting down, what you’re wearing up top.
I like boxy, thick-cut cotton tees with a little bit of a crop on men — that’s elite. When you’re wearing a free T-shirt you got from math club back in high school, it looks like you don’t care.
How to Exude Effortless (Instead of Try-Hard)
When a guy has a really, really tight outfit on — this is so specific, but when a buff-ish guy has a really tiny shirt or jacket on — that’s trying too hard. I get it, you’re fit or maybe want to appear bigger, but it looks like you don’t know your size. It feels old school, like a 2010s vibe with the skinny jeans and the tiny Chelsea boots.
Another thing that does give me “the ick” for men is the Patagonia jacket. Wearing your corporate gifted jacket, or T-shirt, even a sweater — it just feels dull, like you have less personality.
Effortless to me is when a guy wears slightly looser clothing, like a breezy shirt that’s a little unbuttoned and not tucked in all the way. Pair it with baggier jeans that have a flattering structure. It doesn’t have to be insane pieces. It doesn’t have to be selvedge denim. It just has to fit well.
What to Wear: Neighborhood Bar Date Edition
I know it’s casual, but try to steer clear from jeans and a T-shirt. That’s such a daytime look. Save that for the coffee date — during the day, you can go lighter, like light denims, linens, cottons, natural fiber stuff. But for a nighttime date, a nice button-down with a loose boyfriend fit is perfect. Keep it slightly unbuttoned, maybe with a a tank underneath. That with tailored pants, like khakis, slacks or a dark-wash denim, is cool.
For shoes, don’t go for anything too snazzy or outrageous. Be subtle. You don’t want to outshine your girl. A classy sneaker, like an Onitsuka Tiger or Samba, give a casual vibe while still looking good.
If it’s colder, go for a fitted sweater with a polo underneath. Getting the pants right is most important. Something I really hate is when guys are standing up and the fit of their pants is off, so they almost look like a funnel (wide on top, narrow at the bottom). It looks awkward. There’s elegance in a good silhouette. Finding the right pants can be hard, but it’s worth it.
Tips For a Fancier Dinner Date
Ditch the tie and lose the office jacket. I hate office jackets. A leather jacket, or even Carhartt, is much better. I also really like a high-quality cardigan on a guy — that, to me, reads like you’re a sweet, friendly guy with exceptional standards for fabrics. If you’re coming straight from work, you could totally keep your top the same, probably even the pants; just make sure you don’t look too stiff. I always like ‘90s aesthetics as a reference — something more laid-back and loose.
What to Wear: Full Night of Plans Edition
A black T-shirt will always rule. It sounds boring, but a man should have multiple high-quality staples, half of them being white T-shirts and the other half being black T-shirts. Quality matters — you shouldn’t just be grabbing a Hanes tee out of your underwear drawer to go on a date.
For a full night of plans, like a nice dinner and then off to the nearest dive, you should go for a dark-wash denim jean. They’re so classic. That with a sleek black cotton shirt? That’s great. Add a nice black belt, nothing too flashy. For shoes, go with leather sneakers. They have a regular rubber sole, but the rest is leather, so it’s casual but still polished. Try to find a pair that matches most color schemes, so for a black shirt, go for a black or dark-colored shoe. I always try to match shoes with shirts, even for myself. It ties the whole look together. For outerwear, you want a leather jacket. I can’t stress enough how sexy those are.
Products That Are Worth Waiting For a Sale
Basics are always worth the full price point. A linen or cotton T-shirt or tank, jeans, even a cardigan — they’re all worth the splurge when it’s from a solid brand.
When it comes to waiting for the sales rack, hold out on new releases, along with coats and jackets. Outerwear and jewelry can be overpriced. (Most of the time with outerwear, it’s made out of synthetic materials anyway.) You don’t need to spend $1,000, or even $500, for something nice. Buy outerwear six months ahead of colder months, that’s when brands mark those items down. For jewelry, try buying abroad — it’s usually much more discounted.
One Must Skip, and One Must Buy
Skip skinny jeans. That was in style a long time ago, and now it’s just so cheugy — oh my god, I hate using that word. Do not go on a date wearing skinny jeans. Also, for me personally, earrings. I think it’s really cute when it’s a hoop that dangles, but skip the fake chunky diamonds. This is so niche, but I don’t love when men wear gold jewelry. I’m a gold girl, but to me it’s very feminine. Like you’re a queen, royalty, glistening in the sun — I don’t know if I want my guy decked out in a gold chain with a million rings.
If you don’t have them already, you must buy one or two solid accessories: a nice silver chain, a couple rings, maybe a bracelet. You can even opt for a nice pair of sunglasses for daytime dates. I prefer to build on solid basics, and the easiest way to elevate a basic outfit is with cool accessories.
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