Sasha Wears | sashashantel.com
Can we talk about the panic of standing in front of your wardrobe with somewhere to be?
You know the one. You have a whole rail of clothes, and somehow nothing is right. Too casual, too formal, too try-hard, not enough effort. You end up in the same safe thing you always reach for, half-convinced you need to go shopping, half-convinced you just need a stylist on speed dial.
I’ve been there more times than I can count. And over the past couple of years I’ve done a lot of work on my wardrobe not buying more, but buying smarter, so that when I have somewhere to go, I actually know what to wear.
So this is that post. Five occasions, five complete outfits, every single piece linked so you can shop exactly what I’d wear or find something close to it. Consider it your seasonal dressing handbook.
01 — The Work Meeting That Matters
You need to mean business without looking like you’re trying too hard.
The temptation here is to reach for something stiff and corporate, but that rarely feels like you and when you don’t feel like you, it shows. What actually works for a high-stakes meeting is polish with a personal touch. Something that says “I know exactly who I am.”
The outfit: My go-to is a tailored wide-leg trouser in a neutral camel, chocolate, or a warm grey paired with a fitted ribbed top tucked in, and a blazer I can take on or off depending on the room. Heeled mule or pointed flat to finish.
Shop the look:
- Wide-leg tailored trousers — Reiss, & Other Stories, or M&S (the M&S barrel leg trouser is a revelation and costs under £50)
- Longline blazer- Mango, River Island, or John Lewis own brand
- Pointed kitten heel mule — Stradivarius , PLT, or ASOS
The Sasha tip: Invest in the trouser and the shoe, keep the top inexpensive. Nobody remembers a ribbed top, but a great trouser and a good heel carry the whole look.
02 — The First Date (Or Any Date You Actually Care About)
Attractive but not like you tried. Confident but not uncomfortable.
Date dressing is genuinely one of the most asked-about style topics I get and the answer is always the same: wear something you feel good in, not something you think they’ll like. The most attractive thing is someone who’s comfortable in themselves.
That said, there are silhouettes that just work. A midi dress with a defined waist. Wide-leg trousers with a pretty top. A wrap style in a great fabric. These are not fashion moments, they’re just quietly excellent.
The outfit: A satin-finish or washed silk midi dress in a deep tone — rust, burgundy, chocolate, forest green. These colours are rich, flattering on most skin tones, and feel immediately dressed up without screaming “I tried.” Add a simple heel and a small bag.
Shop the look:
- Satin midi dress — ASOS EDITION, & Other Stories, and Reiss.
- Strappy block heel — ASOS Design, Boohoo and Public Desire
- Gold jewellery— Marks & Spencer,
The Sasha tip: If you’re anxious about the occasion, wear something you’ve worn before and felt great in. Save the new purchase for a date you’re more relaxed about.
03 — The Weekend Brunch
Pulled together but absolutely not trying. Cool, comfortable, and still very much yourself.
Brunch is my favourite dressing occasion because the rules are genuinely loose, you can go anywhere from a silk blouse to an oversized blazer to a great pair of jeans and the only requirement is that it looks intentional. Not I-just-rolled-out-of-bed (even if you basically did), but I-woke-up-like-this-and-I-liked-what-I-saw.
The outfit: Barrel-leg or wide-leg jeans, the kind with a slightly higher rise that gives you that relaxed-but-shaped silhouette. Paired with a simple fitted long-sleeve or a soft, slightly oversized knit. A loafer or clean trainer. Minimal jewellery, a great bag.
Shop the look:
- Barrel-leg or wide-leg jeans —ASOS, New Look, or All Saints
- Structured tote — Mango, Charles & Keith, or & Other Stories
The Sasha tip: The bag is doing more work than you think at brunch. A good structured tote or a quality-looking mini bag elevates even the most casual outfit. Spend a little more here.
04 — The Wedding Guest
The one that causes the most stress. I’m here to fix that.
Wedding guest dressing is its own sport and I know more people who’ve had a full outfit crisis over a wedding than any other occasion. The rules feel invisible but somehow everyone knows when you’ve broken them.
My approach: go for something that photographs well (you will be in many photos), that works for the venue (outdoor summer vs winter ballroom are different beasts), and that you won’t be fussing with all day. Movement matters more than you think when you’re going to be in the same thing for 8 hours.
The outfit: A midi or maxi dress in a print or a rich solid colour. Not black (unless explicitly confirmed fine, it’s still divisive at weddings), not white, not anything that competes with the wedding party. Look for a fabric that moves chiffon, satin, crepe. Add a fascinator or a great updo, and comfortable-but-elegant shoes because you will be standing and dancing.
Shop the look:
- Midi print dress- Wallis
- Open toe heel- ASOS, Schuh, or All Saints
- Occasion bag — clutch or mini — ASOS
- Jewellery — PLT,
The Sasha tip: Buy the dress first, then find everything else to match it. Going the other way (shoes first) is a trap that leads to compromise. The dress is the decision.
05 — The Casual Day (But Make It Intentional)
Because not everywhere you go requires an occasion outfit but that doesn’t mean anything goes.
A Saturday with no plans. A coffee with a friend. Running errands but still feeling like yourself. This is actually where most of our daily dressing happens, and it’s where a lot of us put in the least thought, which is why we end up feeling a bit meh by midday.
Intentional casual is not about wearing more, it’s about wearing the right things. One good piece that does the heavy lifting, comfortable basics underneath, and something that makes you feel like a person rather than a pile of clothes.
The outfit: An oversized coat in a great colour, camel, tan, burgundy, or a check over a simple base of straight-leg jeans, a fitted top, and a clean trainer or Chelsea boot. The coat is the look. Everything else just supports it.
Shop the look:
- Straight-leg jeans —Arket, & Marks & Spencer
- Fitted white or neutral long-sleeve — COS, Zara, or ASOS
- Clean leather trainer — New Balance
The Sasha tip: If you feel underdressed, the answer is almost always a better coat, not more outfit underneath. A great coat makes jeans and a white tee look like a decision.
A note on sizing and fit: I’m a UK 12 and 5’6″ for reference , but I’ve tried to include links across retailers who offer a good size range. If something I’ve linked doesn’t work for you, drop me a comment and I’ll find you an alternative.
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